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Tim FerrissTim Ferriss

How to Take Radical Ownership of Your Life and Career — Claire Hughes Johnson

Claire Hughes Johnson currently serves as a corporate officer and advisor for Stripe, a global technology company that builds economic infrastructure for the Internet. Claire previously served as Stripe’s chief operating officer from 2014 to 2021, helping grow the company from fewer than 200 employees to more than 6,000. Her book is Scaling People: Tactics for Management and Company Building: https://www.amazon.com/Scaling-People-Tactics-Management-Building/dp/1953953212/?tag=offsitoftimfe-20 This episode is brought to you by: AG1 all-in-one nutritional supplement: https://drinkag1.com/tim (1-year supply of Vitamin D (and 5 free AG1 travel packs) with your first subscription purchase.) LinkedIn Ads marketing platform with 1B+ users: https://linkedin.com/TFS (free $100 LinkedIn ad credit for your first campaign) Momentous high-quality supplements: https://livemomentous.com/tim (code TIM for 20% off) *** Resources from this episode: https://tim.blog/2024/02/27/claire-hughes-johnson/ [00:00] Preview [01:00] Say the thing you think you cannot say. [07:05] Detoxifying your left-hand column. [15:30] Victim versus player. [25:05] Recommended reading. [31:32] The case for reading fiction. [39:43] Crafting a working-with-me document. [48:11] Make the implicit explicit. [54:01] An Irish Goodbye. [55:11] Email policies. [01:01:03] Renegotiating the terms of expectations. [01:03:28] Listening for the quiet no. [01:06:02] Money versus time. [01:08:02] Good rules can be liberating. [01:11:12] Leadership and disappointment. [01:16:39] Renegotiating past disappointment. [01:37:34] Asking a question versus stating an opinion. [01:41:17] Training wheels for a “no.” [01:42:54] Time, talent, treasure, and testimony. [01:47:29] Spotting bad apples while hiring. [01:49:34] If you’re not self-aware, how would you know? [01:52:34] Work style assessments for self-awareness building. [02:00:10] Paragons of no. [02:02:36] No more boards. [02:06:50] Pushers and pullers. [02:14:20] Parting thoughts. Please enjoy! Tim Ferriss is one of Fast Company’s “Most Innovative Business People” and an early-stage tech investor/advisor in Uber, Facebook, Twitter, Shopify, Duolingo, Alibaba, and 50+ other companies. He is also the author of five #1 New York Times and Wall Street Journal bestsellers: The 4-Hour Workweek, The 4-Hour Body, The 4-Hour Chef, Tools of Titans and Tribe of Mentors. The Observer and other media have named him “the Oprah of audio” due to the influence of his podcast, The Tim Ferriss Show, which has exceeded 900 million downloads and been selected for “Best of Apple Podcasts” three years running. Sign up for "5-Bullet Friday" (Tim's free weekly email newsletter): https://go.tim.blog/5-bullet-friday-yt/ Follow the Tim Ferriss Podcast: https://tim.blog/podcast/ Visit the Tim Ferriss Blog: https://tim.blog/ Follow Tim Ferriss on Twitter: https://twitter.com/tferriss/ Follow Tim Ferriss on Instagram: https://www.instagram.com/timferriss/ Like Tim Ferriss on Facebook: https://www.facebook.com/TimFerriss/

Claire Hughes JohnsonguestTim Ferrisshost
Feb 27, 20242h 16mWatch on YouTube ↗

Summaries, chapters, transcripts, and FAQs on this page are made by uListen, not YouTube.

EVERY SPOKEN WORD

  1. 0:00 – 1:00

    Preview

    1. CJ

      Often we get a request, you have this experience, and you're looking at it, and she says, "Listen for the quiet no."

    2. TF

      Mm-hmm.

    3. CJ

      Because we are often feel like we have to say yes, and her trick is do not respond immediately. Because we often feel, I mean, if you're someone who's prides yourself on being decisive and responsive and empathetic, as I do, I feel like, well, they asked me to be on this panel at this important conference or whatever. I've learned that my response in fact should be, "When do you need to know whether or not I can do- be on this panel?" Or I'll even say, "I need two weeks to get back to you about whether I can be on this panel," because if I don't give myself some space, I will do yes instead of the quiet no. [upbeat music]

  2. 1:00 – 7:05

    Say the thing you think you cannot say.

    1. TF

      Claire, thank you so much for making the time.

    2. CJ

      I'm so glad to be here, Tim. Thank you for having me on.

    3. TF

      And we were talking briefly about how one thing that you've observed [laughs] I'm just joshing here, of course, a lot of cool people go to Brown. I wanna ask about somebody else who seems pretty cool-

    4. CJ

      Yeah

    5. TF

      ... who I'm not sure went to Brown or not, but that is Fred Kofman.

    6. CJ

      Yeah.

    7. TF

      And I guess he is the, the origin of your second favorite operating principle perhaps, say the thing you cannot say. I just love this line.

    8. CJ

      Say the thing you think you cannot say.

    9. TF

      Oh.

    10. CJ

      Yeah.

    11. TF

      There we go. That's actually such a critical distinction, right? That is such a critical distinction. I simplified it. That probably tells you a lot. We could psychoanalyze that later, but say the thing you think you cannot say. Can you provide listeners with a bit of context as to what this means and why it is important?

