AI transcript
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0:05:02 Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode
0:05:06 of The Tim Ferriss Show, where it is my job to sit down with world-class performers from every
0:05:11 field imaginable to tease out the habits, routines, favorite books, and so on that you can apply
0:05:17 and test in your own lives. This episode is a two-for-one, and that’s because the podcast recently
0:05:24 hit its 10th year anniversary, which is insane to think about, and past one billion downloads.
0:05:29 To celebrate, I’ve curated some of the best of the best, some of my favorites
0:05:34 from more than 700 episodes over the last decade. I could not be more excited to give you these
0:05:39 super combo episodes. And internally, we’ve been calling these the super combo episodes
0:05:44 because my goal is to encourage you to, yes, enjoy the household names, the super famous folks,
0:05:51 but to also introduce you to lesser-known people I consider stars. These are people who have
0:05:56 transformed my life, and I feel like they can do the same for many of you. Perhaps they got
0:06:01 lost in a busy news cycle. Perhaps you missed an episode. Just trust me on this one. We went to
0:06:08 great pains to put these pairings together. And for the bios of all guests, you can find
0:06:15 that and more at tim.log/combo. And now, without further ado, please enjoy and thank you for listening.
0:06:23 First up, Coach George Ravelling, the first African-American head basketball coach in the
0:06:29 Pac-8, Nike’s former director of international basketball, inductee of the Naismith Memorial
0:06:35 Basketball Hall of Fame and the National Collegiate Basketball Hall of Fame, and the custodian of
0:06:43 Dr. Martin Luther King Jr.’s original typewritten “I Have a Dream” speech. You can find Coach Ravelling
0:06:50 on Twitter @GeorgeRavelling. I had read, and please feel free to correct this,
0:06:54 that you’ve said the most important conversation is the one you have with yourself.
0:07:01 Yeah. So, could you elaborate on that, please? Because I think that self-talk is,
0:07:05 and I’m not sure that’s what you’re referring to, but it’s so, so terribly important.
0:07:11 So, I’d love to hear you just elaborate on that. The older I’ve gotten, the more I’ve come to the
0:07:18 conclusion that the conversation that you have every day with yourself as you characterize
0:07:25 its self-talk is so vital. It’s far more important than the conversations you have with those around
0:07:31 you. And the best part about the conversation with yourself is you’re in total control of that
0:07:39 conversation. You can craft the conversation any way you want to. And so, I try to have at least
0:07:46 90% of the conversations that I have with myself, which I have two or three times a day,
0:07:55 that it’s positive self-talk. If I start to linger on to something negative, then what I’ll do is
0:08:00 I’ll immediately deal with it and discount it. For example, since I’m Catholic, I’ll make this
0:08:07 confession. So, this morning when I got up, your reputation is so impeccable. I got up at five,
0:08:12 I’m really nervous. I’m thinking to myself, “God, what if I do a bad job? I’ll be so embarrassed.”
0:08:18 And so, the minute I started thinking that, I said, “Nope, that’s not it. Get fired up, man.
0:08:22 You’re going to do it. I’m in the bathroom. I’m doing this motivational talk for myself
0:08:28 to eradicate any doubt that I have.” And then I keep saying to myself, “You got to go in there.
0:08:32 You got to give me a best shot. You can do it.” So, I’m getting myself fired up for it.
0:08:33 And this is out loud.
0:08:41 Yeah, because I really spend as much time as I probably, at least, well, I wouldn’t say probably,
0:08:48 once a day, I’ll find an hour to just go someplace and sit by myself. And all I’ll do is take a
0:08:53 notebook and just put it in the pen in front of me and I’ll just sit there and think. Whatever
0:09:00 comes into my mind, then I start to fixate on those things. And I’ll write down notes as a result
0:09:06 of something that I think or I’ll write out a strategy. For example, the way I govern my day,
0:09:14 Tim, is I get up in the morning and I put my two feet beside the bed and I say to myself,
0:09:19 “Okay, George, you only have two choices today. These are the only two choices that you have
0:09:25 and you got to make one.” And the two choices are to be happy or to be very happy. And there’s no
0:09:32 other choice. And so, then I start to plan out my day. And so, I have these points of focus.
0:09:38 Energy management, time management, environmental management, productivity. And to me,
0:09:45 productivity is a byproduct of the other three. So, how do I manage my energy every day so that
0:09:51 I can be at maximum efficiency? So, one of the things I try to do is declutter my mind. I won’t
0:09:58 do any more than four things a day. And it reverts back to something one of the presidents at Nike,
0:10:02 Charlie Denson said one time in a leadership meeting, he said, “Let me ask you guys this.
0:10:09 Will we be better off doing 25 things good or will we be better off doing six things great?”
0:10:18 And so, to me, to simplify my day, I will not do more than four things. I try to limit the meetings
0:10:24 to two. And if it’s two, one of them is usually a breakfast meeting. When I go into the office,
0:10:31 I have a total commitment. Once I get into the office to be totally focused on business matters,
0:10:38 try to be as disciplined as I can not to get on the telephone. And also, to meet with the two
0:10:45 people that work with me, we meet every single day and we talk as a team because I want us to
0:10:52 function as a team. I want each person’s opinion to be valued. If one person happens to be 50 years
0:10:59 younger than me, so what? Their opinion is valuable to me. I respect everyone’s knowledge and I think
0:11:05 to myself, they know something that I don’t know. And so, I want to value their opinion. So,
0:11:13 we meet every day as a staff. We talk about things and it helps me grow and it keeps my day
0:11:18 simplified. I try to, once a week, have a personal audit. I go back through the week and I audit my
0:11:25 week and make course corrections along the way. So, that’s when I really get into the self-talk
0:11:31 part is having these little mental audits that my life’s just not going on and on and on. I try
0:11:37 to evaluate am I making progress? What am I doing that’s good? What am I doing that’s not working?
0:11:43 And then make those course corrections. And at 80 years old, I try to hold myself to the most
0:11:51 severe standards and I just despise the idea of retirement. I think that it’s the biggest force
0:11:56 that’s ever been predicated on us is this idea of retirement because the first thing that happens,
0:12:02 you retire physically and then you retire mentally and then you’re just taking up residence in
0:12:09 society. And I don’t ever want to be a resident of society. I want to be a contributor to society.
0:12:16 When I was doing homework, I read somewhere that you have a collection of racist mementos
0:12:21 in your house. Wow, you did do some research. Could you, beyond that, I don’t know the details,
0:12:24 but that just stuck in my mind because that’s something I think that a lot of people would
0:12:30 actively avoid. So, why do you have this collection? No one’s ever asked me that question, but I spent,
0:12:36 I probably have over a hundred thousand dollars worth of black collectibles for about eight or
0:12:42 nine years that it became an obsession with me. And so, I would go to antique shows and go to
0:12:49 stores and hunt down all black memorabilia. I have things that date back before I actually have a
0:12:56 first edition of Uncle Tom’s Cabin. So, I started to collect books, figurines, and postcards. Postcards,
0:13:03 I started with figurines. And so, a friend of mine told me about an antique store that was closing
0:13:09 and the gentleman had a huge collection of black collectibles. And so, it was in San Pedro. So,
0:13:15 I went down and I paid him $35,000 for the collectibles. He had, I wore a hundred pieces.
0:13:20 And part of the deal was that he had to mark them and write a little card so I would understand
0:13:27 the historic significance of them. Postcards, Tim, I have them back before you had,
0:13:32 this might surprise you, originally you didn’t have to put a stamp on a postcard to send it
0:13:40 out to mail. So, I have them back in the earliest one I have is 1891. Wow. But what was interesting
0:13:47 about the black postcards was they always made blacks. They pictured them in a derogatory term.
0:13:54 One of the more frequent ones you see is a black person eating watermelon with a smile on his face.
0:14:01 But they were all derogatory. Now, here’s what’s further interesting. We’ve now, you put stamps
0:14:07 on them. I was able to read the messages on some of them. And so, the one that I remember the most
0:14:12 is a lady’s writing to one of her girlfriends and we’ll just make up the name. She says,
0:14:19 Helen, we have a nigger that works at our house that smiles just like him. And so, in those days,
0:14:26 to use the word nigger was commonplace. And I don’t know if you ever learned to accept it,
0:14:32 but it was something that was said commonplace. So, I started to build this historic collection
0:14:39 of memorabilia so that I could have a legacy for my children and their children.
0:14:46 And I have them on display at my home to remind me of where we were and where we are today
0:14:50 and the trials and tribulations that we’ve gone through.
0:14:53 Do you collect anything else or have you collected anything else?
0:15:02 Books and friends. In my library at home, I have well over 2,500 books and probably I have another
0:15:11 six or 700 that are in storage because it just ran out of space. But I just continue to buy books
0:15:18 to read them. I have, as you probably researched, I have an unusual way of going about reading books.
0:15:25 And friends, I don’t have a strategy or anything for friends that most times people,
0:15:30 when I meet them, are not who they ended up being, whether it was Phil Knight, Bob Knight,
0:15:34 John Thompson, Sonny McGregor. I could tell you, tons of people, when I met them,
0:15:40 they were not who they ended up being. But for some reason, we were able to build an
0:15:48 authentic and sustainable relationship. And I’ve always looked upon relationships as a privilege.
0:15:55 And at the end of the day, at the core of all relationships, in my mind, is trust and respect.
0:16:00 And so both of those have to be earned. And so over the years, I’ve met people and
0:16:08 unintentionally, we’ve stayed in touch and there’s been this level of trust that’s allowed the
0:16:13 relationship to endure. But it’s something that’s a lot like marriage. You have to work at it.
0:16:20 You have to understand that there’s a balance in relationships. And with me, the number one
0:16:29 thing that I ask myself continually is, what can I do for you? And your good friend Ryan
0:16:34 Holiday and I had dinner last night. And one of the very last things I said to him, I said,
0:16:39 Ryan, is there anything I can be doing for you in the next 30 days? I’ve always had this theory
0:16:45 that if you help enough people get what they want, you’ll always get what you want. So I’ve
0:16:51 never tried to enter a relationship based on selfish motives that if I know this person,
0:16:57 I’m going to get these benefits. So I try to find out what do we have in common as people?
0:17:03 What is it that we can share? How can I help this person? No matter how famous they are,
0:17:10 how successfully are, everyone has certain needs, even if they’re just psychological needs or
0:17:16 we all need truth tellers in our life. And so in building relationships, I try to make sure that
0:17:23 I surround myself with people who want to see me become better and can help me become better,
0:17:28 that I can learn from them and that I can contribute to their lives. And so most of the
0:17:34 friendships I have in life, they all started by mistake. You’re one of the young men that’s
0:17:42 here today that has taught me almost all I know about technology. I spoke at a clinic in Orlando,
0:17:47 a friend of mine, Kevin Eastman, was running the clinic. And I said to him, I said, who’s going
0:17:53 to put my presentation up on the screen in that? Do you have an IT guy? And he said, yes. And so I
0:17:57 said, well, introduce him to me because I want to put my presentation up. I want to walk to the back
0:18:04 of the room and make sure it’s clear and so forth. So I met Alex Savosier. And during the time I was
0:18:09 there, we just hit it off. And so when he, I’m pretty sure he was taking me back to the airport.
0:18:15 And I asked him if he would be interested in doing a website for me. And he said, yes. And so that’s
0:18:22 how it started. And it’s turned into a lifelong friendship. And I think that was the start of
0:18:31 me recognizing that I needed to be around more young people. And so I don’t associate, and maybe
0:18:36 it’s bad to say this, but I don’t hang out with many people my own age. Most of the people that I
0:18:42 associate with are younger people because I think they’re the future. They’re smart. They’re naive
0:18:47 enough that they’ll tell you the truth. And they’re not afraid to tell you if they think you’re wrong.
0:18:54 And when I hang around people my own age, it tends to always revert back to the past. And I don’t
0:18:59 want to talk about coaching that Washington state of being the first black, this or the first black,
0:19:06 that. What I want to do is figure out at 80 years old, what is it that I don’t know but need to know
0:19:12 and how is this going to help me stay relevant in this ever-changing world? And so I’ve tend to
0:19:20 spend most of my time with younger people who inspire me, who I can have a partnership with.
0:19:26 That’s the other thing about relationships. I think relationships at their most authentic stage,
0:19:32 it’s a partnership. We share common vision, common goals, common objectives, common strategy,
0:19:40 common execution plan. It’s a we mentality. It’s not a me mentality. And it’s a win-win mentality.
0:19:47 It’s not I win, you lose or you lose, I win. It’s not about that. We were in this thing together
0:19:51 and we’re in the boat together. We’re going to row in the same direction and we’re going to get
0:19:58 the boat ashore. You mentioned books. I want to make sure we give reading at least a few minutes
0:20:06 because you are known as a voracious reader, the human Google, one nickname. And you’ve read,
0:20:13 probably, I’m sure, thousands of books at this point. You were very kind when we first got here,
0:20:17 we’re recording this right now. You said, “I learned from the wise men.” It’s always
0:20:20 a good thing to bear gifts or something along those lines. And you gave me several books.
0:20:25 You’ve also gifted many, many different books. How did this love affair with books start? And
0:20:30 could you tell us about how you read books? Because as you alluded to earlier, you have a
0:20:36 particular way of reading books. As I look back on it now, Tim, and with a point of reference to
0:20:42 so many times as we speak, it’s always going to be my grandma. Well, my grandma told me one time
0:20:47 when she’d be in the kitchen cooking, she’d tell me stories. And one time my grandma told me,
0:20:52 she said, “George, you know, back in the days of slavery, the plantation owners used to put their
0:20:58 money in books and hide them up on the bookshelves because the banking system wasn’t as sophisticated
0:21:04 as it is today.” And so I said, “Grandma, why did they do that?” And she said, “Because they didn’t
0:21:09 have to worry about the slaves stealing the money because the slaves would never take the books off
0:21:18 the shelf because they couldn’t read.” And so from that, I began to understand that as long as someone
0:21:26 can control your mind, they can control who you are in your body. And so I decided that I was never
0:21:34 going to allow myself to be in a position where someone can control my mind and control my body
0:21:41 because of my lack of information and knowledge. And so I decided that I was going to try to read
0:21:49 and learn as much as I possibly could on a continual basis because I believe that people will have a
0:21:57 greater respect for you if they respect you intellectually. And I’ve often felt in life,
0:22:05 if I had the choice between Tim liking me or Tim respecting me, I’d far more hope that you respect
0:22:11 me than like me. And I figured the byproduct of you respecting me will be that you’ll learn
0:22:17 to like me. So I don’t work at trying to get people to like me. So I’ve been on this mission
0:22:25 for a reading for years and years and years, and it’s become an obsession now with me. I don’t go
0:22:31 anywhere without a book and a notebook. If I go to a doctor’s office, I take a book with me. If I’m
0:22:37 in, I have a new system now. If I go to a bookstore and I’m in Barnes & Noble and the line has got
0:22:43 eight or nine people and rather than stand there for 10 minutes waiting, I’ll start reading the book
0:22:50 right there in line and start underlining things. So I have all these quirks that I’ve acquired over
0:22:56 the years with reading books. First of all, I divide the book into messages. I don’t spend any time
0:23:02 now trying to read a whole book because there’s probably in most books, there’s probably maybe
0:23:09 eight to 10 chapters that are really powerful and influential. And the others I skim through. So I
0:23:14 never start a book from the front and go to the back. I just, I’ll open the index and I’ll find
0:23:20 what I believe is an interesting chapter and I start there. And that’s actually how I purchase
0:23:25 a book. When I’m in the bookstore, I have this routine that I go through that. And if it passes,
0:23:30 I buy the book. And if it doesn’t, I don’t buy the book. What’s your routine? So if I, let’s say,
0:23:37 I’m going to envision this one. So our office is in El Segundo, which is outside of Los Angeles.
0:23:42 And so I go to Barnes & Noble there. One thing I found out that because there’s so many corporate
0:23:50 offices within a two mile radius that they tend to house really excellent business books. So I’ll
0:23:55 go in and as soon as I go in, I look at the books that are on reduction sale to see if there’s
0:24:01 something there that might be a good buy. Then I go to the new releases, nonfiction. By the way,
0:24:06 I go to a bookstore four to five days out of the week. I’m constantly going in and I just call it
0:24:12 search and discovery. So I’ll go to the new releases in a nonfiction and I’ll look through the books.
0:24:17 There’s usually 20 books on the table. I’d say eight out of 10 times. I’m going to find a book
0:24:24 that I had never heard of before. And so I’ll pick the book up. I go to the back. I read about the
0:24:29 author and I go to the front part and I read the promos down the side. And then the next thing I do
0:24:36 is I go to the chapters and I’ll find a chapter and I’ll open it up and I’ll see the writer’s
0:24:43 style. I look at the style. Is this someone that’s a book filled with a lot of statistics or stories?
0:24:50 Because I know what I’m looking for. The books that have had the most impact are the ones that
0:24:56 make me change the way I think or act or behave. Those are the books that ultimately end up being
0:25:02 the best for me. So I’ll go through the book and then once I find this one chapter, I start to read
0:25:08 some of it and I can tell if this is going to be me or not. And at that point, I’ll purchase the
0:25:14 book. But I just don’t go in and buy a book based on the top 10. Not that there’s anything wrong
0:25:21 with that. It’s just that I’ve had better success. So now here at 80 years old, two of my favorite
0:25:27 authors are Ryan Holiday and Walter Isison. They’ve both taken me on interesting intellectual
0:25:35 journeys. The first book I read by Walter Isison was Steve Jobs. And I was so blown away. I had
0:25:40 underlined about three quarters of the book. I was quoting and writing down quotes. And as you
0:25:45 know, the Steve Jobs book couldn’t be anything you want it to be. It can be a thesis on leadership,
0:25:53 but it was just utterly fascinating. I loved Walter Isison’s writing style. So when I finished a book,
0:25:57 I went back, I said, “Damn, I’d like the way he writes.” So I go back and I looked to see what
0:26:03 else he had written. And so then I see he’s done a book on Benjamin Franklin. He’s done a book on
0:26:10 Einstein and subsequently Kissinger and others. So I go to the bookstore and I buy the Benjamin
0:26:17 Franklin book. And I am blown away and a little sad because I feel like, “God damn, I went through
0:26:22 all this education. No one ever taught me any of this stuff other than the kite.” And so before
0:26:29 that, I think if you’d have asked me who was the most important American of all time, I think I would
0:26:35 have probably tended to say Abraham Lincoln. But after I read Isison’s book on Benjamin Franklin,
0:26:44 I would now feel, I mean, the lottery system, banking, schools, streets. He did so many unbelievable
0:26:52 things. And then from there, I went to Einstein. And anybody who can write a book on Einstein that
0:26:58 an idiot like me can understand the physics, and it was absolutely, it was a miracle.
0:27:07 So in the book Tim, I read that Einstein was very active in what they would capture in those times
0:27:13 as the Negro movement. And it says that he wrote a book on Einstein in the Negro movement. Well,
0:27:20 I had never heard of this. So I immediately stopped reading and go Google Einstein on the Negro problem
0:27:28 and lo and behold, it comes up. So I chased the book down. So what I find that a lot of times in
0:27:33 reading books and in your book, Tools of the Titan, I’m reading and I see this, you mentioned in there
0:27:40 about masterminds. And I had never heard of masterminds. So I circle it and I write Google behind
0:27:45 it. So I go back and I go online and I find out, wow. So I’m thinking to myself, oh my God, how
0:27:51 did I never knew about this? So how do I become part of it? So I sent some information to Ryan
0:27:56 Holiday about this mastermind. So he gets back to me. He says, oh, I’m surprised you didn’t know
0:28:02 about that. He says, you want to go, I’ll get you in. So the next thing I know, I get this invite to
0:28:11 go to masterminds in Carmel Valley. And my eight years on earth, that was the greatest collection
0:28:16 of intellects that I’ve ever been around in my life. I was so intimidated. And what was marvelous?
0:28:21 That was when I knew I was on the right path. Because I’m 80 years old. The next oldest person
0:28:30 there is probably 49. They’re all young energetic people. And I was readily admit I was so intimidated.
0:28:36 I didn’t think I was thinking to myself, God, how am I going to fit in? And every night I went to bed
0:28:42 with the worst headaches that I ever had, because I couldn’t process all this stuff. By the second
0:28:49 day, I’ve already filled up a notebook of notes. And it was one of those life changing experiences.
0:28:56 So you helped me grow as a person just by what you mentioned in Tools of the Titan.
0:29:00 Well, thank you for reading it. First of all, I’m sure that with all my notes here,
0:29:05 today, I’m going to have to figure out a way to have another conversation with you for sure.
0:29:10 So hopefully, I won’t blow it between now and the end of the interview. But books that you’ve
0:29:18 reread the most yourself or gifted to other people the most, are there any books that come to mind?
0:29:25 Being 80 years old, it’s a long span of reading. The books that I’ve given out the most, rarely
0:29:31 do I go to meet anyone. I can’t tell you the last time I met someone and I didn’t bring them a book,
0:29:38 it’s just become a habit now to give them a book. In most cases, I give them two or three books.
0:29:45 But the books that I’ve given away the most lately are Ryan’s two books, Obstacles and Ego is the
0:29:51 Enemy. I give Ryan’s books away a lot. One thing that I like about Ryan’s book, it’s easier to carry
0:29:56 because it’s smaller, so I can get a little bag and I can put 12 of them in there.
0:30:00 Yeah, mine are not as user-friendly from carrying perspective.
0:30:05 One thing I found with your two books is I take them on as a personal challenge. I said,
0:30:12 if he spent this much time with this many pages, I am not going to allow the length of the book
0:30:18 to intimidate me. I’m going to see this as an opportunity. And so what I did with Tools of the
0:30:26 Titan, I call that my China book. So it’s 13 hours of Shanghai or 13 hours of Hong Kong and
0:30:33 13 coming back. That’s 26 hours, man. I can knock that sucker out. Some books, you just have to find
0:30:39 the right environment in which to read them. But most of the books I read, they’re very few of them
0:30:44 that I don’t come away and feel that I’m a better person. One of the things I like to ask myself
0:30:51 at the close of every day is, what did I do to make myself a better person than I was yesterday?
0:30:59 What did I learn today? And so from a talk that I do, I say that every day is composed of 86,400
0:31:07 seconds of opportunities. And how shameful is it for me at the close of my day to say that I didn’t
0:31:13 do anything today to make myself a better person than I was yesterday? And that’s shame on me
0:31:21 because I had 86,400 seconds of opportunities to do something, even if it’s no more than a thank you,
0:31:27 a random smile, a pat on the back. Think about this, Tim, there are a lot of people in this country
0:31:33 who go through 24 hours and never have anyone say anything to them positive. You might be the only
0:31:40 person that day who said something to that person that was positive. Or I know we’re in a different
0:31:47 culture now. And I always think I’m running a little risk. But if I’m in a restaurant or somewhere
0:31:55 and a person’s waiting on me, and he or she has a great smile, I invariably say, hey, you have a
0:32:00 great smile. I sometimes I feel a little uneasy when I say it to a female because I don’t want
0:32:04 someone might think you’re trying to come on to them. But at the same time, I’m willing to take
0:32:10 that risk. So earlier, when we were leaving breakfast, as we were leaving, the two waitresses
0:32:14 said, thanks for coming. And they had a big smile on their face. So I said to both of them,
0:32:22 two of you have a great smile. Well, to me, I like practicing random acts of kindness because
0:32:31 so much today, we’re cruel and unintentionally cruel. We don’t think how valuable the little
0:32:38 things are, the thank yous, the smiles, the taking time to listen. I had a situation that I still
0:32:43 grapple with this when people stop you on the street and ask for money. We were having lunch
0:32:48 yesterday and a lady came up and she asked if we could spare some money. She wanted to get
0:32:56 something to eat or drink. So I gave her $5 and I said, now I hope you used the $5 on what you
0:33:02 said you were going to do. So she points and there’s a little grocery store a few doors down.
0:33:10 She comes back, shows me the drink and the $3 change. So it was a win for both of us.
0:33:17 But I grapple with this thing about, do I give them some money or do I not? In this case,
0:33:23 I mean, I really felt good that I was able to do something for her and she did something for me
0:33:30 because she made me feel good. What she really did is help fortify my mind that I should probably be
0:33:37 giving more instead of less. Well, you’ve given a lot in a lot of ways in many years of your life
0:33:45 and certainly one capacity is that of coach or educator or teacher and we could spend days
0:33:49 and hopefully we will, hopefully we’ll get to know each other even better and spend more time
0:33:55 together. But for now, I thought we might jump forward at least from your childhood stories
0:34:07 to the Olympics 1984. And there are many different angles we could take to get into this. But I
0:34:12 suppose where I want to start, there’s so many different things that I want to touch on. But
0:34:17 since we were talking about communicating and phrasing and words, could you share the motivational
0:34:23 quote that you came up with at that time? And I think it’s each one of us has a relative who gave
0:34:28 his life for this country, the least we can do is give 40 minutes of ourselves. Yes, that was,
0:34:35 that’s actually a Bob Knight quote. And it was a motivating force because when you stop and think
0:34:43 about it, very seldom in our lifetime does our country ever come to us and say, we need you.
0:34:49 It’s always the exact opposite. We’re looking for something from the government. But I felt that
0:34:57 this was a unique opportunity that the country was basically saying to the team and the coaches
0:35:03 that we need you and we need you to bring back a gold medal for us. And so this was a unique
0:35:10 opportunity for us to serve our country. And I can remember vividly in the months leading up to
0:35:17 the 84 Olympics in Los Angeles, I would envision that we were going to win the gold medal and we
0:35:24 were going to be standing there and hear the national anthem play and to be at attention and
0:35:28 look at the American flag. I know that we’re in a different era now in a different time,
0:35:36 but the reality was this is how I felt. And so I grew up in an era where my grandma taught America
0:35:41 right or wrong, America, whatever the problems are, we’ll work them out. But at the end of the
0:35:47 day, we’re an American. And so I envisioned what was it going to be like when we stood there and
0:35:53 received the gold medal and heard the national anthem played and you had the satisfaction of
0:36:01 saying to yourself, mission accomplished. And it was one of the most unique experiences I’ve ever
0:36:08 had in my life to be in a position where you could represent your country and you could have a good
0:36:15 feeling about it. I’m sure there’ll be a lot of people who will question why I felt that way,
0:36:17 but that’s the truth of the matter.
0:36:24 Just a quick thanks to one of our sponsors and we’ll be right back to the show.
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0:37:38 And now, Claire Hughes-Johnson, a corporate officer and advisor for Stripe, and its chief
0:37:47 operating officer from 2014 to 2021, and the author of Scaling People, Tactics for Management
0:37:53 and Company Building. You can find Claire on Twitter @chuesjohnson.
0:37:56 Claire, thank you so much for making the time.
0:37:58 I’m so glad to be here, Tim. Thank you for having me on.
0:38:04 And we were talking briefly about how one thing that you’ve observed, I’m just joshing here,
0:38:08 of course. A lot of cool people go to Brown. I want to ask about somebody else who seems
0:38:14 pretty cool, who I’m not sure went to Brown or not, but that is Fred Kauffman. And I guess
0:38:19 he is the origin of your second favorite operating principle, perhaps? Say the thing you
0:38:25 cannot say. I just love this line. Say the thing you think you cannot say. Oh, there we go. That’s
0:38:30 actually such a critical distinction, right? That is such a critical distinction. I simplified it.
0:38:36 That probably tells you a lot. We could psychoanalyze that later. But say the thing you think you cannot
0:38:44 say. Can you provide listeners with a bit of context as to what this means and why it is important?
0:38:49 I laid out, and I had to think about this for myself, for operating principles
0:38:52 for me as a leader and a person. And I shared them with others because I think actually everybody
0:38:58 should authentically come up with their own. But this one was the second one. The first one
0:39:03 about self-awareness is the one I probably talk about the most with everyone and myself. But
0:39:07 the second one is say the thing you think you cannot say. That’s why I started with the second one.
0:39:14 Yeah, because no one asked me about it now. And it’s a lesson that I’ve learned. And I think there’s
0:39:18 a journey that people go on with this lesson so we can share about that. But I’ve certainly
0:39:24 gone on the journey. And the person who was probably one of the most pivotal to me stepping
0:39:28 from square one, which is we often just don’t say the thing. We just don’t say it, was Fred
0:39:34 Kaufman. And Fred was… I’m going to get some of this wrong. But as I understand it, he was an
0:39:40 accountant by training. He became a professor at MIT. He was teaching accounting. He grew up
0:39:47 in Argentina, by the way. I don’t think he went to Brown. And he had some sort of life revelation
0:39:54 that he was not living with the true dimensions of his being and his values. And what he needed
0:40:02 to do was stop teaching accounting and become a leadership coach and advisor. And he wrote this
0:40:06 book, Conscious Business, which I recommend. I don’t recommend a lot of business books. I’m
0:40:10 just going to be perfectly honest to him. I often read the beginning of business books,
0:40:15 and then I never finished them. But Conscious Business, I have read all of it. And he formed
0:40:23 this firm called Excellent at the time that Sheryl Sandberg hired at Google. So Fred and his team
0:40:29 come in to start working with Sheryl Sandberg’s organization, of which I was a member of
0:40:34 management and then leadership. But initially, I was sort of one of the senior managers,
0:40:38 like not anyone, particularly special. And to Sheryl’s great credit, because not a lot of
0:40:43 companies at the stage Google was at were investing two, three days of management training and
0:40:48 leadership training. We all went through these 360 assessments. They gave us these report outs,
0:40:51 and then they put us in these boot camps with Fred and his team.
0:40:56 Just for a snapshot in time, when you say at that scale, what was the status of Google at that time,
0:41:05 roughly? I joined Google in May of 2004, and it was maybe around 1800 people. I mean,
0:41:08 there was a lot of contractors, I’m going to be honest, but I think in terms of full-time
0:41:11 employees. And it was, by the way, for me, the biggest place I’d ever worked. So I was like,
0:41:17 this place is huge. And then just fast forward, I left Google in 2014, and it was almost 60,000
0:41:24 people. So whoa. So I would say that the excellent engagement with Sheryl and her team was probably,
0:41:28 I joined right before the IPO, which was in August of ’04. And then in ’05, I would say,
0:41:36 is when we had, so Google actually was doubling every year. Probably 3,000 to 4,000. But Google
0:41:42 had gone public, but was still maturing and establishing, especially on the sort of
0:41:47 investment and management and organizational skills. But Sheryl, of course, ahead of her
0:41:52 time on things like that, was making the investment and had the budget that was a benefit of Google,
0:41:56 as we certainly had nice margins, Tim, that we could spend on management training.
0:42:02 And so we did this bootcamp with Excellent. But one of the things that Fred has, as he has some
0:42:06 really great frameworks, he has one about being a victim versus being a player. But one of his
0:42:11 frameworks is, how do you take what he calls your left-hand column? So you and I are talking right
0:42:16 now, say we’re having a conversation in the workplace, our brain is always operating in
0:42:21 the background. And it’s often thinking some things about the conversation, about the person,
0:42:26 about sometimes it’s thinking, what should I be doing? What do I want to have for dinner?
0:42:32 But we have this ongoing monologue in our brain. And the left-hand column, with respect to,
0:42:36 look, it’s about our conversation, Fred was really pushing us as a group. He’s like,
0:42:42 how do you, he’d say, detoxify, I can’t do his accent, detoxify the left-hand column and actually
0:42:48 say, like say the thing. And then he’d go through these exercises. And so this was sort of a light
0:42:52 bulb for me, which is like really about giving hard feedback. At that time, I was in management
0:42:57 training. But what I’ve come to learn is not only is say the thing you think you cannot say,
0:43:02 certainly about giving feedback and being more direct in your management conversations.
0:43:08 But I actually think it’s a really tremendous leadership skill, which is to get in a room.
0:43:13 And I don’t care if I’m in charge of the team or I’m just a person on a board. I’m on some boards
0:43:19 now. And we’re sitting there. And there’s often an unspoken thing. You’ve been there. You’ve been
0:43:23 in the like, Tim, you seem like someone who would actually put the thing on the table. Like I think
0:43:28 you and I are sometimes to my detriment. But yes, well, I think I need help. And this is where I’m
0:43:34 going to ask you if you could give an example, could be hypothetical or real of this type of
0:43:40 experience. And also the detoxifying, sort of like, how do you detoxify the like gentrifying
0:43:45 your inner language so that you don’t sound like a complete asshole?
0:43:50 Right. And I think, I mean, the short answer is you got to ask some stuff as a question often
0:43:55 to stop yourself from making a big judgment. But Tim, yeah, I think what I pick up in you
0:44:00 and from listening to you is you’re willing to take some risks. And so I think this is really
0:44:05 about risk taking and saying something that you’re not sure you should say, but you’re going to put
0:44:09 it out there. And then the question is, how do you do it with as much finesse as possible so that
0:44:13 you don’t end up having blowback, which believe me, I’ve sometimes said the thing I think I cannot
0:44:18 say and had people look at me like, oh my goodness. But most of the time I’m reading the room right.
0:44:23 Here’s an example, which is, I mean, just classic, more of a business example, but certainly happens
0:44:28 in my personal life too. So we went through various business planning types of tactics at Stripe,
0:44:33 but one of them we were using for a while was your classic quarterly business review. You have
0:44:38 teams come in, we’ve given them a template and we say, please fill out these things. Let’s see your
0:44:42 data. Let’s see where you are versus your goals. What’s your strategy? What’s your plan? Write this
0:44:45 memo. We’re all going to read the memo and then we’re going to have this discussion about how
0:44:49 you’re doing. And often teams come in and they want more resources or they want us to solve
0:44:52 something or decide something. And we’re of course saying like, well, it’s actually you,
0:44:56 you’re supposed to be deciding and solving, but it’s a discussion with the executive team.
0:45:01 And I’m sitting in one of these reviews with a team that’s primarily working on an area of the
0:45:06 product. So it’s product and engineering leaders. It’s not my part of the org that I run, but I’m
0:45:09 invited to be there and I like to be there. I like to be close to the product.
0:45:15 And I’m listening to the discussion and it starts to become incredibly clear to me that the team
0:45:22 is feeling defensive or blocked or angry. I couldn’t quite tell what it was that there’s
0:45:27 another team doing some similar work. And by the way, if you’ve read any Jack Welch stuff,
0:45:32 he actually had this tactic as a leader where he’d put two teams on the same problem and sort of
0:45:37 like get them to compete these tiger teams. That was not stripes tactic. I just want to be clear.
0:45:40 We were not interested. We’d never had enough people. There’s no way we would put
0:45:44 engineers on the same, believe me. So it was mystifying. And I think by the way,
0:45:50 I could hear it because I wasn’t in the room super close to the material. This wasn’t my part of the
0:45:55 org. I hadn’t heard about the details of some of these projects until this meeting. I’m reading
0:46:00 the document. I’m listening to them talk. And I just said, can I just ask if there’s something
0:46:05 we’re not talking about here? And they’re all looking at me because I rarely poke in on certain
0:46:09 moments with respect to what’s our product roadmap. And is there something we’re not talking about?
0:46:16 And everyone looks at me and I said, I feel like you’re really concerned about this other team,
0:46:20 what they’re building or what they’re up to. Are you concerned? And initially, no, no, no,
0:46:25 I mean, it’s fine. It’s fine. They’ve got this thing they’re doing that I said, well, is it?
0:46:30 Do you think it’s the same thing? Is that what I’m hearing? And I just started to ask
0:46:35 a bunch of questions of the leader of the discussion. And I said, well, should that team
0:46:40 be in the room right now? Should we have a meeting with both of you? Because it feels like there’s
0:46:47 asymmetrical information and that you all don’t feel confident in what they’re building and that
0:46:51 you’re either dependent on them or competing with them with what you’re building. And they were like,
0:46:56 maybe. I mean, it eventually became like, we don’t have the right people in the room to have a
0:47:01 conversation about the problem. And so we sort of stopped it and said, let’s go do that to the
0:47:05 credit of the rest of the people in the room. But as we left, one of the engineers who was
0:47:10 sitting on the sort of periphery walked up to me on the stairs and he was like, that was refreshing.
0:47:14 But why I’m bringing it up is, to me, that was a moment of leadership, which by the way,
0:47:21 you don’t have to be a VP or a COO to do that. The leadership is to say, I am observing a thing
0:47:26 that people are clearly not saying and are uncomfortable and is actually,
0:47:32 seems to me like a bad practice happening. And I am going to just call it, I’m going to ask,
0:47:37 is this going on? Am I seeing this correctly? And it’s going to change the whole trajectory of
0:47:42 the meeting and the conversation and maybe of the team and their work. It did result in some
0:47:46 de-duping ultimately. But I think that’s what I mean by saying the thing.
0:47:53 De-duping meaning having people working on less similar, overlapping Venn diagrams of
0:47:58 responsibilities. Exactly. And I think really what it was is they both had a part of their team that
0:48:02 was sort of doing the same thing and they were feeling dependent on each other. It was almost
0:48:05 like a yin-yang and they didn’t have the whole picture. And I was like, all right, someone needs
0:48:10 to have the whole thing under their control. So it was almost duplicate plus dependency,
0:48:15 which is sort of worse. Sounds like a recipe for lots of headaches. Exactly. But there’s also,
0:48:20 Tim, I’m sure you can picture an example in a personal situation where you take a risk
0:48:25 with a friend and you say, hey, have you told your husband that you feel that way?
0:48:32 So the detoxifying, though, in any of these examples is in your mind, you’re having a judgment.
0:48:37 We’re always judging. The brain looks for shortcuts. We know this. I’m judging and I’m like,
0:48:41 oh, I’m convinced that they’re pissed at this other team or I’m convinced my friend and her
0:48:45 husband are having problems and I’m going to solve them. But to detoxify it, you have to
0:48:50 sort of float above yourself and say, it is not going to be productive for me to open my mouth
0:48:55 and issue a judgment on another person or someone else’s work product. Yeah, people take that really
0:49:06 well. Yeah, exactly. People super don’t like that. So what can I do? What can I say? And my
0:49:14 feeling is it’s usually a question that opens the aperture of the conversation there, but keeps them
0:49:20 in a mode of curiosity, openness. How can I ask? And the problem and the art here, and this is why
0:49:26 you have to practice it and it’s uncomfortable, is sometimes you say something too general. You’re
0:49:29 like, is there something you’re not telling me? That’s not going to work because that’s going
0:49:35 to make them think, wait a minute, is there some paranoid thing? So it has to be more like,
0:49:39 you can use the words, I’m hearing a concern about the work of this other team. Say more,
0:49:45 are you concerned? And I’m all about hypotheses. I love management by hypothesis, which is like,
0:49:49 I think this is happening. I’m going to name it. I’m going to name the hypothesis I have. And then
0:49:54 I want you to validate it. Or by the way, fight with me. Say to me, no, no, no, I have data to the
0:50:00 contrary. And I’m happy to revise my hypothesis. But if you don’t state it, you’re not going to get
0:50:06 anywhere. We’re going to come back to what people might perceive as uncomfortable conversations.
0:50:13 And I want to ask later, we’re going to take a side quest for a minute about giving feedback to
0:50:17 direct reports. Because a lot of people who listen to this, or who are watching this,
0:50:26 have smaller teams. And my experience is that often people who are good at having these direct
0:50:33 conversations in a personal context or a business context are sometimes compartmentalized in their
0:50:37 capability in the sense that they’re very good. For instance, I think I’m better on the personal
0:50:44 side than I am in the business side, specifically when it is team members of my employees. If it’s
0:50:50 with contractors or joint venture partners, I can do that. For whatever reason, I think it’s
0:50:56 probably we could also do years of psychotherapy on this, but a fear of someone say abruptly
0:51:00 quitting or something if I don’t deliver the message properly. Whereas I’m not worried about
0:51:05 my friend quitting our friendship. They might get pissed and put me on ice for a week and give me
0:51:08 the silent treatment, but it’s not going to be a forever thing. So I want to come back to that.
0:51:17 But before we go there, I want to come back for a second to Fred Kaufman and victim versus player.
0:51:21 Can you explain what this is? I love this one because I think it’s so
0:51:28 simplifying and clarifying really about are you managing someone or interacting with someone who
0:51:34 has agency takes responsibility. Fred, when he introduces this framework tells the story of
0:51:38 how young children and he’s the I think he has six or seven children, by the way, but how young
0:51:45 children when something has happened that they know is bad will not take responsibility. So
0:51:52 they will say things like the coat is at school. So not I left my coat at school, right? Or a thing
0:51:57 has happened. Things have happened. The toy is broken. You’re like, well, did you break it? You
0:52:01 know, so he has this really disarming way of introducing this concept, which is we’re all
0:52:05 laughing. Just like you and I were like, haha, the toy is broken. But then he’s like, okay,
0:52:10 now let’s talk about if one of your direct reports came to you and said the report was not written.
0:52:16 And you’re like the report that you were meant to write, but how it actually manifests is you’re
0:52:21 supposed to write some report up or some summary of a meeting and you say, oh, tell me where that is.
0:52:26 And the player says completely my fault. I had planned to get it to you by five o’clock yesterday.
0:52:33 I prioritized this emergency that came up, didn’t tell you my bad. Can we renegotiate?
0:52:37 Can I get it to you at five o’clock today? And you’re like, fine, I wish you told me that you
0:52:43 weren’t going to get it. But the victim says, let me tell you about that report. Lucy owes me her
0:52:49 notes. And I can’t finish it without Lucy. And Lucy, you know, super slow at getting her notes.
0:52:54 And I’m sorry, I don’t know when I’m going to get it. But that actually is pretty common. People
0:52:59 are like, well, it’s this other person that I’m depending on. And therefore I have no responsibility.
0:53:05 And they’re a victim. And they’re going to play the victim. And I think that’s a very hard person
0:53:11 to coach. How much do you have to select that in your hiring process versus coach people from
0:53:15 one side to the other? Have you had much success or seen much success in moving people
0:53:21 from the victim side to the player side? And that’s a bit of a leading question by my tone,
0:53:28 I guess. I suspect there are a lot of instances where that’s hard. But in the success cases,
0:53:34 what does that coaching process look like? I’ve seen both. I feel like with people who are earlier
0:53:39 in their career, they’re more, I’m all growth mindset, but they’re a little more moldable.
0:53:44 And you can actually coach people out of this as like a way of operating. If they’re later in
0:53:49 their career, it’s a little more ingrained. And it’s quite hard, especially because they tend to
0:53:54 not be aware of it because they’ve somehow been successful operating in that mode. And so they’re
0:53:58 kind of like, what are you saying? You see leaders who, you know, how they behave to him is they
0:54:04 say, well, if it’s not under my direct control, then I am not responsible. And so they become
0:54:09 empire builders. And some organizations let them get away with it. They’re like, sure, you can
0:54:14 have all the infrastructure teams then. Like it becomes this weird, failing upward problem,
0:54:17 where people say, well, if I can control it, I’ll take responsibility.
0:54:22 If it’s within my house, then I’ll take responsibility. So people satisfy that
0:54:24 checkbox by giving them more and more resources. What a nightmare.
0:54:29 Exactly. And it becomes this weird expanded scope of this person who actually doesn’t take
0:54:34 responsibility. It’s a pattern I’ve seen. For people earlier in their career, the easiest coaching
0:54:38 move you do, which I’m sure you’ve heard, or someone’s done it to you, I’ve certainly had it
0:54:43 done to me. They’re saying, Lucy didn’t send me her notes. And you’re saying, what could you have
0:54:49 done differently? And you have to let uncomfortable silence then. And some people will then say,
0:54:54 what do you mean? You’re like, oh, my gosh. But some people will say, well, I guess I could have
0:54:59 helped Lucy write the notes. So what I try to do is stay in the discomfort, which is hard,
0:55:03 and just sort of like, let’s list out a few things you could have done differently.
0:55:07 And not be judgmental, like not judge the things. Just say what it was. So you could have helped
0:55:12 Lucy write the notes. You could have set a deadline with her that was ahead of your deadline.
0:55:15 Right. Put a deadline in a sauna where people can actually see it.
0:55:19 You could use a productivity tool where you could see, I love those tools, because that’s
0:55:24 sunshine. Sunshine is a great disinfectant, Tim. If everybody can see that Lucy has not
0:55:29 done her action item, that is going to help Lucy be more accountable. But the point is,
0:55:34 you come up with this list, and the person often is like, wow, you’re right. Really,
0:55:38 what you’re, they’re kind of going to have to admit to you is they’re being a little lazy.
0:55:40 They’re not helping others do the work. They’re not a good collaborator.
0:55:44 And that’s what I sometimes do with someone is like, you know, if this is a pattern, I say,
0:55:49 you know, I see this pattern. Do you see this pattern where you’re waiting for other people
0:55:53 all the time? Tell me more about why you think that’s happening. Why are the people not delivering
0:55:58 for you? And the question is like, either it’s because they haven’t figured out how to do action
0:56:04 items or accountability or be clear about deadlines, or there’s someone people don’t like to work with.
0:56:07 I always call it like going meta. Like you’re looking from the balcony at the situation,
0:56:11 which is a term from adaptive leadership. Are you on the balcony or are you on the dance floor?
0:56:14 And if you’re on the balcony, you try to get the person up there with you and say,
0:56:21 why do you have this pattern of people not helping you get your work done? And then I think of it
0:56:25 as going to the basement. I know this is, I’m a very visual person. So we look down and they sort
0:56:29 of, if they acknowledge it, they say, yeah, I guess I see that. And I say, well, let’s talk
0:56:33 about a few examples. And we come up with some examples. Then we go down and we’re in the scenario.
0:56:37 And I say, let’s do the five wise. I mean, everyone loves the five wise. I’m like,
0:56:43 why do you think Lucy didn’t send you the notes? Well, she’s not good at deadlines. Okay. And then
0:56:47 this is a wonderful expression that I learned from some coach I had a million years ago.
0:56:51 Be that as it may, which is not normal English language, but I don’t know it worked.
0:56:57 Sort of like, be that as it may. Okay. Maybe Lucy’s terrible at deadlines. But why else? Well,
0:57:02 I didn’t ask her to get it to me at a specific time. Okay. So maybe there’s a thing. Why else?
0:57:07 You know, and you’re sort of pushing them and sometimes not every time they’ll sort of say,
0:57:14 well, I don’t know Lucy and I don’t work that well together. And you’re like, oh,
0:57:18 say more about that. What do you think’s going on? And of course, by the way,
0:57:23 your left hand column, Tim, is it’s because Lucy doesn’t like you because you blame her
0:57:30 for all of your missed deadlines. But I can’t say that because that person is going to go from
0:57:34 learning to barely in learning mode. I’m trying to bring them along with me and they’re going to
0:57:39 just shut down. And by the way, they may never admit that Lucy doesn’t like them because they
0:57:44 blame her for missed deadlines. But they’re going to realize that their manager, who’s me,
0:57:49 is not letting them off the hook. If they can’t get into an agency, a player mindset,
0:57:55 I’m a responsible party for my work and others, then they are going to be off my team. If I can’t
0:58:00 coach them out of it, to your point, there’s two gaps that I think are really hard. One is people
0:58:05 who can’t stop being victims. And the other gap, I call it self-awareness gap, where they think
0:58:11 they are the best in the world. I once worked with this BD person who was like, I can negotiate a
0:58:16 deal better than anyone. And talk about not being in a learning mindset. I’m like, do you not think
0:58:22 we should get any outside advice? I’m exaggerating a little bit, but really unaware that they had
0:58:28 any potential blind spot or had never done a deal like this deal. And I’m like, how are we going to
0:58:33 close this awareness gap? Because the people around you are saying you are not the best person to
0:58:38 negotiate this deal. And I’m trying to hand it to someone else. And you’re like, what? You have no
0:58:44 one better than me. And that’s a very hard gap to close. Yeah, totally. And I promise we are going
0:58:50 to spend some time on self-awareness. The book I’ve probably gifted most to my friends and house
0:58:54 guests and so on in the last few years is actually a very short book called Awareness by Anthony
0:58:58 DeMello, which is outstanding. I need to read it again. I read it probably once or twice a year.
0:59:05 So we are going to spend some time there. I’m kind of tiptoeing around the edges of the dance floor,
0:59:12 as it were, and tiptoeing and side stepping on the balcony because I want to paint a picture
0:59:18 of you also as a person, not just the concepts. So we are going to spend some time there. I’d also
0:59:25 just as a side note, if you decide to write another book, I think the toy is broken as the title and
0:59:31 then the subtitle could be like a high performers guide to taking responsibility. Oh my God,
0:59:37 so good. The toy is broken. Tim, you’re hired for my marketing team. I gotta tell you, we’re not
0:59:41 always the best at naming things. It’s right. So you’re invited. That’s the one thing that I am
0:59:47 good at. You’re on the team. Congratulations. Thank you. As a hell of a team. I mean, my boss
0:59:52 sucks. Oh wait, I’m my boss. Oh, you’re the boss. Terrible. Terrible. You said you don’t recommend
0:59:56 a lot of business books, and I am going to come back to share all an excellent in a little bit,
0:59:59 but you don’t recommend a lot of business books. Sometimes you read the introduction and you’re
1:00:06 like, “That’s enough. Thank you.” Let’s talk about a non-business book. And that book is To the
1:00:13 Lighthouse by Virginia Woolf. What is your history with this book and why do you recommend it?
1:00:20 I love great literature. I think that’s how I grew up. My parents are both teachers. My
1:00:24 father was a high school English department chair and teacher and baseball coach. By the way,
1:00:29 he would probably say he was a baseball coach, and then he would say I’m a teacher. And my mom
1:00:36 was a college professor for a long time. And I wish more people loved literature because I think,
1:00:40 how do you understand the human condition? Literature is like the best shortcut to that
1:00:46 in your life. But I think there are some authors for someone who becomes a student of literature
1:00:53 that change their worldview about really what’s possible with writing. So not just the book changes
1:00:58 how they feel and think, but actually the process. Sort of like when you see a product. I think you
1:01:04 love innovative products. When you see something, you’re like, “That is going to change my life.”
1:01:10 And so I think that to the Lighthouse represents. I mean, Virginia Woolf is a writer that
1:01:16 resonated for me. And I think if you understand, if you’ve also studied history and you think,
1:01:24 okay, she’s writing some stuff in like the early 1900s, 1920s, not a lot of women publishing a lot
1:01:30 in that time in Britain. She gets herself into this writer’s collective with men and women.
1:01:36 She also has relationships with men and women. She’s like pretty avant-garde person. But if you
1:01:44 read A Room of One’s Own, it’s basically one of the earliest feminist manifestos that exist.
1:01:48 And this is where I think, Tim, you’re like me, I love people who are polymaths. You’re like,
1:01:54 not just this amazing novelist, thank you, Virginia Woolf, but you’re also writing
1:01:59 just your thoughts on things like women should have a room of their own. I mean,
1:02:05 actually figuratively, you know, not just literally. And I think that she is fascinating,
1:02:10 her life is fascinating. And I want to acknowledge not all of her personal views are great on some
1:02:16 things. As that happens, I worry that we started to not study certain artists because they’ve said
1:02:21 some things or done some things, which I would disagree with. I think people think she was an
1:02:25 anti-Semite and it does appear that she said some very anti-Semitic things in some of her writing.
1:02:31 I still think you should study Virginia Woolf. And I will own that as my position on her. But
1:02:37 I think To the Lighthouse, most people would say is her most important novel. I will be honest
1:02:43 with you and say, when I wrote my thesis in college, I was going to write it on To the Lighthouse.
1:02:48 And then I actually decided to write it on Mrs. Dalloway, which is another one of her novels,
1:02:54 because I love the parallels from Mrs. Dalloway with a book called The Passion by Jeanette Winterson.
1:03:01 So Jeanette Winterson is a female British writer, more in the modern era, who had broken through
1:03:06 with a memoir called Oranges Are Not the Only Fruit and then had published
1:03:10 this book, The Passion, and then a book called Sexing the Cherry. She’s published now several
1:03:14 books. But Jeanette Winterson, I think, is a descendant, in my opinion, of Virginia Woolf.
1:03:19 And I was like, I’m going to examine these two novels. And I didn’t choose To the Lighthouse.
1:03:23 But I will say that, and To the Lighthouse is not an easy read. And I want to own that also.
1:03:27 I think it’s very, Mrs. Dalloway, much more digestible, shorter book.
1:03:31 It has some repetition in it, some beautiful rhythm in the writing where you’re like, oh,
1:03:36 and I’m coming back around in the circular way to the way the story sort of moves you.
1:03:39 To the Lighthouse is like a dream state. You feel like you’re in a dream state.
1:03:45 You’re like, the points of view are shifting. Who’s the real narrator here? What is the story?
1:03:51 There’s not like, you’re not being driven by your classic plot or character driven story.
1:03:52 It is much more internal.
1:03:55 It’s like John Wick, in some sense. I’m kidding, I’m kidding.
1:04:02 I feel like the plot of John Wick is pretty clear. You know, I am going to take vengeance.
1:04:06 Excuse me now. I’m going to come out of retirement and kill everyone.
1:04:07 Oh, what a great work of art.
1:04:11 I’ll be the first one to tell you. I read a lot of mysteries and thrillers. And I like
1:04:16 movies like that, actually. So I’m very multi-dimensional. But I think for To the Lighthouse,
1:04:20 you find something new every time you read it. You think about life, death, the human condition,
1:04:25 what is love? What is family? What does it mean to connect with other human beings?
1:04:29 And there’s something about the way the writing works. I mean, it’s set in this island in Scotland
1:04:33 and there’s a lighthouse and they go out in the boat. Like you literally feel like you’re surfing
1:04:39 in a boat. Like that feeling when you’re like, I’m not really connected to firm land, but I’m in
1:04:45 this inner sanctum of people’s heads. So I think that it changed me because of the way it felt to
1:04:51 read it. Frankly, the themes are much more sophisticated than my 19-year-old self probably
1:04:54 could have handled. Like I should actually, you just said you should read awareness again. I should
1:05:00 go read To the Lighthouse again because now that I am a mother and a wife of a certain age,
1:05:05 I’m like, this book is going to resonate a lot more for me. But what’s amazing is Virginia Woolf was
1:05:10 never that. She didn’t have children and she unfortunately did kill herself. Like she had
1:05:16 a lot of demons and actually the way that she killed herself, brutal. When she filled her pockets
1:05:21 with rocks and drowned herself. And I think that a lot of artists are tortured, but the fact that
1:05:28 she could project into this Mrs. Ramsey and this woman, this very maternal figure, was a sign of
1:05:33 true artistry. Sorry, that was very long. That’s why I have a long podcast. So I’m not going to let
1:05:38 it go. I’m going to continue to chew on this bone a little bit. And for the record, I actually love
1:05:43 John Wick. But I don’t want to dwell on John Wick. I was going to say first, if you like dream state
1:05:52 evoking novels, the one that blew my mind and nine out of 10 people hate this book. So it’s a very
1:05:58 strong caveat, but it’s a little big by John Crowley. There’s actually a poet by training. It is so
1:06:05 unbelievably good. You have to slog through the first 150 pages, but beyond that, it’s absolutely
1:06:11 stunning. So what are the reasons to read fiction aside from the, as I think you put earlier, the
1:06:16 insight into the human condition? If you were trying to get someone to take that first bite of
1:06:22 forbidden apple of fiction, are there any other points that you would make?
1:06:28 How do you build empathy? How do you understand everybody has a story? I mean, you’ve traveled a
1:06:33 lot, Tim, but a lot of people you and I both know haven’t traveled the world. They haven’t been to
1:06:38 that many countries. You want to go to another country, find a great novel that’s been translated
1:06:43 from that country and read it and like you will understand that country in a way that no travel
1:06:49 guide will ever give you in my opinion. So I think it’s a very cheap way. And there’s also to build
1:06:59 like emotional intelligence. I’ve worked now in tech companies for over 20 years. And when you
1:07:04 sort of get to certain levels of responsibility with management and leadership, you could be
1:07:10 technically the smartest person in the room. But if you have no emotional intelligence or
1:07:16 dimensionality in contemplating emotional states, you are going to struggle. You are going to struggle
1:07:21 to lead. And so when I say understand the human condition, I don’t just mean like, I’m reading a
1:07:25 book and I understand, wow, that’s how it might feel to be in a divorce, or that’s how it might feel
1:07:31 to lose your child. Or, you know, I’m saying, no, you yourself as the reader, if the book is really
1:07:38 good, start to feel the feelings. You start to feel like, oh, I lost a child. Emotional exercise
1:07:46 is hard. It’s either happening to you. So you’re going through an emotional situation in your own
1:07:51 life, which is hard, but doesn’t happen every day to most people. Or you’re going to get
1:07:57 emotional exercise from, in my experience, a lot of people get it from film. They get it from video
1:08:03 content. Short form video gives you like a dopamine hit, in my opinion, but not an actual
1:08:10 deep story emotional resonant hit. We think we’re getting it when we see, oh, that dog fell
1:08:14 through the ice and then that guy rescued the dog and you’re sort of like crying and you’re so happy.
1:08:19 But like in a 30 second YouTube video, like, no, that’s not an emotional arc. That’s just, I like
1:08:26 to see people rescue animals who are drowning. But like, no, I really want, I think it’s a serious
1:08:30 film. Maybe it’s John Wick. John Wick might be a way to detoxify your left-hand collar.
1:08:35 I almost cried. I said to my friend who’d seen him before, I was like, if they touch that dog,
1:08:39 I’m going to lose it. And he just stayed silent. I was like, oh, no, here it comes.
1:08:46 But anyway, point is, I think it’s emotional workout. Literature, great films.
1:08:53 Yeah. The other thing I would say is fiction is often much more efficient and elegant in delivering
1:09:01 truths than nonfiction. And that’s speaking as someone who is a militant, nonfiction purist for
1:09:08 decades. And I really wish I’d started earlier with reading very, very high quality fiction.
1:09:12 So what was your gateway fiction? What got you, I’m so glad to hear your convert.
1:09:18 Oh, a gateway fiction. I mean, I would say that early on, I was an avid fiction reader. So as a
1:09:25 kid, there were books like The Neverending Story, and then later Dune, for instance, Science Fiction,
1:09:33 A Stranger in a Strange Land by Heinlein, which were also very condensed thought experiments.
1:09:40 This is part of the reason why I like sci-fi quite a lot. So for folks who are male, also female,
1:09:47 but if they’re male tech on the spectrum over performers, I’ll usually steer them to say
1:09:54 Ted Chiang short stories like Exhalation is a second collection. Then I stopped for a long
1:09:59 time because it was time to get serious and follows rules and be a business guy and so on and so
1:10:05 forth. So I read all the nonfiction stuff. And then I would say later on, now that I’m reflecting
1:10:10 on it, because I’m trying to pinpoint and maybe it’s because you seeded me with the Argentina.
1:10:15 I used to live in Argentina for about nine months in 2004. And in an effort, this is going to sound
1:10:22 ridiculous to people who are familiar with this work, but I wanted to read fiction in an effort
1:10:30 to get better at Spanish. So I found side by side Jorge Luis Borges, which is incredibly challenging
1:10:36 in Spanish, I will say right up front. But that ethereal kind of magic
1:10:47 realism. Yes. Fever dream type of conjuring that he was able to accomplish was intoxicating to me
1:10:55 because it’s effectively mind control, right? Like language on some level is mind control.
1:10:59 If you said to me, like, what’s the other to the lighthouse? I would say a hundred years of
1:11:04 solitude. Gabriel Garcia Marquez and my introduction to magical realism. And what’s interesting is
1:11:09 you went to this because a lot of guys I talked to, they’re like Neil Stevenson, three body problem,
1:11:14 like it’s like there’s a sci fi dune is always in their contact, you know, like whatever,
1:11:19 he depends on when they were born. But like you get this sort of sci fi. But what you just did,
1:11:26 I love, which is where else is there sci fi in a lot of Latin American literature? Isabella Yende,
1:11:33 Orres Marquez. And that’s where like maybe the genders can meet, which is like really emotional,
1:11:40 gripping multi era stories, but really wild stuff is like dream state is happening. And you’re
1:11:44 wondering like, are they on drugs? Like what’s happening here? Of course they were on drugs.
1:11:50 I 100% love that you went there. Because I think it’s when you’re pushing the sci fi
1:11:55 into like a different realm is magical realism. The most creative people I know this includes
1:12:00 business for sure. The most creative if they’re the most creative deal makers, they read and consume
1:12:06 very widely. They’re not going to this huge buffet and always eating the shredded carrots. Okay,
1:12:10 fine, like shredded carrots. Yeah, they’re healthy for you. Easy to eat. I get it. There’s a whole
1:12:18 buffet. And they end up being able to connect disparate fields and ideas in a way that end up
1:12:23 being ultimately incredibly interesting and sometimes very profitable. And I would say who
1:12:29 was it? He works with Daniel Kahneman. Let’s say this aim was very scary, something like that.
1:12:35 But he said something along the lines of researchers waste years not being able to waste
1:12:42 hours. I’m butchering the quote. But it’s like if you feel so rushed that you cannot read a short
1:12:48 fiction book, that is a symptom of a much larger problem, I would say. And so proving to yourself
1:12:54 like creating the slack in the system to do that has its own benefits. Alright, fiction conversation
1:12:59 check. We believe in it. Yeah, we believe, we believe. Alright, so let’s come back to,
1:13:04 I’m going to take a further not digression because this is just a natural conversation,
1:13:09 but we are going to come back to feedback for direct reports. But I feel like we need a smoother
1:13:16 off ramp. So what might make a nice off ramp from the fiction is something that is highly, highly,
1:13:21 highly personal and nonfiction. And that is a working with me document. So I want to ask about
1:13:25 questions that you might answer in a working with me document, you could explain what a working
1:13:32 with me document is. And there are a number that come to mind that I have in front of me here.
1:13:36 But perhaps you could just give a little bit of context on what a working with me document is
1:13:43 and how it is helpful. A working with me document is basically trying to write your own user manual.
1:13:48 And I don’t think you have to be a people manager, but I’ve come to believe it’s a best
1:13:53 practice if you are going to be managing people to do your best to write a user manual to working
1:13:58 with you. The idea came to me actually, I was moderating a panel at Google, Google had then
1:14:02 involved to a point where it’s trying to celebrate management. So we’ve done this great manager award.
1:14:08 And I was the moderator interviewing the great managers that we’d selected across several teams
1:14:13 in front of this big room of people at Google. And I asked them, you know, you ask, what are some
1:14:18 practices that you think have really benefited you as a manager? And one of the panelists said,
1:14:23 well, I copied this thing that oars, and this is oars who’s who’s who’s along many, many decades
1:14:28 at Google, I think he’s only retiring like now, who worked in infrastructure and building the servers
1:14:34 and the like a lot of what really makes your Google results come very quickly, you can think oars.
1:14:40 And then at Google Cloud, a lot of work, but he wrote a user manual. And this person described
1:14:43 it. And then they went on to say they wrote one and they shared it with their team and their teams
1:14:47 response. And I was like, I should write one like here, I am moderating this great manager panel.
1:14:53 I haven’t done this. So like any good learner, I go back and I sort of like bang out this document.
1:14:58 I mean, this is the thing that’s the most interesting to me in this maybe anti growth mindset. But
1:15:04 this was probably, I don’t know, 2009, 2008, whatever, it was like many years ago. I bang out
1:15:10 this document. And I call it the unauthorized guide because I don’t work for me. So I invited
1:15:14 comment. I said, for those who actually have had me as a manager, like, please tell me how
1:15:20 on base I am or not. And then I gave it actually, I had the time had this really amazing woman who
1:15:25 had been a manager in my organization. And then she went on maternity leave and came back and asked
1:15:29 to be my assistant. She said, I want to change sort of, I think I could be kind of a chief of staff
1:15:33 to you. And she was very talented. And we got very close. And she worked for me for like,
1:15:38 at least half my career at Google. And I was like, Maeve, read this, am I anywhere near like,
1:15:43 am I on base here? You know, she was actually, she’s Irish, which is a theme somehow in my life.
1:15:48 Like, I really bond with the Irish. And she said, well, I feel like at the end,
1:15:53 you know, you don’t even acknowledge that you like good crack. And crack, which I’m saying
1:15:58 wrong in Irish is like sort of kind of fun, Joe, humor. Yeah, she’s like, you know, your meetings,
1:16:02 she said, I’ve never been in a meeting with you where we didn’t laugh at least once.
1:16:06 That’s the kind of thing, by the way, that you don’t know, because you’re never not in a meeting
1:16:11 with you. Right. And so I was like, Oh, that was super helpful. But I feel embarrassed that I’m
1:16:15 like, I said, am I saying I’m funny? She’s like, no, you like a good laugh. It’s true. I’m not
1:16:19 particularly that funny, but I really enjoy humor. Anyway, so we added a section at the end.
1:16:22 But she said, no, I think this is pretty good. I think you should send it to the team and see
1:16:27 what they think. But what’s amazing, Tim, is that document has not changed markedly.
1:16:34 Since 2009 or whenever it was like 2009, it has not changed very much. And we can decide how we
1:16:38 feel about that. But I think it’s a great exercise in self awareness. It’s a great exercise. And
1:16:42 also sort of thinking about, okay, when I have to make a decision. So to your point, what kind of
1:16:48 content is there? Some of it’s very tactical. It’s like, how do I like what communication channels
1:16:54 work best for me? So how to use our one on one versus send me a Slack versus a text versus call me.
1:16:59 In today’s world, you know that like, I literally have people that I work with. Actually, I think,
1:17:04 you know, I work with Patrick and John Collison, the Stripe Co founders, of course, they contact
1:17:08 me on every channel. Like, how is it that you’re texting me, what’s happening me, calling me,
1:17:13 slacking me, rarely emailing me, actually emailing is probably like the least interesting channel to
1:17:17 them. So you give guidance, like what are the best channels, like how to use our one on one,
1:17:22 but also things like how do I tend to make decisions. So if you’re coming to me for a decision,
1:17:26 here’s what you can expect. If it’s this kind of decision, how long will I need, what kind of data
1:17:31 might I like, like I have a section in my doc, which is, I tend to be intuitive. So I’ve taken a
1:17:35 lot of different personality assessments. And I actually don’t really spike in a lot of areas,
1:17:41 but I spike as highly intuitive, meaning you come to me with something I intuitively have an opinion,
1:17:46 I’m like, Oh, I think this is going to be the right thing to do. Or I think I say, I’m intuitive.
1:17:51 And then I write dot dot dot, don’t worry, but data driven. So I’ll tell you my intuition. And
1:17:56 then I’ll say you bring me data. So we either can validate it, or you tell me your intuition,
1:18:01 but let’s get some data. So I don’t just get out there and start operating without any basis.
1:18:06 But I think that you’re trying to reflect that, but I think it’s important to reflect that.
1:18:11 Like, for example, in my first version, one thing that did change when my team read it was,
1:18:17 I said, I’m not a mic, by the way, every manager’s like, I’m not a micromanager. It’s like a common
1:18:20 everyone’s like, well, don’t worry, I’m not a micromanager. Unfortunately, a lot of us are.
1:18:26 And I said, I’m not a micromanager, I will delegate, I will trust you. But if I’m concerned,
1:18:29 you’re going to know, and I’ll get more involved. Right. And so I thought I was being pretty honest,
1:18:33 like when I do get involved, we should have a conversation because it means I’m having an issue
1:18:37 with trust, which means I’m not sure I’m happy with the product. So this guy who worked for me,
1:18:41 he said, I’m not sure that you’re accurate about this. And I said, well, are you saying I’m a
1:18:46 micromanager? And he said, well, there was this one thing and he named this project that I had
1:18:52 delegated to him. And he’s like, then you proceeded to show up in every meeting, read every document,
1:18:58 be in the spreadsheet. And that was, to me, felt pretty micromanagy. I was like, yeah,
1:19:02 I bet it did feel that way. I said, I did that because that project was the first time it was
1:19:07 like a sales compensation scheme. I was like, that’s the first time I’d ever built one. And I was
1:19:12 really like wanting to learn. And he said, well, you never told me that. So as far as he was concerned,
1:19:17 I showed up in every damn thing this poor guy had scheduled, and he’s supposed to be leading,
1:19:22 and he’s supposed to make a recommendation to me. And I’m like reading all the same stuff,
1:19:26 participating. I mean, I was looking back, I’m really embarrassed. I was like, I can’t believe
1:19:30 I didn’t tell you, because I had full confidence in this. He was probably, by the way, better
1:19:35 positioned than I was to build this thing. And I was counting on him, but then I went and undermined
1:19:39 him. And so that’s why, by the way, the working with me documents also helpful is because if you
1:19:43 have a good relationships with people you work with, they will tell you, yeah, you think you
1:19:47 act this way, but you really don’t. So then I had to add a section about sometimes when it feels
1:19:52 like I’m micromanaging you, it’s because I’m trying to learn the first time I’ve ever done a thing,
1:19:57 you are going to see me hyper involved. But what we should do is establish that ahead of time. And
1:20:01 if I don’t, please call me on it. Anyway, the point is, yeah, the working with me document
1:20:06 became something I just shared today with anyone who starts to work with me closely. And what happens
1:20:11 in high growth environments like Google and Stripe is like your team changes a lot. There’s new people,
1:20:16 people’s managers change is hard. You don’t love that, but like I’ve had people come to me and say
1:20:20 you’re my fourth manager in a year. So what are you trying to do? You’re trying to create a shortcut
1:20:24 because there’s anxiety when we first work with someone. Well, should I call you if I have some
1:20:29 kind of crisis? When you’re at night and Slack looks like you’re available, should I slack you
1:20:33 stuff? Or should I wait till the next morning? Or like you’re looking for guidance, you’re looking
1:20:36 to read the person. I’m like, just tell them. Tell them how to work with you.
1:20:42 And then that reduces the anxiety. And ideally, they write their own manual. And then you’ve both
1:20:46 sort of shortcut some of the get to know you stuff. So you can just jump right into working together.
1:20:56 This is something I wanted to explore because jumping expose to something you explore at some
1:21:01 length in your book, which I definitely recommend people check out. I underlined this a couple of
1:21:07 times for myself because I still feel like I have room to improve here. And that is strive to make
1:21:14 implicit structures and beliefs explicit, make the implicit explicit. And that shows up in so many
1:21:20 different ways. It can manifest in so many different ways. And I want to stick with the working with
1:21:26 me document for a minute. This first came to my attention because I had Dustin Moskovitz on the
1:21:34 podcast from Facebook fame, and then certainly of Sana. And he shared his working with me document.
1:21:40 And I’ve since seen a few versions of this. But I wanted to get your take on what might
1:21:46 be worth adding to this list of questions. Here are a few. What do I want to be involved in?
1:21:50 When do I want to hear from you? When you already mentioned, what are my preferred
1:21:56 communication modes? What makes me impatient? Are there other questions that you have found
1:22:05 helpful to address or topic areas worth including? Having seen these letters, having crafted your own
1:22:11 working with me document. My working with me document was published in Elad Gill’s book,
1:22:16 High Growth Handbook, and went a little bit viral, viral for Claire, not for Tim Ferriss. But still,
1:22:23 I was shocked at how many people that I’ve never met had seen it. And I also got some criticisms
1:22:28 on the interwebs that was very egotistical in some way. It was sort of like, here’s how you
1:22:34 make me happy. Which I was like, okay, that’s a totally fair criticism and not the intention.
1:22:39 By the way, I’m pretty highly empathetic. I’m trying to reduce anxiety and help people feel
1:22:44 comfortable being honest with me, whatever. But I get it. It seems very self-absorbed.
1:22:49 So one of the things that I’m reacting to is the question, I guess, if I were going to phrase it
1:22:55 as a question, it would be, how do I help you make great decisions? Or how do you like to make
1:22:59 decisions? But I think in my document, I just sort of have headers, like decision making, because
1:23:04 I’m not, that’s why yours called it user manual, which is a very technical, like an engineer is
1:23:08 going to be like, I’m going to write a user manual to me. And I just called it working with me.
1:23:15 There’s a section on what types of information do you like to see? Because that’s different than
1:23:19 how do I want to be communicated with. And it’s different than when should I get in touch with
1:23:24 you, which is like, yeah, if there’s a crisis, get in touch with me. But there’s something in mine
1:23:27 where I talk about the fact that if someone on your team is having a major life event,
1:23:33 I’d like to know about it. I’d like to send them a note. I’d like to say, I’m sorry, or celebrate
1:23:37 their child. Or I think, what types of information do you like to have? I also get really explicit
1:23:42 about things like email protocols mean different things to people, especially in different
1:23:48 generations. I’m sure you’ve seen this. But I used to work with someone who would send FYI
1:23:56 and really, really feel strongly that you need to process that information and have a response.
1:24:02 Whereas for me, I’m like, if you send me FYI. That means no response. That means for me anyway.
1:24:08 Yeah, I can read it later. And it’s interesting, but I don’t need to respond. And I’m like,
1:24:12 I can’t believe this. But I think I have to back to, I think you asked your guest the question
1:24:16 of like, if you were going to have a billboard. I think the fight for me in my billboard would be,
1:24:23 is it make the implicit explicit, or is it undermine the superstructure from within?
1:24:27 I’m not sure. But one of those, one of those is my billboard. But the first one,
1:24:33 I think I get the first one, making the implicit explicit is so valuable. By the way,
1:24:37 so many, a lot of people are like, I love that your book is like so humanistic about people
1:24:44 and how to care for, I was like, folks, my book is about getting results. I do appreciate other
1:24:48 humans. And I love working with them, even though sometimes Patrick calls and I would be like,
1:24:53 Oh my gosh, this is like the hardest problem. And we’d go, Oh, if there were no humans involved,
1:24:59 it would be so cheesy. But point is, I love humans and the human condition. But I really am talking
1:25:04 about how do you get results? And how do you get results? You get super clear and transparent
1:25:08 about anything implicit, you make it explicit. And you’re like clear, like this is a process,
1:25:12 we’re going to go through it to get to this outcome. And what is the outcome we want?
1:25:16 Make it explicit. I mean, Tim, you, I think are the master of this. What are we measuring?
1:25:21 Why are we measuring it? How will we know if we won? And I would add to that. And what process
1:25:27 will we go through together to get there? So that no one is guessing or reading the tea leaves or
1:25:32 wondering why another team is doing the same project, put it all on the table so that we
1:25:38 can get to the end faster. And frankly, more inclusively, and why do I care about inclusion?
1:25:43 Yes, inclusion is a good thing for people to feel better and included. But actually, because
1:25:48 if you’ve hired a bunch of smart people, and yet they don’t feel included, they will not share
1:25:52 their opinion. And the reason you hired them is because they’re smart people who bring diverse
1:25:58 opinions. And if they won’t say them, then you’re like not really benefiting from all that work
1:26:03 hiring them, because you want a better outcome. This is all about results. But I think it’s a
1:26:10 little windy to get there sometimes. Yeah, totally. Until you make it explicit. I wanted to piggyback
1:26:16 off of your Irish pattern in life and recommend a short film that I think won an Oscar. I might
1:26:21 be making that up, but I won some slew of fancy awards. And I watched it last night, called an
1:26:26 Irish goodbye. It’s about 20 to 23 minutes long. If I don’t Vimeo, I think you might be able to
1:26:32 watch on YouTube as well. It is hilarious and profound and outstanding. I think based on the
1:26:38 little that I feel like I’ve sort of felt out with our fiction love fest, I think you would
1:26:43 really enjoy this. It is one of the better short films I’ve ever seen. It’s really good. It’s really
1:26:49 really good. So an Irish goodbye. What is it? Little big and Irish goodbye. Start with an Irish goodbye,
1:26:52 because then you’ll be like, wow, Tim really recommends good stuff. And then if you hate
1:26:58 little big, at least I’ll have some redemption preemptively. Yeah, so it’s like the Moose
1:27:03 Boosh before you try to chew on the fever dream. And I’d also say also, I’d love a good Irish
1:27:10 goodbye. I used to find it a little offensive, but now I’m like, gosh, there’s some real beauty
1:27:16 and just disappear. Oh, I do that all the time. I do it all the time. So email policies. I had a request
1:27:22 from Kevin Kelly recently who’s been on the podcast and is a close friend. I asked him if I
1:27:25 could help him with anything. We’re having a conversation. He said, well, I do have one request,
1:27:29 and it’s not for him. It’s because he gets asked about it so much. He doesn’t have any issues
1:27:35 with email. But he’s like, I want you to ask everyone of your guests about email policies slash
1:27:42 rules, systems, anything that they have ended up using that they have found helpful. And I will
1:27:48 say in advance, my assumption is that almost, well, it’s not my assumption, I’ve also run into this,
1:27:52 even though this podcast has some of the top performing people in the world of every discipline
1:27:58 imaginable, they all claim to kind of suck at email, they’re behind and it’s hard. So I understand
1:28:03 that being that as it may. See, it’s a beautiful change. There we go. Be that as it may. Be that
1:28:08 as it may. You are still going to have to answer this. Yeah. Are there any sort of email policy
1:28:14 systems, rules, implicit things that you make explicit that you found helpful? I actually
1:28:19 worked on Gmail right after it launched at Google and like you should think I would be like a power
1:28:24 email organizer and I’m okay, but I’m not great. But one thing that just stuck out of my mind as
1:28:30 you brought this up is I had a good friend who was a executive at Genentech and she rose up with
1:28:35 Genentech as it got big and she got more and more responsibility and she told me about this leadership
1:28:39 training they put them in Tim. Honestly, whenever I look at my inbox, I think of this training
1:28:46 where they gave them some 30 minutes, some window, they gave them an inbox. And they were like,
1:28:54 you need to process all this and kind of do the right things, right? Okay. And so in this inbox
1:29:00 of like 100 emails, whatever they have 30 minutes, you have to find there’s like a massive legal
1:29:05 issue. There’s an HR violation, but it’s like not in the headline of the subject of like an
1:29:11 anxiety dream. Like a bunch of bombs in these messages and you have to like open them, skim
1:29:16 them, decide you have to come back to it, right? Yeah. And I kind of was like feeling like Japanese
1:29:21 game show. I’m like, what does show that people might want to watch? And I think there is a
1:29:26 sector of people who might find that like really interesting to watch. So sometimes I look at my
1:29:33 inbox and I’m like, oh my gosh, I have 30 minutes and I need to find all of the legal time bomb.
1:29:38 But one of the things that I think I’m very good at an email is it’s a set of people in my both
1:29:44 professional and personal life, like they get opened immediately. And I’ll open it. And if it’s
1:29:49 by the way read FYI, I’ll read it later. I really want to make sure I mean, it’s easy. Some of these
1:29:53 people is like easy. It’s like your kids. By the way, my kids are teenagers. They never email me.