    12. CJ

      I laid out, and I had to think about this for myself, four operating principles for me as a leader and a person, and I shared them with others 'cause I think actually everybody should authentically come up with their own, but this one was the second one. The first one about self-awareness is, is the one I probably talk about the most with-

    13. TF

      Mm-hmm

    14. CJ

      ... with everyone and myself, but-

    15. TF

      Mm-hmm

    16. CJ

      ... the second one is say the thing you think you cannot say.

    17. TF

      That's why I started with the second one. [laughs]

    18. CJ

      Yeah, 'cause no one asked me about it. It's a lesson that I've learned, and I think there's a journey that, that people go on with this lesson, so we can share about that.

    19. TF

      Mm-hmm.

    20. CJ

      But I've certainly gone on the journey, and the person who was probably one of the most pivotal to me stepping from square one, which is we often just don't say the thing, right?

    21. TF

      Mm-hmm.

    22. CJ

      We just don't say it, was Fred Kofman. And Fred was... I'm gonna get some of this wrong, but as I understand it, he was an accountant by training.

    23. TF

      Mm.

    24. CJ

      He became a professor at MIT. He was teaching accounting, and he, he grew up in Argentina, by the way. I, I don't think he went to Brown.

    25. TF

      [laughs]

    26. CJ

      And he had some sort of life revelation that he was not living with the dimension, like the true dimensions of his being and his values, and what he needed to do was stop teaching accounting and become a leadership coach and advisor.

    27. TF

      Mm.

    28. CJ

      And he wrote this book, Conscious Business, which I recommend to... I don't recommend a lot of business books. I'm just gonna be perfectly honest, Tim. I often read the beginning of business books, and then I never finish them.

    29. TF

      [laughs]

    30. CJ

      But Conscious Business, I have read all of it, and he formed this firm called Axcellent at the time that Sheryl Sandberg hired at Google.

  3. 7:05 – 15:30

    Detoxifying your left-hand column.

    1. TF

      yes.

    2. CJ

      Well-

    3. TF

      I think I need help, and this is where I'm gonna ask you if you could give an example, it could be hypothetical or real-

    4. CJ

      Yeah

    5. TF

      ... of this type of experience and also the detoxifying, right?

    6. CJ

      Yeah.

    7. TF

      Which is sort of like the-

    8. CJ

      How do you detoxify, right

    9. TF

      ... the like gentrifying your inner language so that you don't sound like a complete asshole. [laughs]

    10. CJ

      Right. Right. So totally, and I think, I mean, the short answer is you gotta ask some stuff as a question often to, to stop-

    11. TF

      Yeah

    12. CJ

      ... yourself from making a big judgment.

    13. TF

      [laughs]

    14. CJ

      But, but Tim, yeah, I think what I pick up in you and, and from listening to you is you're willing to take some risks, right?

    15. TF

      Mm-hmm.

    16. CJ

      And so I think this is really about risk-taking and saying something that you're not sure you should say, but you're gonna put it out there, and then the question is how do you do it with as much finesse as possible so that you don't end up having blowback, which, you know-

    17. TF

      Mm

    18. CJ

      ... I've have... Believe me, I've sometimes said the thing I think I cannot say and had people look at me like, "Oh my goodness," you know? But, but most of the time I'm reading the room right. Here's an example, which is, I mean, just classic more of a business example, but certainly happens in my personal life too. So we went through various business planning types of tactics at Stripe, but one of them we were using for a while was your classic quarterly business review, right? You have teams come in, we've given them a template, and we say, "Please fill out these things. Let's see your data. Let's see where you are versus your goals. What's your strategy? What's your plan? Write this memo. We're all gonna read the memo, and then we're gonna have this discussion about how you're doing and like do you..." And often teams come in, and they want more resources, or they want us to solve something or decide something, and we're of course saying like, "Well, it's actually you. You're supposed to be deciding and solving." But, but it's a discussion with the executive team, and I'm sitting in one of these reviews with a team that's primarily working on an area of the product, so it's product and engineering leaders. It's not my part of the org that I run, but I'm f- invited to be there, and I, I like to be there. I like to be close to the product. And I'm listening to the discussion, and it starts to become incredibly clear to me that the team is feeling defensive or blocked or angry, I couldn't quite tell what it was, that there's another team doing some similar work. And by the way, if you've read any Jack Welch stuff, he actually had this tactic as a leader where he'd put two teams on the same problem and sort of like get them to compete.

    19. TF

      Mm.

    20. CJ

      These tiger teams. That was not Stripe's tactic. I just wanted to be clear. We were not interested. We had n- we never had enough people. There's no way we would put engineers on the same pro... Like, believe me. And so, so it was mystifying. I'm like, "How is this..." And I think, by the way, I could hear it because I wasn't in the room super close to the material, right? I, this wasn't my part of the org. I hadn't heard about the details of some of these projects until this meeting. I'm reading the document. I'm listening to them talk, and I just said, I said, "Can I just ask if there's something we're not talking about here?" And they're all looking at me 'cause I rarely poke in on certain moments with respect to like what's our product roadmap and what do we... And is there something we're not talking about? And everyone looks at me, and I said, "I feel like you're really concerned about this other team and what, what they're building or what they're up to. Are you concerned?" And initially, "No, no, no. I mean, you know, it's fine. It's fine. Like they've got this thing they're doing that, you know, it's, it's clo..." I said, "Well, is it, do you think it's the same thing? Is that, is that what I'm hearing?" And I just started to ask a bunch of questions of the leader of the discussion, and I said, "Well, should that team be in the room right now? Like, should we have a meeting with both of you? Because feels like there's asymmetrical information and that you all don't feel confident in what they're building and that you're either dependent on them or competing with them with what you're building." And they were like, "Maybe." [laughs] You know? It eventually became like we don't have the right people in the room to have a conversation about the problem.