1:29:58 So that’s like easy. But you know, certainly if you’re the COO of a company, even if you’re not
1:30:03 the COO anymore, if the founders of Stripe emailed me directly, I’m going to open the email pretty
1:30:08 freaking quickly just to make sure like, you know, so it’s sort of like your boss or but I do think
1:30:16 that some people have a methodology, which is either LIFO or FIFO lasted first out. Yeah. And I
1:30:20 think that that’s tempting. My husband does this a little bit. It bothers me. I’m like,
1:30:28 you have cues, which is who is it from? And is a group or is it in direct to you? And use those
1:30:34 cues to prioritize. And so if you only have 30 minutes, you know where to start. That’s one
1:30:38 of the things and it is a combination of the people and what’s being sent to you directly.
1:30:42 So I think that’s like a number one rule I have that I’m pretty actually good at.
1:30:46 So there’s certain people who feel I’m very responsive on email because I I am very responsive
1:30:54 to them. Yeah, I’m not maybe responsive to everyone as consistently. The other is I have,
1:30:59 this is like more of a cheat, but you’re an investor, I think, right? So I’m I’ve invested
1:31:05 in some companies. And a lot of them send these investor newsletters or investor updates. And
1:31:11 of course, I’m because I do have some Gmail skills. I label them. I know there’s a folder full of them.
1:31:19 And I have every intention to him. On Friday, for like two hours, I’m going to read those investor
1:31:26 updates. Okay. You know what? That is not correct. Sometimes when I’m on an airplane and I’m trapped,
1:31:30 I like open and start reading them. But like, I am not reading them in a timely fashion. And I’m
1:31:36 sorry, all the founders I’ve invested in, I’m sorry, I’m not reading your investor updates in a
1:31:40 timely fashion. But what I’ve learned to do, and this goes back to making the implicit explicit
1:31:46 and also to another rule I have, which is strive to set expectations with people. So now when I
1:31:52 invest in a company, I say to them, I say, look, you may email me, I’ll give you my email. I said,
1:31:57 I’ll give you my cell phone. I’m quite good on text, but please don’t abuse it. And if you want
1:32:01 to WhatsApp me and not tech, whatever, either of those is going to work. And then I say to them,
1:32:05 I want you to know, I really appreciate getting the investor updates. I will not read them in a
1:32:11 timely fashion. I may not read them at all. If you need something from me directly, like you need
1:32:16 help me interview this person, or I have a crowd, you should get in touch with me directly,
1:32:21 not as like at the end of an investor email, it says, please help us hire some way to scientists.
1:32:28 And cognitive load wise, I’m like, I have been feeling so much guilt about not reading there.
1:32:34 By the way, they spend so much time on them. And it’s terrible sometimes. But I no longer feel
1:32:38 guilt. I’ve told them, you must contact me directly. Set expectations. But this is actually
1:32:42 a management lesson, which is why not this goes back to the user manual, or they’re working with
1:32:48 Claire guide, like why not tell people, I have this habit of ignoring this kind of thing. And
1:32:54 if you need my attention, please, you have my permission, please use it, please text me even.
1:32:57 I mean, for these founders, they have my phone number. I’m like, if you need me,
1:33:01 you can call me. But it’s sort of a human lesson we learn over and over again,
1:33:05 which is we’re like, dying inside that we’re disappointing someone. And I’m like, no,
1:33:09 just renegotiate the terms of what expectations they should have of you.
1:33:13 How else does this renegotiating show up? This has become
1:33:21 it’s embarrassing to say, but I’d say maybe in the last two years has become such a revelation for
1:33:25 me in a sense, because I was thought about negotiating as the thing you did in the beginning.
1:33:31 And I got, I think pretty good at that. And at times, though, I would have who knows, like,
1:33:35 maybe I’ve had two glasses of wine or I had two little sleep or whatever. And I would agree to
1:33:39 these things. And then later I’d look at my calendar. And my blood pressure would go up
1:33:46 being a 30 points, because I felt trapped by these commitments that I made when I was compromised or
1:33:54 rushed or lazy fill in the blank. And this renegotiating has become an invisible option
1:33:59 made visible for me in the last two years. Could you talk a little bit more about how
1:34:06 you have used that in your life, personal or professional, how that shows up like examples
1:34:09 would be really helpful here. So people can really get a grasp on it.
1:34:13 I’m having like almost a physical reaction to relating to you about this calendar. It’s
1:34:18 like your past self. I used to say, oh my gosh, I just milled myself a letter bomb.
1:34:23 So one is, of course, we all strive to improve, which is do not make a decision in the moment
1:34:30 about a time or a commitment of resources or time without trying to project your future self.
1:34:33 But of course, we all do because you’re right, we’re rushed, we’re trying to be responsive,
1:34:37 we’re trying to move through our inbox, by the way, because we’ve only got 30 minutes,
1:34:39 so we might fail the corporate training test.
1:34:41 Or the Japanese TV show, I don’t want to come in last.
1:34:46 Yeah. So one thing is trying to be better about projecting. And I also had a friend
1:34:50 who’s like a very kind of spiritually in touch person. And she said,
1:34:57 when something is requested of you, she said, you need to sometimes listen for the quiet no.
1:34:59 Can you say that one more time?
1:35:03 So she said, when something’s requested of you, a person, I mean, she’s like sort of like,
1:35:09 sometimes your reaction is, wow, yes, right? You’ve had this. I mean, hey, Tim Ferriss asked
1:35:15 me to be on his podcast. I was like, yes, emphatically, that is something I want to do.
1:35:20 That is easy. My future self is very happy to be, my past and future selves are very happy
1:35:26 to be here. But often we get a request, you have this experience and you’re looking at it.
1:35:33 And she says, listen for the quiet no. Because we are often feel like we have to say yes.
1:35:37 And her trick is, and I know this wasn’t the question you asked me, which I will answer,
1:35:38 but her trick is-
1:35:41 These are really closely related. I’m so interested in this.
1:35:41 Yeah.
1:35:46 I think they are. Do not respond immediately. Because we often feel, I mean, if you’re someone
1:35:50 who prides yourself on being decisive and responsive and empathetic as I do,
1:35:56 I feel like, well, they asked me to be on this panel at this important conference or whatever.
1:36:00 And I’m like, I’ve learned that my response in fact should be,
1:36:04 when do you need to know whether or not I can be on this panel?
1:36:09 Or I’ll even say, I need two weeks to get back to you about whether I can be on this panel.
1:36:15 Because if I don’t give myself some space, I will do yes instead of the quiet no.
1:36:21 Because I didn’t give myself time to really think about, is this my priority? Should I spend my time?
1:36:26 Oh my gosh, I have to fly to the city. Like you have to really think. So I think
1:36:31 when you are renegotiating, so I’m proud of you that you found this as a skill. And by the way,
1:36:36 I have the same problem. I had a delayed travel earlier this week, and I was looking at my next
1:36:40 day, and I was thinking, well, I am going to get home, but I’m going to get home at like now two
1:36:45 in the morning. And then I looked at it, and I was like, I should not even be doing that stuff.
1:36:49 I was like, why did I even agree to go into Boston and have lunch with this person and then talk to
1:36:55 this other person. And so I was like, I am going to renegotiate those commitments. I don’t even have
1:37:01 to say that I was delayed. So it’s a good skill. But what I look for is a pattern, a pattern of
1:37:05 why am I renegotiating this stuff. It means I’m not making the right decision in the first place.
1:37:11 So I listen for the quiet no. But if I find myself renegotiating, it is often about, yeah,
1:37:17 commitments I’ve made. Commitments, especially of time. My mom was a very talented, apparently
1:37:22 mathematician in college, and my mom went to Harvard, well, Radcliffe then. But I think it was
1:37:30 pretty rare for a woman to be like a star in the math department. And she decided to go get her PhD
1:37:37 in history and to major in history. And I said, why did you switch? Why did you make the switch?
1:37:45 And she said, I realized that there is a trade-off that most people find themselves making between
1:37:53 money and time. And she said, I knew that if I prioritized math, it would likely lead to a more
1:37:58 lucrative career. By the way, my mom was like, out there, she was going to work, and she did,
1:38:01 and she was going to have kids and work. But she was like, it would lead to a more lucrative career,
1:38:06 but I would not have time. So I decided to become, she became an academic. She got her PhD. She
1:38:11 became a professor. And why? Because professors have more control over their time. And they have
1:38:15 the summers off. And they have time to think and write. And that’s what she knew she wanted,
1:38:20 which by the way is pretty aware for like a 19 or 20 year old to realize you’re going to trade
1:38:26 money and time. I think it’s Peter Thiel, who says people don’t value their time highly enough.
1:38:32 They just don’t get, every hour is costing you something. And I’ve taken me so long to come
1:38:36 to this point where I’m like, oh my gosh, I just threw away and said, sure, I’ll meet with you
1:38:42 to give you advice about that thing. And I’m like, oh, so I’ve become less responsive on email
1:38:52 because I am trying to stop myself from mortgaging my time. You may or may not have had the same
1:38:58 experience. But all right, here’s an example, you’re looking for concrete. I have a woman who I
1:39:03 highly value personally in my life. She’s a founder. And she asked me to be on her board.
1:39:08 By the way, to stop myself from saying yes to stuff, I make rules. I made a rule. I was like,
1:39:11 no more boards. I also have a rule about travel right now. I’m like, my daughter’s going to
1:39:16 college soon, no more travel unless it meets these criteria, because I want to be home. Of
1:39:19 course, she doesn’t want to hang out with me, but I want to hang out with her.
1:39:23 What are the criteria to study curiosity? Could be just a few examples.
1:39:28 Really important to Stripe. I still actually work part-time for Stripe and they get bids on my time.
1:39:32 And if Stripe said the most important thing you can do for Stripe is go to, this happened to me
1:39:38 recently, go to Helsinki to slush to this conference. I was like, fine, I will do it.
1:39:42 I will go to Helsinki for Stripe. And by the way, I had a great time and I met a great number of
1:39:47 founders and it was actually a blast. So is it important to Stripe? Is it a personal connection
1:39:54 that is meaningful to me that is asking of my time treasure talents? My criteria is not to
1:40:00 say yes to default, but it is to number one, is there a way I could do it that is less friction?
1:40:07 As in, am I flying to California anyway? Therefore, I can do that commitment if I bundle it. So can I
1:40:12 control when it is? And if I can control when it is and it’s a personal connection that’s meaningful
1:40:16 to me, I will make it happen, but it will not happen quickly. But if it’s not something I can
1:40:22 control where and when it is, then I have a subset of criteria of like, but I often will say like,
1:40:26 could this thing, maybe it’s a conference, can I do this next year and get back to you later?
1:40:32 So I can actually think for a minute. A lot of it is buying time. But I have these rules
1:40:36 about things because it stops me. So I said to her, I said, I have made a commitment to myself
1:40:41 that I will not join another board. And she, because she’s a talented founder, she’s persistent.
1:40:45 And she said, why don’t you just come and be an observer? Why don’t you just come to, I know,
1:40:50 I know, come to the board meeting. And then she told me why she really needed help in this particular
1:40:55 moment. And there was a situation where having someone who was sort of a friendly, who was neutral
1:41:00 in the room was going to be valuable. So I said, okay, I will come, but I will not,
1:41:03 like I really want to set your expectations right back. I was like, I am not, this is not
1:41:08 going to reel me in. I’m not going to join the board. And I did go and she actually convinced
1:41:12 someone else. And the two of us went and we actually, I think helped her through a particular
1:41:18 moment by being sort of board participants. But then she said, I’d like you to come to every,
1:41:21 you know, first every board meeting. And I said, I don’t think I can commit to that,
1:41:27 but I can try when it’s virtual. And if it’s in person, I’m pretty sure I won’t, but you can
1:41:33 invite me. And I went to a couple, I did pretty well. And then I started to look at my calendar.
1:41:39 And I was like, I can’t do this. I can’t even take three, four hours. And so I needed to renegotiate
1:41:44 it. There’s a quote that I have in my book that that people find, I think the most compelling
1:41:50 line in the book. And I keep having to remind them it is not my line. Yeah, I know this problem
1:41:54 where I’m like, no, no, no, no, no, don’t attribute it to me. That was Mark Twain or whatever.
1:42:00 Exactly. Exactly. The line is from Ron Heifetz or Marty Linsky. These are the adaptive leadership
1:42:05 guys who do the balcony and the dance floor analogy. And it is leadership is disappointing
1:42:10 people at a rate that they can absorb. Yeah. I had that line underlined. It’s very catchy.
1:42:14 Because it really makes you think and it’s kind of dark too. Yeah. What does that mean in like
1:42:19 concrete terms? Yeah. And then I’m not going to let go of the renegotiating because I’m going to
1:42:23 come back to that. I want to ask you about phrasing and wording that you use. But let’s
1:42:27 talk about leadership and disappointing people. Well, I think one of the ways that leaders
1:42:33 disappoint people is their time. You don’t have unlimited time. You’re the CEO of a company.
1:42:38 There’s no way you’re going to be at all the things or do all the things. But the key is how
1:42:44 do you create enough leadership buy-in that people understand? And also you get a little bit of
1:42:48 forgiveness when you’re the CEO, I think. But leadership is disappointing people at a rate
1:42:54 that can absorb. To me, it’s about management is very knowable. It’s like, how do I get from
1:42:59 point A to point B? What people do I need? What’s the scope? How are we going to measure it? Here’s
1:43:03 the project plan. Here’s the milestones. Here’s the talents I need. And now I’m going to deploy
1:43:11 and delegate. And I think leadership is very unknowable because it is essentially having a
1:43:17 vision and idea, a goal that you haven’t even fully understood yourself, right, often? Yeah.
1:43:23 It’s like, we’re going to climb this mountain that no one has ever climbed before, by the way.
1:43:29 And you have to be really convincing to build followership. You’re painting a picture of the
1:43:36 top of that mountain, man. And it is awesome. And the climb is going to be really challenging,
1:43:42 but really rewarding. And you are going to get on that journey with those people. And you are
1:43:47 going to be wrong about a lot of what you just said, right? No, actually, it wasn’t as easy up the
1:43:54 south face as we thought it was. Yes, we did actually need special equipment. I mean, come on.
1:43:58 You don’t even know how you’re going to get up there. The analogy that’s more concrete that I
1:44:05 use is, I came into Stripe and look, it’s a product that has people’s money. And you need to have
1:44:11 good support experiences when something is wrong with any kind of payment. I’m expecting money.
1:44:16 I’m trying to take money. I’m moving money. There’s a high expectation. And Patrick is like,
1:44:22 we need to build 24/7 global support. We had really good ambitions. And by the way,
1:44:29 I want to be clear. One of the things that Stripe has as a value is to be users first. It is always
1:44:34 our most important operating principle. It is actually deeply in the culture of the company.
1:44:38 So much so, Tim, that when the support team would get behind, the entire company
1:44:45 would stop and answer support emails. And so, this was becoming an existential problem because
1:44:50 we had to do engineering work and other work to build the company. But we were ending up on
1:44:56 Fridays before the weekend because you want to get back to people quickly answering support tickets.
1:45:00 By the way, you hit product market fit. You get traction. This is a super normal problem.
1:45:04 But it is not great because the product is people’s money. It’s a quality problem,
1:45:07 but it’s a problem nonetheless. And so, Patrick is like, look,
1:45:12 we need to have this 24/7. And I had to get up as the leader and say, I will build this.
1:45:17 And I had built similar things for Google. So, I wasn’t completely describing the mountain I’d
1:45:24 never seen. But I certainly didn’t join Google when it was only 160 people with 21 support people.
1:45:30 And I was like, we are now going to do a set of things to solve this. And it took me a few years
1:45:35 and it’s not perfect. And it involved hiring very talented people. I don’t get credit for
1:45:42 what we built. But I still look back on that and I say, I can’t believe I declared that I would get
1:45:46 it done. And I didn’t have a plan because I’m more of a manager. I’m more of like, I need to have a
1:45:50 clear plan on how I’m going to get this done. Instead, I was like, yep, we’re going to have it.
1:45:57 Public announcement. And I mean, Patrick kind of pushed me there. But I was like, this is uncomfortable.
1:46:01 And I’ll tell you, I did disappoint. Did I deliver it by the end of that year? Oh, no, Tim,
1:46:04 I did not deliver it by the end of that first year. Like, let’s not kid ourselves.
1:46:11 I disappointed. But I did figure out a way to do it. And I think people followed me. They
1:46:15 kept following me. They kept believing we were going to do it, which is some combination of me
1:46:20 being authentic, I think, me being honest about where we were, me having a plan eventually,
1:46:25 me demonstrating that it mattered, whatever. So I think that’s what it means is like,
1:46:29 you will not live up to everything you said, all the expectations of you,
1:46:36 with your time, with your ideas. We’re all humans. We’re not perfect. And we’re not
1:46:41 fortune tellers. I’m not a fortune teller. So this ties into the renegotiating, actually,
1:46:47 pretty well, because there are many different species of renegotiating. One was, you gave an
1:46:51 example very early on in the conversation, when Lucy was getting thrown under the bus,
1:46:59 the dog ate my homework situation. And then we segmented from that to the player versus victim.
1:47:03 And the player would say, you know what, you’re right. I committed to get this to you by 5pm.
1:47:08 I didn’t. And because this emergency popped up, and I didn’t let you know, I should let you know
1:47:16 how about 5pm tomorrow, or whatever the example was, renegotiations. So in this particular example,
1:47:21 when it becomes clear to you that by whatever deadline had been agreed, you are not going to
1:47:25 be able to deliver what you’re going to hope to deliver. What does that conversation look like?
1:47:30 I mean, it’s not exactly semiotics, but I know you like language, and I know you consume a lot
1:47:36 of language. So what is the language that you use to have that conversation, whether it’s verbal
1:47:41 or in email? I think you made the connection, and then you didn’t finish making a connection,
1:47:46 but it is so easy to sound like a victim when you are facing this kind of a situation. And if
1:47:50 you’re someone who prides themselves on being a player, on taking ownership, and you’ve made this
1:47:56 commitment, and you’re like, oh my gosh, there’s no way I’m either coming to that meeting or
1:48:02 delivering 24/7 global support in six months. And so what does it look like? I think what it looks
1:48:08 like, the first thing I did that was probably the smartest thing I did when I joined Stripe was I
1:48:14 listened, and I did my first 90 days, and I talked to everybody, and I heard sort of here’s priorities,
1:48:18 here’s what people need, here’s what need my attention. And then I sat down with Patrick,
1:48:22 and I said, I’m hearing these four things. One of them was the support thing, by the way,
1:48:29 that really need my attention. And I am going to rank them, and then I want you to see my ranking,
1:48:34 and I want to agree on my level of priority. I said, because I can’t make meaningful progress on four
1:48:42 things at once, I can maybe keep, and I actually predicted in that moment, I said, because we had
1:48:46 to build sales, we had to build recruiting, we had some internal operational stuff that
1:48:52 needed to be fixed, and then we had this support smoldering fire. And I said, I think I actually
1:48:58 need to build sales and recruiting ahead of fixing support. But I predict support is going to
1:49:03 implode within the next six months. And at that point, you were COO. Is that right?
1:49:07 I was COO. I was actually hired as Chief of Business Operations, and then I became,
1:49:11 we just swapped titles with someone else, but it’s a long story. But yes, I was basically COO.
1:49:16 And remember, we’re users first. This was a painful, because we were also not getting back
1:49:21 to sales leads though, Tim. I was like, I’m also here to build some revenue. I’m here to build,
1:49:25 go to market, and I’m here to deliver some revenue for this company. And I’m like,
1:49:29 we have this other thing where we’re not getting back to our prospects. And so,
1:49:34 it was a very Sophie’s choice kind of moment, honestly. Oh, and then we couldn’t hire people
1:49:38 to build the company, so we couldn’t get back to sales leads. This is normal, by the way,
1:49:43 this happens, and especially for people like me coming into that kind of opportunity. But what
1:49:47 I loved about that conversation was Patrick was, one, first of all, supportive. He was like, great,
1:49:52 this is good for us to talk out now. And then he had to admit, he’s like, I can’t believe I’m
1:49:57 doing this, but I agree, you’re not going to fix support in the first six months. We made an
1:50:04 agreement. And then, by the way, Tim, four months in, complete explosion. And I was thinking in my
1:50:08 head, thank goodness, this goes back to expectation setting. I’m like, thank goodness, I said out
1:50:12 loud that I thought it was going to explode. And then, I mean, by the way, it’s still terrible.
1:50:16 I was so sad. I was like, oh my gosh, I had to go then put it at the top of the priority list,
1:50:22 basically. But I had at least four months to build some other things. Point is, one is try to set
1:50:27 the priorities, align on them, and set expectations ahead of time. Even if you haven’t done that,
1:50:29 you’re going to reach a moment where you’re like, there’s no way we’re going to the top of this
1:50:37 mountain. And so what you try to do is not come up and make a bunch of excuses. So what I, I think
1:50:42 I did in those moments, we had written public goals in the company, we had plans, and I just
1:50:46 want to be clear, none of the plans, this is where when you’re working with founders, maybe this is
1:50:51 a side, what do you call them side quests? This is a little bit of a side quest. Love side quests.
1:50:57 When you’re working with founders, people describe this reality distortion experience,
1:51:03 which often is more that they have a version of reality. And they’re like, no, no, no, we can ship
1:51:08 the iPhone in five minutes or whatever, you know, and like everyone’s like, yes, Steve, yes, we can.
1:51:14 Right. There’s another version of reality distortion I find, which is you can fix that
1:51:18 thing in five minutes. It’s now a joke between Patrick and I, because he’ll be like, yeah,
1:51:24 we could just like code that up. And I say in five minutes, you know, it’s not five minutes.
1:51:30 So we had a consistent conflict where I would say to him, no, that mountain is not going to be
1:51:34 climbed by the end of this year. I never actually said I was going to build that thing by the end
1:51:39 of the year. And he refused to hear it. He was like, no, it really needs to be the goal.
1:51:46 This actually needs to be the goal. Be that as it may, Claire. Yeah, be that as it may, Claire.
1:51:53 I’m making it your goal. And I was like, okay, under duress, I am going to like take this goal
1:51:59 and try to put some language in it. I mean, I’m going to get a red, right? Whatever on your,
1:52:04 I mean, that doesn’t feel good. This is the other thing. It’s beneficial to walk into a situation
1:52:10 like that after some amount of career success, so that you have some amount of self actualization.
1:52:14 So I was like, luckily, my whole identity is not tied up in this goal, because I would have been
1:52:18 destroyed. I would have really lost confidence. By the way, a lot of leaders you hire into a
1:52:24 startup environment end up losing confidence just because you’re getting pummeled, totally pummeled.
1:52:28 And like, you need to sort of be like, no, no, no, I have identity outside of the success of this
1:52:31 moment. But I was like, all right, I’m going to publicly get up in front of the company and
1:52:36 have failed on this goal. But we disagree. We agreed to disagree that this is possible.
1:52:41 What’s also funny, though, is I was like, I think he really believed it was possible and he’s very
1:52:45 smart. And of course, then I’m going home, I’m like driving home at night. I’m like, has he ever
1:52:51 built anything like this? No, why am I even listening to them? But they reality distort you
1:52:55 into thinking, yes, it’s completely possible. Like, I don’t know how I got fooled. But what I did
1:52:59 sort of commit to myself is like, I have to make meaningful progress. So what are some of the
1:53:04 milestones we can point to? So what you do is you go in and you say, well, I was not convinced
1:53:10 this was the right goal. But I agreed to it. Here are the milestones that I’m glad we hit. So you
1:53:13 kind of don’t forget to point out you made progress. I think sometimes people get defense,
1:53:17 they’re like, I don’t want to be defensive. But you have to be like, look, it’s like nothing happened.
1:53:23 And then you try to be data driven. And what I think, because this is where the context matters,
1:53:29 Stripes founders and Stripes culture is very learning oriented. Very, very, more so than
1:53:35 almost maybe any startup I’ve come across. Yes. At an early stage too. Yes. So think about the
1:53:40 cultural context you’re in. What did we learn? What did we not know? And what did we learn
1:53:45 trying to get there on this goal? What did I learn? And by the way, some of them are mistakes I made.
1:53:50 And so try to be humble. Stripes is also very humble culture. Say, here’s some things I thought
1:53:53 I knew. By the way, I thought I did know. I was like, we were going to outsource certain things
1:53:58 that I thought was going to be easier than it was. And that is true. And here’s what I learned.
1:54:01 Here’s what I thought. Here’s what the truth was. Here’s what I learned. Here’s now what we’re
1:54:05 going to do differently. And by the way, everyone’s nodding in the room, because they’re like, cool,
1:54:10 cool. We had a plan. We tried it. I mean, they’re engineers. They know it like did not work the way
1:54:15 we thought it was going to work. We’re going to try this other thing. So you basically do a retro
1:54:20 postmortem, whatever you want to call it, sort of publicly in front of everyone in the language
1:54:26 they like speaking. So the language stripe like speaking is learning. I made mistakes. What am
1:54:31 I doing differently? What do I see next? How are we going to get there now? You know what I mean?
1:54:37 Like it’s I’m confident, but humbled by this experience. And I’ve learned a lot. And here’s
1:54:41 some data that shows we have made some progress because that also people want to make sure like,
1:54:45 are we actually know what we’re doing? So that’s what you do. And I think it depends on your context
1:54:51 instead of what language do you speak. So that is a big example. And that is, I think, a very
1:55:00 effective way to, as a player, offer a miacopa in a way. Yeah. Yeah. At that point then. And this
1:55:06 may be if this is going to require a dissertation, then tell me and I can read jig. But how did you
1:55:12 decide to scope the thing and then make a counter offer effectively? Or was that even your decision
1:55:16 to make? I don’t know. In terms of like, okay, we’ve learned these things. These were some
1:55:22 assumptions. And then leading into the kind of now what? I won’t do the dissertation version, Tim,
1:55:27 but I will tell you one bind I found myself in consistently that I’m sure you have also
1:55:33 is it’s a talent bind, which is I can only do so many things at once individually me alone.
1:55:38 And I did feel like a victim, I’m going to be honest, because I had been trying to hire someone,
1:55:44 I had hired someone they hadn’t worked out, partly my fault, partly not my fault. And I’m in a meeting,
1:55:48 this happened so many times, but I’m talking to Patrick and I’m like, look, we know so and so
1:55:55 didn’t work out. Here’s what happened with that. We now have face a choice, which is you have Claire
1:56:00 as a resource me alone. Am I going to go lead support directly? Like, am I going to go start
1:56:06 building this thing with all my most of my time? And what is the opportunity cost of that? What is
1:56:11 the tradeoff of me not leading sales? By the way, at that moment, which I was also leading. And this
1:56:15 is where I fell into a trap because I had like a few too many needing to clone myself problems.
1:56:20 And this happens when you’re growing quickly, but it’s still I got into an egregious case of
1:56:26 needing cloning. Then we’re having a renegotiation conversation, not even a reasonable case of
1:56:31 needing cloning egregious. It was egregious. It was egregious. There was one point where I mean,
1:56:35 I think it’s important that people, especially because they seem to think I have some like
1:56:40 storied career. I’m like, there was a moment where I had taken a former colleague from Google who I
1:56:45 was admittedly, I’ll be honest, was trying to recruit to strike out for a coffee. You’re just
1:56:51 going to be a board observer. Just come once. Yeah, right. Exactly. Exactly. And he says to me,
1:56:55 he used to actually work for me and he knew how much I pride myself on good management practices.
1:57:00 And he asked me, how many direct reports do you have? And I told him, and he almost like,
1:57:04 I had to peel him off the ground. He’s like, I can’t believe you let that happen to you.
1:57:08 He was like, what happened to the Claire Johnson? Then I know, I’m like, I know, I’m so sorry.
1:57:14 Like I had so many direct reports. How many direct reports? It was a crime. At peak. I think the
1:57:19 peak, I want to say the peak two was 23, but it might have been 27. And I just like lost control
1:57:26 of, I really don’t. Tim, I didn’t want to go here. I didn’t want to go here. It’s so many
1:57:32 one-on-ones. And of course, I do actually make one-on-ones happen. So point is, I got schooled
1:57:38 by my former direct report for violating my own rules in the need for cloning. But the point is,
1:57:47 the negotiation turns from we’re negotiating you getting this massive goal done to what’s the
1:57:53 cost of me getting that goal done for the other priorities. And then you’re making a joint
1:57:58 decision. By the way, the outcome of that negotiation could have been, let’s not build out
1:58:03 sales any further. Let’s not keep internationalizing. Let’s not open new markets. Let’s wait on those
1:58:08 other things because we decided you should just go and be the directly the head of support.
1:58:14 Honestly, that was not where the conversation went. It was like, okay, what creative ideas
1:58:21 do we have to somehow do both because we’re reality distorting? That’s fine. But actually,
1:58:26 you got to push yourself. And so I think in that exact moment, if I’m remembering the scenario,
1:58:30 we talked about some talented people I had hired, some people into the org,
1:58:38 who were like, could we lean on them? Could we put some newer leaders, managers into the deep end
1:58:44 and get them to take on more of this plan? And in the end, that was part of the solution,
1:58:49 which is, let’s take some risks with some people we have, give them more than they probably are
1:58:54 ready for and see if they can swim, which I’m not always a fan of because I have seen people
1:58:59 not make it out of the pool. By the way, a lot of young companies find themselves in that situation.
1:59:04 And if you have great hiring, which we did, I’m proud to say that actually that’s where
1:59:08 opportunities and magic can happen for people. I’m going to get to build out the global support
1:59:13 org. But anyway, so we ended up sort of compromising, but we weren’t going to trade off my other
1:59:18 responsibilities. And that became a more important discussion about how do I deploy? Anyone who’s
1:59:23 the CEO has got to be thinking, well, who are my most important resources and how am I deploying
1:59:28 them against the most important priorities? So take the negotiation up to that level would
1:59:36 be my advice. That’s a great macro renegotiation example. And we’re not going to stay on this
1:59:41 forever, but I want to spend a little, little, little more time on it when you’re renegotiating
1:59:46 the next day. So we’re moving down to the micro here. What language do you use? Like you have a
1:59:50 meeting booked, you got a lunch booked in Boston, you got this, you got that. And the other thing,
1:59:56 when you reach out to these folks, what do you say? I think you want to, again, be a player,
2:00:03 not a victim, and you got to take responsibility. So I think there is a version of saying,
2:00:07 I don’t love if it’s the next day, that’s rough. Yeah, it could be the next week too,
2:00:12 right? It’s just broadly speaking. I do actually tend to look at my calendar at least a week ahead
2:00:16 and sort of start renegotiating because I don’t like to be the one who’s like the morning of or
2:00:23 the day before. But I think you sort of own it, whether this is an email, it’s probably an email,
2:00:29 it might be a text and you say, first of all, I am very sorry. I know we had time tomorrow
2:00:34 on the calendar. I am staring at a list of priorities and I’ve realized you’re saying
2:00:38 something that doesn’t hopefully make them feel diminished. I mean, I often will tell them there’s
2:00:44 this thing. I am on this board in the middle of a transaction and I have to be on a phone call for
2:00:49 four hours tomorrow. And unfortunately, I think I need some time to prep. I need some time to prep
2:00:54 and I booked our lunch and it’s not realistic. I’m not going to be able to be present
2:00:59 at that lunch. It’s not great. I try to give like, I’m probably overcontext people,
2:01:04 but I think it makes you more human. It’s like, look, I did this thing. I’m sorry.
2:01:08 What if you don’t have like a house fire at a point too? What if you just look at it and you’re
2:01:13 like, oh, you’re like, you’re not important. Yeah, I mean, you get it. Like, you’re like, why did I
2:01:18 agree to why did I mail myself the letter bomb? Yeah, there goes to Christmas past is coming to
2:01:23 scratch my door and I’m realizing I don’t want to moderate this panel in Tuscaloosa. No offense
2:01:27 to Tuscaloosa, but you get the idea because I’ve got all this other stuff going on and I just don’t
2:01:32 want to spend the energy. Yeah. What do you do in a case like that? So again, I try not to be the
2:01:35 day before. Sure. No, let’s say you look out and you’re like, okay, this thing isn’t two weeks.
2:01:41 I’m not doing this thing. Yeah. So my instinct is always to offer context and be a little bit
2:01:46 vulnerable, which maybe is not expected. I think you also know there’s a, I think women will get
2:01:52 judged more for certain things. And in particular, like not being conscientious is the thing that
2:02:00 gets a little more beaten into you is my feeling as a woman. And so you have to also watch out for
2:02:06 creating some reputational issue that I think maybe not everyone has to watch out for. So maybe some
2:02:12 of my instinct to offer more information is to like try to avoid that hit. But I’ve been saying
2:02:20 to people recently actually that I have reworked my personal priorities and the demands of my time
2:02:26 are higher than I’ve actually seen in my professional life, which is true. And I have realized that I
2:02:34 cannot do a good job of some of the commitments I’ve made. And unfortunately, I can’t travel
2:02:39 and be on this panel and be effective for you. And this is where I feel sometimes I’m a little
2:02:43 weak. I’ll try to offer, I mean, I try to think, do I know anyone locally who could do that? I’ll
2:02:48 be like, I think I have an idea if you want an idea on someone who could sub in. Like I’ll try to
2:02:53 find some solution for them if I’m really leaving them in the lurch, right? Because I don’t love
2:02:59 that. But I kind of am just honest about like, I can’t do this well. And I think you want someone
2:03:04 at their best. It’s not going to be my best. Yeah, that’s good language. That’s really good
2:03:08 language. I’m not going to drag us back into the swamp of selling literature, but it’s good
2:03:12 language. That’s good word smithing, right? Right. And I think you’re showing, look, I looked at
2:03:17 priorities. I realized, and also you’re showing context, which is this is true statement. I’m
2:03:23 like, I have more demands on my time than I’ve ever had in my life. And I’m learning to cope with it.
2:03:28 And I’m learning that I can’t perform at the level I’d like to perform. And I don’t want you to
2:03:32 suffer for that. You want to show respect for people. They want a good panel. They want your
2:03:37 best. You know, you’re saying like, please, just you have to trust me, I’m not going to be great.
2:03:42 And they’ll be disappointed. One thing that I do think, I think Cheryl’s an example of this,
2:03:46 they’re people I’ve come to respect. They’re the people who protect their time,
2:03:49 like demons, right? The other people I’ve come to respect are the people who are like,
2:03:55 very comfortable just saying no. You know what? No, I’m sorry, I can’t do that. My hope for myself,
2:04:00 my future self is I am not in the situation where I’m doing that renegotiation. Again,
2:04:05 it goes back to being honest, taking time before you make the commitment to saying no.
2:04:09 But it’s also with investments. Like a lot of founders will be like, or even nonprofits,
2:04:12 they come and they’re like, I want to tell you about our organization. And you’re like,
2:04:17 oh, that organization sounds amazing. But then do you want to waste an hour of your time and their
2:04:22 time learning about it when you realize, I don’t have time to commit a lot to this organization?
2:04:28 What they would rather have is one, no, it’s not on my list of causes that I support. Or by the way,
2:04:32 two, I will give you X amount of money. You never have to meet with me. I don’t actually have time,
2:04:37 but it sounds good. Here’s some money. Goodbye. And they’ll say, well, can you make that commitment
2:04:42 for multiple years in a row? Maybe, maybe not. But I think getting faster at like, there’s a pattern
2:04:47 here, which is you want my money and my time. Am I willing to give any money or time? Yes,
2:04:52 no. If I’m willing to get a little bit, just tell them and get out. Don’t have a dog and pony show
2:04:57 about it. Or investments. I just don’t really invest in a lot of B2C. I’ll just write back and say,
2:05:02 this is not for me. I don’t really do B2C. Good luck. And they’re like, thank you,
2:05:05 because they didn’t waste their time sending you a deck, sending you, you know.
2:05:10 Yeah, they’re not chasing the Glengarry leads. Right. And so you think you’re being an empath
2:05:15 by saying, oh, let me hear your story. This is my trap. My personal trap is,
2:05:20 I think I’m being an empath, giving them 30 minutes. Let me hear your story. And in fact,
2:05:24 the empathic thing to do is to say, I’m going to do a probability assessment. The chance that
2:05:32 I’m going to invest/make a donation are sub 5%. No. No for you. No for me. And you don’t have to
2:05:35 think about it ever again. You don’t have to email me tomorrow and ask me again, right? Like,
2:05:41 they’re going to keep coming back. Yeah, yeah, absolutely. I love that. I’m so glad I asked.
2:05:47 And a great answer. Also, very useful, useful answer. What are some other rules we are going
2:05:54 to back the car into the garage of self-awareness? Because a lot of this pulls at the hem of
2:05:57 self-awareness from a bunch of different directions. But you mentioned that there are
2:06:05 certain rules you have because your kid is going off to college and therefore X, Y, and Z.
2:06:10 What are some of the other rules that you have for yourself around what you will or will not do?
2:06:16 Well, I have a rule. This is more of just a self-awareness. I do get intuitive and I do jump
2:06:21 to sort of judgments, conclusions, solutions quickly. So I have a rule that, like, especially
2:06:25 if I’m in a position of leadership and I’m in a meeting and there’s other people,
2:06:30 instead of stating my opinion, I have to ask a question. Because if you’re the senior person
2:06:35 and you state your opinion, like, the whole thing is over. Yeah, right. Yes, Steve, we can ship it
2:06:42 in five minutes. Uh-huh, exactly. Here’s an iPhone. So that’s a rule. Could you give an example of what
2:06:49 that would, because you could also ask a question in a way that makes it clear. It’s your strong
2:06:55 opinion, right? So what might that look like? So what it looks like is they’re kind of looking
2:06:59 to you. You know, I think we need to actually, you’re like looking at you and you say,
2:07:05 I have a thought. I do. I’ll share it. But actually, I’m interested in what you all think we should do.
2:07:10 Got it. You know, like, I want to learn from your thought before I share mine. You know,
2:07:13 and that’s, by the way, the benefit of seniority is you can be like, no, I’m not going to like.
2:07:18 I appreciate and refuse to ask you a question. I’m not going to perform right now. I will perform
2:07:23 later because I actually want you to participate. I’m often now in a position of sort of coaching
2:07:28 leaders. And because I’m more of an operator, not a professional coach, I have the same problem.
2:07:32 I’ll be like, oh my God, this is obvious. Like, here’s what you’re going to do. And then I think,
2:07:36 no, no, no, no, no. So I’ll say to them, all right, give me the bones of the situation.
2:07:41 And then I’ll start to tell them what I think. And I’m like, no. And I’ll say, you know what?
2:07:46 And I totally commentate. I’m like a sports color commentator. I’m like, I was about to jump in
2:07:51 and tell you exactly what I would do if I were you. And they’re at the edge of their seat because
2:07:54 that’s what they came for. Like, that’s what they want. And I say, we’re not going to learn from
2:07:59 that. What I want you to do is tell me your instinct. What is it you think you’re doing next?
2:08:02 And I don’t even say, give me the whole answer. I’m like, what would you do next? Because it’s
2:08:07 often a situation there’s an executive they think is underperforming. There’s a team off the rails,
2:08:12 whatever. I’m like, what are you going to do next? Then I get them talking. And then I sort of get
2:08:16 out from them. And I’ll tell you to him most of this. I mean, there’s a reason these people are
2:08:21 leaders. Most of the time, they’re like 80% of the way there. They’re just not confident in their
2:08:28 instinct. And so my job is not to tell them what to do or how to do it. It is to build their confidence
2:08:34 in their instinct. And then, yeah, we can brainstorm the last 20%. And I mean, it’s just like,
2:08:39 this is a total digression, but good pedagogy, right? Like, how do people learn? People do not
2:08:45 learn by being told answers. We all know this. But yet, we get some amount of experience in our
2:08:50 life. And we think, I’m going to go tell some people some answers. No, what you’re going to do,
2:08:56 if you’re a good leader, good teacher, is you’re going to lead them through learning with you.
2:09:00 And they are going to get to the answer. And you are going to celebrate them doing that.
2:09:09 But I cannot tell you how many times I myself have to create a rule to shut my own mouth.
2:09:14 Because I love helping people. Luckily, I don’t think it’s the know it all version of this. I
2:09:18 think it’s the, I can help you. Oh, my God, I see how to help you. And I just want to tell
2:09:25 them the answer. And I got to zip it, zip it. So one rule is like, yeah, I make a travel rule.
2:09:30 Another rule I make is, as I already told you, which is don’t say yes immediately. It has to be
2:09:35 very rare for me to say yes immediately. And as a pleaser, that’s very hard to be like, no,
2:09:39 I’m sorry, I have to get back to you next week. How often do you say I have to get back to you
2:09:46 next week versus I’m not sure can you get back to me next week versus in other words, like,
2:09:52 where does the ball fall and who’s court? Good feedback for me, Tim. And I take it. Thank you.
2:09:58 Now, I think that is actually a really good tactic that I don’t do enough of is to say,
2:10:04 I think this is unlikely that I’m going to be able to do this. I’m willing to consider it.
2:10:10 But what I’d like you to do is go look at your other options. And if you’re not finding something,
2:10:14 feel free to get back to me by the end of the month. And I will consider it. But it’s like,
2:10:19 basically telegraphing, like, I kind of want to try to help you, but I can’t. You got to go to
2:10:23 your plan B. I’m not going to be your keynote speaker. And that’s a great feedback. I think
2:10:28 that’s a good, maybe even it’s just, if you find yourself doing that, you should be asking yourself,
2:10:33 why isn’t it just not a no? It’s a no. Yeah. It’s a no for me. It’s a no. Tim, right? But
2:10:39 maybe it’s a way to trial yourself into realizing, oh, this is a no. This is the training wheels.
2:10:43 Yeah. I like your idea, which is like, put the ball in their court. Maybe again,
2:10:48 it’s back to some donation request or something like, this is not for me now. Feel free to get
2:10:53 in touch in the future. A lot of those people might just not ever. And I mean, sorry for them
2:10:57 because they’re not assisted. But is that being a player? Is that being a player enough? I don’t know.
2:11:04 Yeah. Hitting the snooze button can lead to like a delayed 24 car pile up later in my experience,
2:11:08 right? Good analogy. I was chatting with a friend of mine about this, because I’m fascinated by rules
2:11:16 for folks who handle a lot of inbound of any type. And his rule for the charitable stuff,
2:11:20 specifically like, oh, here’s my go fund me or this or this. He’s like, well, look,
2:11:24 he’s done very, very well professionally. And he’s like, okay, look, if it’s a friend,
2:11:30 and it’s basically any cause that’s not going to entail reputational risk, if it’s like, ah,
2:11:35 my buddy is doing a climbing Kilimanjaro for prostate cancer, and he’s has a go fund me,
2:11:40 they’ll basically give 5k to anything side unseen, because the universe of possible
2:11:45 acquaintances or friends who’s going to come to them with that is pretty limited. But the rule is
2:11:51 like 5k, that’s it. That’s our rule. And then for anything large, it’s just like, we focus on this
2:11:56 and this and this. And outside of that, we are not involved. That’s it. Yeah. No, I think that
2:12:00 is so powerful. That would be another rule is like, for something that’s a major commitment
2:12:08 of my time or my resources, someone said to me, it’s time, treasure, talent. But there’s another
2:12:17 one that’s like testimony. Ooh, okay. So time, treasures, capital, talent and testimony. And
2:12:21 testimony is interesting, right? Because you could, Tim, care about something that you can’t
2:12:25 give time to and you could say, if you need a quote from me, again, now we’re like in this weird,
2:12:31 rarefied air where someone might want a quote from, probably not me. But I think that that’s
2:12:36 another thing you can do. But the thing that for any of those categories, you need some criteria.
2:12:41 Yeah. Which is like, you know, some people, it’s about climate. If it’s not related to climate
2:12:46 and working on the climate crisis, it’s a no. And I think those people actually make more friends
2:12:49 than I probably make. Because I’m like, I’m not sure that sounds so important.
2:12:56 Just to ask a clarifying question on one time, I get, that seems pretty straightforward,
2:13:01 hours, minutes, treasure, like financial resources, things of that type, testimony,
2:13:05 okay, like endorsing something or some version of that.
2:13:09 By the way, a version of that might be like, can I introduce you to someone and endorse you?
2:13:14 Yeah, totally. What is talent? I mean, I understand the word, but I think of talent as
2:13:17 if they’re utilizing your talent, wouldn’t that kind of fall into the time bucket or is it a
2:13:21 separate thing? You know, I had a similar question because this was a friend of mine who was like
2:13:26 facilitating this workshop with people trying to think about what their criteria were for like,
2:13:34 what am I going to spend my time on? I think that the version of it is you say to someone,
2:13:39 I agree with you, like I can’t really deploy my particular talent without putting some time in.
2:13:47 But the example was, say you are very good at some specific thing and the thing takes you
2:13:51 less than 30 minutes, they’re like, all right, I don’t want you to join my board,
2:13:57 but can you read this press release and tell me is it good or not? I think it’s like,
2:14:02 you know what, I can’t give you my time. I can’t join a board. I can’t commit to a regular meeting.
2:14:05 It’s almost what I say to some of the founders I work with. I’m like, don’t expect me to read
2:14:10 the newsletter and try to volunteer for all the things you need. But if you think
2:14:16 my particular talent is going to be useful, and here’s what it often looks like, Tim, is
2:14:22 they send me profiles of people they’re thinking of hiring and I give them a five minute Claire
2:14:27 assessment. And so that is my time, but I don’t get on the phone. I’m just like, here’s the questions.
2:14:32 Usually how it comes back because I’m all about questions is here’s the three to five questions
2:14:37 I’d have about this background. If I’m you and I’m hiring for this role, why did they move around
2:14:43 five times? Why did they stop doing that job? I would just give them interview questions and
2:14:49 then I would back away. So you’re right. It takes me a minute. You probably have a version of that.
2:14:54 I’ve heard people like text you with very specific, which supplement should I take or which, you know,
2:15:01 should I intermittent fast? Yeah, you could probably like text back this one. No, this one,
2:15:05 you know, that’s probably still time and you probably should count how much time it is,
2:15:11 but it’s a way to stay it’s compressed because of the expertise. Right. You already know the
2:15:15 answer. You have the talent. You don’t have to go do extra work and you can answer quickly.
2:15:24 Quick add on, because I realize you’ve done so much hiring and develop so much talent. I’m so
2:15:32 curious how you spot bad apples or illicit negative feedback or infer negative feedback
2:15:40 when in the U.S. it is so incredibly difficult to get honest negative feedback from anyone
2:15:44 because they’re so concerned about liability. You’re talking about like references. Hiring,
2:15:52 yes, references. Exactly. The non dissertation answer is one, people have trouble giving hard
2:15:56 feedback. People have trouble asking this question, which is I think a question you just ask, which
2:16:01 is like, is this someone in the top 20% of people you’ve ever worked with? And then they say yes,
2:16:06 you say top 10. And then if they say yes, oh, so is it top five? Because what happens is when
2:16:12 people are asked for a very specific quantifiable ranking of something, they don’t like lying.
2:16:16 And so what I think happens is we’re not comfortable asking for ranking questions sometimes
2:16:21 about humans and I don’t love them actually in most contexts. But in this case, I’m like,
2:16:27 I’m going to pin you down on how good this person really is and how they handle and you could go
2:16:34 just to top five. But I think that’s the short answer. I think the other answer is you say to
2:16:39 someone, you put them again in the role of you say, look, I’m going to be their manager,
2:16:43 you are their manager. What’s the thing I can do that’s most important to help them?
2:16:50 That’s a good question. And people will say some very revealing things because all of a sudden
2:16:55 they’re back. Yeah. Being the manager of the person. And they’re like, well, I’ll tell them to
2:17:02 really be more truthful when things are off the rails. You’re like, what? Yeah. And then you’ll
2:17:07 sort of get going. Tell me a situation where you had to use that advice. Like what, you know,
2:17:13 anyway, so those are two, one very specific pin them down and one a little more tricky.
2:17:20 So good. Oh, deft. Very, very elegant. All right. As promised, the garage of self-awareness.
2:17:26 That is the very strained analogy that I used. And tell me if this ties in. And I’m curious
2:17:31 what good answers to this question might be. But I do want to talk about self-awareness so we
2:17:36 can go into it however you would like. Because it’s sort of the foundational layer for everything
2:17:42 that is built upon it. Or it seems that way to me. Yeah. That’s my hypothesis. Yeah. So actually,
2:17:46 I was going to ask you about the question. When have you seen me do my best and worst work? But
2:17:49 we can come back to that. We can come back to that. I’m going to bookmark that. Maybe we’ll
2:17:54 get to it. Maybe we won’t. But how should people think about self-awareness? And I’m just going
2:18:00 to share something that I found in the course of doing homework. And you can certainly fact-check
2:18:05 this. But I thought it was quite thought-provoking. This is from CNBC. And I think it was an interview
2:18:09 with you. So this is, you know, if you’re not self-aware, how would you know? That’s a hell
2:18:13 of a question. It’s kind of like, you know, the tree falling in the forest. No one to hear it
2:18:18 kind of question. Here are some telltale signs. You consistently get feedback that you disagree
2:18:23 with. This doesn’t mean the feedback is correct. But it does mean how others perceive you differs
2:18:28 from how you perceive yourself. Interesting. I added the interesting. You often feel frustrated
2:18:33 and annoyed because you don’t agree with your team’s direction or decisions. You feel drained at the
2:18:37 end of a work day and can’t pinpoint why. You can’t describe what kinds of work you do and don’t
2:18:41 enjoy doing. So that’s setting the table or maybe just peaking people’s curiosity. How would you
2:18:47 suggest people think about self-awareness? Why is this important in the world in which you operate?
2:18:53 I spent a lot of time thinking about how do you get results through people, through teams. Like,
2:18:58 I’m not actually the one building the product. So I got to do it through kind of brute force human
2:19:04 brain power and human time. And I think that most people who think that way start with the
2:19:10 individuals you’re managing or the team or the organization. And my argument is where you started
2:19:15 this section of the garage is the foundation is self-awareness. It actually has to start with you.
2:19:20 You’re not going to get great results from the people around you until you understand yourself.
2:19:26 And I mean, I think there’s some obvious reasons why which is like, look, I alone can’t move the
2:19:32 mountain. I need you and I need to complement myself. How am I going to complement myself
2:19:37 with other capabilities and skills if I don’t understand what I’m bringing to the table?
2:19:41 By the way, a lot of people think they’re the director in every scene. No, you’re not. You’re
2:19:46 often an extra. And just knowing that will make you more effective. So that’s a side piece of
2:19:52 advice for you. But a lot of self-awareness building to me, a lot of these work style assessments you
2:19:57 can take are just trying to help you figure out your defaults. Like, right to my default setting.
2:20:01 A lot of them are asking you, you know, are you more introverted or extroverted?
2:20:05 So you’re talking about, I guess, for maybe lack of a better descriptor, almost like personality
2:20:11 typing tests, like Myers-Briggs. Yeah, like Myers-Briggs, Disk, Enneagram. I mean, there’s
2:20:16 discovery insights. There’s the Hogan assessment, like whatever. That’s like 170 questions. Like,
2:20:22 there’s all these different, there’s the Big Five personality test. There’s a lot of
2:20:26 Strengths Finder goes on and on. Strengths Finder, good one. Like, there’s so many.
2:20:31 To me, they all boil down to on one axis, let’s call it the horizontal axis. You’ve got,
2:20:38 are you more introverted or extroverted? And the litmus test is sort of introverts think to talk
2:20:44 and extroverts talk to think. So where do you fall in that continuum? And then the other thing is the
2:20:48 vertical axis, which is, are you more task-oriented or people-oriented? Which, by the way, doesn’t
2:20:53 mean you can’t get a task done. And my litmus test for this is like, if someone comes to you with,
2:21:00 like, a massive problem in some organization, is the first thing you think of the first task that
2:21:04 has to get done or, oh my God, the people. And it’s just what do you lead with? For me, I’ll be
2:21:10 like, oh my gosh, someone’s getting fired, which is sort of a task and a person answer, but you’re
2:21:16 kind of, anyway, but I would say, sorry, I’m being very negative today, but I would say,
2:21:22 it sort of boils down then. And then you think, okay, what quadrant am I in? Am I a more extroverted
2:21:27 task-oriented type person or extroverted people? By the way, a lot of extroverted people-oriented
2:21:33 people are excellent at sales. Makes sense. Their default is, I love getting stuff done,
2:21:38 talking to you. Like, that’s, yay, BSL. And then you’ve got your introverted task-oriented people.
2:21:43 Where do a lot of those people work? Tim, do you think introverted task-oriented people?
2:21:49 Engineering. Programming. Engineering finance. Finance. Give me a spreadsheet and I will rule
2:21:54 the world. I do not, you know, need to talk to you to finish this model, right? Like, in fact,
2:21:59 you often do. And I know that. And so that’s the other thing is you have to be really careful not
2:22:05 to stereotype with any of this and not to generalize. But I think it helps any human frameworks are
2:22:10 useful for a reason, which is I am comfortable sort of saying, okay, where can I place myself
2:22:15 in these quadrants? And then what does that mean? My default setting is, and by the way,
2:22:19 the people around me have different default settings. One of my big, this is such a dumb
2:22:25 tactical lesson. But I’m one of those people where if I trust who I’m meeting with, I don’t need the
2:22:29 agenda ahead of time. I’ll be like, let’s meet. And then at the very beginning of the meeting,
2:22:34 bang out the agenda, make sure we know what we’re going to get done. I still like to run it well.
2:22:39 But I’m kind of loose with the prep. I have people who’ve worked for me who are like, frozen.
2:22:44 If they’re like, I don’t have time to think ahead of this meeting, what we’re going to talk about.
2:22:47 And I’m thinking there’s something wrong with them. I’m like, well, come on, we trust each other,
2:22:51 we’ve worked together, we’re just going to spit ball about this. And they’re like, no,
2:22:56 I had to learn that there are humans in the world who if they don’t have time to think before a
2:23:02 meeting will not be effective in the meeting and will be uncomfortable. Because my water is really
2:23:07 different than that. Really different. But you, if you’re trying to create an environment that’s
2:23:14 conducive to different styles, different defaults, you got to be aware of your own, and then realize,
2:23:19 and I have to operate aware of others, because I want that meeting to be really effective.
2:23:24 And I’ve got to email Richard the day before and tell him we’re going to spit ball ideas for
2:23:28 this new marketing campaign. That’s what it all boils down to. It’s really cultivating awareness,
2:23:33 but starting at home in the sense. Start at home and then start to map the other people.
2:23:37 Guinea pig is always in the cage right next to you in that case, right? It’s just easier to,
2:23:40 in some cases, a little easier study. Coming back to the personality test for a second,
2:23:44 or these, I’m not sure if that’s the right way to categorize them, Myers-Briggs,
2:23:49 Disk, any other… Work style assessments. There we go. Work style assessments.
2:23:53 If you could only choose one or two that have been most helpful to you personally,
2:23:59 what would you choose? I would say there’s one that’s called, I think if you just Google,
2:24:05 it’s Insights Discovery, which is sort of, to me, more effective than Myers-Briggs.
2:24:09 Myers-Briggs has a lot of interpretive work you have to do on your results. Like,
2:24:15 understand what sensing is. Understand what the decision-making process of a sensing
2:24:19 judge or whatever. Insights maps you more and they have some shading and colors,
2:24:25 but it’s sort of like more straightforward. That is one I’m a fan of. The other is more of a simple
2:24:31 one, but Patrick Collison, obviously, who I’ve worked with, I think I brought him around. He felt
2:24:34 like these things are like horoscopes. He’s like, “They’re just going to give you a report and it’s
2:24:38 going to sound like a plausible prediction of you.” And I said, “I get it. I get the skepticism.”
2:24:42 And I really do, by the way, for anyone. And actually, I think there’s value in getting a
2:24:47 horoscope. How does it actually make me feel? Like, do I agree with it or not? What am I really?
2:24:49 Like, it actually is part of a process, in my opinion.
2:24:51 Yeah, it’s a prompt, like a Rorschach prompt.
2:24:55 Yes, it’s a prompt. And how you react to it is interesting, right? Like, you’re like,
2:25:02 “I really, yes. I am finding love this year.” Or am I not? But the point is,
2:25:08 he then did some research, and the big five personality test is very simple. It’s available
2:25:15 for free online, as far as I can tell or I’ve seen. And it’s just these five factors like neuroticism,
2:25:22 agreeableness, conscientiousness. There’s one that’s sort of entrepreneurial comfort with ambiguity,
2:25:28 like whatever. And you can tell a lot from, well, one, the research supports that they’re pretty
2:25:34 indicative of certain human behaviors. You and I have had a lot of conversations in this
2:25:41 discussion about things like saying yes too easily. But if you’re like very high agreeableness and very
2:25:46 high conscientiousness, guess what? You’re going to end up committing to too much stuff.
2:25:47 Yeah, for sure.
2:25:51 And so, when I’m saying, “Oh, I’m jealous of those people who protect their time,” you know what?
2:25:56 They’re pretty comfortable being disagreeable. They’re pretty comfortable being like, “No.”
2:26:00 Or frankly, canceling at the last minute, saying, “Sorry, I don’t have time today for you.”
2:26:03 And if they’re not very conscientious, they’re like, “I don’t even feel bad.”
2:26:10 But by the way, no judgment. A lot of founders are really good about being like, “Look,
2:26:15 I’m doing the most important thing that I got to be doing today, and I’m the operator.” I’m like,
2:26:19 “Oh, but we made a bunch of commitments and we made a plan and we got to stick to the plan.”
2:26:26 And that meeting of those styles is very powerful. That’s why you want a diverse team.
2:26:28 But anyway, I would say those two.
2:26:32 Yeah, Patrick is endlessly fascinating. He’s been on the show probably a couple years ago.
2:26:40 But boy, oh boy, does that man read. He really is a voracious consumer of knowledge.
2:26:44 Yes, he puts the rest of us to shame. You know what, though, Tim? I bet he’s never seen John Wick.
2:26:50 So we have that. We have that going for us. We do.
2:26:54 One zero fairest cousin, but Wick on the scoreboard.
2:26:59 Yeah, we were actually in a meeting and he said something about Greg Popovich.
2:27:02 And two of us looked at each other and were like, “Do you really know who Greg Popovich is?”
2:27:10 It was amazing because Patrick also is not super up on sports, popular culture. We all have our
2:27:15 strengths. Popovich also incredible. Somebody I would love to have on the show at some point.
2:27:17 Oh, yeah, absolutely. Yeah, well, that’s why he knew.
2:27:22 So going to the kind of black belts of no, I’m wondering if there are people who stand out
2:27:29 outside of the Colossians as people who are sort of paragons of no. People who are really good at
2:27:35 saying no or defending their time where you’re like, “Wow, that person’s really good at keeping
2:27:39 their eye on the one puck that matters.” Anybody come to mind?
2:27:44 Well, I mentioned you. I think Cheryl’s very good at getting back, being very accessible and fast
2:27:49 and sort of decisive, like no efficient. She’s very efficient. And sometimes that efficiency
2:27:55 is a no, right? I mean, my version of it is someone who I think is least doing it carefully with
2:28:01 others, others like feelings. I think I don’t love the person who has an assistant, for example,
2:28:07 who cancels everything. No, there’s a model here, Tim. You’ve seen it where they agree to
2:28:11 everything and then they have a cleanup crew. Super lame. They have a cleanup crew.
2:28:14 Like the wolf from Pulp Fiction. They send it out to do the dirty work.
2:28:19 Yeah. Yeah. I think what’s happening is I’m doing left-hand column filtering names of people
2:28:23 right now in my mind where I’m like, “Nope, can’t mention them because I think they actually have
2:28:29 a cleanup crew.” They use the cleanup crew. They use the cleanup crew. There aren’t that many who
2:28:34 seem, I mean, I think you have some good, I think it’s in four-hour work week, you have some good
2:28:40 models of pushing people on not just being busy but being productive. There’s some engineering
2:28:45 leaders I worked with at Google who I thought was very bold, but it of course makes sense.
2:28:50 They would look at what were we planning in a meeting and they’d be like, “I don’t need to be
2:28:56 here,” or, “This meeting doesn’t seem important.” To me, those are paragons of no, though,
2:29:00 because it was very open, very direct, very honest. It was like, “I see what you’re trying
2:29:05 to do with this one hour and I am not giving you my hour. Why can’t more people just call it?”
2:29:11 Uncomfortable. There’s a finance guy that I’m on a board with and he’ll be like, “What are we
2:29:18 trying to accomplish in this and how long do we need?” He’ll set his, “I’m here for that objective
2:29:24 and I’m only here for this long.” I admire it because he’s like, “Don’t be chatting away about
2:29:28 other stuff. I want to be productive.” Don’t hear about your fishing trip right now, Ralph.
2:29:35 Exactly. Just because you mentioned the board, why no more boards? Just the thinking behind it.
2:29:38 I think there are different motivations for being on boards. I don’t know if you
2:29:43 are serve on boards. No, I basically, from the beginning, I have a number of friends who have
2:29:50 policies that they won’t join any more boards and I took that as an indicator. I’ve only done
2:29:54 advising. I’ve never been on boards. I would say there’s a sector of the world that feels it is
2:29:58 a service and I do think it’s a valuable service. By the way, I serve on some boards with some people
2:30:03 who are Jedi master board members and I’m like, “Wow, you are serving these companies because you
2:30:11 are awesome at governance and proxy statements, politics, and you get it.” I think there’s a
2:30:17 service motivation. There’s a motivation that has to do with maybe a personal CEO who really trusts
2:30:23 you. You want to help them. That’s mostly what happens to me. I want to be there for that person,
2:30:28 but it is a big commitment. If you’re someone who’s realized that time is your most precious
2:30:34 resource, which my mom realized somehow when she was 19, but I did not, boards can stomp all over
2:30:40 your calendar. They can just say, “You know what? All day Friday, someone just made an acquisition
2:30:45 offer.” You’re like, “Goodbye.” You realize you think you’re controlling your time because they
2:30:52 don’t meet that often, but no, no, no. Really what I’ve decided is I need to go on a board
2:30:57 diet and then rebuild. I’m not going to say no ever. I’m never doing it again,
2:31:04 but I’ve realized the bar has to be extremely high. I’m on one of my favorite boards,
2:31:08 and I would do it forever. I don’t know if I’m adding that much value, but it’s the Atlantic,
2:31:14 which is private, so it’s easier. The quality of the people involved, we’re doing the business
2:31:20 brain stuff, but you get to meet these amazing writers. You get to be part of exchange of ideas
2:31:27 about the future of democracy. Yes, that’s enriching me. That’s the other thing is making sure there’s
2:31:31 an exchange in the board of your learning. You’re getting enriched. They’re benefiting,
2:31:36 and I don’t think it’s easy to always get that balance right. You just have to be careful.
2:31:43 I think you just have to be. I think I just didn’t realize the level of commitment,
2:31:48 not just time, but to do it well. It goes back to renegotiating. What I’m doing is I’m saying no
2:31:54 more boards until I’ve renegotiated some of my current commitments, and then we’ll see.
2:31:59 That’s also a very powerful language right there. Categorically, I have a policy of saying no to
2:32:04 X until I have A, B, and C. That’s right. Done deal. By the way, people can’t argue with that,
2:32:09 because they’re like, “That does sound like a very same thing to do.” I have a lot of appreciation
2:32:15 more than I did before of folks who do this in service. Governance matters, right? It matters
2:32:21 for institutions, not just companies. It should be done well, but gosh, it’s a big commitment.
2:32:24 Be careful with those big commitments, folks. They sneak up on you.
2:32:28 Anything that has multiple years attached to it?
2:32:36 Yeah. Oh, boy. It’s kind of like the scope creep time-evaporating version of the best business
2:32:40 model of all time, which is being a venture capitalist, where you have these stacked funds.
2:32:46 That’s great if you’re taking your 2 and 20, but if it’s a commitment of your time over multiple
2:32:52 years, and then they start to stack, and oh my god, then you’re like 27 snow layers deep in the
2:32:59 avalanche of time requests. That’s right. And you get a 10-year horizon. I mean, at minimum.
2:33:06 That seems exciting at the beginning. Then you stack another 10 and another 10, and you’re like,
2:33:13 “Wait a minute. All of a sudden, I’m like 65 years old.” Anyway, I think it’s yes,
2:33:18 some funds have closed, and hopefully you’ve done well, but you made commitments before those things
2:33:24 happened to another set of them. Yeah, totally. So it’s like a rolling avalanche. The avalanche
2:33:30 is not ending. Do not say yes right away, folks. Yeah, especially to multi-year commitments. That’s
2:33:34 probably the headline. That and the toy is broken. I’m telling you, that’s your next book.
2:33:40 I really think it could do well. I have to ask this because it’s of acute interest for me,
2:33:47 personally, also because it might help me individually, but also with employees of mine.
2:33:51 Managing high performers, how do you get extraordinary output from extraordinary
2:33:55 people without burning them out or letting them burn themselves out?
2:34:00 If I was like, what are the pantheon of management lessons? So one of them is you’ve got to manage
2:34:06 different people differently. Another pantheon lesson is spend disproportionate amount of time
2:34:11 with your high performers because instead what we all do is get all of our time sucked by the
2:34:16 folks who are struggling and then we don’t invest in the high performers and then they’re either
2:34:21 burning themselves out or finding a new opportunity because they’re not realizing their high performers
2:34:24 and benefiting or they know they are and they’re not getting investment and they’re like,
2:34:28 I’m going to go get investment somewhere else. So number one is how do you manage them is you
2:34:33 make sure that they are a priority of yours even though they are perfectly good on their own,
2:34:38 which is the sort of dilemma, right? Like, how do I help them? In my book, I mean, I don’t steal,
2:34:43 I credit, I source a lot of frameworks. The book, Scaling People, Tactics for Management and
2:34:49 Company Building. Oh yes, thank you. Just to throw it in there. So there are a lot of QR codes. You
2:34:53 can scan and look at the sites where I reference a lot of materials and books, Conscious Business,
2:34:58 Fred Kaufman’s in there. One framework, I think, I mean, as far as I can tell, I made up myself
2:35:05 was a top talent framework, which is, again, I try to like simplify things. But I think
2:35:12 high performers fall into two categories and I call them pushers and pullers. And so the pusher
2:35:17 is the one who’s like, give me more, give me more. They’re often wanting to get more comp too,
2:35:21 but they’re like, I want recognition, I want responsibility, I want scope, I want to move
2:35:26 the needle. I’m high impact. They’re very impatient with themselves, with other people. They can be
2:35:31 a little high friction for the team because they’re like going for it, grabbing it, grabbing it.
2:35:35 But you know, it’s fun because you load them up and they’re just like carrying the whole
2:35:41 thing up the hill without you. But they can be tough. My main coaching often ends up with them
2:35:49 is saying, until I believe that the people working with you love working with you,
2:35:53 I don’t think you’re succeeding. And they’re like, what? What? Because they’re all keeping score,
2:35:58 but they’re keeping score in the sort of maybe early in his life, Tim Ferriss version? I don’t
2:36:05 know. Oh, no, that’s a fair assessment. I mean, I think I am a pusher as an entrepreneur for sure,
2:36:10 and I’ve learned how that can be a liability. It can be a huge superpower and it can be a huge
2:36:15 liability. Right. And your job is to sort of, like I said, giving direct feedback is holding up a
2:36:20 mirror and just being like, here’s the beauty of you and here’s the liability part. And if you
2:36:27 can’t show me that you can work on the liability part, I can’t keep loading you up. Because in the
2:36:32 case of the pusher, yeah, they might burn themselves out, but they actually burn out the people around
2:36:38 them. So that’s the pusher. So the puller, it’s funny, this happened to me in a couple of conversations
2:36:42 I’ve had is I’m usually being interviewed by someone who’s like the pusher and I’m the puller.
2:36:49 But anyway, I’m the puller is someone who, no complaints, you load them up and they’re like,
2:36:54 yep, yep, I got it. But they’re not asking for it. They’re not grabbing it. They’re not pushing,
2:36:58 but they’re highly competent. They’re very organized. They’re very consistent, reliable,
2:37:02 and they have good judgment. And you’re like, okay, I know that person won’t screw that up. I
2:37:06 know that person will get the people to the party and the, you know, whatever it is. And you just
2:37:14 start loading them. And they don’t renegotiate. They don’t know how to say no. And then they
2:37:20 explode. Like they basically implode or that’s what I’ve run into with past employees. Yep.
2:37:24 And there’s some like, I went through a period of my own development where I was like, I think
2:37:32 of it as my martyr period where I literally, I don’t know who I thought I was bartering myself
2:37:38 for like everyone else. I like, I would be doing all this stuff for my colleagues, for my team.
2:37:43 And I was like, no one appreciates like, I don’t know. And I eventually had a really good open
2:37:47 conversation with a guy, not my boss, who worked with me. And he’s like, did I ask you to take
2:37:52 that on? Like, you just started running that project? Or you run our planning process? Or like,
2:37:57 did someone ask you? And I’m like, well, no, no one was doing it. So I’m doing it. And I was like,
2:38:02 and he’s like, and why do you feel like you have to do that? I was martyring myself for nothing.
2:38:08 Like, I think martyrs at least are celebrating like a God. I was like, I’m sacrificing myself on
2:38:15 the altar of someone didn’t do the work. So I’ll do it. It was very bad, very bad. And I was resenting
2:38:19 the hell out of my colleagues. For sure. I’m like, does, I mean, this happens in relationships.
2:38:24 I mean, it’s like the who’s going to take out the garbage thing. I designated myself the garbage
2:38:28 collector for like a whole set of things, partly because I thought it was that was part of my job,
2:38:35 but still it was not good, not good. Anyway, the polar will implode slash explode. And you might
2:38:40 not be able to save them if it gets too far. So your job with them is like, look, let’s work on
2:38:44 delegation skills. Let’s work on saying no, let’s work on boundary, like, look at me, let’s work
2:38:51 on rules, boundaries. How do you not be the person carrying everything and doing three jobs? And I
2:38:56 think that once you know those two archetypes, you can sort of look for the signs of them. And
2:39:00 then you can think, well, what’s their classic development area? And then your job is to be
2:39:07 all over them on that development area, because they will collapse. If you don’t get them to see
2:39:13 that part of their job, like the pusher, especially part of your job is to stop creating friction
2:39:19 for everyone. And like for me, I really started to take exercise seriously when I decided it’s
2:39:24 part of my job to be like a better leader. I need to get a certain amount of exercise. And now I
2:39:29 will make time for it. And I think a lot of these types are like, I’m going to do everything to win
2:39:34 these pushers. And you’re like, you know what, part of winning is avoiding a Pyrrhic victory,
2:39:39 avoiding one where everyone wins, but dies on the field, right? And they’re like, oh, well,
2:39:43 then how do I do that? Because it doesn’t come naturally to them. And then they’ll say, I don’t
2:39:48 want to work with low performers. And this is the problem. They’re so good that, I mean,
2:39:54 now we’re going deeper on this, they’re so good that you can’t quite say back to them, no, those
2:40:00 people are the same as you. So instead, you’re like, yeah, okay, we all have different strengths
2:40:05 and weaknesses. What I feel like you’re doing is not even appreciating what anyone else is
2:40:10 bringing to the table. Why do you think that is? And it’s like, they don’t stay up all night like
2:40:15 I do getting the thing done. You’re like, no, they don’t. And I actually don’t think sometimes you
2:40:19 should stay up all night getting the thing done. But what do they do well? And then you get them
2:40:25 trying to think about assets. And you’re like, how can you use that asset to get the things done?
2:40:28 And they’re like, hmm, but they really don’t think that way because it’s all in their own shoulders.
2:40:35 Takes practice like so many things. Claire, this has been a fantastic conversation. Thank you so
2:40:40 much. I’ve had so much fun. I’ve taken copious notes. I’m going to be following up on a million
2:40:45 site quests, as we call them, but important site quests. I’ve taken notes of phrasing that you’ve
2:40:50 used all sorts of things. So I am looking forward to actually digging into my homework. I will not
2:40:55 stay up all night for the record. I’m trying to also help first sort of foundational along with
2:41:00 the awareness, having the vehicle to do the things you want to do. Your book, which I highly recommend
2:41:05 to folks is incredibly tactical, scaling people tactics for management and company building,
2:41:12 tons of templates, tons of frameworks, lots of specifics that you can apply immediately.
2:41:18 People can find you, correct me if I’m getting this wrong, but on Twitter @ChuseJohnson.
2:41:24 We’ll link to LinkedIn as well. Are there any other websites or anything else that you’d like
2:41:28 to point people to? The Stripe Press website, you can find scaling people and you can find,
2:41:33 actually, I did interviews with a bunch of leaders that there’s digital only content,
2:41:37 which we can give you all the link to that. But no, thank you, Tim. This has been
2:41:43 wide ranging as promised and stimulating and I’ve got some recommendations I’m walking away with.
2:41:47 So thank you. Thank you so much, Claire. And for everybody listening, we will link to everything
2:41:54 in the show notes. This will be encyclopedic and you can find that at tim.blog/podcast.
2:41:58 So you just search for Claire and this will pop right up and you will find everything that we
2:42:03 discussed. And it’s the next time be a little bit kinder than is necessary, not only to others,
2:42:09 but also to yourself. And as always, thanks for tuning in. Hey, guys, this is Tim again,
2:42:14 just one more thing before you take off and that is Five Bullet Friday. Would you enjoy
2:42:19 getting a short email from me every Friday that provides a little fun before the weekend?
2:42:22 Between one and a half and two million people subscribe to my free newsletter,
2:42:28 my super short newsletter called Five Bullet Friday. Easy to sign up, easy to cancel. It is
2:42:33 basically a half page that I send out every Friday to share the coolest things I’ve found or
2:42:38 discovered or have started exploring over that week. It’s kind of like my diary of cool things.
2:42:44 It often includes articles I’m reading, books I’m reading, albums, perhaps gadgets, gizmos,
2:42:50 all sorts of tech tricks and so on that get sent to me by my friends, including a lot of podcast
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2:43:02 I share them with you. So if that sounds fun, again, it’s very short, a little tiny bite of
2:43:06 goodness before you head off for the weekend, something to think about. If you’d like to try
2:43:12 it out, just go to tim.vlog/friday, type that into your browser, tim.vlog/friday,
2:43:15 drop in your email and you’ll get the very next one. Thanks for listening.
2:43:22 This episode is brought to you by Shopify. Shopify is the all-in-one commerce platform
2:43:26 that powers millions of businesses worldwide, including me, including mine. What business
2:43:31 you might ask? Well, one way I’ve scratched my own itch is by creating cockpunch coffee. It’s a
2:43:37 long story, all proceeds on my end go to my foundation, Saise Foundation, fund research for
2:43:42 mental health, etc. Anyway, cockpunch coffee, it’s delicious. The first coffee I’ve ever produced
2:43:46 myself, I drink it every morning. Check it out. We use Shopify for the online storefront and my
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2:43:57 Whether you’re a garage entrepreneur or getting ready for your IPO, Shopify is the only tool you
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2:44:39 across more than 170 countries. Plus, Shopify’s award-winning help is there to support your success
2:44:45 every step of the way if you have questions. This is possibility powered by Shopify. So check it out.
2:44:52 Sign up for a $1 per month trial period at Shopify, that’s S-H-O-P-I-F-Y, Shopify.com/Tim.
2:44:57 Go to Shopify.com/Tim to take your business to the next level today. One more time,
2:45:06 all lowercase, Shopify.com/Tim. This episode is brought to you by AG1, the daily foundational
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2:46:36 and adaptogens to help manage stress. Now, I do my best, always, to eat nutrient-dense meals.
2:46:42 That is the basic, basic, basic requirement, right? That is why things are called supplements.
2:46:48 Of course, that’s what I focus on, but it is not always possible. It is not always easy. So part
2:46:54 of my routine is using AG1 daily. If I’m on the road, on the run, it just makes it easy to get a
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2:47:34 Vitamin D and five free AG1 travel packs with your first subscription purchase. So learn more,
2:47:44 check it out. Go to drinkag1.com/tim. That’s drinkag1, the number one. Drinkag1.com/tim.
2:47:54 Last time, drinkag1.com/tim. Check it out.
0:00:11 whole body health. I view AG1 as comprehensive nutritional insurance and that is nothing new.
0:00:18 I actually recommended AG1 in my 2010 best seller more than a decade ago, the 4-hour body,
0:00:24 and I did not get paid to do so. I simply loved the product and felt like it was the ultimate
0:00:29 nutritionally dense supplement that you could use conveniently while on the run, which is,
0:00:34 for me, a lot of the time. I have been using it a very, very long time indeed, and I do get asked
0:00:40 a lot what I would take if I could only take one supplement, and the true answer is invariably AG1.
0:00:45 It simply covers a ton of bases. I usually drink it in the mornings and frequently take their travel
0:00:52 packs with me on the road. So what is AG1? What is this stuff? AG1 is a science-driven formulation
0:00:57 of vitamins, probiotics, and whole food-sourced nutrients. In a single scoop, AG1 gives you
0:01:04 support for the brain, gut, and immune system. Since 2010, they have improved the formula 52 times
0:01:09 in pursuit of making the best foundational nutrition supplement possible using rigorous
0:01:15 standards and high-quality ingredients. How many ingredients? 75. And you would be hard-pressed
0:01:20 to find a more nutrient-dense formula on the market. It has a multivitamin, multi-mineral
0:01:26 superfood complex, probiotics and prebiotics for gut health, and antioxidant immune support formula
0:01:32 digestive enzymes and adaptogens to help manage stress. Now, I do my best, always, to eat nutrient
0:01:39 dense meals. That is the basic, basic, basic requirement. That is why things are called supplements.
0:01:44 Of course, that’s what I focus on, but it is not always possible. It is not always easy,
0:01:51 so part of my routine is using AG1 daily. If I’m on the road, on the run, it just makes it easy to
0:01:56 get a lot of nutrients at once and to sleep easy knowing that I am checking a lot of important
0:02:02 boxes. So, each morning, AG1. That’s just like brushing my teeth, part of the routine. It’s also
0:02:08 NSF-certified for sports, so professional athletes trust it to be safe. And each pouch of AG1 contains
0:02:14 exactly what is on the label, does not contain harmful levels of microbes or heavy metals,
0:02:20 and is free of 280-band substances. It’s the ultimate nutritional supplement in one easy scoop.