    21. TF

      Mm-hmm.

    22. CJ

      And so we sort of stopped it and said, "Let's go do that," to the credit of the rest of the people in the room. But as we left, one of the engineers who was sitting on the sort of periphery walked up to me on the stairs, and he was like, "That was refreshing."

    23. TF

      Hmm.

    24. CJ

      But why I'm bringing it up is to me that was a moment of leadership, which by the way, you don't have to be a VP or a COO to do that. Like the leadership is to say, "I am observing a thing that people are clearly not saying and are uncomfortable and is actually seems to me like a bad practice happening, and I am gonna just call it. Like, I'm gonna ask, 'Is this going on? Am I seeing this correctly?'" And it's gonna change the whole trajectory of the meeting and the conversation and maybe of the team and their work.

    25. TF

      Hmm.

    26. CJ

      And there may be a... I mean, it did result in some deduping ultimately, but I think that's what I mean by say the thing.

    27. TF

      [laughs] Deduping meaning having people working on less similar-

    28. CJ

      Yeah

    29. TF

      ... overlapping Venn diagrams-

    30. CJ

      Right

  4. 15:30 – 25:05

    Victim versus player.

    1. TF

      come back to that, but before we go there, I want to come back for a second to Fred Kofman and Victim versus player. Can you explain what this is?

    2. CJ

      I love this one because I think it's so simplifying and clarifying really about are you managing someone or interacting with someone who has agency, takes responsibility? And Fred, when he introduces this framework, tells the story of how young children, and he's the... I think he has six or seven children, by the way, but how young children when something has happened that they know is bad will not take responsibility. So they will say things like, "The coat is at school."

    3. TF

      [laughs]

    4. CJ

      So not, "I left my coat at school," right? Or, "The toy-

    5. TF

      A thing has happened. Things have happened

    6. CJ

      ... the toy is broken."

    7. TF

      [laughs]

    8. CJ

      You're like, "Well, did you break it?" You know?

    9. TF

      [laughs]

    10. CJ

      So he has this really disarming way of introducing this concept, which is we're all laughing, just like you and I.

    11. TF

      Yeah.

    12. CJ

      We're like, "Ha ha, the toy is broken." But then he's like, "Okay, now let's talk about you couldn't... If one of your direct reports came to you and said, 'The report was not written'" [laughs]

    13. TF

      Yeah. [laughs]

    14. CJ

      And you're like, "The report that you were meant to write?"

    15. TF

      Yeah. [laughs]

    16. CJ

      You know? But how it actually manifests is, I mean, yeah, here... Like, you're supposed to write some report up or some summary of a meeting, right? And you say, "Oh, tell me where that is," and the player says, "Completely my fault. I had planned to get it to you by 5:00 yesterday. I prioritized this emergency that came up. Didn't tell you. My bad. Can we renegotiate? Like, can I get it to you at 5:00 today?" And you're like, "Fine. I wish you'd told me that you weren't gonna get it, but like, you know." The victim says, "Let me tell you about that report. Lucy owes me her notes, and I can't finish it without Lucy, and Lucy, you know, is super slow at getting her notes and I'm sorry. Like, it's, it's, I don't know when I'm gonna get it."

    17. TF

      Mm-hmm.

    18. CJ

      But that actually is pretty common. People are like, "Well, it's-

    19. TF

      Super common

    20. CJ

      ... this other person that I'm depending on-

    21. TF

      Mm-hmm

    22. CJ

      ... and therefore I have no responsibility," and they're a victim, and they're gonna play the victim, and I think that's a very hard person to coach.

    23. TF

      How much do you have to select that in your hiring process versus coach people from one side to the other? Have you had much success or seen much success in moving people from the victim side to the player side? And that's a bit of a leading question by my tone, I guess. I suspect there are a lot of instances where that's hard, but in the success cases, what does that coaching process look like?

    24. CJ

      I've seen both. Like, I feel like with people who are earlier in their career, they're more... I mean, I'm, I'm all growth mindset, but they're a little more moldable, and you can actually coach people out of this as, like, a way of operating. If they're later in their career- It's a little more ingrained, and it's quite hard, especially 'cause they tend to not be aware of it, because they've somehow been successful operating in that mode, and so they're kinda like, "What are you saying?" You see leaders, and you know how they behave, Tim, is they say, "Well, if it's not under my direct control, then I am not responsible."

    25. TF

      Mm-hmm.

    26. CJ

      And so they become empire builders-

    27. TF

      Mm

    28. CJ

      ... and some organizations let them get away with it. They're like, "Sure, you can have all the infrastructure teams then, and then I'll hold you account..." Like, it becomes this weird failing upward problem-

    29. TF

      I see

    30. CJ

      ... where people say, "Well, if I can control it, I'll take responsibility."