0:02:25 So, take ownership of your health and try AG1 today. You will get a free one-year supply of
0:02:31 vitamin D and five free AG1 travel packs with your first subscription purchase. So, learn more,
0:02:41 check it out. Go to drinkag1.com/tim. That’s drinkag1, the number one. Drinkag1.com/tim.
0:02:46 Last time, drinkag1.com/tim. Check it out.
0:02:54 This episode is brought to you by Shopify. Shopify is the all-in-one commerce platform that powers
0:02:59 millions of businesses worldwide, including me, including mine. What business you might ask?
0:03:05 Well, one way I’ve scratched my own itch is by creating Cockpunch Coffee. It’s a long story.
0:03:10 All proceeds on my end go to my foundation, SciSafe Foundation, Fund Research for Mental
0:03:14 Health, etc. Anyway, Cockpunch Coffee, it’s delicious. The first coffee I’ve ever produced
0:03:19 myself, I drink it every morning. Check it out. We use Shopify for the online storefront and my
0:03:24 team raves about how simple and easy it is to use. It has everything we need and nothing we don’t.
0:03:29 Whether you’re a garage entrepreneur or getting ready for your IPO, Shopify is the only tool
0:03:34 you need to start, run, and grow your business without the struggle. Shopify puts you in control
0:03:38 of every sales channel. Doesn’t matter if you’re selling satin sheets from Shopify’s
0:03:44 in-person POS system or offering organic olive oil on Shopify’s all-in-one e-commerce platform.
0:03:48 However you interact with your customers, you’re covered. And once you’ve reached your audience,
0:03:53 Shopify has the internet’s best converting checkout to help you turn browsers into buyers.
0:03:59 Shopify powers 10% of all e-commerce in the United States. And Shopify is truly a global
0:04:04 force as the e-commerce solution behind Allbirds, Rothes, Brooklyn, and millions of other entrepreneurs
0:04:10 of every size across more than 170 countries. Plus, Shopify’s award-winning help is there to support
0:04:16 your success every step of the way if you have questions. This is Possibility Powered by Shopify.
0:04:22 So check it out. Sign up for a $1 per month trial period at Shopify. That’s S-H-O-P-I-F-Y.
0:04:29 Shopify.com/Tim. Go to Shopify.com/Tim to take your business to the next level today.
0:04:33 One more time, all lowercase Shopify.com/Tim.
0:05:02 Hello, boys and girls, ladies and germs. This is Tim Ferriss. Welcome to another episode
0:05:06 of The Tim Ferriss Show, where it is my job to sit down with world-class performers from every
0:05:11 field imaginable to tease out the habits, routines, favorite books, and so on that you can apply
0:05:17 and test in your own lives. This episode is a two-for-one, and that’s because the podcast recently
0:05:24 hit its 10th year anniversary, which is insane to think about, and past one billion downloads.
0:05:29 To celebrate, I’ve curated some of the best of the best, some of my favorites
0:05:34 from more than 700 episodes over the last decade. I could not be more excited to give you these
0:05:39 super combo episodes. And internally, we’ve been calling these the super combo episodes
0:05:44 because my goal is to encourage you to, yes, enjoy the household names, the super famous folks,
0:05:51 but to also introduce you to lesser-known people I consider stars. These are people who have
0:05:56 transformed my life, and I feel like they can do the same for many of you. Perhaps they got
0:06:01 lost in a busy news cycle. Perhaps you missed an episode. Just trust me on this one. We went to
0:06:08 great pains to put these pairings together. And for the bios of all guests, you can find
0:06:15 that and more at tim.log/combo. And now, without further ado, please enjoy and thank you for listening.
0:06:23 First up, Coach George Ravelling, the first African-American head basketball coach in the
0:06:29 Pac-8, Nike’s former director of international basketball, inductee of the Naismith Memorial
0:06:35 Basketball Hall of Fame and the National Collegiate Basketball Hall of Fame, and the custodian of
0:06:43 Dr. Martin Luther King Jr.’s original typewritten “I Have a Dream” speech. You can find Coach Ravelling
0:06:50 on Twitter @GeorgeRavelling. I had read, and please feel free to correct this,
0:06:54 that you’ve said the most important conversation is the one you have with yourself.
0:07:01 Yeah. So, could you elaborate on that, please? Because I think that self-talk is,
0:07:05 and I’m not sure that’s what you’re referring to, but it’s so, so terribly important.
0:07:11 So, I’d love to hear you just elaborate on that. The older I’ve gotten, the more I’ve come to the
0:07:18 conclusion that the conversation that you have every day with yourself as you characterize
0:07:25 its self-talk is so vital. It’s far more important than the conversations you have with those around
0:07:31 you. And the best part about the conversation with yourself is you’re in total control of that
0:07:39 conversation. You can craft the conversation any way you want to. And so, I try to have at least
0:07:46 90% of the conversations that I have with myself, which I have two or three times a day,
0:07:55 that it’s positive self-talk. If I start to linger on to something negative, then what I’ll do is
0:08:00 I’ll immediately deal with it and discount it. For example, since I’m Catholic, I’ll make this
0:08:07 confession. So, this morning when I got up, your reputation is so impeccable. I got up at five,
0:08:12 I’m really nervous. I’m thinking to myself, “God, what if I do a bad job? I’ll be so embarrassed.”
0:08:18 And so, the minute I started thinking that, I said, “Nope, that’s not it. Get fired up, man.
0:08:22 You’re going to do it. I’m in the bathroom. I’m doing this motivational talk for myself
0:08:28 to eradicate any doubt that I have.” And then I keep saying to myself, “You got to go in there.
0:08:32 You got to give me a best shot. You can do it.” So, I’m getting myself fired up for it.
0:08:33 And this is out loud.
0:08:41 Yeah, because I really spend as much time as I probably, at least, well, I wouldn’t say probably,
0:08:48 once a day, I’ll find an hour to just go someplace and sit by myself. And all I’ll do is take a
0:08:53 notebook and just put it in the pen in front of me and I’ll just sit there and think. Whatever
0:09:00 comes into my mind, then I start to fixate on those things. And I’ll write down notes as a result
0:09:06 of something that I think or I’ll write out a strategy. For example, the way I govern my day,
0:09:14 Tim, is I get up in the morning and I put my two feet beside the bed and I say to myself,
0:09:19 “Okay, George, you only have two choices today. These are the only two choices that you have
0:09:25 and you got to make one.” And the two choices are to be happy or to be very happy. And there’s no
0:09:32 other choice. And so, then I start to plan out my day. And so, I have these points of focus.
0:09:38 Energy management, time management, environmental management, productivity. And to me,
0:09:45 productivity is a byproduct of the other three. So, how do I manage my energy every day so that
0:09:51 I can be at maximum efficiency? So, one of the things I try to do is declutter my mind. I won’t
0:09:58 do any more than four things a day. And it reverts back to something one of the presidents at Nike,
0:10:02 Charlie Denson said one time in a leadership meeting, he said, “Let me ask you guys this.
0:10:09 Will we be better off doing 25 things good or will we be better off doing six things great?”
0:10:18 And so, to me, to simplify my day, I will not do more than four things. I try to limit the meetings
0:10:24 to two. And if it’s two, one of them is usually a breakfast meeting. When I go into the office,
0:10:31 I have a total commitment. Once I get into the office to be totally focused on business matters,
0:10:38 try to be as disciplined as I can not to get on the telephone. And also, to meet with the two
0:10:45 people that work with me, we meet every single day and we talk as a team because I want us to
0:10:52 function as a team. I want each person’s opinion to be valued. If one person happens to be 50 years
0:10:59 younger than me, so what? Their opinion is valuable to me. I respect everyone’s knowledge and I think
0:11:05 to myself, they know something that I don’t know. And so, I want to value their opinion. So,
0:11:13 we meet every day as a staff. We talk about things and it helps me grow and it keeps my day
0:11:18 simplified. I try to, once a week, have a personal audit. I go back through the week and I audit my
0:11:25 week and make course corrections along the way. So, that’s when I really get into the self-talk
0:11:31 part is having these little mental audits that my life’s just not going on and on and on. I try
0:11:37 to evaluate am I making progress? What am I doing that’s good? What am I doing that’s not working?
0:11:43 And then make those course corrections. And at 80 years old, I try to hold myself to the most
0:11:51 severe standards and I just despise the idea of retirement. I think that it’s the biggest force
0:11:56 that’s ever been predicated on us is this idea of retirement because the first thing that happens,
0:12:02 you retire physically and then you retire mentally and then you’re just taking up residence in
0:12:09 society. And I don’t ever want to be a resident of society. I want to be a contributor to society.
0:12:16 When I was doing homework, I read somewhere that you have a collection of racist mementos
0:12:21 in your house. Wow, you did do some research. Could you, beyond that, I don’t know the details,
0:12:24 but that just stuck in my mind because that’s something I think that a lot of people would
0:12:30 actively avoid. So, why do you have this collection? No one’s ever asked me that question, but I spent,
0:12:36 I probably have over a hundred thousand dollars worth of black collectibles for about eight or
0:12:42 nine years that it became an obsession with me. And so, I would go to antique shows and go to
0:12:49 stores and hunt down all black memorabilia. I have things that date back before I actually have a
0:12:56 first edition of Uncle Tom’s Cabin. So, I started to collect books, figurines, and postcards. Postcards,
0:13:03 I started with figurines. And so, a friend of mine told me about an antique store that was closing
0:13:09 and the gentleman had a huge collection of black collectibles. And so, it was in San Pedro. So,
0:13:15 I went down and I paid him $35,000 for the collectibles. He had, I wore a hundred pieces.
0:13:20 And part of the deal was that he had to mark them and write a little card so I would understand
0:13:27 the historic significance of them. Postcards, Tim, I have them back before you had,
0:13:32 this might surprise you, originally you didn’t have to put a stamp on a postcard to send it
0:13:40 out to mail. So, I have them back in the earliest one I have is 1891. Wow. But what was interesting
0:13:47 about the black postcards was they always made blacks. They pictured them in a derogatory term.
0:13:54 One of the more frequent ones you see is a black person eating watermelon with a smile on his face.
0:14:01 But they were all derogatory. Now, here’s what’s further interesting. We’ve now, you put stamps
0:14:07 on them. I was able to read the messages on some of them. And so, the one that I remember the most
0:14:12 is a lady’s writing to one of her girlfriends and we’ll just make up the name. She says,
0:14:19 Helen, we have a nigger that works at our house that smiles just like him. And so, in those days,
0:14:26 to use the word nigger was commonplace. And I don’t know if you ever learned to accept it,
0:14:32 but it was something that was said commonplace. So, I started to build this historic collection
0:14:39 of memorabilia so that I could have a legacy for my children and their children.
0:14:46 And I have them on display at my home to remind me of where we were and where we are today
0:14:50 and the trials and tribulations that we’ve gone through.
0:14:53 Do you collect anything else or have you collected anything else?
0:15:02 Books and friends. In my library at home, I have well over 2,500 books and probably I have another
0:15:11 six or 700 that are in storage because it just ran out of space. But I just continue to buy books
0:15:18 to read them. I have, as you probably researched, I have an unusual way of going about reading books.
0:15:25 And friends, I don’t have a strategy or anything for friends that most times people,
0:15:30 when I meet them, are not who they ended up being, whether it was Phil Knight, Bob Knight,
0:15:34 John Thompson, Sonny McGregor. I could tell you, tons of people, when I met them,
0:15:40 they were not who they ended up being. But for some reason, we were able to build an
0:15:48 authentic and sustainable relationship. And I’ve always looked upon relationships as a privilege.
0:15:55 And at the end of the day, at the core of all relationships, in my mind, is trust and respect.
0:16:00 And so both of those have to be earned. And so over the years, I’ve met people and
0:16:08 unintentionally, we’ve stayed in touch and there’s been this level of trust that’s allowed the
0:16:13 relationship to endure. But it’s something that’s a lot like marriage. You have to work at it.
0:16:20 You have to understand that there’s a balance in relationships. And with me, the number one
0:16:29 thing that I ask myself continually is, what can I do for you? And your good friend Ryan
0:16:34 Holiday and I had dinner last night. And one of the very last things I said to him, I said,
0:16:39 Ryan, is there anything I can be doing for you in the next 30 days? I’ve always had this theory
0:16:45 that if you help enough people get what they want, you’ll always get what you want. So I’ve
0:16:51 never tried to enter a relationship based on selfish motives that if I know this person,
0:16:57 I’m going to get these benefits. So I try to find out what do we have in common as people?
0:17:03 What is it that we can share? How can I help this person? No matter how famous they are,
0:17:10 how successfully are, everyone has certain needs, even if they’re just psychological needs or
0:17:16 we all need truth tellers in our life. And so in building relationships, I try to make sure that
0:17:23 I surround myself with people who want to see me become better and can help me become better,
0:17:28 that I can learn from them and that I can contribute to their lives. And so most of the
0:17:34 friendships I have in life, they all started by mistake. You’re one of the young men that’s
0:17:42 here today that has taught me almost all I know about technology. I spoke at a clinic in Orlando,
0:17:47 a friend of mine, Kevin Eastman, was running the clinic. And I said to him, I said, who’s going
0:17:53 to put my presentation up on the screen in that? Do you have an IT guy? And he said, yes. And so I
0:17:57 said, well, introduce him to me because I want to put my presentation up. I want to walk to the back
0:18:04 of the room and make sure it’s clear and so forth. So I met Alex Savosier. And during the time I was
0:18:09 there, we just hit it off. And so when he, I’m pretty sure he was taking me back to the airport.
0:18:15 And I asked him if he would be interested in doing a website for me. And he said, yes. And so that’s
0:18:22 how it started. And it’s turned into a lifelong friendship. And I think that was the start of
0:18:31 me recognizing that I needed to be around more young people. And so I don’t associate, and maybe
0:18:36 it’s bad to say this, but I don’t hang out with many people my own age. Most of the people that I
0:18:42 associate with are younger people because I think they’re the future. They’re smart. They’re naive
0:18:47 enough that they’ll tell you the truth. And they’re not afraid to tell you if they think you’re wrong.
0:18:54 And when I hang around people my own age, it tends to always revert back to the past. And I don’t
0:18:59 want to talk about coaching that Washington state of being the first black, this or the first black,
0:19:06 that. What I want to do is figure out at 80 years old, what is it that I don’t know but need to know
0:19:12 and how is this going to help me stay relevant in this ever-changing world? And so I’ve tend to
0:19:20 spend most of my time with younger people who inspire me, who I can have a partnership with.
0:19:26 That’s the other thing about relationships. I think relationships at their most authentic stage,
0:19:32 it’s a partnership. We share common vision, common goals, common objectives, common strategy,
0:19:40 common execution plan. It’s a we mentality. It’s not a me mentality. And it’s a win-win mentality.
0:19:47 It’s not I win, you lose or you lose, I win. It’s not about that. We were in this thing together
0:19:51 and we’re in the boat together. We’re going to row in the same direction and we’re going to get
0:19:58 the boat ashore. You mentioned books. I want to make sure we give reading at least a few minutes
0:20:06 because you are known as a voracious reader, the human Google, one nickname. And you’ve read,
0:20:13 probably, I’m sure, thousands of books at this point. You were very kind when we first got here,
0:20:17 we’re recording this right now. You said, “I learned from the wise men.” It’s always
0:20:20 a good thing to bear gifts or something along those lines. And you gave me several books.
0:20:25 You’ve also gifted many, many different books. How did this love affair with books start? And
0:20:30 could you tell us about how you read books? Because as you alluded to earlier, you have a
0:20:36 particular way of reading books. As I look back on it now, Tim, and with a point of reference to
0:20:42 so many times as we speak, it’s always going to be my grandma. Well, my grandma told me one time
0:20:47 when she’d be in the kitchen cooking, she’d tell me stories. And one time my grandma told me,
0:20:52 she said, “George, you know, back in the days of slavery, the plantation owners used to put their
0:20:58 money in books and hide them up on the bookshelves because the banking system wasn’t as sophisticated
0:21:04 as it is today.” And so I said, “Grandma, why did they do that?” And she said, “Because they didn’t
0:21:09 have to worry about the slaves stealing the money because the slaves would never take the books off
0:21:18 the shelf because they couldn’t read.” And so from that, I began to understand that as long as someone
0:21:26 can control your mind, they can control who you are in your body. And so I decided that I was never
0:21:34 going to allow myself to be in a position where someone can control my mind and control my body
0:21:41 because of my lack of information and knowledge. And so I decided that I was going to try to read
0:21:49 and learn as much as I possibly could on a continual basis because I believe that people will have a
0:21:57 greater respect for you if they respect you intellectually. And I’ve often felt in life,
0:22:05 if I had the choice between Tim liking me or Tim respecting me, I’d far more hope that you respect
0:22:11 me than like me. And I figured the byproduct of you respecting me will be that you’ll learn
0:22:17 to like me. So I don’t work at trying to get people to like me. So I’ve been on this mission
0:22:25 for a reading for years and years and years, and it’s become an obsession now with me. I don’t go
0:22:31 anywhere without a book and a notebook. If I go to a doctor’s office, I take a book with me. If I’m
0:22:37 in, I have a new system now. If I go to a bookstore and I’m in Barnes & Noble and the line has got
0:22:43 eight or nine people and rather than stand there for 10 minutes waiting, I’ll start reading the book
0:22:50 right there in line and start underlining things. So I have all these quirks that I’ve acquired over
0:22:56 the years with reading books. First of all, I divide the book into messages. I don’t spend any time
0:23:02 now trying to read a whole book because there’s probably in most books, there’s probably maybe
0:23:09 eight to 10 chapters that are really powerful and influential. And the others I skim through. So I
0:23:14 never start a book from the front and go to the back. I just, I’ll open the index and I’ll find
0:23:20 what I believe is an interesting chapter and I start there. And that’s actually how I purchase
0:23:25 a book. When I’m in the bookstore, I have this routine that I go through that. And if it passes,
0:23:30 I buy the book. And if it doesn’t, I don’t buy the book. What’s your routine? So if I, let’s say,
0:23:37 I’m going to envision this one. So our office is in El Segundo, which is outside of Los Angeles.
0:23:42 And so I go to Barnes & Noble there. One thing I found out that because there’s so many corporate
0:23:50 offices within a two mile radius that they tend to house really excellent business books. So I’ll
0:23:55 go in and as soon as I go in, I look at the books that are on reduction sale to see if there’s
0:24:01 something there that might be a good buy. Then I go to the new releases, nonfiction. By the way,
0:24:06 I go to a bookstore four to five days out of the week. I’m constantly going in and I just call it
0:24:12 search and discovery. So I’ll go to the new releases in a nonfiction and I’ll look through the books.
0:24:17 There’s usually 20 books on the table. I’d say eight out of 10 times. I’m going to find a book
0:24:24 that I had never heard of before. And so I’ll pick the book up. I go to the back. I read about the
0:24:29 author and I go to the front part and I read the promos down the side. And then the next thing I do
0:24:36 is I go to the chapters and I’ll find a chapter and I’ll open it up and I’ll see the writer’s
0:24:43 style. I look at the style. Is this someone that’s a book filled with a lot of statistics or stories?
0:24:50 Because I know what I’m looking for. The books that have had the most impact are the ones that
0:24:56 make me change the way I think or act or behave. Those are the books that ultimately end up being
0:25:02 the best for me. So I’ll go through the book and then once I find this one chapter, I start to read
0:25:08 some of it and I can tell if this is going to be me or not. And at that point, I’ll purchase the
0:25:14 book. But I just don’t go in and buy a book based on the top 10. Not that there’s anything wrong
0:25:21 with that. It’s just that I’ve had better success. So now here at 80 years old, two of my favorite
0:25:27 authors are Ryan Holiday and Walter Isison. They’ve both taken me on interesting intellectual
0:25:35 journeys. The first book I read by Walter Isison was Steve Jobs. And I was so blown away. I had
0:25:40 underlined about three quarters of the book. I was quoting and writing down quotes. And as you
0:25:45 know, the Steve Jobs book couldn’t be anything you want it to be. It can be a thesis on leadership,
0:25:53 but it was just utterly fascinating. I loved Walter Isison’s writing style. So when I finished a book,
0:25:57 I went back, I said, “Damn, I’d like the way he writes.” So I go back and I looked to see what
0:26:03 else he had written. And so then I see he’s done a book on Benjamin Franklin. He’s done a book on
0:26:10 Einstein and subsequently Kissinger and others. So I go to the bookstore and I buy the Benjamin
0:26:17 Franklin book. And I am blown away and a little sad because I feel like, “God damn, I went through
0:26:22 all this education. No one ever taught me any of this stuff other than the kite.” And so before
0:26:29 that, I think if you’d have asked me who was the most important American of all time, I think I would
0:26:35 have probably tended to say Abraham Lincoln. But after I read Isison’s book on Benjamin Franklin,
0:26:44 I would now feel, I mean, the lottery system, banking, schools, streets. He did so many unbelievable
0:26:52 things. And then from there, I went to Einstein. And anybody who can write a book on Einstein that
0:26:58 an idiot like me can understand the physics, and it was absolutely, it was a miracle.
0:27:07 So in the book Tim, I read that Einstein was very active in what they would capture in those times
0:27:13 as the Negro movement. And it says that he wrote a book on Einstein in the Negro movement. Well,
0:27:20 I had never heard of this. So I immediately stopped reading and go Google Einstein on the Negro problem
0:27:28 and lo and behold, it comes up. So I chased the book down. So what I find that a lot of times in
0:27:33 reading books and in your book, Tools of the Titan, I’m reading and I see this, you mentioned in there
0:27:40 about masterminds. And I had never heard of masterminds. So I circle it and I write Google behind
0:27:45 it. So I go back and I go online and I find out, wow. So I’m thinking to myself, oh my God, how
0:27:51 did I never knew about this? So how do I become part of it? So I sent some information to Ryan
0:27:56 Holiday about this mastermind. So he gets back to me. He says, oh, I’m surprised you didn’t know
0:28:02 about that. He says, you want to go, I’ll get you in. So the next thing I know, I get this invite to
0:28:11 go to masterminds in Carmel Valley. And my eight years on earth, that was the greatest collection
0:28:16 of intellects that I’ve ever been around in my life. I was so intimidated. And what was marvelous?
0:28:21 That was when I knew I was on the right path. Because I’m 80 years old. The next oldest person
0:28:30 there is probably 49. They’re all young energetic people. And I was readily admit I was so intimidated.
0:28:36 I didn’t think I was thinking to myself, God, how am I going to fit in? And every night I went to bed
0:28:42 with the worst headaches that I ever had, because I couldn’t process all this stuff. By the second
0:28:49 day, I’ve already filled up a notebook of notes. And it was one of those life changing experiences.
0:28:56 So you helped me grow as a person just by what you mentioned in Tools of the Titan.
0:29:00 Well, thank you for reading it. First of all, I’m sure that with all my notes here,
0:29:05 today, I’m going to have to figure out a way to have another conversation with you for sure.
0:29:10 So hopefully, I won’t blow it between now and the end of the interview. But books that you’ve
0:29:18 reread the most yourself or gifted to other people the most, are there any books that come to mind?
0:29:25 Being 80 years old, it’s a long span of reading. The books that I’ve given out the most, rarely
0:29:31 do I go to meet anyone. I can’t tell you the last time I met someone and I didn’t bring them a book,
0:29:38 it’s just become a habit now to give them a book. In most cases, I give them two or three books.
0:29:45 But the books that I’ve given away the most lately are Ryan’s two books, Obstacles and Ego is the
0:29:51 Enemy. I give Ryan’s books away a lot. One thing that I like about Ryan’s book, it’s easier to carry
0:29:56 because it’s smaller, so I can get a little bag and I can put 12 of them in there.
0:30:00 Yeah, mine are not as user-friendly from carrying perspective.
0:30:05 One thing I found with your two books is I take them on as a personal challenge. I said,
0:30:12 if he spent this much time with this many pages, I am not going to allow the length of the book
0:30:18 to intimidate me. I’m going to see this as an opportunity. And so what I did with Tools of the
0:30:26 Titan, I call that my China book. So it’s 13 hours of Shanghai or 13 hours of Hong Kong and
0:30:33 13 coming back. That’s 26 hours, man. I can knock that sucker out. Some books, you just have to find
0:30:39 the right environment in which to read them. But most of the books I read, they’re very few of them
0:30:44 that I don’t come away and feel that I’m a better person. One of the things I like to ask myself
0:30:51 at the close of every day is, what did I do to make myself a better person than I was yesterday?
0:30:59 What did I learn today? And so from a talk that I do, I say that every day is composed of 86,400
0:31:07 seconds of opportunities. And how shameful is it for me at the close of my day to say that I didn’t
0:31:13 do anything today to make myself a better person than I was yesterday? And that’s shame on me
0:31:21 because I had 86,400 seconds of opportunities to do something, even if it’s no more than a thank you,
0:31:27 a random smile, a pat on the back. Think about this, Tim, there are a lot of people in this country
0:31:33 who go through 24 hours and never have anyone say anything to them positive. You might be the only
0:31:40 person that day who said something to that person that was positive. Or I know we’re in a different
0:31:47 culture now. And I always think I’m running a little risk. But if I’m in a restaurant or somewhere
0:31:55 and a person’s waiting on me, and he or she has a great smile, I invariably say, hey, you have a
0:32:00 great smile. I sometimes I feel a little uneasy when I say it to a female because I don’t want
0:32:04 someone might think you’re trying to come on to them. But at the same time, I’m willing to take
0:32:10 that risk. So earlier, when we were leaving breakfast, as we were leaving, the two waitresses
0:32:14 said, thanks for coming. And they had a big smile on their face. So I said to both of them,
0:32:22 two of you have a great smile. Well, to me, I like practicing random acts of kindness because
0:32:31 so much today, we’re cruel and unintentionally cruel. We don’t think how valuable the little
0:32:38 things are, the thank yous, the smiles, the taking time to listen. I had a situation that I still
0:32:43 grapple with this when people stop you on the street and ask for money. We were having lunch
0:32:48 yesterday and a lady came up and she asked if we could spare some money. She wanted to get
0:32:56 something to eat or drink. So I gave her $5 and I said, now I hope you used the $5 on what you
0:33:02 said you were going to do. So she points and there’s a little grocery store a few doors down.
0:33:10 She comes back, shows me the drink and the $3 change. So it was a win for both of us.
0:33:17 But I grapple with this thing about, do I give them some money or do I not? In this case,
0:33:23 I mean, I really felt good that I was able to do something for her and she did something for me
0:33:30 because she made me feel good. What she really did is help fortify my mind that I should probably be
0:33:37 giving more instead of less. Well, you’ve given a lot in a lot of ways in many years of your life
0:33:45 and certainly one capacity is that of coach or educator or teacher and we could spend days
0:33:49 and hopefully we will, hopefully we’ll get to know each other even better and spend more time
0:33:55 together. But for now, I thought we might jump forward at least from your childhood stories
0:34:07 to the Olympics 1984. And there are many different angles we could take to get into this. But I
0:34:12 suppose where I want to start, there’s so many different things that I want to touch on. But
0:34:17 since we were talking about communicating and phrasing and words, could you share the motivational
0:34:23 quote that you came up with at that time? And I think it’s each one of us has a relative who gave
0:34:28 his life for this country, the least we can do is give 40 minutes of ourselves. Yes, that was,
0:34:35 that’s actually a Bob Knight quote. And it was a motivating force because when you stop and think
0:34:43 about it, very seldom in our lifetime does our country ever come to us and say, we need you.
0:34:49 It’s always the exact opposite. We’re looking for something from the government. But I felt that
0:34:57 this was a unique opportunity that the country was basically saying to the team and the coaches
0:35:03 that we need you and we need you to bring back a gold medal for us. And so this was a unique
0:35:10 opportunity for us to serve our country. And I can remember vividly in the months leading up to
0:35:17 the 84 Olympics in Los Angeles, I would envision that we were going to win the gold medal and we
0:35:24 were going to be standing there and hear the national anthem play and to be at attention and
0:35:28 look at the American flag. I know that we’re in a different era now in a different time,
0:35:36 but the reality was this is how I felt. And so I grew up in an era where my grandma taught America
0:35:41 right or wrong, America, whatever the problems are, we’ll work them out. But at the end of the
0:35:47 day, we’re an American. And so I envisioned what was it going to be like when we stood there and
0:35:53 received the gold medal and heard the national anthem played and you had the satisfaction of
0:36:01 saying to yourself, mission accomplished. And it was one of the most unique experiences I’ve ever
0:36:08 had in my life to be in a position where you could represent your country and you could have a good
0:36:15 feeling about it. I’m sure there’ll be a lot of people who will question why I felt that way,
0:36:17 but that’s the truth of the matter.
0:36:24 Just a quick thanks to one of our sponsors and we’ll be right back to the show.
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0:37:38 And now, Claire Hughes-Johnson, a corporate officer and advisor for Stripe, and its chief
0:37:47 operating officer from 2014 to 2021, and the author of Scaling People, Tactics for Management
0:37:53 and Company Building. You can find Claire on Twitter @chuesjohnson.
0:37:56 Claire, thank you so much for making the time.
0:37:58 I’m so glad to be here, Tim. Thank you for having me on.
0:38:04 And we were talking briefly about how one thing that you’ve observed, I’m just joshing here,
0:38:08 of course. A lot of cool people go to Brown. I want to ask about somebody else who seems
0:38:14 pretty cool, who I’m not sure went to Brown or not, but that is Fred Kauffman. And I guess
0:38:19 he is the origin of your second favorite operating principle, perhaps? Say the thing you
0:38:25 cannot say. I just love this line. Say the thing you think you cannot say. Oh, there we go. That’s
0:38:30 actually such a critical distinction, right? That is such a critical distinction. I simplified it.
0:38:36 That probably tells you a lot. We could psychoanalyze that later. But say the thing you think you cannot
0:38:44 say. Can you provide listeners with a bit of context as to what this means and why it is important?
0:38:49 I laid out, and I had to think about this for myself, for operating principles
0:38:52 for me as a leader and a person. And I shared them with others because I think actually everybody
0:38:58 should authentically come up with their own. But this one was the second one. The first one
0:39:03 about self-awareness is the one I probably talk about the most with everyone and myself. But
0:39:07 the second one is say the thing you think you cannot say. That’s why I started with the second one.
0:39:14 Yeah, because no one asked me about it now. And it’s a lesson that I’ve learned. And I think there’s
0:39:18 a journey that people go on with this lesson so we can share about that. But I’ve certainly
0:39:24 gone on the journey. And the person who was probably one of the most pivotal to me stepping
0:39:28 from square one, which is we often just don’t say the thing. We just don’t say it, was Fred
0:39:34 Kaufman. And Fred was… I’m going to get some of this wrong. But as I understand it, he was an
0:39:40 accountant by training. He became a professor at MIT. He was teaching accounting. He grew up
0:39:47 in Argentina, by the way. I don’t think he went to Brown. And he had some sort of life revelation
0:39:54 that he was not living with the true dimensions of his being and his values. And what he needed
0:40:02 to do was stop teaching accounting and become a leadership coach and advisor. And he wrote this
0:40:06 book, Conscious Business, which I recommend. I don’t recommend a lot of business books. I’m
0:40:10 just going to be perfectly honest to him. I often read the beginning of business books,
0:40:15 and then I never finished them. But Conscious Business, I have read all of it. And he formed
0:40:23 this firm called Excellent at the time that Sheryl Sandberg hired at Google. So Fred and his team
0:40:29 come in to start working with Sheryl Sandberg’s organization, of which I was a member of
0:40:34 management and then leadership. But initially, I was sort of one of the senior managers,
0:40:38 like not anyone, particularly special. And to Sheryl’s great credit, because not a lot of
0:40:43 companies at the stage Google was at were investing two, three days of management training and
0:40:48 leadership training. We all went through these 360 assessments. They gave us these report outs,
0:40:51 and then they put us in these boot camps with Fred and his team.
0:40:56 Just for a snapshot in time, when you say at that scale, what was the status of Google at that time,
0:41:05 roughly? I joined Google in May of 2004, and it was maybe around 1800 people. I mean,
0:41:08 there was a lot of contractors, I’m going to be honest, but I think in terms of full-time
0:41:11 employees. And it was, by the way, for me, the biggest place I’d ever worked. So I was like,
0:41:17 this place is huge. And then just fast forward, I left Google in 2014, and it was almost 60,000
0:41:24 people. So whoa. So I would say that the excellent engagement with Sheryl and her team was probably,
0:41:28 I joined right before the IPO, which was in August of ’04. And then in ’05, I would say,
0:41:36 is when we had, so Google actually was doubling every year. Probably 3,000 to 4,000. But Google
0:41:42 had gone public, but was still maturing and establishing, especially on the sort of
0:41:47 investment and management and organizational skills. But Sheryl, of course, ahead of her
0:41:52 time on things like that, was making the investment and had the budget that was a benefit of Google,
0:41:56 as we certainly had nice margins, Tim, that we could spend on management training.
0:42:02 And so we did this bootcamp with Excellent. But one of the things that Fred has, as he has some
0:42:06 really great frameworks, he has one about being a victim versus being a player. But one of his
0:42:11 frameworks is, how do you take what he calls your left-hand column? So you and I are talking right
0:42:16 now, say we’re having a conversation in the workplace, our brain is always operating in
0:42:21 the background. And it’s often thinking some things about the conversation, about the person,
0:42:26 about sometimes it’s thinking, what should I be doing? What do I want to have for dinner?
0:42:32 But we have this ongoing monologue in our brain. And the left-hand column, with respect to,
0:42:36 look, it’s about our conversation, Fred was really pushing us as a group. He’s like,
0:42:42 how do you, he’d say, detoxify, I can’t do his accent, detoxify the left-hand column and actually
0:42:48 say, like say the thing. And then he’d go through these exercises. And so this was sort of a light
0:42:52 bulb for me, which is like really about giving hard feedback. At that time, I was in management
0:42:57 training. But what I’ve come to learn is not only is say the thing you think you cannot say,
0:43:02 certainly about giving feedback and being more direct in your management conversations.
0:43:08 But I actually think it’s a really tremendous leadership skill, which is to get in a room.
0:43:13 And I don’t care if I’m in charge of the team or I’m just a person on a board. I’m on some boards
0:43:19 now. And we’re sitting there. And there’s often an unspoken thing. You’ve been there. You’ve been
0:43:23 in the like, Tim, you seem like someone who would actually put the thing on the table. Like I think
0:43:28 you and I are sometimes to my detriment. But yes, well, I think I need help. And this is where I’m
0:43:34 going to ask you if you could give an example, could be hypothetical or real of this type of
0:43:40 experience. And also the detoxifying, sort of like, how do you detoxify the like gentrifying
0:43:45 your inner language so that you don’t sound like a complete asshole?
0:43:50 Right. And I think, I mean, the short answer is you got to ask some stuff as a question often
0:43:55 to stop yourself from making a big judgment. But Tim, yeah, I think what I pick up in you
0:44:00 and from listening to you is you’re willing to take some risks. And so I think this is really
0:44:05 about risk taking and saying something that you’re not sure you should say, but you’re going to put
0:44:09 it out there. And then the question is, how do you do it with as much finesse as possible so that
0:44:13 you don’t end up having blowback, which believe me, I’ve sometimes said the thing I think I cannot
0:44:18 say and had people look at me like, oh my goodness. But most of the time I’m reading the room right.
0:44:23 Here’s an example, which is, I mean, just classic, more of a business example, but certainly happens
0:44:28 in my personal life too. So we went through various business planning types of tactics at Stripe,
0:44:33 but one of them we were using for a while was your classic quarterly business review. You have
0:44:38 teams come in, we’ve given them a template and we say, please fill out these things. Let’s see your
0:44:42 data. Let’s see where you are versus your goals. What’s your strategy? What’s your plan? Write this
0:44:45 memo. We’re all going to read the memo and then we’re going to have this discussion about how
0:44:49 you’re doing. And often teams come in and they want more resources or they want us to solve
0:44:52 something or decide something. And we’re of course saying like, well, it’s actually you,
0:44:56 you’re supposed to be deciding and solving, but it’s a discussion with the executive team.
0:45:01 And I’m sitting in one of these reviews with a team that’s primarily working on an area of the
0:45:06 product. So it’s product and engineering leaders. It’s not my part of the org that I run, but I’m
0:45:09 invited to be there and I like to be there. I like to be close to the product.
0:45:15 And I’m listening to the discussion and it starts to become incredibly clear to me that the team
0:45:22 is feeling defensive or blocked or angry. I couldn’t quite tell what it was that there’s
0:45:27 another team doing some similar work. And by the way, if you’ve read any Jack Welch stuff,
0:45:32 he actually had this tactic as a leader where he’d put two teams on the same problem and sort of
0:45:37 like get them to compete these tiger teams. That was not stripes tactic. I just want to be clear.
0:45:40 We were not interested. We’d never had enough people. There’s no way we would put
0:45:44 engineers on the same, believe me. So it was mystifying. And I think by the way,
0:45:50 I could hear it because I wasn’t in the room super close to the material. This wasn’t my part of the
0:45:55 org. I hadn’t heard about the details of some of these projects until this meeting. I’m reading
0:46:00 the document. I’m listening to them talk. And I just said, can I just ask if there’s something
0:46:05 we’re not talking about here? And they’re all looking at me because I rarely poke in on certain
0:46:09 moments with respect to what’s our product roadmap. And is there something we’re not talking about?
0:46:16 And everyone looks at me and I said, I feel like you’re really concerned about this other team,
0:46:20 what they’re building or what they’re up to. Are you concerned? And initially, no, no, no,
0:46:25 I mean, it’s fine. It’s fine. They’ve got this thing they’re doing that I said, well, is it?
0:46:30 Do you think it’s the same thing? Is that what I’m hearing? And I just started to ask
0:46:35 a bunch of questions of the leader of the discussion. And I said, well, should that team
0:46:40 be in the room right now? Should we have a meeting with both of you? Because it feels like there’s
0:46:47 asymmetrical information and that you all don’t feel confident in what they’re building and that
0:46:51 you’re either dependent on them or competing with them with what you’re building. And they were like,
0:46:56 maybe. I mean, it eventually became like, we don’t have the right people in the room to have a
0:47:01 conversation about the problem. And so we sort of stopped it and said, let’s go do that to the
0:47:05 credit of the rest of the people in the room. But as we left, one of the engineers who was
0:47:10 sitting on the sort of periphery walked up to me on the stairs and he was like, that was refreshing.
0:47:14 But why I’m bringing it up is, to me, that was a moment of leadership, which by the way,
0:47:21 you don’t have to be a VP or a COO to do that. The leadership is to say, I am observing a thing
0:47:26 that people are clearly not saying and are uncomfortable and is actually,
0:47:32 seems to me like a bad practice happening. And I am going to just call it, I’m going to ask,
0:47:37 is this going on? Am I seeing this correctly? And it’s going to change the whole trajectory of
0:47:42 the meeting and the conversation and maybe of the team and their work. It did result in some
0:47:46 de-duping ultimately. But I think that’s what I mean by saying the thing.
0:47:53 De-duping meaning having people working on less similar, overlapping Venn diagrams of
0:47:58 responsibilities. Exactly. And I think really what it was is they both had a part of their team that
0:48:02 was sort of doing the same thing and they were feeling dependent on each other. It was almost
0:48:05 like a yin-yang and they didn’t have the whole picture. And I was like, all right, someone needs
0:48:10 to have the whole thing under their control. So it was almost duplicate plus dependency,
0:48:15 which is sort of worse. Sounds like a recipe for lots of headaches. Exactly. But there’s also,
0:48:20 Tim, I’m sure you can picture an example in a personal situation where you take a risk
0:48:25 with a friend and you say, hey, have you told your husband that you feel that way?
0:48:32 So the detoxifying, though, in any of these examples is in your mind, you’re having a judgment.
0:48:37 We’re always judging. The brain looks for shortcuts. We know this. I’m judging and I’m like,
0:48:41 oh, I’m convinced that they’re pissed at this other team or I’m convinced my friend and her
0:48:45 husband are having problems and I’m going to solve them. But to detoxify it, you have to
0:48:50 sort of float above yourself and say, it is not going to be productive for me to open my mouth
0:48:55 and issue a judgment on another person or someone else’s work product. Yeah, people take that really
0:49:06 well. Yeah, exactly. People super don’t like that. So what can I do? What can I say? And my
0:49:14 feeling is it’s usually a question that opens the aperture of the conversation there, but keeps them
0:49:20 in a mode of curiosity, openness. How can I ask? And the problem and the art here, and this is why
0:49:26 you have to practice it and it’s uncomfortable, is sometimes you say something too general. You’re
0:49:29 like, is there something you’re not telling me? That’s not going to work because that’s going
0:49:35 to make them think, wait a minute, is there some paranoid thing? So it has to be more like,
0:49:39 you can use the words, I’m hearing a concern about the work of this other team. Say more,
0:49:45 are you concerned? And I’m all about hypotheses. I love management by hypothesis, which is like,
0:49:49 I think this is happening. I’m going to name it. I’m going to name the hypothesis I have. And then
0:49:54 I want you to validate it. Or by the way, fight with me. Say to me, no, no, no, I have data to the
0:50:00 contrary. And I’m happy to revise my hypothesis. But if you don’t state it, you’re not going to get
0:50:06 anywhere. We’re going to come back to what people might perceive as uncomfortable conversations.
0:50:13 And I want to ask later, we’re going to take a side quest for a minute about giving feedback to
0:50:17 direct reports. Because a lot of people who listen to this, or who are watching this,
0:50:26 have smaller teams. And my experience is that often people who are good at having these direct
0:50:33 conversations in a personal context or a business context are sometimes compartmentalized in their
0:50:37 capability in the sense that they’re very good. For instance, I think I’m better on the personal
0:50:44 side than I am in the business side, specifically when it is team members of my employees. If it’s
0:50:50 with contractors or joint venture partners, I can do that. For whatever reason, I think it’s
0:50:56 probably we could also do years of psychotherapy on this, but a fear of someone say abruptly
0:51:00 quitting or something if I don’t deliver the message properly. Whereas I’m not worried about
0:51:05 my friend quitting our friendship. They might get pissed and put me on ice for a week and give me
0:51:08 the silent treatment, but it’s not going to be a forever thing. So I want to come back to that.
0:51:17 But before we go there, I want to come back for a second to Fred Kaufman and victim versus player.
0:51:21 Can you explain what this is? I love this one because I think it’s so
0:51:28 simplifying and clarifying really about are you managing someone or interacting with someone who
0:51:34 has agency takes responsibility. Fred, when he introduces this framework tells the story of
0:51:38 how young children and he’s the I think he has six or seven children, by the way, but how young
0:51:45 children when something has happened that they know is bad will not take responsibility. So
0:51:52 they will say things like the coat is at school. So not I left my coat at school, right? Or a thing
0:51:57 has happened. Things have happened. The toy is broken. You’re like, well, did you break it? You
0:52:01 know, so he has this really disarming way of introducing this concept, which is we’re all
0:52:05 laughing. Just like you and I were like, haha, the toy is broken. But then he’s like, okay,
0:52:10 now let’s talk about if one of your direct reports came to you and said the report was not written.
0:52:16 And you’re like the report that you were meant to write, but how it actually manifests is you’re
0:52:21 supposed to write some report up or some summary of a meeting and you say, oh, tell me where that is.
0:52:26 And the player says completely my fault. I had planned to get it to you by five o’clock yesterday.
0:52:33 I prioritized this emergency that came up, didn’t tell you my bad. Can we renegotiate?
0:52:37 Can I get it to you at five o’clock today? And you’re like, fine, I wish you told me that you
0:52:43 weren’t going to get it. But the victim says, let me tell you about that report. Lucy owes me her
0:52:49 notes. And I can’t finish it without Lucy. And Lucy, you know, super slow at getting her notes.
0:52:54 And I’m sorry, I don’t know when I’m going to get it. But that actually is pretty common. People
0:52:59 are like, well, it’s this other person that I’m depending on. And therefore I have no responsibility.
0:53:05 And they’re a victim. And they’re going to play the victim. And I think that’s a very hard person
0:53:11 to coach. How much do you have to select that in your hiring process versus coach people from
0:53:15 one side to the other? Have you had much success or seen much success in moving people
0:53:21 from the victim side to the player side? And that’s a bit of a leading question by my tone,
0:53:28 I guess. I suspect there are a lot of instances where that’s hard. But in the success cases,
0:53:34 what does that coaching process look like? I’ve seen both. I feel like with people who are earlier
0:53:39 in their career, they’re more, I’m all growth mindset, but they’re a little more moldable.
0:53:44 And you can actually coach people out of this as like a way of operating. If they’re later in
0:53:49 their career, it’s a little more ingrained. And it’s quite hard, especially because they tend to
0:53:54 not be aware of it because they’ve somehow been successful operating in that mode. And so they’re
0:53:58 kind of like, what are you saying? You see leaders who, you know, how they behave to him is they
0:54:04 say, well, if it’s not under my direct control, then I am not responsible. And so they become
0:54:09 empire builders. And some organizations let them get away with it. They’re like, sure, you can
0:54:14 have all the infrastructure teams then. Like it becomes this weird, failing upward problem,
0:54:17 where people say, well, if I can control it, I’ll take responsibility.
0:54:22 If it’s within my house, then I’ll take responsibility. So people satisfy that
0:54:24 checkbox by giving them more and more resources. What a nightmare.
0:54:29 Exactly. And it becomes this weird expanded scope of this person who actually doesn’t take
0:54:34 responsibility. It’s a pattern I’ve seen. For people earlier in their career, the easiest coaching
0:54:38 move you do, which I’m sure you’ve heard, or someone’s done it to you, I’ve certainly had it
0:54:43 done to me. They’re saying, Lucy didn’t send me her notes. And you’re saying, what could you have
0:54:49 done differently? And you have to let uncomfortable silence then. And some people will then say,
0:54:54 what do you mean? You’re like, oh, my gosh. But some people will say, well, I guess I could have
0:54:59 helped Lucy write the notes. So what I try to do is stay in the discomfort, which is hard,
0:55:03 and just sort of like, let’s list out a few things you could have done differently.
0:55:07 And not be judgmental, like not judge the things. Just say what it was. So you could have helped
0:55:12 Lucy write the notes. You could have set a deadline with her that was ahead of your deadline.
0:55:15 Right. Put a deadline in a sauna where people can actually see it.
0:55:19 You could use a productivity tool where you could see, I love those tools, because that’s
0:55:24 sunshine. Sunshine is a great disinfectant, Tim. If everybody can see that Lucy has not
0:55:29 done her action item, that is going to help Lucy be more accountable. But the point is,
0:55:34 you come up with this list, and the person often is like, wow, you’re right. Really,
0:55:38 what you’re, they’re kind of going to have to admit to you is they’re being a little lazy.
0:55:40 They’re not helping others do the work. They’re not a good collaborator.
0:55:44 And that’s what I sometimes do with someone is like, you know, if this is a pattern, I say,
0:55:49 you know, I see this pattern. Do you see this pattern where you’re waiting for other people
0:55:53 all the time? Tell me more about why you think that’s happening. Why are the people not delivering
0:55:58 for you? And the question is like, either it’s because they haven’t figured out how to do action
0:56:04 items or accountability or be clear about deadlines, or there’s someone people don’t like to work with.
0:56:07 I always call it like going meta. Like you’re looking from the balcony at the situation,
0:56:11 which is a term from adaptive leadership. Are you on the balcony or are you on the dance floor?
0:56:14 And if you’re on the balcony, you try to get the person up there with you and say,
0:56:21 why do you have this pattern of people not helping you get your work done? And then I think of it
0:56:25 as going to the basement. I know this is, I’m a very visual person. So we look down and they sort
0:56:29 of, if they acknowledge it, they say, yeah, I guess I see that. And I say, well, let’s talk
0:56:33 about a few examples. And we come up with some examples. Then we go down and we’re in the scenario.
0:56:37 And I say, let’s do the five wise. I mean, everyone loves the five wise. I’m like,
0:56:43 why do you think Lucy didn’t send you the notes? Well, she’s not good at deadlines. Okay. And then
0:56:47 this is a wonderful expression that I learned from some coach I had a million years ago.
0:56:51 Be that as it may, which is not normal English language, but I don’t know it worked.
0:56:57 Sort of like, be that as it may. Okay. Maybe Lucy’s terrible at deadlines. But why else? Well,
0:57:02 I didn’t ask her to get it to me at a specific time. Okay. So maybe there’s a thing. Why else?
0:57:07 You know, and you’re sort of pushing them and sometimes not every time they’ll sort of say,
0:57:14 well, I don’t know Lucy and I don’t work that well together. And you’re like, oh,
0:57:18 say more about that. What do you think’s going on? And of course, by the way,
0:57:23 your left hand column, Tim, is it’s because Lucy doesn’t like you because you blame her
0:57:30 for all of your missed deadlines. But I can’t say that because that person is going to go from
0:57:34 learning to barely in learning mode. I’m trying to bring them along with me and they’re going to
0:57:39 just shut down. And by the way, they may never admit that Lucy doesn’t like them because they
0:57:44 blame her for missed deadlines. But they’re going to realize that their manager, who’s me,
0:57:49 is not letting them off the hook. If they can’t get into an agency, a player mindset,
0:57:55 I’m a responsible party for my work and others, then they are going to be off my team. If I can’t
0:58:00 coach them out of it, to your point, there’s two gaps that I think are really hard. One is people
0:58:05 who can’t stop being victims. And the other gap, I call it self-awareness gap, where they think
0:58:11 they are the best in the world. I once worked with this BD person who was like, I can negotiate a
0:58:16 deal better than anyone. And talk about not being in a learning mindset. I’m like, do you not think
0:58:22 we should get any outside advice? I’m exaggerating a little bit, but really unaware that they had
0:58:28 any potential blind spot or had never done a deal like this deal. And I’m like, how are we going to
0:58:33 close this awareness gap? Because the people around you are saying you are not the best person to
0:58:38 negotiate this deal. And I’m trying to hand it to someone else. And you’re like, what? You have no
0:58:44 one better than me. And that’s a very hard gap to close. Yeah, totally. And I promise we are going
0:58:50 to spend some time on self-awareness. The book I’ve probably gifted most to my friends and house
0:58:54 guests and so on in the last few years is actually a very short book called Awareness by Anthony
0:58:58 DeMello, which is outstanding. I need to read it again. I read it probably once or twice a year.
0:59:05 So we are going to spend some time there. I’m kind of tiptoeing around the edges of the dance floor,
0:59:12 as it were, and tiptoeing and side stepping on the balcony because I want to paint a picture
0:59:18 of you also as a person, not just the concepts. So we are going to spend some time there. I’d also
0:59:25 just as a side note, if you decide to write another book, I think the toy is broken as the title and
0:59:31 then the subtitle could be like a high performers guide to taking responsibility. Oh my God,
0:59:37 so good. The toy is broken. Tim, you’re hired for my marketing team. I gotta tell you, we’re not
0:59:41 always the best at naming things. It’s right. So you’re invited. That’s the one thing that I am
0:59:47 good at. You’re on the team. Congratulations. Thank you. As a hell of a team. I mean, my boss
0:59:52 sucks. Oh wait, I’m my boss. Oh, you’re the boss. Terrible. Terrible. You said you don’t recommend
0:59:56 a lot of business books, and I am going to come back to share all an excellent in a little bit,
0:59:59 but you don’t recommend a lot of business books. Sometimes you read the introduction and you’re
1:00:06 like, “That’s enough. Thank you.” Let’s talk about a non-business book. And that book is To the
1:00:13 Lighthouse by Virginia Woolf. What is your history with this book and why do you recommend it?
1:00:20 I love great literature. I think that’s how I grew up. My parents are both teachers. My
1:00:24 father was a high school English department chair and teacher and baseball coach. By the way,
1:00:29 he would probably say he was a baseball coach, and then he would say I’m a teacher. And my mom
1:00:36 was a college professor for a long time. And I wish more people loved literature because I think,
1:00:40 how do you understand the human condition? Literature is like the best shortcut to that
1:00:46 in your life. But I think there are some authors for someone who becomes a student of literature
1:00:53 that change their worldview about really what’s possible with writing. So not just the book changes
1:00:58 how they feel and think, but actually the process. Sort of like when you see a product. I think you
1:01:04 love innovative products. When you see something, you’re like, “That is going to change my life.”
1:01:10 And so I think that to the Lighthouse represents. I mean, Virginia Woolf is a writer that
1:01:16 resonated for me. And I think if you understand, if you’ve also studied history and you think,
1:01:24 okay, she’s writing some stuff in like the early 1900s, 1920s, not a lot of women publishing a lot
1:01:30 in that time in Britain. She gets herself into this writer’s collective with men and women.
1:01:36 She also has relationships with men and women. She’s like pretty avant-garde person. But if you
1:01:44 read A Room of One’s Own, it’s basically one of the earliest feminist manifestos that exist.
1:01:48 And this is where I think, Tim, you’re like me, I love people who are polymaths. You’re like,
1:01:54 not just this amazing novelist, thank you, Virginia Woolf, but you’re also writing
1:01:59 just your thoughts on things like women should have a room of their own. I mean,
1:02:05 actually figuratively, you know, not just literally. And I think that she is fascinating,
1:02:10 her life is fascinating. And I want to acknowledge not all of her personal views are great on some
1:02:16 things. As that happens, I worry that we started to not study certain artists because they’ve said
1:02:21 some things or done some things, which I would disagree with. I think people think she was an
1:02:25 anti-Semite and it does appear that she said some very anti-Semitic things in some of her writing.
1:02:31 I still think you should study Virginia Woolf. And I will own that as my position on her. But
1:02:37 I think To the Lighthouse, most people would say is her most important novel. I will be honest
1:02:43 with you and say, when I wrote my thesis in college, I was going to write it on To the Lighthouse.
1:02:48 And then I actually decided to write it on Mrs. Dalloway, which is another one of her novels,
1:02:54 because I love the parallels from Mrs. Dalloway with a book called The Passion by Jeanette Winterson.
1:03:01 So Jeanette Winterson is a female British writer, more in the modern era, who had broken through
1:03:06 with a memoir called Oranges Are Not the Only Fruit and then had published
1:03:10 this book, The Passion, and then a book called Sexing the Cherry. She’s published now several
1:03:14 books. But Jeanette Winterson, I think, is a descendant, in my opinion, of Virginia Woolf.
1:03:19 And I was like, I’m going to examine these two novels. And I didn’t choose To the Lighthouse.
1:03:23 But I will say that, and To the Lighthouse is not an easy read. And I want to own that also.
1:03:27 I think it’s very, Mrs. Dalloway, much more digestible, shorter book.
1:03:31 It has some repetition in it, some beautiful rhythm in the writing where you’re like, oh,
1:03:36 and I’m coming back around in the circular way to the way the story sort of moves you.
1:03:39 To the Lighthouse is like a dream state. You feel like you’re in a dream state.
1:03:45 You’re like, the points of view are shifting. Who’s the real narrator here? What is the story?
1:03:51 There’s not like, you’re not being driven by your classic plot or character driven story.
1:03:52 It is much more internal.
1:03:55 It’s like John Wick, in some sense. I’m kidding, I’m kidding.
1:04:02 I feel like the plot of John Wick is pretty clear. You know, I am going to take vengeance.
1:04:06 Excuse me now. I’m going to come out of retirement and kill everyone.
1:04:07 Oh, what a great work of art.
1:04:11 I’ll be the first one to tell you. I read a lot of mysteries and thrillers. And I like
1:04:16 movies like that, actually. So I’m very multi-dimensional. But I think for To the Lighthouse,
1:04:20 you find something new every time you read it. You think about life, death, the human condition,
1:04:25 what is love? What is family? What does it mean to connect with other human beings?
1:04:29 And there’s something about the way the writing works. I mean, it’s set in this island in Scotland
1:04:33 and there’s a lighthouse and they go out in the boat. Like you literally feel like you’re surfing
1:04:39 in a boat. Like that feeling when you’re like, I’m not really connected to firm land, but I’m in
1:04:45 this inner sanctum of people’s heads. So I think that it changed me because of the way it felt to
1:04:51 read it. Frankly, the themes are much more sophisticated than my 19-year-old self probably
1:04:54 could have handled. Like I should actually, you just said you should read awareness again. I should
1:05:00 go read To the Lighthouse again because now that I am a mother and a wife of a certain age,
1:05:05 I’m like, this book is going to resonate a lot more for me. But what’s amazing is Virginia Woolf was
1:05:10 never that. She didn’t have children and she unfortunately did kill herself. Like she had
1:05:16 a lot of demons and actually the way that she killed herself, brutal. When she filled her pockets
1:05:21 with rocks and drowned herself. And I think that a lot of artists are tortured, but the fact that
1:05:28 she could project into this Mrs. Ramsey and this woman, this very maternal figure, was a sign of
1:05:33 true artistry. Sorry, that was very long. That’s why I have a long podcast. So I’m not going to let
1:05:38 it go. I’m going to continue to chew on this bone a little bit. And for the record, I actually love
1:05:43 John Wick. But I don’t want to dwell on John Wick. I was going to say first, if you like dream state
1:05:52 evoking novels, the one that blew my mind and nine out of 10 people hate this book. So it’s a very
1:05:58 strong caveat, but it’s a little big by John Crowley. There’s actually a poet by training. It is so
1:06:05 unbelievably good. You have to slog through the first 150 pages, but beyond that, it’s absolutely
1:06:11 stunning. So what are the reasons to read fiction aside from the, as I think you put earlier, the
1:06:16 insight into the human condition? If you were trying to get someone to take that first bite of
1:06:22 forbidden apple of fiction, are there any other points that you would make?
1:06:28 How do you build empathy? How do you understand everybody has a story? I mean, you’ve traveled a
1:06:33 lot, Tim, but a lot of people you and I both know haven’t traveled the world. They haven’t been to
1:06:38 that many countries. You want to go to another country, find a great novel that’s been translated
1:06:43 from that country and read it and like you will understand that country in a way that no travel
1:06:49 guide will ever give you in my opinion. So I think it’s a very cheap way. And there’s also to build
1:06:59 like emotional intelligence. I’ve worked now in tech companies for over 20 years. And when you
1:07:04 sort of get to certain levels of responsibility with management and leadership, you could be
1:07:10 technically the smartest person in the room. But if you have no emotional intelligence or
1:07:16 dimensionality in contemplating emotional states, you are going to struggle. You are going to struggle
1:07:21 to lead. And so when I say understand the human condition, I don’t just mean like, I’m reading a
1:07:25 book and I understand, wow, that’s how it might feel to be in a divorce, or that’s how it might feel
1:07:31 to lose your child. Or, you know, I’m saying, no, you yourself as the reader, if the book is really
1:07:38 good, start to feel the feelings. You start to feel like, oh, I lost a child. Emotional exercise
1:07:46 is hard. It’s either happening to you. So you’re going through an emotional situation in your own
1:07:51 life, which is hard, but doesn’t happen every day to most people. Or you’re going to get
1:07:57 emotional exercise from, in my experience, a lot of people get it from film. They get it from video
1:08:03 content. Short form video gives you like a dopamine hit, in my opinion, but not an actual
1:08:10 deep story emotional resonant hit. We think we’re getting it when we see, oh, that dog fell
1:08:14 through the ice and then that guy rescued the dog and you’re sort of like crying and you’re so happy.
1:08:19 But like in a 30 second YouTube video, like, no, that’s not an emotional arc. That’s just, I like
1:08:26 to see people rescue animals who are drowning. But like, no, I really want, I think it’s a serious
1:08:30 film. Maybe it’s John Wick. John Wick might be a way to detoxify your left-hand collar.
1:08:35 I almost cried. I said to my friend who’d seen him before, I was like, if they touch that dog,
1:08:39 I’m going to lose it. And he just stayed silent. I was like, oh, no, here it comes.
1:08:46 But anyway, point is, I think it’s emotional workout. Literature, great films.
1:08:53 Yeah. The other thing I would say is fiction is often much more efficient and elegant in delivering
1:09:01 truths than nonfiction. And that’s speaking as someone who is a militant, nonfiction purist for
1:09:08 decades. And I really wish I’d started earlier with reading very, very high quality fiction.
1:09:12 So what was your gateway fiction? What got you, I’m so glad to hear your convert.
1:09:18 Oh, a gateway fiction. I mean, I would say that early on, I was an avid fiction reader. So as a
1:09:25 kid, there were books like The Neverending Story, and then later Dune, for instance, Science Fiction,
1:09:33 A Stranger in a Strange Land by Heinlein, which were also very condensed thought experiments.
1:09:40 This is part of the reason why I like sci-fi quite a lot. So for folks who are male, also female,
1:09:47 but if they’re male tech on the spectrum over performers, I’ll usually steer them to say
1:09:54 Ted Chiang short stories like Exhalation is a second collection. Then I stopped for a long
1:09:59 time because it was time to get serious and follows rules and be a business guy and so on and so
1:10:05 forth. So I read all the nonfiction stuff. And then I would say later on, now that I’m reflecting
1:10:10 on it, because I’m trying to pinpoint and maybe it’s because you seeded me with the Argentina.
1:10:15 I used to live in Argentina for about nine months in 2004. And in an effort, this is going to sound
1:10:22 ridiculous to people who are familiar with this work, but I wanted to read fiction in an effort
1:10:30 to get better at Spanish. So I found side by side Jorge Luis Borges, which is incredibly challenging
1:10:36 in Spanish, I will say right up front. But that ethereal kind of magic
1:10:47 realism. Yes. Fever dream type of conjuring that he was able to accomplish was intoxicating to me
1:10:55 because it’s effectively mind control, right? Like language on some level is mind control.
1:10:59 If you said to me, like, what’s the other to the lighthouse? I would say a hundred years of
1:11:04 solitude. Gabriel Garcia Marquez and my introduction to magical realism. And what’s interesting is
1:11:09 you went to this because a lot of guys I talked to, they’re like Neil Stevenson, three body problem,
1:11:14 like it’s like there’s a sci fi dune is always in their contact, you know, like whatever,
1:11:19 he depends on when they were born. But like you get this sort of sci fi. But what you just did,
1:11:26 I love, which is where else is there sci fi in a lot of Latin American literature? Isabella Yende,
1:11:33 Orres Marquez. And that’s where like maybe the genders can meet, which is like really emotional,
1:11:40 gripping multi era stories, but really wild stuff is like dream state is happening. And you’re
1:11:44 wondering like, are they on drugs? Like what’s happening here? Of course they were on drugs.
1:11:50 I 100% love that you went there. Because I think it’s when you’re pushing the sci fi
1:11:55 into like a different realm is magical realism. The most creative people I know this includes
1:12:00 business for sure. The most creative if they’re the most creative deal makers, they read and consume
1:12:06 very widely. They’re not going to this huge buffet and always eating the shredded carrots. Okay,
1:12:10 fine, like shredded carrots. Yeah, they’re healthy for you. Easy to eat. I get it. There’s a whole
1:12:18 buffet. And they end up being able to connect disparate fields and ideas in a way that end up
1:12:23 being ultimately incredibly interesting and sometimes very profitable. And I would say who
1:12:29 was it? He works with Daniel Kahneman. Let’s say this aim was very scary, something like that.
1:12:35 But he said something along the lines of researchers waste years not being able to waste
1:12:42 hours. I’m butchering the quote. But it’s like if you feel so rushed that you cannot read a short
1:12:48 fiction book, that is a symptom of a much larger problem, I would say. And so proving to yourself
1:12:54 like creating the slack in the system to do that has its own benefits. Alright, fiction conversation
1:12:59 check. We believe in it. Yeah, we believe, we believe. Alright, so let’s come back to,
1:13:04 I’m going to take a further not digression because this is just a natural conversation,
1:13:09 but we are going to come back to feedback for direct reports. But I feel like we need a smoother
1:13:16 off ramp. So what might make a nice off ramp from the fiction is something that is highly, highly,
1:13:21 highly personal and nonfiction. And that is a working with me document. So I want to ask about
1:13:25 questions that you might answer in a working with me document, you could explain what a working
1:13:32 with me document is. And there are a number that come to mind that I have in front of me here.
1:13:36 But perhaps you could just give a little bit of context on what a working with me document is
1:13:43 and how it is helpful. A working with me document is basically trying to write your own user manual.
1:13:48 And I don’t think you have to be a people manager, but I’ve come to believe it’s a best
1:13:53 practice if you are going to be managing people to do your best to write a user manual to working
1:13:58 with you. The idea came to me actually, I was moderating a panel at Google, Google had then
1:14:02 involved to a point where it’s trying to celebrate management. So we’ve done this great manager award.
1:14:08 And I was the moderator interviewing the great managers that we’d selected across several teams
1:14:13 in front of this big room of people at Google. And I asked them, you know, you ask, what are some
1:14:18 practices that you think have really benefited you as a manager? And one of the panelists said,
1:14:23 well, I copied this thing that oars, and this is oars who’s who’s who’s along many, many decades
1:14:28 at Google, I think he’s only retiring like now, who worked in infrastructure and building the servers
1:14:34 and the like a lot of what really makes your Google results come very quickly, you can think oars.
1:14:40 And then at Google Cloud, a lot of work, but he wrote a user manual. And this person described
1:14:43 it. And then they went on to say they wrote one and they shared it with their team and their teams
1:14:47 response. And I was like, I should write one like here, I am moderating this great manager panel.
1:14:53 I haven’t done this. So like any good learner, I go back and I sort of like bang out this document.
1:14:58 I mean, this is the thing that’s the most interesting to me in this maybe anti growth mindset. But
1:15:04 this was probably, I don’t know, 2009, 2008, whatever, it was like many years ago. I bang out
1:15:10 this document. And I call it the unauthorized guide because I don’t work for me. So I invited
1:15:14 comment. I said, for those who actually have had me as a manager, like, please tell me how
1:15:20 on base I am or not. And then I gave it actually, I had the time had this really amazing woman who
1:15:25 had been a manager in my organization. And then she went on maternity leave and came back and asked
1:15:29 to be my assistant. She said, I want to change sort of, I think I could be kind of a chief of staff
1:15:33 to you. And she was very talented. And we got very close. And she worked for me for like,
1:15:38 at least half my career at Google. And I was like, Maeve, read this, am I anywhere near like,
1:15:43 am I on base here? You know, she was actually, she’s Irish, which is a theme somehow in my life.
1:15:48 Like, I really bond with the Irish. And she said, well, I feel like at the end,
1:15:53 you know, you don’t even acknowledge that you like good crack. And crack, which I’m saying
1:15:58 wrong in Irish is like sort of kind of fun, Joe, humor. Yeah, she’s like, you know, your meetings,
1:16:02 she said, I’ve never been in a meeting with you where we didn’t laugh at least once.
1:16:06 That’s the kind of thing, by the way, that you don’t know, because you’re never not in a meeting
1:16:11 with you. Right. And so I was like, Oh, that was super helpful. But I feel embarrassed that I’m
1:16:15 like, I said, am I saying I’m funny? She’s like, no, you like a good laugh. It’s true. I’m not
1:16:19 particularly that funny, but I really enjoy humor. Anyway, so we added a section at the end.
1:16:22 But she said, no, I think this is pretty good. I think you should send it to the team and see
1:16:27 what they think. But what’s amazing, Tim, is that document has not changed markedly.
1:16:34 Since 2009 or whenever it was like 2009, it has not changed very much. And we can decide how we
1:16:38 feel about that. But I think it’s a great exercise in self awareness. It’s a great exercise. And
1:16:42 also sort of thinking about, okay, when I have to make a decision. So to your point, what kind of
1:16:48 content is there? Some of it’s very tactical. It’s like, how do I like what communication channels
1:16:54 work best for me? So how to use our one on one versus send me a Slack versus a text versus call me.
1:16:59 In today’s world, you know that like, I literally have people that I work with. Actually, I think,
1:17:04 you know, I work with Patrick and John Collison, the Stripe Co founders, of course, they contact
1:17:08 me on every channel. Like, how is it that you’re texting me, what’s happening me, calling me,
1:17:13 slacking me, rarely emailing me, actually emailing is probably like the least interesting channel to
1:17:17 them. So you give guidance, like what are the best channels, like how to use our one on one,
1:17:22 but also things like how do I tend to make decisions. So if you’re coming to me for a decision,
1:17:26 here’s what you can expect. If it’s this kind of decision, how long will I need, what kind of data
1:17:31 might I like, like I have a section in my doc, which is, I tend to be intuitive. So I’ve taken a
1:17:35 lot of different personality assessments. And I actually don’t really spike in a lot of areas,
1:17:41 but I spike as highly intuitive, meaning you come to me with something I intuitively have an opinion,
1:17:46 I’m like, Oh, I think this is going to be the right thing to do. Or I think I say, I’m intuitive.
1:17:51 And then I write dot dot dot, don’t worry, but data driven. So I’ll tell you my intuition. And
1:17:56 then I’ll say you bring me data. So we either can validate it, or you tell me your intuition,
1:18:01 but let’s get some data. So I don’t just get out there and start operating without any basis.
1:18:06 But I think that you’re trying to reflect that, but I think it’s important to reflect that.
1:18:11 Like, for example, in my first version, one thing that did change when my team read it was,
1:18:17 I said, I’m not a mic, by the way, every manager’s like, I’m not a micromanager. It’s like a common
1:18:20 everyone’s like, well, don’t worry, I’m not a micromanager. Unfortunately, a lot of us are.
1:18:26 And I said, I’m not a micromanager, I will delegate, I will trust you. But if I’m concerned,
1:18:29 you’re going to know, and I’ll get more involved. Right. And so I thought I was being pretty honest,
1:18:33 like when I do get involved, we should have a conversation because it means I’m having an issue
1:18:37 with trust, which means I’m not sure I’m happy with the product. So this guy who worked for me,
1:18:41 he said, I’m not sure that you’re accurate about this. And I said, well, are you saying I’m a
1:18:46 micromanager? And he said, well, there was this one thing and he named this project that I had
1:18:52 delegated to him. And he’s like, then you proceeded to show up in every meeting, read every document,
1:18:58 be in the spreadsheet. And that was, to me, felt pretty micromanagy. I was like, yeah,
1:19:02 I bet it did feel that way. I said, I did that because that project was the first time it was
1:19:07 like a sales compensation scheme. I was like, that’s the first time I’d ever built one. And I was
1:19:12 really like wanting to learn. And he said, well, you never told me that. So as far as he was concerned,
1:19:17 I showed up in every damn thing this poor guy had scheduled, and he’s supposed to be leading,
1:19:22 and he’s supposed to make a recommendation to me. And I’m like reading all the same stuff,
1:19:26 participating. I mean, I was looking back, I’m really embarrassed. I was like, I can’t believe
1:19:30 I didn’t tell you, because I had full confidence in this. He was probably, by the way, better
1:19:35 positioned than I was to build this thing. And I was counting on him, but then I went and undermined
1:19:39 him. And so that’s why, by the way, the working with me documents also helpful is because if you
1:19:43 have a good relationships with people you work with, they will tell you, yeah, you think you
1:19:47 act this way, but you really don’t. So then I had to add a section about sometimes when it feels
1:19:52 like I’m micromanaging you, it’s because I’m trying to learn the first time I’ve ever done a thing,
1:19:57 you are going to see me hyper involved. But what we should do is establish that ahead of time. And
1:20:01 if I don’t, please call me on it. Anyway, the point is, yeah, the working with me document
1:20:06 became something I just shared today with anyone who starts to work with me closely. And what happens
1:20:11 in high growth environments like Google and Stripe is like your team changes a lot. There’s new people,
1:20:16 people’s managers change is hard. You don’t love that, but like I’ve had people come to me and say
1:20:20 you’re my fourth manager in a year. So what are you trying to do? You’re trying to create a shortcut
1:20:24 because there’s anxiety when we first work with someone. Well, should I call you if I have some
1:20:29 kind of crisis? When you’re at night and Slack looks like you’re available, should I slack you
1:20:33 stuff? Or should I wait till the next morning? Or like you’re looking for guidance, you’re looking
1:20:36 to read the person. I’m like, just tell them. Tell them how to work with you.
1:20:42 And then that reduces the anxiety. And ideally, they write their own manual. And then you’ve both
1:20:46 sort of shortcut some of the get to know you stuff. So you can just jump right into working together.
1:20:56 This is something I wanted to explore because jumping expose to something you explore at some
1:21:01 length in your book, which I definitely recommend people check out. I underlined this a couple of
1:21:07 times for myself because I still feel like I have room to improve here. And that is strive to make
1:21:14 implicit structures and beliefs explicit, make the implicit explicit. And that shows up in so many
1:21:20 different ways. It can manifest in so many different ways. And I want to stick with the working with
1:21:26 me document for a minute. This first came to my attention because I had Dustin Moskovitz on the
1:21:34 podcast from Facebook fame, and then certainly of Sana. And he shared his working with me document.
1:21:40 And I’ve since seen a few versions of this. But I wanted to get your take on what might
1:21:46 be worth adding to this list of questions. Here are a few. What do I want to be involved in?
1:21:50 When do I want to hear from you? When you already mentioned, what are my preferred
1:21:56 communication modes? What makes me impatient? Are there other questions that you have found
1:22:05 helpful to address or topic areas worth including? Having seen these letters, having crafted your own
1:22:11 working with me document. My working with me document was published in Elad Gill’s book,
1:22:16 High Growth Handbook, and went a little bit viral, viral for Claire, not for Tim Ferriss. But still,
1:22:23 I was shocked at how many people that I’ve never met had seen it. And I also got some criticisms
1:22:28 on the interwebs that was very egotistical in some way. It was sort of like, here’s how you
1:22:34 make me happy. Which I was like, okay, that’s a totally fair criticism and not the intention.
1:22:39 By the way, I’m pretty highly empathetic. I’m trying to reduce anxiety and help people feel
1:22:44 comfortable being honest with me, whatever. But I get it. It seems very self-absorbed.
1:22:49 So one of the things that I’m reacting to is the question, I guess, if I were going to phrase it
1:22:55 as a question, it would be, how do I help you make great decisions? Or how do you like to make
1:22:59 decisions? But I think in my document, I just sort of have headers, like decision making, because
1:23:04 I’m not, that’s why yours called it user manual, which is a very technical, like an engineer is
1:23:08 going to be like, I’m going to write a user manual to me. And I just called it working with me.
1:23:15 There’s a section on what types of information do you like to see? Because that’s different than
1:23:19 how do I want to be communicated with. And it’s different than when should I get in touch with
1:23:24 you, which is like, yeah, if there’s a crisis, get in touch with me. But there’s something in mine
1:23:27 where I talk about the fact that if someone on your team is having a major life event,
1:23:33 I’d like to know about it. I’d like to send them a note. I’d like to say, I’m sorry, or celebrate
1:23:37 their child. Or I think, what types of information do you like to have? I also get really explicit
1:23:42 about things like email protocols mean different things to people, especially in different
1:23:48 generations. I’m sure you’ve seen this. But I used to work with someone who would send FYI
1:23:56 and really, really feel strongly that you need to process that information and have a response.
1:24:02 Whereas for me, I’m like, if you send me FYI. That means no response. That means for me anyway.
1:24:08 Yeah, I can read it later. And it’s interesting, but I don’t need to respond. And I’m like,
1:24:12 I can’t believe this. But I think I have to back to, I think you asked your guest the question
1:24:16 of like, if you were going to have a billboard. I think the fight for me in my billboard would be,
1:24:23 is it make the implicit explicit, or is it undermine the superstructure from within?
1:24:27 I’m not sure. But one of those, one of those is my billboard. But the first one,
1:24:33 I think I get the first one, making the implicit explicit is so valuable. By the way,
1:24:37 so many, a lot of people are like, I love that your book is like so humanistic about people
1:24:44 and how to care for, I was like, folks, my book is about getting results. I do appreciate other
1:24:48 humans. And I love working with them, even though sometimes Patrick calls and I would be like,
1:24:53 Oh my gosh, this is like the hardest problem. And we’d go, Oh, if there were no humans involved,
1:24:59 it would be so cheesy. But point is, I love humans and the human condition. But I really am talking
1:25:04 about how do you get results? And how do you get results? You get super clear and transparent
1:25:08 about anything implicit, you make it explicit. And you’re like clear, like this is a process,
1:25:12 we’re going to go through it to get to this outcome. And what is the outcome we want?
1:25:16 Make it explicit. I mean, Tim, you, I think are the master of this. What are we measuring?
1:25:21 Why are we measuring it? How will we know if we won? And I would add to that. And what process
1:25:27 will we go through together to get there? So that no one is guessing or reading the tea leaves or
1:25:32 wondering why another team is doing the same project, put it all on the table so that we
1:25:38 can get to the end faster. And frankly, more inclusively, and why do I care about inclusion?