  5. 25:05 – 31:32

    Recommended reading.

    1. TF

      You said you don't recommend a lot of business books, and I am gonna come back to Sheryl and Excellent in a little bit, but-

    2. CJ

      Mm-hmm

    3. TF

      ... you don't recommend a lot of business books. Sometimes you read the introduction, and you're like, "That's enough, thank you." Let's talk about a non-business book, To the Lighthouse by Virginia Woolf. What is your history with this book, and why do you recommend it?

    4. CJ

      I mean, I love great literature. I think that's how I grew up. My parents are both teachers. My father was a high school English department chair and teacher, and baseball coach, by the way. He would probably say he was a baseball coach, and then he would say, "And a teacher." And my mom was a college professor for a long time, and I think that there are just some authors who speak to you as you're starting to... I mean, I wish more people loved literature because I think how do you understand the human condition? Literature is, like, the best shortcut to that in your life. But I think there are some authors for someone who becomes a student of literature that sort of, sort of change their worldview about really what's possible with writing. So not just the book changes how they feel and think, but actually the process. Like, sort of like when you see a product that's super... I think you love innovative products. You know, when you see something and you're like, "That is going to change my life," right? Like, you're like... And so I think that To the Lighthouse represents... I mean, Virginia Woolf is a writer that resonated for me, and I think if you understand, if you've also studied history and you think, "Okay, she's writing some stuff in, like, the early 1900s, 1920s," there's not a lot of women publishing a lot in that time in Britain. She gets herself into this writer's collective with men and women. She also has relationships with men and women. She's, like, pretty avant-garde person, but if you read A Room of One's Own, like, it's basically one of the earliest feminist manifestos that, like, exist. And, and this is where I think, Tim, you're like me. I love people who are polymaths. You're, like, not just this amazing novelist, thank you, Virginia Woolf, but you're also writing just your thoughts on things like women should have a room of their own. I mean, but actually figuratively, you know, not just literally. And I think that she is fascinating. Her life is fascinating, and I want to acknowledge not all of her personal views are great on some things, as that happens. I- I worry that we've started to not study certain artists because they've said some things or, or done some things, uh, that are not... which I would disagree with. Like, I think people think she was an anti-Semite, and it does appear that she said some very anti-Semitic things in some of her writing. I still think you should study Virginia Woolf.

    5. TF

      Mm-hmm.

    6. CJ

      And I will own that as my position on her, but I think To the Lighthouse, most people would say, is her most important novel. I will be honest with you and say when I wrote my thesis in college, I was gonna write it on To the Lighthouse, and then I actually decided to write it on Mrs. Dalloway, which is another one of her novels, because I loved the parallels from Mrs. Dalloway with a book called The Passion by Jeanette Winterson. So Jeanette Winterson is a female British writer more in the modern era who had broken through with a memoir called Oranges Are Not the Only Fruit, and then had published a couple of, of this book, The Passion, and then a book called Sexing the Cherry, and she's, she's published now several books. But Jeanette Winterson, I think, is a descendant, in my opinion, of Virginia Woolf.

    7. TF

      Right.

    8. CJ

      And I was like, "I'm gonna examine these two novels," and I didn't choose To the Lighthouse. But I will say that anyone who... And To the Lighthouse is not an easy read, and I wanna own that also. I think it's very... Mrs. Dalloway, much more digestible, shorter book. It has some repetition in it, some beautiful rhythm in the writing where you're like, "Oh," and I'm coming back around in this circular way to the way the story sort of moves you. To the Lighthouse is like a dream state. You feel like you're in a dream state. [laughs] You're like, the points of view are shifting. Who's the real narrator here? What is the story? There's not... Like, you're not being driven by your classic plot or character-driven story. It is much more internal.

    9. TF

      It's like John Wick in some sense. [laughs] I'm kidding, I'm kidding.

    10. CJ

      I feel like the plot of John Wick is pretty clear. [laughs] Um, you know, I am gonna take vengeance. Excuse me now. I'm gonna come out of retirement and kill everyone.

    11. TF

      Oh, what a great work of art.

    12. CJ

      I'll be the first one to tell you I love a good plot driven... I read a lot of mysteries and thrillers, and, and I like-

    13. TF

      Mm-hmm

    14. CJ

      ... movies like that, actually, so I'm very multidimensional.

    15. TF

      [laughs]

    16. CJ

      But I think for To the Lighthouse, you find something new every time you read it. You think about life, death, the human condition. What is love? What is family? What does it mean to connect with other human beings? And there's something about the way the writing works. I mean, it's set in this island in Scotland, and there's a, a lighthouse, and they go out in the boat. Like, you literally feel like you're surfing in a boat. That feeling when you're like, "I'm not really connected to firm land, but I'm in this inner set, like sanctum of people's heads." So I think that it changed me 'cause of the way it felt to read it. The, uh, frankly, the themes are much more sophisticated than my 19-year-old self probably could have handled. Like, I should actually... You just said you should read Awareness again. I should go read-

    17. TF

      Mm-hmm

    18. CJ

      ... To the Lighthouse again because now that I am a mother and a wife of a certain age, [laughs] I'm like, "This book is gonna resonate a lot more for me."

    19. TF

      [laughs]

    20. CJ

      But what's amazing is Virginia Woolf was never that. She-

    21. TF

      Mm-hmm

    22. CJ

      ... she didn't have children. She really barely was in a, you know, and she unfortunately did kill herself. Like, she had a lot of demons.