1:25:43 Yes, inclusion is a good thing for people to feel better and included. But actually, because
1:25:48 if you’ve hired a bunch of smart people, and yet they don’t feel included, they will not share
1:25:52 their opinion. And the reason you hired them is because they’re smart people who bring diverse
1:25:58 opinions. And if they won’t say them, then you’re like not really benefiting from all that work
1:26:03 hiring them, because you want a better outcome. This is all about results. But I think it’s a
1:26:10 little windy to get there sometimes. Yeah, totally. Until you make it explicit. I wanted to piggyback
1:26:16 off of your Irish pattern in life and recommend a short film that I think won an Oscar. I might
1:26:21 be making that up, but I won some slew of fancy awards. And I watched it last night, called an
1:26:26 Irish goodbye. It’s about 20 to 23 minutes long. If I don’t Vimeo, I think you might be able to
1:26:32 watch on YouTube as well. It is hilarious and profound and outstanding. I think based on the
1:26:38 little that I feel like I’ve sort of felt out with our fiction love fest, I think you would
1:26:43 really enjoy this. It is one of the better short films I’ve ever seen. It’s really good. It’s really
1:26:49 really good. So an Irish goodbye. What is it? Little big and Irish goodbye. Start with an Irish goodbye,
1:26:52 because then you’ll be like, wow, Tim really recommends good stuff. And then if you hate
1:26:58 little big, at least I’ll have some redemption preemptively. Yeah, so it’s like the Moose
1:27:03 Boosh before you try to chew on the fever dream. And I’d also say also, I’d love a good Irish
1:27:10 goodbye. I used to find it a little offensive, but now I’m like, gosh, there’s some real beauty
1:27:16 and just disappear. Oh, I do that all the time. I do it all the time. So email policies. I had a request
1:27:22 from Kevin Kelly recently who’s been on the podcast and is a close friend. I asked him if I
1:27:25 could help him with anything. We’re having a conversation. He said, well, I do have one request,
1:27:29 and it’s not for him. It’s because he gets asked about it so much. He doesn’t have any issues
1:27:35 with email. But he’s like, I want you to ask everyone of your guests about email policies slash
1:27:42 rules, systems, anything that they have ended up using that they have found helpful. And I will
1:27:48 say in advance, my assumption is that almost, well, it’s not my assumption, I’ve also run into this,
1:27:52 even though this podcast has some of the top performing people in the world of every discipline
1:27:58 imaginable, they all claim to kind of suck at email, they’re behind and it’s hard. So I understand
1:28:03 that being that as it may. See, it’s a beautiful change. There we go. Be that as it may. Be that
1:28:08 as it may. You are still going to have to answer this. Yeah. Are there any sort of email policy
1:28:14 systems, rules, implicit things that you make explicit that you found helpful? I actually
1:28:19 worked on Gmail right after it launched at Google and like you should think I would be like a power
1:28:24 email organizer and I’m okay, but I’m not great. But one thing that just stuck out of my mind as
1:28:30 you brought this up is I had a good friend who was a executive at Genentech and she rose up with
1:28:35 Genentech as it got big and she got more and more responsibility and she told me about this leadership
1:28:39 training they put them in Tim. Honestly, whenever I look at my inbox, I think of this training
1:28:46 where they gave them some 30 minutes, some window, they gave them an inbox. And they were like,
1:28:54 you need to process all this and kind of do the right things, right? Okay. And so in this inbox
1:29:00 of like 100 emails, whatever they have 30 minutes, you have to find there’s like a massive legal
1:29:05 issue. There’s an HR violation, but it’s like not in the headline of the subject of like an
1:29:11 anxiety dream. Like a bunch of bombs in these messages and you have to like open them, skim
1:29:16 them, decide you have to come back to it, right? Yeah. And I kind of was like feeling like Japanese
1:29:21 game show. I’m like, what does show that people might want to watch? And I think there is a
1:29:26 sector of people who might find that like really interesting to watch. So sometimes I look at my
1:29:33 inbox and I’m like, oh my gosh, I have 30 minutes and I need to find all of the legal time bomb.
1:29:38 But one of the things that I think I’m very good at an email is it’s a set of people in my both
1:29:44 professional and personal life, like they get opened immediately. And I’ll open it. And if it’s
1:29:49 by the way read FYI, I’ll read it later. I really want to make sure I mean, it’s easy. Some of these
1:29:53 people is like easy. It’s like your kids. By the way, my kids are teenagers. They never email me.
1:29:58 So that’s like easy. But you know, certainly if you’re the COO of a company, even if you’re not
1:30:03 the COO anymore, if the founders of Stripe emailed me directly, I’m going to open the email pretty
1:30:08 freaking quickly just to make sure like, you know, so it’s sort of like your boss or but I do think
1:30:16 that some people have a methodology, which is either LIFO or FIFO lasted first out. Yeah. And I
1:30:20 think that that’s tempting. My husband does this a little bit. It bothers me. I’m like,
1:30:28 you have cues, which is who is it from? And is a group or is it in direct to you? And use those
1:30:34 cues to prioritize. And so if you only have 30 minutes, you know where to start. That’s one
1:30:38 of the things and it is a combination of the people and what’s being sent to you directly.
1:30:42 So I think that’s like a number one rule I have that I’m pretty actually good at.
1:30:46 So there’s certain people who feel I’m very responsive on email because I I am very responsive
1:30:54 to them. Yeah, I’m not maybe responsive to everyone as consistently. The other is I have,
1:30:59 this is like more of a cheat, but you’re an investor, I think, right? So I’m I’ve invested
1:31:05 in some companies. And a lot of them send these investor newsletters or investor updates. And
1:31:11 of course, I’m because I do have some Gmail skills. I label them. I know there’s a folder full of them.
1:31:19 And I have every intention to him. On Friday, for like two hours, I’m going to read those investor
1:31:26 updates. Okay. You know what? That is not correct. Sometimes when I’m on an airplane and I’m trapped,
1:31:30 I like open and start reading them. But like, I am not reading them in a timely fashion. And I’m
1:31:36 sorry, all the founders I’ve invested in, I’m sorry, I’m not reading your investor updates in a
1:31:40 timely fashion. But what I’ve learned to do, and this goes back to making the implicit explicit
1:31:46 and also to another rule I have, which is strive to set expectations with people. So now when I
1:31:52 invest in a company, I say to them, I say, look, you may email me, I’ll give you my email. I said,
1:31:57 I’ll give you my cell phone. I’m quite good on text, but please don’t abuse it. And if you want
1:32:01 to WhatsApp me and not tech, whatever, either of those is going to work. And then I say to them,
1:32:05 I want you to know, I really appreciate getting the investor updates. I will not read them in a
1:32:11 timely fashion. I may not read them at all. If you need something from me directly, like you need
1:32:16 help me interview this person, or I have a crowd, you should get in touch with me directly,
1:32:21 not as like at the end of an investor email, it says, please help us hire some way to scientists.
1:32:28 And cognitive load wise, I’m like, I have been feeling so much guilt about not reading there.
1:32:34 By the way, they spend so much time on them. And it’s terrible sometimes. But I no longer feel
1:32:38 guilt. I’ve told them, you must contact me directly. Set expectations. But this is actually
1:32:42 a management lesson, which is why not this goes back to the user manual, or they’re working with
1:32:48 Claire guide, like why not tell people, I have this habit of ignoring this kind of thing. And
1:32:54 if you need my attention, please, you have my permission, please use it, please text me even.
1:32:57 I mean, for these founders, they have my phone number. I’m like, if you need me,
1:33:01 you can call me. But it’s sort of a human lesson we learn over and over again,
1:33:05 which is we’re like, dying inside that we’re disappointing someone. And I’m like, no,
1:33:09 just renegotiate the terms of what expectations they should have of you.
1:33:13 How else does this renegotiating show up? This has become
1:33:21 it’s embarrassing to say, but I’d say maybe in the last two years has become such a revelation for
1:33:25 me in a sense, because I was thought about negotiating as the thing you did in the beginning.
1:33:31 And I got, I think pretty good at that. And at times, though, I would have who knows, like,
1:33:35 maybe I’ve had two glasses of wine or I had two little sleep or whatever. And I would agree to
1:33:39 these things. And then later I’d look at my calendar. And my blood pressure would go up
1:33:46 being a 30 points, because I felt trapped by these commitments that I made when I was compromised or
1:33:54 rushed or lazy fill in the blank. And this renegotiating has become an invisible option
1:33:59 made visible for me in the last two years. Could you talk a little bit more about how
1:34:06 you have used that in your life, personal or professional, how that shows up like examples
1:34:09 would be really helpful here. So people can really get a grasp on it.
1:34:13 I’m having like almost a physical reaction to relating to you about this calendar. It’s
1:34:18 like your past self. I used to say, oh my gosh, I just milled myself a letter bomb.
1:34:23 So one is, of course, we all strive to improve, which is do not make a decision in the moment
1:34:30 about a time or a commitment of resources or time without trying to project your future self.
1:34:33 But of course, we all do because you’re right, we’re rushed, we’re trying to be responsive,
1:34:37 we’re trying to move through our inbox, by the way, because we’ve only got 30 minutes,
1:34:39 so we might fail the corporate training test.
1:34:41 Or the Japanese TV show, I don’t want to come in last.
1:34:46 Yeah. So one thing is trying to be better about projecting. And I also had a friend
1:34:50 who’s like a very kind of spiritually in touch person. And she said,
1:34:57 when something is requested of you, she said, you need to sometimes listen for the quiet no.
1:34:59 Can you say that one more time?
1:35:03 So she said, when something’s requested of you, a person, I mean, she’s like sort of like,
1:35:09 sometimes your reaction is, wow, yes, right? You’ve had this. I mean, hey, Tim Ferriss asked
1:35:15 me to be on his podcast. I was like, yes, emphatically, that is something I want to do.
1:35:20 That is easy. My future self is very happy to be, my past and future selves are very happy
1:35:26 to be here. But often we get a request, you have this experience and you’re looking at it.
1:35:33 And she says, listen for the quiet no. Because we are often feel like we have to say yes.
1:35:37 And her trick is, and I know this wasn’t the question you asked me, which I will answer,
1:35:38 but her trick is-
1:35:41 These are really closely related. I’m so interested in this.
1:35:41 Yeah.
1:35:46 I think they are. Do not respond immediately. Because we often feel, I mean, if you’re someone
1:35:50 who prides yourself on being decisive and responsive and empathetic as I do,
1:35:56 I feel like, well, they asked me to be on this panel at this important conference or whatever.
1:36:00 And I’m like, I’ve learned that my response in fact should be,
1:36:04 when do you need to know whether or not I can be on this panel?
1:36:09 Or I’ll even say, I need two weeks to get back to you about whether I can be on this panel.
1:36:15 Because if I don’t give myself some space, I will do yes instead of the quiet no.
1:36:21 Because I didn’t give myself time to really think about, is this my priority? Should I spend my time?
1:36:26 Oh my gosh, I have to fly to the city. Like you have to really think. So I think
1:36:31 when you are renegotiating, so I’m proud of you that you found this as a skill. And by the way,
1:36:36 I have the same problem. I had a delayed travel earlier this week, and I was looking at my next
1:36:40 day, and I was thinking, well, I am going to get home, but I’m going to get home at like now two
1:36:45 in the morning. And then I looked at it, and I was like, I should not even be doing that stuff.
1:36:49 I was like, why did I even agree to go into Boston and have lunch with this person and then talk to
1:36:55 this other person. And so I was like, I am going to renegotiate those commitments. I don’t even have
1:37:01 to say that I was delayed. So it’s a good skill. But what I look for is a pattern, a pattern of
1:37:05 why am I renegotiating this stuff. It means I’m not making the right decision in the first place.
1:37:11 So I listen for the quiet no. But if I find myself renegotiating, it is often about, yeah,
1:37:17 commitments I’ve made. Commitments, especially of time. My mom was a very talented, apparently
1:37:22 mathematician in college, and my mom went to Harvard, well, Radcliffe then. But I think it was
1:37:30 pretty rare for a woman to be like a star in the math department. And she decided to go get her PhD
1:37:37 in history and to major in history. And I said, why did you switch? Why did you make the switch?
1:37:45 And she said, I realized that there is a trade-off that most people find themselves making between
1:37:53 money and time. And she said, I knew that if I prioritized math, it would likely lead to a more
1:37:58 lucrative career. By the way, my mom was like, out there, she was going to work, and she did,
1:38:01 and she was going to have kids and work. But she was like, it would lead to a more lucrative career,
1:38:06 but I would not have time. So I decided to become, she became an academic. She got her PhD. She
1:38:11 became a professor. And why? Because professors have more control over their time. And they have
1:38:15 the summers off. And they have time to think and write. And that’s what she knew she wanted,
1:38:20 which by the way is pretty aware for like a 19 or 20 year old to realize you’re going to trade
1:38:26 money and time. I think it’s Peter Thiel, who says people don’t value their time highly enough.
1:38:32 They just don’t get, every hour is costing you something. And I’ve taken me so long to come
1:38:36 to this point where I’m like, oh my gosh, I just threw away and said, sure, I’ll meet with you
1:38:42 to give you advice about that thing. And I’m like, oh, so I’ve become less responsive on email
1:38:52 because I am trying to stop myself from mortgaging my time. You may or may not have had the same
1:38:58 experience. But all right, here’s an example, you’re looking for concrete. I have a woman who I
1:39:03 highly value personally in my life. She’s a founder. And she asked me to be on her board.
1:39:08 By the way, to stop myself from saying yes to stuff, I make rules. I made a rule. I was like,
1:39:11 no more boards. I also have a rule about travel right now. I’m like, my daughter’s going to
1:39:16 college soon, no more travel unless it meets these criteria, because I want to be home. Of
1:39:19 course, she doesn’t want to hang out with me, but I want to hang out with her.
1:39:23 What are the criteria to study curiosity? Could be just a few examples.
1:39:28 Really important to Stripe. I still actually work part-time for Stripe and they get bids on my time.
1:39:32 And if Stripe said the most important thing you can do for Stripe is go to, this happened to me
1:39:38 recently, go to Helsinki to slush to this conference. I was like, fine, I will do it.
1:39:42 I will go to Helsinki for Stripe. And by the way, I had a great time and I met a great number of
1:39:47 founders and it was actually a blast. So is it important to Stripe? Is it a personal connection
1:39:54 that is meaningful to me that is asking of my time treasure talents? My criteria is not to
1:40:00 say yes to default, but it is to number one, is there a way I could do it that is less friction?
1:40:07 As in, am I flying to California anyway? Therefore, I can do that commitment if I bundle it. So can I
1:40:12 control when it is? And if I can control when it is and it’s a personal connection that’s meaningful
1:40:16 to me, I will make it happen, but it will not happen quickly. But if it’s not something I can
1:40:22 control where and when it is, then I have a subset of criteria of like, but I often will say like,
1:40:26 could this thing, maybe it’s a conference, can I do this next year and get back to you later?
1:40:32 So I can actually think for a minute. A lot of it is buying time. But I have these rules
1:40:36 about things because it stops me. So I said to her, I said, I have made a commitment to myself
1:40:41 that I will not join another board. And she, because she’s a talented founder, she’s persistent.
1:40:45 And she said, why don’t you just come and be an observer? Why don’t you just come to, I know,
1:40:50 I know, come to the board meeting. And then she told me why she really needed help in this particular
1:40:55 moment. And there was a situation where having someone who was sort of a friendly, who was neutral
1:41:00 in the room was going to be valuable. So I said, okay, I will come, but I will not,
1:41:03 like I really want to set your expectations right back. I was like, I am not, this is not
1:41:08 going to reel me in. I’m not going to join the board. And I did go and she actually convinced
1:41:12 someone else. And the two of us went and we actually, I think helped her through a particular
1:41:18 moment by being sort of board participants. But then she said, I’d like you to come to every,
1:41:21 you know, first every board meeting. And I said, I don’t think I can commit to that,
1:41:27 but I can try when it’s virtual. And if it’s in person, I’m pretty sure I won’t, but you can
1:41:33 invite me. And I went to a couple, I did pretty well. And then I started to look at my calendar.
1:41:39 And I was like, I can’t do this. I can’t even take three, four hours. And so I needed to renegotiate
1:41:44 it. There’s a quote that I have in my book that that people find, I think the most compelling
1:41:50 line in the book. And I keep having to remind them it is not my line. Yeah, I know this problem
1:41:54 where I’m like, no, no, no, no, no, don’t attribute it to me. That was Mark Twain or whatever.
1:42:00 Exactly. Exactly. The line is from Ron Heifetz or Marty Linsky. These are the adaptive leadership
1:42:05 guys who do the balcony and the dance floor analogy. And it is leadership is disappointing
1:42:10 people at a rate that they can absorb. Yeah. I had that line underlined. It’s very catchy.
1:42:14 Because it really makes you think and it’s kind of dark too. Yeah. What does that mean in like
1:42:19 concrete terms? Yeah. And then I’m not going to let go of the renegotiating because I’m going to
1:42:23 come back to that. I want to ask you about phrasing and wording that you use. But let’s
1:42:27 talk about leadership and disappointing people. Well, I think one of the ways that leaders
1:42:33 disappoint people is their time. You don’t have unlimited time. You’re the CEO of a company.
1:42:38 There’s no way you’re going to be at all the things or do all the things. But the key is how
1:42:44 do you create enough leadership buy-in that people understand? And also you get a little bit of
1:42:48 forgiveness when you’re the CEO, I think. But leadership is disappointing people at a rate
1:42:54 that can absorb. To me, it’s about management is very knowable. It’s like, how do I get from
1:42:59 point A to point B? What people do I need? What’s the scope? How are we going to measure it? Here’s
1:43:03 the project plan. Here’s the milestones. Here’s the talents I need. And now I’m going to deploy
1:43:11 and delegate. And I think leadership is very unknowable because it is essentially having a
1:43:17 vision and idea, a goal that you haven’t even fully understood yourself, right, often? Yeah.
1:43:23 It’s like, we’re going to climb this mountain that no one has ever climbed before, by the way.
1:43:29 And you have to be really convincing to build followership. You’re painting a picture of the
1:43:36 top of that mountain, man. And it is awesome. And the climb is going to be really challenging,
1:43:42 but really rewarding. And you are going to get on that journey with those people. And you are
1:43:47 going to be wrong about a lot of what you just said, right? No, actually, it wasn’t as easy up the
1:43:54 south face as we thought it was. Yes, we did actually need special equipment. I mean, come on.
1:43:58 You don’t even know how you’re going to get up there. The analogy that’s more concrete that I
1:44:05 use is, I came into Stripe and look, it’s a product that has people’s money. And you need to have
1:44:11 good support experiences when something is wrong with any kind of payment. I’m expecting money.
1:44:16 I’m trying to take money. I’m moving money. There’s a high expectation. And Patrick is like,
1:44:22 we need to build 24/7 global support. We had really good ambitions. And by the way,
1:44:29 I want to be clear. One of the things that Stripe has as a value is to be users first. It is always
1:44:34 our most important operating principle. It is actually deeply in the culture of the company.
1:44:38 So much so, Tim, that when the support team would get behind, the entire company
1:44:45 would stop and answer support emails. And so, this was becoming an existential problem because
1:44:50 we had to do engineering work and other work to build the company. But we were ending up on
1:44:56 Fridays before the weekend because you want to get back to people quickly answering support tickets.
1:45:00 By the way, you hit product market fit. You get traction. This is a super normal problem.
1:45:04 But it is not great because the product is people’s money. It’s a quality problem,
1:45:07 but it’s a problem nonetheless. And so, Patrick is like, look,
1:45:12 we need to have this 24/7. And I had to get up as the leader and say, I will build this.
1:45:17 And I had built similar things for Google. So, I wasn’t completely describing the mountain I’d
1:45:24 never seen. But I certainly didn’t join Google when it was only 160 people with 21 support people.
1:45:30 And I was like, we are now going to do a set of things to solve this. And it took me a few years
1:45:35 and it’s not perfect. And it involved hiring very talented people. I don’t get credit for
1:45:42 what we built. But I still look back on that and I say, I can’t believe I declared that I would get
1:45:46 it done. And I didn’t have a plan because I’m more of a manager. I’m more of like, I need to have a
1:45:50 clear plan on how I’m going to get this done. Instead, I was like, yep, we’re going to have it.
1:45:57 Public announcement. And I mean, Patrick kind of pushed me there. But I was like, this is uncomfortable.
1:46:01 And I’ll tell you, I did disappoint. Did I deliver it by the end of that year? Oh, no, Tim,
1:46:04 I did not deliver it by the end of that first year. Like, let’s not kid ourselves.
1:46:11 I disappointed. But I did figure out a way to do it. And I think people followed me. They
1:46:15 kept following me. They kept believing we were going to do it, which is some combination of me
1:46:20 being authentic, I think, me being honest about where we were, me having a plan eventually,
1:46:25 me demonstrating that it mattered, whatever. So I think that’s what it means is like,
1:46:29 you will not live up to everything you said, all the expectations of you,
1:46:36 with your time, with your ideas. We’re all humans. We’re not perfect. And we’re not
1:46:41 fortune tellers. I’m not a fortune teller. So this ties into the renegotiating, actually,
1:46:47 pretty well, because there are many different species of renegotiating. One was, you gave an
1:46:51 example very early on in the conversation, when Lucy was getting thrown under the bus,
1:46:59 the dog ate my homework situation. And then we segmented from that to the player versus victim.
1:47:03 And the player would say, you know what, you’re right. I committed to get this to you by 5pm.
1:47:08 I didn’t. And because this emergency popped up, and I didn’t let you know, I should let you know
1:47:16 how about 5pm tomorrow, or whatever the example was, renegotiations. So in this particular example,
1:47:21 when it becomes clear to you that by whatever deadline had been agreed, you are not going to
1:47:25 be able to deliver what you’re going to hope to deliver. What does that conversation look like?
1:47:30 I mean, it’s not exactly semiotics, but I know you like language, and I know you consume a lot
1:47:36 of language. So what is the language that you use to have that conversation, whether it’s verbal
1:47:41 or in email? I think you made the connection, and then you didn’t finish making a connection,
1:47:46 but it is so easy to sound like a victim when you are facing this kind of a situation. And if
1:47:50 you’re someone who prides themselves on being a player, on taking ownership, and you’ve made this
1:47:56 commitment, and you’re like, oh my gosh, there’s no way I’m either coming to that meeting or
1:48:02 delivering 24/7 global support in six months. And so what does it look like? I think what it looks
1:48:08 like, the first thing I did that was probably the smartest thing I did when I joined Stripe was I
1:48:14 listened, and I did my first 90 days, and I talked to everybody, and I heard sort of here’s priorities,
1:48:18 here’s what people need, here’s what need my attention. And then I sat down with Patrick,
1:48:22 and I said, I’m hearing these four things. One of them was the support thing, by the way,
1:48:29 that really need my attention. And I am going to rank them, and then I want you to see my ranking,
1:48:34 and I want to agree on my level of priority. I said, because I can’t make meaningful progress on four
1:48:42 things at once, I can maybe keep, and I actually predicted in that moment, I said, because we had
1:48:46 to build sales, we had to build recruiting, we had some internal operational stuff that
1:48:52 needed to be fixed, and then we had this support smoldering fire. And I said, I think I actually
1:48:58 need to build sales and recruiting ahead of fixing support. But I predict support is going to
1:49:03 implode within the next six months. And at that point, you were COO. Is that right?
1:49:07 I was COO. I was actually hired as Chief of Business Operations, and then I became,
1:49:11 we just swapped titles with someone else, but it’s a long story. But yes, I was basically COO.
1:49:16 And remember, we’re users first. This was a painful, because we were also not getting back
1:49:21 to sales leads though, Tim. I was like, I’m also here to build some revenue. I’m here to build,
1:49:25 go to market, and I’m here to deliver some revenue for this company. And I’m like,
1:49:29 we have this other thing where we’re not getting back to our prospects. And so,
1:49:34 it was a very Sophie’s choice kind of moment, honestly. Oh, and then we couldn’t hire people
1:49:38 to build the company, so we couldn’t get back to sales leads. This is normal, by the way,
1:49:43 this happens, and especially for people like me coming into that kind of opportunity. But what
1:49:47 I loved about that conversation was Patrick was, one, first of all, supportive. He was like, great,
1:49:52 this is good for us to talk out now. And then he had to admit, he’s like, I can’t believe I’m
1:49:57 doing this, but I agree, you’re not going to fix support in the first six months. We made an
1:50:04 agreement. And then, by the way, Tim, four months in, complete explosion. And I was thinking in my
1:50:08 head, thank goodness, this goes back to expectation setting. I’m like, thank goodness, I said out
1:50:12 loud that I thought it was going to explode. And then, I mean, by the way, it’s still terrible.
1:50:16 I was so sad. I was like, oh my gosh, I had to go then put it at the top of the priority list,
1:50:22 basically. But I had at least four months to build some other things. Point is, one is try to set
1:50:27 the priorities, align on them, and set expectations ahead of time. Even if you haven’t done that,
1:50:29 you’re going to reach a moment where you’re like, there’s no way we’re going to the top of this
1:50:37 mountain. And so what you try to do is not come up and make a bunch of excuses. So what I, I think
1:50:42 I did in those moments, we had written public goals in the company, we had plans, and I just
1:50:46 want to be clear, none of the plans, this is where when you’re working with founders, maybe this is
1:50:51 a side, what do you call them side quests? This is a little bit of a side quest. Love side quests.
1:50:57 When you’re working with founders, people describe this reality distortion experience,
1:51:03 which often is more that they have a version of reality. And they’re like, no, no, no, we can ship
1:51:08 the iPhone in five minutes or whatever, you know, and like everyone’s like, yes, Steve, yes, we can.
1:51:14 Right. There’s another version of reality distortion I find, which is you can fix that
1:51:18 thing in five minutes. It’s now a joke between Patrick and I, because he’ll be like, yeah,
1:51:24 we could just like code that up. And I say in five minutes, you know, it’s not five minutes.
1:51:30 So we had a consistent conflict where I would say to him, no, that mountain is not going to be
1:51:34 climbed by the end of this year. I never actually said I was going to build that thing by the end
1:51:39 of the year. And he refused to hear it. He was like, no, it really needs to be the goal.
1:51:46 This actually needs to be the goal. Be that as it may, Claire. Yeah, be that as it may, Claire.
1:51:53 I’m making it your goal. And I was like, okay, under duress, I am going to like take this goal
1:51:59 and try to put some language in it. I mean, I’m going to get a red, right? Whatever on your,
1:52:04 I mean, that doesn’t feel good. This is the other thing. It’s beneficial to walk into a situation
1:52:10 like that after some amount of career success, so that you have some amount of self actualization.
1:52:14 So I was like, luckily, my whole identity is not tied up in this goal, because I would have been
1:52:18 destroyed. I would have really lost confidence. By the way, a lot of leaders you hire into a
1:52:24 startup environment end up losing confidence just because you’re getting pummeled, totally pummeled.
1:52:28 And like, you need to sort of be like, no, no, no, I have identity outside of the success of this
1:52:31 moment. But I was like, all right, I’m going to publicly get up in front of the company and
1:52:36 have failed on this goal. But we disagree. We agreed to disagree that this is possible.
1:52:41 What’s also funny, though, is I was like, I think he really believed it was possible and he’s very
1:52:45 smart. And of course, then I’m going home, I’m like driving home at night. I’m like, has he ever
1:52:51 built anything like this? No, why am I even listening to them? But they reality distort you
1:52:55 into thinking, yes, it’s completely possible. Like, I don’t know how I got fooled. But what I did
1:52:59 sort of commit to myself is like, I have to make meaningful progress. So what are some of the
1:53:04 milestones we can point to? So what you do is you go in and you say, well, I was not convinced
1:53:10 this was the right goal. But I agreed to it. Here are the milestones that I’m glad we hit. So you
1:53:13 kind of don’t forget to point out you made progress. I think sometimes people get defense,
1:53:17 they’re like, I don’t want to be defensive. But you have to be like, look, it’s like nothing happened.
1:53:23 And then you try to be data driven. And what I think, because this is where the context matters,
1:53:29 Stripes founders and Stripes culture is very learning oriented. Very, very, more so than
1:53:35 almost maybe any startup I’ve come across. Yes. At an early stage too. Yes. So think about the
1:53:40 cultural context you’re in. What did we learn? What did we not know? And what did we learn
1:53:45 trying to get there on this goal? What did I learn? And by the way, some of them are mistakes I made.
1:53:50 And so try to be humble. Stripes is also very humble culture. Say, here’s some things I thought
1:53:53 I knew. By the way, I thought I did know. I was like, we were going to outsource certain things
1:53:58 that I thought was going to be easier than it was. And that is true. And here’s what I learned.
1:54:01 Here’s what I thought. Here’s what the truth was. Here’s what I learned. Here’s now what we’re
1:54:05 going to do differently. And by the way, everyone’s nodding in the room, because they’re like, cool,
1:54:10 cool. We had a plan. We tried it. I mean, they’re engineers. They know it like did not work the way
1:54:15 we thought it was going to work. We’re going to try this other thing. So you basically do a retro
1:54:20 postmortem, whatever you want to call it, sort of publicly in front of everyone in the language
1:54:26 they like speaking. So the language stripe like speaking is learning. I made mistakes. What am
1:54:31 I doing differently? What do I see next? How are we going to get there now? You know what I mean?
1:54:37 Like it’s I’m confident, but humbled by this experience. And I’ve learned a lot. And here’s
1:54:41 some data that shows we have made some progress because that also people want to make sure like,
1:54:45 are we actually know what we’re doing? So that’s what you do. And I think it depends on your context
1:54:51 instead of what language do you speak. So that is a big example. And that is, I think, a very
1:55:00 effective way to, as a player, offer a miacopa in a way. Yeah. Yeah. At that point then. And this
1:55:06 may be if this is going to require a dissertation, then tell me and I can read jig. But how did you
1:55:12 decide to scope the thing and then make a counter offer effectively? Or was that even your decision
1:55:16 to make? I don’t know. In terms of like, okay, we’ve learned these things. These were some
1:55:22 assumptions. And then leading into the kind of now what? I won’t do the dissertation version, Tim,
1:55:27 but I will tell you one bind I found myself in consistently that I’m sure you have also
1:55:33 is it’s a talent bind, which is I can only do so many things at once individually me alone.
1:55:38 And I did feel like a victim, I’m going to be honest, because I had been trying to hire someone,
1:55:44 I had hired someone they hadn’t worked out, partly my fault, partly not my fault. And I’m in a meeting,
1:55:48 this happened so many times, but I’m talking to Patrick and I’m like, look, we know so and so
1:55:55 didn’t work out. Here’s what happened with that. We now have face a choice, which is you have Claire
1:56:00 as a resource me alone. Am I going to go lead support directly? Like, am I going to go start
1:56:06 building this thing with all my most of my time? And what is the opportunity cost of that? What is
1:56:11 the tradeoff of me not leading sales? By the way, at that moment, which I was also leading. And this
1:56:15 is where I fell into a trap because I had like a few too many needing to clone myself problems.
1:56:20 And this happens when you’re growing quickly, but it’s still I got into an egregious case of
1:56:26 needing cloning. Then we’re having a renegotiation conversation, not even a reasonable case of
1:56:31 needing cloning egregious. It was egregious. It was egregious. There was one point where I mean,
1:56:35 I think it’s important that people, especially because they seem to think I have some like
1:56:40 storied career. I’m like, there was a moment where I had taken a former colleague from Google who I
1:56:45 was admittedly, I’ll be honest, was trying to recruit to strike out for a coffee. You’re just
1:56:51 going to be a board observer. Just come once. Yeah, right. Exactly. Exactly. And he says to me,
1:56:55 he used to actually work for me and he knew how much I pride myself on good management practices.
1:57:00 And he asked me, how many direct reports do you have? And I told him, and he almost like,
1:57:04 I had to peel him off the ground. He’s like, I can’t believe you let that happen to you.
1:57:08 He was like, what happened to the Claire Johnson? Then I know, I’m like, I know, I’m so sorry.
1:57:14 Like I had so many direct reports. How many direct reports? It was a crime. At peak. I think the
1:57:19 peak, I want to say the peak two was 23, but it might have been 27. And I just like lost control
1:57:26 of, I really don’t. Tim, I didn’t want to go here. I didn’t want to go here. It’s so many
1:57:32 one-on-ones. And of course, I do actually make one-on-ones happen. So point is, I got schooled
1:57:38 by my former direct report for violating my own rules in the need for cloning. But the point is,
1:57:47 the negotiation turns from we’re negotiating you getting this massive goal done to what’s the
1:57:53 cost of me getting that goal done for the other priorities. And then you’re making a joint
1:57:58 decision. By the way, the outcome of that negotiation could have been, let’s not build out
1:58:03 sales any further. Let’s not keep internationalizing. Let’s not open new markets. Let’s wait on those
1:58:08 other things because we decided you should just go and be the directly the head of support.
1:58:14 Honestly, that was not where the conversation went. It was like, okay, what creative ideas
1:58:21 do we have to somehow do both because we’re reality distorting? That’s fine. But actually,
1:58:26 you got to push yourself. And so I think in that exact moment, if I’m remembering the scenario,
1:58:30 we talked about some talented people I had hired, some people into the org,
1:58:38 who were like, could we lean on them? Could we put some newer leaders, managers into the deep end
1:58:44 and get them to take on more of this plan? And in the end, that was part of the solution,
1:58:49 which is, let’s take some risks with some people we have, give them more than they probably are
1:58:54 ready for and see if they can swim, which I’m not always a fan of because I have seen people
1:58:59 not make it out of the pool. By the way, a lot of young companies find themselves in that situation.
1:59:04 And if you have great hiring, which we did, I’m proud to say that actually that’s where
1:59:08 opportunities and magic can happen for people. I’m going to get to build out the global support
1:59:13 org. But anyway, so we ended up sort of compromising, but we weren’t going to trade off my other
1:59:18 responsibilities. And that became a more important discussion about how do I deploy? Anyone who’s
1:59:23 the CEO has got to be thinking, well, who are my most important resources and how am I deploying
1:59:28 them against the most important priorities? So take the negotiation up to that level would
1:59:36 be my advice. That’s a great macro renegotiation example. And we’re not going to stay on this
1:59:41 forever, but I want to spend a little, little, little more time on it when you’re renegotiating
1:59:46 the next day. So we’re moving down to the micro here. What language do you use? Like you have a
1:59:50 meeting booked, you got a lunch booked in Boston, you got this, you got that. And the other thing,
1:59:56 when you reach out to these folks, what do you say? I think you want to, again, be a player,
2:00:03 not a victim, and you got to take responsibility. So I think there is a version of saying,
2:00:07 I don’t love if it’s the next day, that’s rough. Yeah, it could be the next week too,
2:00:12 right? It’s just broadly speaking. I do actually tend to look at my calendar at least a week ahead
2:00:16 and sort of start renegotiating because I don’t like to be the one who’s like the morning of or
2:00:23 the day before. But I think you sort of own it, whether this is an email, it’s probably an email,
2:00:29 it might be a text and you say, first of all, I am very sorry. I know we had time tomorrow
2:00:34 on the calendar. I am staring at a list of priorities and I’ve realized you’re saying
2:00:38 something that doesn’t hopefully make them feel diminished. I mean, I often will tell them there’s
2:00:44 this thing. I am on this board in the middle of a transaction and I have to be on a phone call for
2:00:49 four hours tomorrow. And unfortunately, I think I need some time to prep. I need some time to prep
2:00:54 and I booked our lunch and it’s not realistic. I’m not going to be able to be present
2:00:59 at that lunch. It’s not great. I try to give like, I’m probably overcontext people,
2:01:04 but I think it makes you more human. It’s like, look, I did this thing. I’m sorry.
2:01:08 What if you don’t have like a house fire at a point too? What if you just look at it and you’re
2:01:13 like, oh, you’re like, you’re not important. Yeah, I mean, you get it. Like, you’re like, why did I
2:01:18 agree to why did I mail myself the letter bomb? Yeah, there goes to Christmas past is coming to
2:01:23 scratch my door and I’m realizing I don’t want to moderate this panel in Tuscaloosa. No offense
2:01:27 to Tuscaloosa, but you get the idea because I’ve got all this other stuff going on and I just don’t
2:01:32 want to spend the energy. Yeah. What do you do in a case like that? So again, I try not to be the
2:01:35 day before. Sure. No, let’s say you look out and you’re like, okay, this thing isn’t two weeks.
2:01:41 I’m not doing this thing. Yeah. So my instinct is always to offer context and be a little bit
2:01:46 vulnerable, which maybe is not expected. I think you also know there’s a, I think women will get
2:01:52 judged more for certain things. And in particular, like not being conscientious is the thing that
2:02:00 gets a little more beaten into you is my feeling as a woman. And so you have to also watch out for
2:02:06 creating some reputational issue that I think maybe not everyone has to watch out for. So maybe some
2:02:12 of my instinct to offer more information is to like try to avoid that hit. But I’ve been saying
2:02:20 to people recently actually that I have reworked my personal priorities and the demands of my time
2:02:26 are higher than I’ve actually seen in my professional life, which is true. And I have realized that I
2:02:34 cannot do a good job of some of the commitments I’ve made. And unfortunately, I can’t travel
2:02:39 and be on this panel and be effective for you. And this is where I feel sometimes I’m a little
2:02:43 weak. I’ll try to offer, I mean, I try to think, do I know anyone locally who could do that? I’ll
2:02:48 be like, I think I have an idea if you want an idea on someone who could sub in. Like I’ll try to
2:02:53 find some solution for them if I’m really leaving them in the lurch, right? Because I don’t love
2:02:59 that. But I kind of am just honest about like, I can’t do this well. And I think you want someone
2:03:04 at their best. It’s not going to be my best. Yeah, that’s good language. That’s really good
2:03:08 language. I’m not going to drag us back into the swamp of selling literature, but it’s good
2:03:12 language. That’s good word smithing, right? Right. And I think you’re showing, look, I looked at
2:03:17 priorities. I realized, and also you’re showing context, which is this is true statement. I’m
2:03:23 like, I have more demands on my time than I’ve ever had in my life. And I’m learning to cope with it.
2:03:28 And I’m learning that I can’t perform at the level I’d like to perform. And I don’t want you to
2:03:32 suffer for that. You want to show respect for people. They want a good panel. They want your
2:03:37 best. You know, you’re saying like, please, just you have to trust me, I’m not going to be great.
2:03:42 And they’ll be disappointed. One thing that I do think, I think Cheryl’s an example of this,
2:03:46 they’re people I’ve come to respect. They’re the people who protect their time,
2:03:49 like demons, right? The other people I’ve come to respect are the people who are like,
2:03:55 very comfortable just saying no. You know what? No, I’m sorry, I can’t do that. My hope for myself,
2:04:00 my future self is I am not in the situation where I’m doing that renegotiation. Again,
2:04:05 it goes back to being honest, taking time before you make the commitment to saying no.
2:04:09 But it’s also with investments. Like a lot of founders will be like, or even nonprofits,
2:04:12 they come and they’re like, I want to tell you about our organization. And you’re like,
2:04:17 oh, that organization sounds amazing. But then do you want to waste an hour of your time and their
2:04:22 time learning about it when you realize, I don’t have time to commit a lot to this organization?
2:04:28 What they would rather have is one, no, it’s not on my list of causes that I support. Or by the way,
2:04:32 two, I will give you X amount of money. You never have to meet with me. I don’t actually have time,
2:04:37 but it sounds good. Here’s some money. Goodbye. And they’ll say, well, can you make that commitment
2:04:42 for multiple years in a row? Maybe, maybe not. But I think getting faster at like, there’s a pattern
2:04:47 here, which is you want my money and my time. Am I willing to give any money or time? Yes,
2:04:52 no. If I’m willing to get a little bit, just tell them and get out. Don’t have a dog and pony show
2:04:57 about it. Or investments. I just don’t really invest in a lot of B2C. I’ll just write back and say,
2:05:02 this is not for me. I don’t really do B2C. Good luck. And they’re like, thank you,
2:05:05 because they didn’t waste their time sending you a deck, sending you, you know.
2:05:10 Yeah, they’re not chasing the Glengarry leads. Right. And so you think you’re being an empath
2:05:15 by saying, oh, let me hear your story. This is my trap. My personal trap is,
2:05:20 I think I’m being an empath, giving them 30 minutes. Let me hear your story. And in fact,
2:05:24 the empathic thing to do is to say, I’m going to do a probability assessment. The chance that
2:05:32 I’m going to invest/make a donation are sub 5%. No. No for you. No for me. And you don’t have to
2:05:35 think about it ever again. You don’t have to email me tomorrow and ask me again, right? Like,
2:05:41 they’re going to keep coming back. Yeah, yeah, absolutely. I love that. I’m so glad I asked.
2:05:47 And a great answer. Also, very useful, useful answer. What are some other rules we are going
2:05:54 to back the car into the garage of self-awareness? Because a lot of this pulls at the hem of
2:05:57 self-awareness from a bunch of different directions. But you mentioned that there are
2:06:05 certain rules you have because your kid is going off to college and therefore X, Y, and Z.