    23. TF

      Mm-hmm.

    24. CJ

      And actually, the way that she killed herself, brutal, right?

    25. TF

      What'd she do?

    26. CJ

      Like, I mean, she filled her pockets with rocks and, like, drowned herself.

    27. TF

      Hmm.

    28. CJ

      You know, and I think that a lot of artists are, are tortured, but the fact that she could project into this Mrs. Ramsay and this woman, this very maternal figure, was the sign of true art- artistry. Sorry, that was very long.

    29. TF

      That's why I have a long podcast. [laughs]

    30. CJ

      [laughs]

  6. 31:32 – 39:43

    The case for reading fiction.

    1. TF

      I'm gonna continue to chew on this bone a little bit, and for the record, I actually love John Wick. [laughs] But I don't wanna dwell on John Wick. I was gonna say, first, if you like dream state evoking novels, the one that blew my mind, and 9 out of 10 people hate this book, so it's a very strong caveat, but it's Little, Big by John Crowley.

    2. CJ

      Ooh.

    3. TF

      He's actually a-

    4. CJ

      Have not read it

    5. TF

      ... poet by training. It is so unbelievably good. You have to slog through the first 150 pages, but beyond that, it's absolutely stunning. What are the reasons to read fiction, aside from the, as I think you put it earlier, the insight into the human condition?

    6. CJ

      Yes.

    7. TF

      If you were, if you were trying to get someone to take that first bite of the forbidden apple [laughs] of fiction, are there any other points that you would make?

    8. CJ

      How do you build empathy?

    9. TF

      Yeah.

    10. CJ

      How do you understand everybody has a story? How do you... I mean, you've traveled a lot, Tim, but a lot of people you and I both know haven't traveled the world. They haven't been to that many countries. Like, you wanna go to another country, find a great novel that's been translated from that country and read it, and, like, you will understand that country in a way that no travel guide will ever give you, in my opinion.

    11. TF

      Mm-hmm.

    12. CJ

      So I think it's a very cheap way, and there's also to build, like, emotional intelligence, right? I think, you know, I've worked now in tech companies for over 20 years, and when you sort of get to certain levels of responsibility with management and leadership, you could be technically the smartest person in the room, but if you have no emotional intelligence or dimensionality in contemplating emotional states, you are gonna struggle. You are gonna-

    13. TF

      Mm-hmm

    14. CJ

      ... struggle to lead. And so when I say understand the human condition, I don't just mean, like, I'm reading a book and I understand, wow, that's how it might feel to be in a divorce, or that's how it might feel to lose your child, or, you know. I'm saying, no, you yourself as the reader, if the book is really good, start to feel the feelings, right?

    15. TF

      Mm-hmm.

    16. CJ

      You start to feel like, "Oh, I lost a child." Emotional exercise is hard. It's either happening to you-

    17. TF

      Yeah

    18. CJ

      ... so you're going through an emotional situation in your own life, which is hard, but doesn't happen every day to most people, or you're gonna get emotional exercise from, in my experience, a lot of people get it from film, right? They get it from video.

    19. TF

      Uh-huh.

    20. CJ

      They get it from video content. Uh, I worry we don't... Short-form video gives you, like, a dopamine hit, in my opinion, but not an actual deep story, emotional resonant hit. We think we're getting it when we see, oh, that dog fell through the ice, and then that guy rescued the dog, and you're sorta, like, la- crying, and you're so happy, but, like, in a 30-second YouTube video, like, no. That's not an emotional arc. That's just, like, I like to see people rescue animals who are drowning.

    21. TF

      [laughs]

    22. CJ

      No, I really want... I think it's a serious film. It's, maybe it's John Wick. John Wick might be a way to detoxify your left-hand column.

    23. TF

      I almost cried. I said to my friend who'd seen it before, I was like, "If they touch that dog, I'm gonna lose it." And he just stayed silent, and I was like, "Oh, no."

    24. CJ

      Uh-oh. Uh-oh.

    25. TF

      "Here it comes."

    26. CJ

      Uh-oh.

    27. TF

      Yeah. Anyway. [laughs]

    28. CJ

      But anyway, point is, I think it's emotional workout. Literature, great films, you know.

    29. TF

      The other thing I would say is I think that fiction is often much more efficient and elegant in delivering truths than nonfiction, and that's speaking as someone who was a militant nonfiction purist for decades. Uh, and I really wish I'd started earlier with reading very, very high-quality fiction.

    30. CJ

      So what was your gateway fiction? What got you... I'm so glad to hear you're a convert.

  7. 39:43 – 48:11

    Crafting a working-with-me document.

    1. TF

      believe. All right. So let's come back to ... I'm ac- actually gonna, I'm gonna take a, a further, not digression, 'cause this is just a natural conversation, but we are gonna come back to feedback for direct reports.

    2. CJ

      Mm-hmm.

    3. TF

      But I feel like we need a smoother off-ramp. [laughs] So what might make a nice off-ramp from the fiction [laughs] is something that is highly, highly, highly personal and nonfiction, and that is a working-with-me document.

    4. CJ

      Oh, yeah.

    5. TF

      So I wanna ask about questions that you might answer in a working-with-me document. You could explain what a working-with-me document is, and there are a, a number that come to mind that I have in front of me here, but perhaps you could just give a little bit of context on what a working-with-me document is and how it is helpful.

    6. CJ

      A working-with-me document is basically trying to write your own user manual.

    7. TF

      Mm-hmm.

    8. CJ

      And so I don't think you have to be a people manager, but I've come to believe it's a best practice if you are gonna be managing people to do your best to write a user manual to working with you. The idea came to me, actually, I was moderating a panel at Google. Google had then evolved to a point where it was trying to celebrate management, so we'd done this great manager award, and I was the moderator interviewing the great managers that we'd selected across several teams in front of this big room of people at Google. And I asked them, you know, "You ask what are some practices that you think have really benefited you as a manager?" And one of the panelists said, "Well, I copied this thing that Urs," and this is Urs Holzle, who's a long many, many decades at Google, I think he's only retiring, like, now, who worked in infrastructure and building the servers and the, like, a lot of what really makes your Google results come very quickly, [laughs] you can thank Urs. But anyway, and then at Google Cloud, a lot of work. But he wrote a user manual, and this person described it, and then they went on to say they wrote one, and they shared it with their team, and their team's response, and I was like, "I should write one." Like, here I am moderating this great manager panel. I don't, I haven't done this. So like any good learner, I go back and I sort of, like, bang out this document. I mean, this is the thing that's the most interesting to me in this maybe anti-growth mindset, but this was probably, I don't know, 20- 2009, 2008, whatever. It was, like, many years ago. I bang out this document, and I call it the unauthorized guide, because I don't work for me. Like, I, I said ... So I invited comment. I said, "For those who actually have had me as a manager, like, please tell me how, like, on base I am or not." And then I, I gave it ... Actually, I had the time, had this really amazing woman who had been a manager in my organization and then she went on maternity leave and came back and asked to be my assistant. She said, "I wanna change sort of ... I think I could be kind of a chief of staff to you," and she was very talented, and we got very close, and she worked for me for, like, at least half my career at Google. And I was like, "Maeve, read this. Am I anywhere near, like, am I on base here?" You know. And she, she was actually, uh, she's Irish, which is a theme somehow in my life. Like, I, I really-

    9. TF

      [laughs]

    10. CJ

      ... bond with the Irish. And she said, "Well, I feel like at the end-" You don't even acknowledge that you like good craic, and craic, which I'm saying wrong in Irish-

    11. TF

      [laughs] Good fun

    12. CJ

      ... is like sort of fun, joke humor.

    13. TF

      Mm-hmm.

    14. CJ

      Yeah. She's like-

    15. TF

      Yep

    16. CJ

      ... "You know, your meetings," she said, "I've never been in a meeting with you where we didn't laugh at least once." And th- that's the kinda thing, by the way, that you don't know, 'cause you're never not in a meeting with you, right?

    17. TF

      [laughs] Yeah.

    18. CJ

      And so I was like, "Oh, that was super helpful," but I feel embarrassed that I'm like... I, I said, "Am I saying I'm funny?" She's like, "No, you like a good laugh. Like, you're not trying to..." It's true, I'm not particularly that funny, but I really enjoy humor. Anyway, so, so we added a section at the end. But she said, "No, I think this is pretty good. I think you should send it to the team and see what they think." But what's amazing, Tim, is that document has not changed markedly.

    19. TF

      Huh. Since 2009 or whenever it was.

    20. CJ

      Since like 2009. It has not changed very much, and we can decide how we feel about that, but I think it's, it's a great exercise in self-awareness. It's a great exercise in also sort of thinking about, okay, when I have to make a decision, so to your point, what kinda content is there? Some of it's very tactical. It's like how do I, like, what communication channels work best for me? So how to use our one-on-one versus send me a Slack versus a text versus call me. Like, in today's world, you know th- like, I literally have people that I work with, actually, I think you know, I work with Patrick and John Collison, the Stripe co-founders.

    21. TF

      Mm-hmm. Of course.

    22. CJ

      They contact me on every channel. [laughs] Like-

    23. TF

      Oh, boy

    24. CJ

      ... how is it that you're texting me, WhatsApping me, calling me, Slacking me, rarely emailing me? Actually, emailing is probably like the least interesting channel to them. Anyway, you give guidance, like what are the best channels, like how to use our one-on-one, but also things like how do I tend to make decisions? So if you're coming to me for a decision, here's what you can expect. If it's, you know, this kinda decision, how long will I need? What kinda data might I like? Like, I have a section in my doc which is I tend to be intuitive, so I've taken a lot of different personality assessments, and I actually don't really spike in a lotta areas, but I spike as highly intuitive, meaning you come to me with something, I intuitively have an opin- I'm like, "Oh, I think this is gonna be the right thing to do," or I think... I say, "I'm intuitive," and then I write dot, dot, dot, "Don't worry, I won't jump to..." But data-driven. So I'll tell you my intuition, and then I'll say to you, "Bring me data so we either can validate it or you tell me your intuition, but let's get some data so I don't, like, just get out there and start operating without any basis," right? But I think that you're trying to reflect that, but I think it's important to reflect that. Like, for example, in my first version, one thing that did change when my team read it was I said, "I'm not a mi-" By the way, every manager's like, "I'm not a micromanager."

    25. TF

      [laughs] Yeah.