2:06:10 What are some of the other rules that you have for yourself around what you will or will not do?
2:06:16 Well, I have a rule. This is more of just a self-awareness. I do get intuitive and I do jump
2:06:21 to sort of judgments, conclusions, solutions quickly. So I have a rule that, like, especially
2:06:25 if I’m in a position of leadership and I’m in a meeting and there’s other people,
2:06:30 instead of stating my opinion, I have to ask a question. Because if you’re the senior person
2:06:35 and you state your opinion, like, the whole thing is over. Yeah, right. Yes, Steve, we can ship it
2:06:42 in five minutes. Uh-huh, exactly. Here’s an iPhone. So that’s a rule. Could you give an example of what
2:06:49 that would, because you could also ask a question in a way that makes it clear. It’s your strong
2:06:55 opinion, right? So what might that look like? So what it looks like is they’re kind of looking
2:06:59 to you. You know, I think we need to actually, you’re like looking at you and you say,
2:07:05 I have a thought. I do. I’ll share it. But actually, I’m interested in what you all think we should do.
2:07:10 Got it. You know, like, I want to learn from your thought before I share mine. You know,
2:07:13 and that’s, by the way, the benefit of seniority is you can be like, no, I’m not going to like.
2:07:18 I appreciate and refuse to ask you a question. I’m not going to perform right now. I will perform
2:07:23 later because I actually want you to participate. I’m often now in a position of sort of coaching
2:07:28 leaders. And because I’m more of an operator, not a professional coach, I have the same problem.
2:07:32 I’ll be like, oh my God, this is obvious. Like, here’s what you’re going to do. And then I think,
2:07:36 no, no, no, no, no. So I’ll say to them, all right, give me the bones of the situation.
2:07:41 And then I’ll start to tell them what I think. And I’m like, no. And I’ll say, you know what?
2:07:46 And I totally commentate. I’m like a sports color commentator. I’m like, I was about to jump in
2:07:51 and tell you exactly what I would do if I were you. And they’re at the edge of their seat because
2:07:54 that’s what they came for. Like, that’s what they want. And I say, we’re not going to learn from
2:07:59 that. What I want you to do is tell me your instinct. What is it you think you’re doing next?
2:08:02 And I don’t even say, give me the whole answer. I’m like, what would you do next? Because it’s
2:08:07 often a situation there’s an executive they think is underperforming. There’s a team off the rails,
2:08:12 whatever. I’m like, what are you going to do next? Then I get them talking. And then I sort of get
2:08:16 out from them. And I’ll tell you to him most of this. I mean, there’s a reason these people are
2:08:21 leaders. Most of the time, they’re like 80% of the way there. They’re just not confident in their
2:08:28 instinct. And so my job is not to tell them what to do or how to do it. It is to build their confidence
2:08:34 in their instinct. And then, yeah, we can brainstorm the last 20%. And I mean, it’s just like,
2:08:39 this is a total digression, but good pedagogy, right? Like, how do people learn? People do not
2:08:45 learn by being told answers. We all know this. But yet, we get some amount of experience in our
2:08:50 life. And we think, I’m going to go tell some people some answers. No, what you’re going to do,
2:08:56 if you’re a good leader, good teacher, is you’re going to lead them through learning with you.
2:09:00 And they are going to get to the answer. And you are going to celebrate them doing that.
2:09:09 But I cannot tell you how many times I myself have to create a rule to shut my own mouth.
2:09:14 Because I love helping people. Luckily, I don’t think it’s the know it all version of this. I
2:09:18 think it’s the, I can help you. Oh, my God, I see how to help you. And I just want to tell
2:09:25 them the answer. And I got to zip it, zip it. So one rule is like, yeah, I make a travel rule.
2:09:30 Another rule I make is, as I already told you, which is don’t say yes immediately. It has to be
2:09:35 very rare for me to say yes immediately. And as a pleaser, that’s very hard to be like, no,
2:09:39 I’m sorry, I have to get back to you next week. How often do you say I have to get back to you
2:09:46 next week versus I’m not sure can you get back to me next week versus in other words, like,
2:09:52 where does the ball fall and who’s court? Good feedback for me, Tim. And I take it. Thank you.
2:09:58 Now, I think that is actually a really good tactic that I don’t do enough of is to say,
2:10:04 I think this is unlikely that I’m going to be able to do this. I’m willing to consider it.
2:10:10 But what I’d like you to do is go look at your other options. And if you’re not finding something,
2:10:14 feel free to get back to me by the end of the month. And I will consider it. But it’s like,
2:10:19 basically telegraphing, like, I kind of want to try to help you, but I can’t. You got to go to
2:10:23 your plan B. I’m not going to be your keynote speaker. And that’s a great feedback. I think
2:10:28 that’s a good, maybe even it’s just, if you find yourself doing that, you should be asking yourself,
2:10:33 why isn’t it just not a no? It’s a no. Yeah. It’s a no for me. It’s a no. Tim, right? But
2:10:39 maybe it’s a way to trial yourself into realizing, oh, this is a no. This is the training wheels.
2:10:43 Yeah. I like your idea, which is like, put the ball in their court. Maybe again,
2:10:48 it’s back to some donation request or something like, this is not for me now. Feel free to get
2:10:53 in touch in the future. A lot of those people might just not ever. And I mean, sorry for them
2:10:57 because they’re not assisted. But is that being a player? Is that being a player enough? I don’t know.
2:11:04 Yeah. Hitting the snooze button can lead to like a delayed 24 car pile up later in my experience,
2:11:08 right? Good analogy. I was chatting with a friend of mine about this, because I’m fascinated by rules
2:11:16 for folks who handle a lot of inbound of any type. And his rule for the charitable stuff,
2:11:20 specifically like, oh, here’s my go fund me or this or this. He’s like, well, look,
2:11:24 he’s done very, very well professionally. And he’s like, okay, look, if it’s a friend,
2:11:30 and it’s basically any cause that’s not going to entail reputational risk, if it’s like, ah,
2:11:35 my buddy is doing a climbing Kilimanjaro for prostate cancer, and he’s has a go fund me,
2:11:40 they’ll basically give 5k to anything side unseen, because the universe of possible
2:11:45 acquaintances or friends who’s going to come to them with that is pretty limited. But the rule is
2:11:51 like 5k, that’s it. That’s our rule. And then for anything large, it’s just like, we focus on this
2:11:56 and this and this. And outside of that, we are not involved. That’s it. Yeah. No, I think that
2:12:00 is so powerful. That would be another rule is like, for something that’s a major commitment
2:12:08 of my time or my resources, someone said to me, it’s time, treasure, talent. But there’s another
2:12:17 one that’s like testimony. Ooh, okay. So time, treasures, capital, talent and testimony. And
2:12:21 testimony is interesting, right? Because you could, Tim, care about something that you can’t
2:12:25 give time to and you could say, if you need a quote from me, again, now we’re like in this weird,
2:12:31 rarefied air where someone might want a quote from, probably not me. But I think that that’s
2:12:36 another thing you can do. But the thing that for any of those categories, you need some criteria.
2:12:41 Yeah. Which is like, you know, some people, it’s about climate. If it’s not related to climate
2:12:46 and working on the climate crisis, it’s a no. And I think those people actually make more friends
2:12:49 than I probably make. Because I’m like, I’m not sure that sounds so important.
2:12:56 Just to ask a clarifying question on one time, I get, that seems pretty straightforward,
2:13:01 hours, minutes, treasure, like financial resources, things of that type, testimony,
2:13:05 okay, like endorsing something or some version of that.
2:13:09 By the way, a version of that might be like, can I introduce you to someone and endorse you?
2:13:14 Yeah, totally. What is talent? I mean, I understand the word, but I think of talent as
2:13:17 if they’re utilizing your talent, wouldn’t that kind of fall into the time bucket or is it a
2:13:21 separate thing? You know, I had a similar question because this was a friend of mine who was like
2:13:26 facilitating this workshop with people trying to think about what their criteria were for like,
2:13:34 what am I going to spend my time on? I think that the version of it is you say to someone,
2:13:39 I agree with you, like I can’t really deploy my particular talent without putting some time in.
2:13:47 But the example was, say you are very good at some specific thing and the thing takes you
2:13:51 less than 30 minutes, they’re like, all right, I don’t want you to join my board,
2:13:57 but can you read this press release and tell me is it good or not? I think it’s like,
2:14:02 you know what, I can’t give you my time. I can’t join a board. I can’t commit to a regular meeting.
2:14:05 It’s almost what I say to some of the founders I work with. I’m like, don’t expect me to read
2:14:10 the newsletter and try to volunteer for all the things you need. But if you think
2:14:16 my particular talent is going to be useful, and here’s what it often looks like, Tim, is
2:14:22 they send me profiles of people they’re thinking of hiring and I give them a five minute Claire
2:14:27 assessment. And so that is my time, but I don’t get on the phone. I’m just like, here’s the questions.
2:14:32 Usually how it comes back because I’m all about questions is here’s the three to five questions
2:14:37 I’d have about this background. If I’m you and I’m hiring for this role, why did they move around
2:14:43 five times? Why did they stop doing that job? I would just give them interview questions and
2:14:49 then I would back away. So you’re right. It takes me a minute. You probably have a version of that.
2:14:54 I’ve heard people like text you with very specific, which supplement should I take or which, you know,
2:15:01 should I intermittent fast? Yeah, you could probably like text back this one. No, this one,
2:15:05 you know, that’s probably still time and you probably should count how much time it is,
2:15:11 but it’s a way to stay it’s compressed because of the expertise. Right. You already know the
2:15:15 answer. You have the talent. You don’t have to go do extra work and you can answer quickly.
2:15:24 Quick add on, because I realize you’ve done so much hiring and develop so much talent. I’m so
2:15:32 curious how you spot bad apples or illicit negative feedback or infer negative feedback
2:15:40 when in the U.S. it is so incredibly difficult to get honest negative feedback from anyone
2:15:44 because they’re so concerned about liability. You’re talking about like references. Hiring,
2:15:52 yes, references. Exactly. The non dissertation answer is one, people have trouble giving hard
2:15:56 feedback. People have trouble asking this question, which is I think a question you just ask, which
2:16:01 is like, is this someone in the top 20% of people you’ve ever worked with? And then they say yes,
2:16:06 you say top 10. And then if they say yes, oh, so is it top five? Because what happens is when
2:16:12 people are asked for a very specific quantifiable ranking of something, they don’t like lying.
2:16:16 And so what I think happens is we’re not comfortable asking for ranking questions sometimes
2:16:21 about humans and I don’t love them actually in most contexts. But in this case, I’m like,
2:16:27 I’m going to pin you down on how good this person really is and how they handle and you could go
2:16:34 just to top five. But I think that’s the short answer. I think the other answer is you say to
2:16:39 someone, you put them again in the role of you say, look, I’m going to be their manager,
2:16:43 you are their manager. What’s the thing I can do that’s most important to help them?
2:16:50 That’s a good question. And people will say some very revealing things because all of a sudden
2:16:55 they’re back. Yeah. Being the manager of the person. And they’re like, well, I’ll tell them to
2:17:02 really be more truthful when things are off the rails. You’re like, what? Yeah. And then you’ll
2:17:07 sort of get going. Tell me a situation where you had to use that advice. Like what, you know,
2:17:13 anyway, so those are two, one very specific pin them down and one a little more tricky.
2:17:20 So good. Oh, deft. Very, very elegant. All right. As promised, the garage of self-awareness.
2:17:26 That is the very strained analogy that I used. And tell me if this ties in. And I’m curious
2:17:31 what good answers to this question might be. But I do want to talk about self-awareness so we
2:17:36 can go into it however you would like. Because it’s sort of the foundational layer for everything
2:17:42 that is built upon it. Or it seems that way to me. Yeah. That’s my hypothesis. Yeah. So actually,
2:17:46 I was going to ask you about the question. When have you seen me do my best and worst work? But
2:17:49 we can come back to that. We can come back to that. I’m going to bookmark that. Maybe we’ll
2:17:54 get to it. Maybe we won’t. But how should people think about self-awareness? And I’m just going
2:18:00 to share something that I found in the course of doing homework. And you can certainly fact-check
2:18:05 this. But I thought it was quite thought-provoking. This is from CNBC. And I think it was an interview
2:18:09 with you. So this is, you know, if you’re not self-aware, how would you know? That’s a hell
2:18:13 of a question. It’s kind of like, you know, the tree falling in the forest. No one to hear it
2:18:18 kind of question. Here are some telltale signs. You consistently get feedback that you disagree
2:18:23 with. This doesn’t mean the feedback is correct. But it does mean how others perceive you differs
2:18:28 from how you perceive yourself. Interesting. I added the interesting. You often feel frustrated
2:18:33 and annoyed because you don’t agree with your team’s direction or decisions. You feel drained at the
2:18:37 end of a work day and can’t pinpoint why. You can’t describe what kinds of work you do and don’t
2:18:41 enjoy doing. So that’s setting the table or maybe just peaking people’s curiosity. How would you
2:18:47 suggest people think about self-awareness? Why is this important in the world in which you operate?
2:18:53 I spent a lot of time thinking about how do you get results through people, through teams. Like,
2:18:58 I’m not actually the one building the product. So I got to do it through kind of brute force human
2:19:04 brain power and human time. And I think that most people who think that way start with the
2:19:10 individuals you’re managing or the team or the organization. And my argument is where you started
2:19:15 this section of the garage is the foundation is self-awareness. It actually has to start with you.
2:19:20 You’re not going to get great results from the people around you until you understand yourself.
2:19:26 And I mean, I think there’s some obvious reasons why which is like, look, I alone can’t move the
2:19:32 mountain. I need you and I need to complement myself. How am I going to complement myself
2:19:37 with other capabilities and skills if I don’t understand what I’m bringing to the table?
2:19:41 By the way, a lot of people think they’re the director in every scene. No, you’re not. You’re
2:19:46 often an extra. And just knowing that will make you more effective. So that’s a side piece of
2:19:52 advice for you. But a lot of self-awareness building to me, a lot of these work style assessments you
2:19:57 can take are just trying to help you figure out your defaults. Like, right to my default setting.
2:20:01 A lot of them are asking you, you know, are you more introverted or extroverted?
2:20:05 So you’re talking about, I guess, for maybe lack of a better descriptor, almost like personality
2:20:11 typing tests, like Myers-Briggs. Yeah, like Myers-Briggs, Disk, Enneagram. I mean, there’s
2:20:16 discovery insights. There’s the Hogan assessment, like whatever. That’s like 170 questions. Like,
2:20:22 there’s all these different, there’s the Big Five personality test. There’s a lot of
2:20:26 Strengths Finder goes on and on. Strengths Finder, good one. Like, there’s so many.
2:20:31 To me, they all boil down to on one axis, let’s call it the horizontal axis. You’ve got,
2:20:38 are you more introverted or extroverted? And the litmus test is sort of introverts think to talk
2:20:44 and extroverts talk to think. So where do you fall in that continuum? And then the other thing is the
2:20:48 vertical axis, which is, are you more task-oriented or people-oriented? Which, by the way, doesn’t
2:20:53 mean you can’t get a task done. And my litmus test for this is like, if someone comes to you with,
2:21:00 like, a massive problem in some organization, is the first thing you think of the first task that
2:21:04 has to get done or, oh my God, the people. And it’s just what do you lead with? For me, I’ll be
2:21:10 like, oh my gosh, someone’s getting fired, which is sort of a task and a person answer, but you’re
2:21:16 kind of, anyway, but I would say, sorry, I’m being very negative today, but I would say,
2:21:22 it sort of boils down then. And then you think, okay, what quadrant am I in? Am I a more extroverted
2:21:27 task-oriented type person or extroverted people? By the way, a lot of extroverted people-oriented
2:21:33 people are excellent at sales. Makes sense. Their default is, I love getting stuff done,
2:21:38 talking to you. Like, that’s, yay, BSL. And then you’ve got your introverted task-oriented people.
2:21:43 Where do a lot of those people work? Tim, do you think introverted task-oriented people?
2:21:49 Engineering. Programming. Engineering finance. Finance. Give me a spreadsheet and I will rule
2:21:54 the world. I do not, you know, need to talk to you to finish this model, right? Like, in fact,
2:21:59 you often do. And I know that. And so that’s the other thing is you have to be really careful not
2:22:05 to stereotype with any of this and not to generalize. But I think it helps any human frameworks are
2:22:10 useful for a reason, which is I am comfortable sort of saying, okay, where can I place myself
2:22:15 in these quadrants? And then what does that mean? My default setting is, and by the way,
2:22:19 the people around me have different default settings. One of my big, this is such a dumb
2:22:25 tactical lesson. But I’m one of those people where if I trust who I’m meeting with, I don’t need the
2:22:29 agenda ahead of time. I’ll be like, let’s meet. And then at the very beginning of the meeting,
2:22:34 bang out the agenda, make sure we know what we’re going to get done. I still like to run it well.
2:22:39 But I’m kind of loose with the prep. I have people who’ve worked for me who are like, frozen.
2:22:44 If they’re like, I don’t have time to think ahead of this meeting, what we’re going to talk about.
2:22:47 And I’m thinking there’s something wrong with them. I’m like, well, come on, we trust each other,
2:22:51 we’ve worked together, we’re just going to spit ball about this. And they’re like, no,
2:22:56 I had to learn that there are humans in the world who if they don’t have time to think before a
2:23:02 meeting will not be effective in the meeting and will be uncomfortable. Because my water is really
2:23:07 different than that. Really different. But you, if you’re trying to create an environment that’s
2:23:14 conducive to different styles, different defaults, you got to be aware of your own, and then realize,
2:23:19 and I have to operate aware of others, because I want that meeting to be really effective.
2:23:24 And I’ve got to email Richard the day before and tell him we’re going to spit ball ideas for
2:23:28 this new marketing campaign. That’s what it all boils down to. It’s really cultivating awareness,
2:23:33 but starting at home in the sense. Start at home and then start to map the other people.
2:23:37 Guinea pig is always in the cage right next to you in that case, right? It’s just easier to,
2:23:40 in some cases, a little easier study. Coming back to the personality test for a second,
2:23:44 or these, I’m not sure if that’s the right way to categorize them, Myers-Briggs,
2:23:49 Disk, any other… Work style assessments. There we go. Work style assessments.
2:23:53 If you could only choose one or two that have been most helpful to you personally,
2:23:59 what would you choose? I would say there’s one that’s called, I think if you just Google,
2:24:05 it’s Insights Discovery, which is sort of, to me, more effective than Myers-Briggs.
2:24:09 Myers-Briggs has a lot of interpretive work you have to do on your results. Like,
2:24:15 understand what sensing is. Understand what the decision-making process of a sensing
2:24:19 judge or whatever. Insights maps you more and they have some shading and colors,
2:24:25 but it’s sort of like more straightforward. That is one I’m a fan of. The other is more of a simple
2:24:31 one, but Patrick Collison, obviously, who I’ve worked with, I think I brought him around. He felt
2:24:34 like these things are like horoscopes. He’s like, “They’re just going to give you a report and it’s
2:24:38 going to sound like a plausible prediction of you.” And I said, “I get it. I get the skepticism.”
2:24:42 And I really do, by the way, for anyone. And actually, I think there’s value in getting a
2:24:47 horoscope. How does it actually make me feel? Like, do I agree with it or not? What am I really?
2:24:49 Like, it actually is part of a process, in my opinion.
2:24:51 Yeah, it’s a prompt, like a Rorschach prompt.
2:24:55 Yes, it’s a prompt. And how you react to it is interesting, right? Like, you’re like,
2:25:02 “I really, yes. I am finding love this year.” Or am I not? But the point is,
2:25:08 he then did some research, and the big five personality test is very simple. It’s available
2:25:15 for free online, as far as I can tell or I’ve seen. And it’s just these five factors like neuroticism,
2:25:22 agreeableness, conscientiousness. There’s one that’s sort of entrepreneurial comfort with ambiguity,
2:25:28 like whatever. And you can tell a lot from, well, one, the research supports that they’re pretty
2:25:34 indicative of certain human behaviors. You and I have had a lot of conversations in this
2:25:41 discussion about things like saying yes too easily. But if you’re like very high agreeableness and very
2:25:46 high conscientiousness, guess what? You’re going to end up committing to too much stuff.
2:25:47 Yeah, for sure.
2:25:51 And so, when I’m saying, “Oh, I’m jealous of those people who protect their time,” you know what?
2:25:56 They’re pretty comfortable being disagreeable. They’re pretty comfortable being like, “No.”
2:26:00 Or frankly, canceling at the last minute, saying, “Sorry, I don’t have time today for you.”
2:26:03 And if they’re not very conscientious, they’re like, “I don’t even feel bad.”
2:26:10 But by the way, no judgment. A lot of founders are really good about being like, “Look,
2:26:15 I’m doing the most important thing that I got to be doing today, and I’m the operator.” I’m like,
2:26:19 “Oh, but we made a bunch of commitments and we made a plan and we got to stick to the plan.”
2:26:26 And that meeting of those styles is very powerful. That’s why you want a diverse team.
2:26:28 But anyway, I would say those two.
2:26:32 Yeah, Patrick is endlessly fascinating. He’s been on the show probably a couple years ago.
2:26:40 But boy, oh boy, does that man read. He really is a voracious consumer of knowledge.
2:26:44 Yes, he puts the rest of us to shame. You know what, though, Tim? I bet he’s never seen John Wick.
2:26:50 So we have that. We have that going for us. We do.
2:26:54 One zero fairest cousin, but Wick on the scoreboard.
2:26:59 Yeah, we were actually in a meeting and he said something about Greg Popovich.
2:27:02 And two of us looked at each other and were like, “Do you really know who Greg Popovich is?”
2:27:10 It was amazing because Patrick also is not super up on sports, popular culture. We all have our
2:27:15 strengths. Popovich also incredible. Somebody I would love to have on the show at some point.
2:27:17 Oh, yeah, absolutely. Yeah, well, that’s why he knew.
2:27:22 So going to the kind of black belts of no, I’m wondering if there are people who stand out
2:27:29 outside of the Colossians as people who are sort of paragons of no. People who are really good at
2:27:35 saying no or defending their time where you’re like, “Wow, that person’s really good at keeping
2:27:39 their eye on the one puck that matters.” Anybody come to mind?
2:27:44 Well, I mentioned you. I think Cheryl’s very good at getting back, being very accessible and fast
2:27:49 and sort of decisive, like no efficient. She’s very efficient. And sometimes that efficiency
2:27:55 is a no, right? I mean, my version of it is someone who I think is least doing it carefully with
2:28:01 others, others like feelings. I think I don’t love the person who has an assistant, for example,
2:28:07 who cancels everything. No, there’s a model here, Tim. You’ve seen it where they agree to
2:28:11 everything and then they have a cleanup crew. Super lame. They have a cleanup crew.
2:28:14 Like the wolf from Pulp Fiction. They send it out to do the dirty work.
2:28:19 Yeah. Yeah. I think what’s happening is I’m doing left-hand column filtering names of people
2:28:23 right now in my mind where I’m like, “Nope, can’t mention them because I think they actually have
2:28:29 a cleanup crew.” They use the cleanup crew. They use the cleanup crew. There aren’t that many who
2:28:34 seem, I mean, I think you have some good, I think it’s in four-hour work week, you have some good
2:28:40 models of pushing people on not just being busy but being productive. There’s some engineering
2:28:45 leaders I worked with at Google who I thought was very bold, but it of course makes sense.
2:28:50 They would look at what were we planning in a meeting and they’d be like, “I don’t need to be
2:28:56 here,” or, “This meeting doesn’t seem important.” To me, those are paragons of no, though,
2:29:00 because it was very open, very direct, very honest. It was like, “I see what you’re trying
2:29:05 to do with this one hour and I am not giving you my hour. Why can’t more people just call it?”
2:29:11 Uncomfortable. There’s a finance guy that I’m on a board with and he’ll be like, “What are we
2:29:18 trying to accomplish in this and how long do we need?” He’ll set his, “I’m here for that objective
2:29:24 and I’m only here for this long.” I admire it because he’s like, “Don’t be chatting away about
2:29:28 other stuff. I want to be productive.” Don’t hear about your fishing trip right now, Ralph.
2:29:35 Exactly. Just because you mentioned the board, why no more boards? Just the thinking behind it.
2:29:38 I think there are different motivations for being on boards. I don’t know if you
2:29:43 are serve on boards. No, I basically, from the beginning, I have a number of friends who have
2:29:50 policies that they won’t join any more boards and I took that as an indicator. I’ve only done
2:29:54 advising. I’ve never been on boards. I would say there’s a sector of the world that feels it is
2:29:58 a service and I do think it’s a valuable service. By the way, I serve on some boards with some people
2:30:03 who are Jedi master board members and I’m like, “Wow, you are serving these companies because you
2:30:11 are awesome at governance and proxy statements, politics, and you get it.” I think there’s a
2:30:17 service motivation. There’s a motivation that has to do with maybe a personal CEO who really trusts
2:30:23 you. You want to help them. That’s mostly what happens to me. I want to be there for that person,
2:30:28 but it is a big commitment. If you’re someone who’s realized that time is your most precious
2:30:34 resource, which my mom realized somehow when she was 19, but I did not, boards can stomp all over
2:30:40 your calendar. They can just say, “You know what? All day Friday, someone just made an acquisition
2:30:45 offer.” You’re like, “Goodbye.” You realize you think you’re controlling your time because they
2:30:52 don’t meet that often, but no, no, no. Really what I’ve decided is I need to go on a board
2:30:57 diet and then rebuild. I’m not going to say no ever. I’m never doing it again,
2:31:04 but I’ve realized the bar has to be extremely high. I’m on one of my favorite boards,
2:31:08 and I would do it forever. I don’t know if I’m adding that much value, but it’s the Atlantic,
2:31:14 which is private, so it’s easier. The quality of the people involved, we’re doing the business
2:31:20 brain stuff, but you get to meet these amazing writers. You get to be part of exchange of ideas
2:31:27 about the future of democracy. Yes, that’s enriching me. That’s the other thing is making sure there’s
2:31:31 an exchange in the board of your learning. You’re getting enriched. They’re benefiting,
2:31:36 and I don’t think it’s easy to always get that balance right. You just have to be careful.
2:31:43 I think you just have to be. I think I just didn’t realize the level of commitment,
2:31:48 not just time, but to do it well. It goes back to renegotiating. What I’m doing is I’m saying no
2:31:54 more boards until I’ve renegotiated some of my current commitments, and then we’ll see.
2:31:59 That’s also a very powerful language right there. Categorically, I have a policy of saying no to
2:32:04 X until I have A, B, and C. That’s right. Done deal. By the way, people can’t argue with that,
2:32:09 because they’re like, “That does sound like a very same thing to do.” I have a lot of appreciation
2:32:15 more than I did before of folks who do this in service. Governance matters, right? It matters
2:32:21 for institutions, not just companies. It should be done well, but gosh, it’s a big commitment.
2:32:24 Be careful with those big commitments, folks. They sneak up on you.
2:32:28 Anything that has multiple years attached to it?
2:32:36 Yeah. Oh, boy. It’s kind of like the scope creep time-evaporating version of the best business
2:32:40 model of all time, which is being a venture capitalist, where you have these stacked funds.
2:32:46 That’s great if you’re taking your 2 and 20, but if it’s a commitment of your time over multiple
2:32:52 years, and then they start to stack, and oh my god, then you’re like 27 snow layers deep in the
2:32:59 avalanche of time requests. That’s right. And you get a 10-year horizon. I mean, at minimum.
2:33:06 That seems exciting at the beginning. Then you stack another 10 and another 10, and you’re like,
2:33:13 “Wait a minute. All of a sudden, I’m like 65 years old.” Anyway, I think it’s yes,
2:33:18 some funds have closed, and hopefully you’ve done well, but you made commitments before those things
2:33:24 happened to another set of them. Yeah, totally. So it’s like a rolling avalanche. The avalanche
2:33:30 is not ending. Do not say yes right away, folks. Yeah, especially to multi-year commitments. That’s
2:33:34 probably the headline. That and the toy is broken. I’m telling you, that’s your next book.
2:33:40 I really think it could do well. I have to ask this because it’s of acute interest for me,
2:33:47 personally, also because it might help me individually, but also with employees of mine.
2:33:51 Managing high performers, how do you get extraordinary output from extraordinary
2:33:55 people without burning them out or letting them burn themselves out?
2:34:00 If I was like, what are the pantheon of management lessons? So one of them is you’ve got to manage
2:34:06 different people differently. Another pantheon lesson is spend disproportionate amount of time
2:34:11 with your high performers because instead what we all do is get all of our time sucked by the
2:34:16 folks who are struggling and then we don’t invest in the high performers and then they’re either
2:34:21 burning themselves out or finding a new opportunity because they’re not realizing their high performers
2:34:24 and benefiting or they know they are and they’re not getting investment and they’re like,
2:34:28 I’m going to go get investment somewhere else. So number one is how do you manage them is you
2:34:33 make sure that they are a priority of yours even though they are perfectly good on their own,
2:34:38 which is the sort of dilemma, right? Like, how do I help them? In my book, I mean, I don’t steal,
2:34:43 I credit, I source a lot of frameworks. The book, Scaling People, Tactics for Management and
2:34:49 Company Building. Oh yes, thank you. Just to throw it in there. So there are a lot of QR codes. You
2:34:53 can scan and look at the sites where I reference a lot of materials and books, Conscious Business,
2:34:58 Fred Kaufman’s in there. One framework, I think, I mean, as far as I can tell, I made up myself
2:35:05 was a top talent framework, which is, again, I try to like simplify things. But I think
2:35:12 high performers fall into two categories and I call them pushers and pullers. And so the pusher
2:35:17 is the one who’s like, give me more, give me more. They’re often wanting to get more comp too,
2:35:21 but they’re like, I want recognition, I want responsibility, I want scope, I want to move
2:35:26 the needle. I’m high impact. They’re very impatient with themselves, with other people. They can be
2:35:31 a little high friction for the team because they’re like going for it, grabbing it, grabbing it.
2:35:35 But you know, it’s fun because you load them up and they’re just like carrying the whole
2:35:41 thing up the hill without you. But they can be tough. My main coaching often ends up with them
2:35:49 is saying, until I believe that the people working with you love working with you,
2:35:53 I don’t think you’re succeeding. And they’re like, what? What? Because they’re all keeping score,
2:35:58 but they’re keeping score in the sort of maybe early in his life, Tim Ferriss version? I don’t
2:36:05 know. Oh, no, that’s a fair assessment. I mean, I think I am a pusher as an entrepreneur for sure,
2:36:10 and I’ve learned how that can be a liability. It can be a huge superpower and it can be a huge
2:36:15 liability. Right. And your job is to sort of, like I said, giving direct feedback is holding up a
2:36:20 mirror and just being like, here’s the beauty of you and here’s the liability part. And if you
2:36:27 can’t show me that you can work on the liability part, I can’t keep loading you up. Because in the
2:36:32 case of the pusher, yeah, they might burn themselves out, but they actually burn out the people around
2:36:38 them. So that’s the pusher. So the puller, it’s funny, this happened to me in a couple of conversations
2:36:42 I’ve had is I’m usually being interviewed by someone who’s like the pusher and I’m the puller.
2:36:49 But anyway, I’m the puller is someone who, no complaints, you load them up and they’re like,
2:36:54 yep, yep, I got it. But they’re not asking for it. They’re not grabbing it. They’re not pushing,
2:36:58 but they’re highly competent. They’re very organized. They’re very consistent, reliable,
2:37:02 and they have good judgment. And you’re like, okay, I know that person won’t screw that up. I
2:37:06 know that person will get the people to the party and the, you know, whatever it is. And you just
2:37:14 start loading them. And they don’t renegotiate. They don’t know how to say no. And then they
2:37:20 explode. Like they basically implode or that’s what I’ve run into with past employees. Yep.
2:37:24 And there’s some like, I went through a period of my own development where I was like, I think
2:37:32 of it as my martyr period where I literally, I don’t know who I thought I was bartering myself
2:37:38 for like everyone else. I like, I would be doing all this stuff for my colleagues, for my team.
2:37:43 And I was like, no one appreciates like, I don’t know. And I eventually had a really good open
2:37:47 conversation with a guy, not my boss, who worked with me. And he’s like, did I ask you to take
2:37:52 that on? Like, you just started running that project? Or you run our planning process? Or like,
2:37:57 did someone ask you? And I’m like, well, no, no one was doing it. So I’m doing it. And I was like,
2:38:02 and he’s like, and why do you feel like you have to do that? I was martyring myself for nothing.
2:38:08 Like, I think martyrs at least are celebrating like a God. I was like, I’m sacrificing myself on
2:38:15 the altar of someone didn’t do the work. So I’ll do it. It was very bad, very bad. And I was resenting
2:38:19 the hell out of my colleagues. For sure. I’m like, does, I mean, this happens in relationships.
2:38:24 I mean, it’s like the who’s going to take out the garbage thing. I designated myself the garbage
2:38:28 collector for like a whole set of things, partly because I thought it was that was part of my job,
2:38:35 but still it was not good, not good. Anyway, the polar will implode slash explode. And you might
2:38:40 not be able to save them if it gets too far. So your job with them is like, look, let’s work on
2:38:44 delegation skills. Let’s work on saying no, let’s work on boundary, like, look at me, let’s work
2:38:51 on rules, boundaries. How do you not be the person carrying everything and doing three jobs? And I
2:38:56 think that once you know those two archetypes, you can sort of look for the signs of them. And
2:39:00 then you can think, well, what’s their classic development area? And then your job is to be
2:39:07 all over them on that development area, because they will collapse. If you don’t get them to see
2:39:13 that part of their job, like the pusher, especially part of your job is to stop creating friction
2:39:19 for everyone. And like for me, I really started to take exercise seriously when I decided it’s
2:39:24 part of my job to be like a better leader. I need to get a certain amount of exercise. And now I
2:39:29 will make time for it. And I think a lot of these types are like, I’m going to do everything to win
2:39:34 these pushers. And you’re like, you know what, part of winning is avoiding a Pyrrhic victory,
2:39:39 avoiding one where everyone wins, but dies on the field, right? And they’re like, oh, well,
2:39:43 then how do I do that? Because it doesn’t come naturally to them. And then they’ll say, I don’t
2:39:48 want to work with low performers. And this is the problem. They’re so good that, I mean,
2:39:54 now we’re going deeper on this, they’re so good that you can’t quite say back to them, no, those
2:40:00 people are the same as you. So instead, you’re like, yeah, okay, we all have different strengths
2:40:05 and weaknesses. What I feel like you’re doing is not even appreciating what anyone else is
2:40:10 bringing to the table. Why do you think that is? And it’s like, they don’t stay up all night like
2:40:15 I do getting the thing done. You’re like, no, they don’t. And I actually don’t think sometimes you
2:40:19 should stay up all night getting the thing done. But what do they do well? And then you get them
2:40:25 trying to think about assets. And you’re like, how can you use that asset to get the things done?
2:40:28 And they’re like, hmm, but they really don’t think that way because it’s all in their own shoulders.
2:40:35 Takes practice like so many things. Claire, this has been a fantastic conversation. Thank you so
2:40:40 much. I’ve had so much fun. I’ve taken copious notes. I’m going to be following up on a million
2:40:45 site quests, as we call them, but important site quests. I’ve taken notes of phrasing that you’ve
2:40:50 used all sorts of things. So I am looking forward to actually digging into my homework. I will not
2:40:55 stay up all night for the record. I’m trying to also help first sort of foundational along with
2:41:00 the awareness, having the vehicle to do the things you want to do. Your book, which I highly recommend
2:41:05 to folks is incredibly tactical, scaling people tactics for management and company building,
2:41:12 tons of templates, tons of frameworks, lots of specifics that you can apply immediately.
2:41:18 People can find you, correct me if I’m getting this wrong, but on Twitter @ChuseJohnson.
2:41:24 We’ll link to LinkedIn as well. Are there any other websites or anything else that you’d like
2:41:28 to point people to? The Stripe Press website, you can find scaling people and you can find,
2:41:33 actually, I did interviews with a bunch of leaders that there’s digital only content,
2:41:37 which we can give you all the link to that. But no, thank you, Tim. This has been
2:41:43 wide ranging as promised and stimulating and I’ve got some recommendations I’m walking away with.
2:41:47 So thank you. Thank you so much, Claire. And for everybody listening, we will link to everything
2:41:54 in the show notes. This will be encyclopedic and you can find that at tim.blog/podcast.
2:41:58 So you just search for Claire and this will pop right up and you will find everything that we
2:42:03 discussed. And it’s the next time be a little bit kinder than is necessary, not only to others,
2:42:09 but also to yourself. And as always, thanks for tuning in. Hey, guys, this is Tim again,
2:42:14 just one more thing before you take off and that is Five Bullet Friday. Would you enjoy
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2:46:42 That is the basic, basic, basic requirement, right? That is why things are called supplements.
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This episode is a two-for-one, and that’s because the podcast recently hit its 10-year anniversary and passed one billion downloads. To celebrate, I’ve curated some of the best of the best—some of my favorites—from more than 700 episodes over the last decade. I could not be more excited.
The episode features segments from episode #332 “Coach George Raveling — A Legend on Sports, Business, and The Great Game of Life” and #724 “Claire Hughes Johnson — How to Take Responsibility for Your Life, Create Rules That Work, Stop Being a Victim, Set Strong Boundaries, and More.“
Please enjoy!
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Timestamps:
[00:00] Start
[05:14] Notes about this supercombo format.
[06:17] Enter George Raveling.
[06:48] The most important conversation is the one you have with yourself.
[09:03] The only two choices George has when he gets out of bed in the morning
[11:13] A personal audit once per week.
[11:40] Retirement at 80?
[12:10] George’s controversial collection.
[14:50] George’s less controversial collections.
[15:44] Relationships as a privilege.
[17:28] Most of George’s best friendships started by mistake.
[18:20] The importance of maintaining friendships with younger people.
[19:22] Relationships as a patnership.
[19:52] A voracious reading habit.
[23:28] How George selects his next book.
[25:17] How George continues to grow in his 80s.
[29:09] Recommended reading.
[30:42] Kindness as an opportunity.
[33:32] The 1984 Olympics.
[37:32] Enter Claire Hughes Johnson.
[37:54] Say the thing you think you cannot say.
[43:26] Detoxifying your left-hand column.
[51:11] Victim versus player.
[58:43] Recommended reading.
[1:05:32] The case for reading fiction.
[1:12:57] Crafting a working-with-me document.
[1:20:47] Make the implicit explicit.
[1:26:07] An Irish Goodbye.
[1:27:13] Email policies.
[1:32:37] Renegotiating the terms of expectations.
[1:34:41] Listening for the quiet no.
[1:37:06] Money versus time.
[1:38:53] Good rules can be liberating.
[1:41:39] Leadership and disappointment.
[1:46:38] Renegotiating past disappointment.
[2:05:45] Asking a question versus stating an opinion.
[2:09:37] Training wheels for a “no.”
[2:11:06] Time, talent, treasure, and testimony.
[2:15:16] Spotting bad apples while hiring.
[2:17:16] If you’re not self-aware, how would you know?
[2:20:01] Work style assessments for self-awareness building.
[2:27:17] Paragons of no.
[2:29:30] No more boards.
[2:33:37] Pushers and pullers.
[2:40:32] Parting thoughts.
*
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