    26. CJ

      It's like a common... Everyone's like-

    27. TF

      Yeah

    28. CJ

      ... "Well, don't worry. I'm not a micromanager." Unfortunately, a lot of us are. And I said, "I'm not a micromanager. I will delegate. I will trust you, but if I, if I'm concerned, you're gonna know, and I'll get more involved," right? And so I thought I was being pretty honest, like, "When I do get involved, we should have a conversation, 'cause it means I'm having an issue with trust, which means I'm not sure I'm happy with the product," you know? So this guy who worked for me, he said, "I'm not sure that you're accurate about this." And I said-

    29. TF

      [laughs]

    30. CJ

      ... "Well, tell me, are you saying I'm a micromanager?" And he said, "Well, there was this one thing," and he named this project that I had delegated to him, and he's like, "Then you proceeded to show up in every meeting, read every document, be in the spreadsheet." And he's like, "That, to me, felt pretty micromanaging." I was like, "Yeah, I bet it did feel that way." I said, "I did that because that project was the first time..." It was like a compensation, sales compensation scheme. I was like, "That's the first time I'd ever built one, and I was really, like, wanting to learn." And he said, "Well, you never told me that." So-

  8. 48:11 – 54:01

    Make the implicit explicit.

    1. TF

      This is something I wanted to explore because jumping, I suppose, to, uh, something you explore at some length in your book, which I definitely recommend people check out, and I, I underlined this a couple of times for myself, because I still feel like I have room to improve here, and that is, "Strive to make implicit structures and beliefs explicit," right? Make the implicit explicit, and that shows up in so many different ways. It can manifest in so many different ways, and I wanna stick with the working-with-me document for a minute.

    2. CJ

      Mm.

    3. TF

      This first came to my attention because I had Dustin Moskovitz on the podcast-

    4. CJ

      Yep

    5. TF

      ... from Facebook fame, and then certainly of Asana And he shared his working-with-me document, and I've s- I've since seen a few versions of this.

    6. CJ

      Mm-hmm.

    7. TF

      But I wanted to get your take on what might be worth adding to this list of questions. Here are a few. S- what do I want to be involved in? When do I want to hear from you? One you already mentioned, what are my preferred communication modes? What makes me impatient?

    8. CJ

      Mm-hmm.

    9. TF

      Right? Are there other questions that you have found helpful to address or kinda topic areas worth including, having seen these letters, having crafted your own working-with-me document?

    10. CJ

      My working-with-me document was published in Elad Gil's book, High Growth Handbook, and went, like, a little bit viral. Like, viral for Claire, not for Tim Ferriss. But, like, still I was, like, shocked at how many people-

    11. TF

      Yeah

    12. CJ

      ... that I've never met had, like, seen it. And I also got some criticisms on the internet webs, on the interwebs, that it was, like, very egotistical in some way. It was sort of like, here's how you, you know, make me happy, which I was like-

    13. TF

      Mm

    14. CJ

      ... okay, that's, like, a totally fair criticism, and not the intention. By the way, I'm, like, pretty highly empathe- I'm like I'm trying to reduce anxiety and help people feel comfortable being honest with me, like-

    15. TF

      Mm-hmm

    16. CJ

      ... whatever, but it, I get it. It's, it seems very self-absorbed. So one of the things that I'm reacting to is, like, the question, I guess if I were gonna phrase it as a question, it would be how do I help you make great decisions, or how, how do you like to make decisions, you know? But I think in my document I just sort of have headers. Like, decision-making, 'cause I'm not telling... Like, that's why yours called it user manual, which is a very techn- Like, an engineer is gonna be like, "I'm gonna write a user manual"

    17. TF

      Mm-hmm

    18. CJ

      ... to me, and I, I just called it working with me [laughs] . Um, working with Claire. There's a section on what types of information do you like to see.

    19. TF

      Mm-hmm.

    20. CJ

      Because that's different than how do I wanna be communicated with, and it's different than when should I get in touch with you, which is like, yeah, if there's a crisis, get in touch with me. But there's something in mine where I talk about the fact that if someone on your team is having a major life event, 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 their child, or, you know. I think that, you know, what types of information do you like to have? I also get really explicit about things like email protocols mean different things to people, especially in different generations. I'm sure you've seen this.

    21. TF

      Mm-hmm.

    22. CJ

      But I used to work with someone who would send FYI and really, really feel strongly that you need to process that information and, like, have a response, whereas for me-

    23. TF

      [laughs]

    24. CJ

      ... I'm like, if you send me FYI-

    25. TF

      That means no response [laughs] .

    26. CJ

      That means... Well, it means-

    27. TF

      For me anyway.

    28. CJ

      Yeah. Like, I can read it later, and it's interesting-

    29. TF

      Yeah

    30. CJ

      ... but I don't need to respond.

  9. 54:01 – 55:11

    An Irish Goodbye.

    1. TF

      I wanted to piggyback off of your Irish pattern in life and recommend a short film that I think won an Oscar. I might be making that up, but it won some slew of fancy awards, and I watched it last night [laughs] called An Irish Goodbye. It's about 22, 23 minutes long. You can find it on Vimeo. I think you might be able to watch it on YouTube as well. It is hilarious and profound and outstanding I think.

    2. CJ

      Ooh.

    3. TF

      Based on the little that I feel like I've sort of felt out with our-

    4. CJ

      Yeah

    5. TF

      ... fiction love fest, I think, I think you would really enjoy this. It is, it is one of the better short films I've ever seen.

    6. CJ

      Oh.

    7. TF

      It's really good. It's really, really good. So An Irish Goodbye.

    8. CJ

      I've got, what is it, Little Big and Irish Goodbye.

    9. TF

      Start with An Irish Goodbye 'cause then you'll be like, wow, Tim really recommends good stuff, and then if you hate Little Big, at least I'll have some redemption preemptively.

    10. CJ

      Okay. All right. That's fair.

    11. TF

      Yeah.

    12. CJ

      That's fair. I'll do it.

    13. TF

      So it's, that's like the amuse-bouche before you try to chew on the [laughs] The fever dream

    14. CJ

      And I, I'll say also, I love a good Irish goodbye. I used to be find it a little offensive, but now I-

    15. TF

      [laughs]

    16. CJ

      Now I'm like, gosh, there's some real beauty in just

  10. 55:11 – 1:01:03

    Email policies.

    1. CJ

      disappearing.

    2. TF

      Oh, I do that all the time. I do it all the time. So email policies. I had a request from Kevin Kelly recently, who's been on the podcast and is a close friend, and, and he's... I asked him if I could help him with anything. We're having a conversation. He said, "Well, I do have one request," and it's not for him. It's because he gets asked about it so much. He doesn't have any issues with email, but he's like, "I want you to ask every one of your guests about email policies/rules, systems, anything that they have ended up using that they have found helpful." And I will say in advance, my, my assumption is that almost... Well, it's not my assumption. I've also run into this. Even though this podcast has some of the top performing people in the world of every discipline imaginable, they all claim to kind of suck at email, they're behind-

    3. CJ

      Yeah

    4. TF

      ... and it's hard.

    5. CJ

      Yeah.

    6. TF

      So I, I understand that. Being that as it may-

    7. CJ

      See? It's a beautiful expression

    8. TF

      Yep. Here we go

    9. CJ

      Be that as it may.

    10. TF

      Be that as it may.

    11. CJ

      You are still gonna have to answer this. [laughs]

    12. TF

      Yeah. Are there any sort of email policies, systems, rules, implicit things that you make explicit that you found helpful?

    13. CJ

      I actually worked on Gmail right after it launched at Google, and, like, you should think I would be, like, a power email organizer, and I'm okay, but I'm not great. But one thing that, that just stuck out of my mind as you brought this up is I, I had a good friend who was executive at Genentech, and she rose up with Genentech as it got big, and she got more and more responsibility, and she told me about this leadership training they put them in, Tim, that st- like, honestly, whenever I look at my inbox, I think of this training, where they gave them some 30 minute... some window. They gave them an inbox, and they were like, "You need to process all this, and, like, kinda do the right things," right? Okay. And so in this inbox of, like, 100 emails, whatever, they have 30 minutes. You have to find... There's, like, a massive legal issue. There's an HR violation, but it's, like, not in the headline of the subject of the email.

    14. TF

      [laughs] Sounds like an anxiety dream. [laughs]

    15. CJ

      There's, like, a bunch of bombs in these messages, and you have to, like, open them, skim them, decide you have to come back to it, right? Like-

    16. TF

      Yeah

    17. CJ

      ... and I kind of was, like, feeling like Japanese game show. I'm like, "Would this-

    18. TF

      [laughs]

    19. CJ

      ... a show that people might wanna watch?" And I think there is a sector of people who might find that, like, really interesting to watch. So sometimes I look at my inbox and I'm like, "Oh my gosh, I have 30 minutes [laughs] and I need to find all of the, like, legal time bombs." But-

    20. TF

      [laughs]

    21. CJ

      ... one of the things that I think I'm very good at on email-

    22. TF

      Mm-hmm

    23. CJ

      ... is there is a set of people in my both professional and personal life where no matter... like, they get opened immediately, right? Like, and I'll open it, and if it's by the way read, FYI, I'll read it later, but, like, I really wanna make sure-

    24. TF

      [laughs]

    25. CJ

      I mean, it's easy. Some of these people, it's, like, easy. It's like your kids, right? By the way-

    26. TF

      Right

    27. CJ

      ... my kids are so... They're teenagers. They never email me, so that's, like, easy. But, you know, certainly if you're the COO of a company, even if you're not the COO anymore, if the founders of Stripe email me directly, I'm gonna open the email, you know?

    28. TF

      Right. Mm-hmm.

    29. CJ

      Like, pretty freaking quickly, just to make sure.

    30. TF

      Mm-hmm.

  11. 1:01:03 – 1:03:28

    Renegotiating the terms of expectations.

    1. CJ

      I, I no longer feel guilt.

    2. TF

      Yeah.

    3. CJ

      I've told them, "You must contact me directly."

    4. TF

      Set expectations.

    5. CJ

      But this is actually a management lesson, which is why not... This goes back to the user manual or the Working with Claire guide. Like, why not tell people, "I have this habit-

    6. TF

      Mm-hmm

    7. CJ

      ... of ignoring this kind of thing, and if you need my attention, you have my permission. Please use it. Please text me even." I mean, for these founders, they have my phone number. I'm like, "If you need me, you can call me," right? But it's sort of a human lesson we learn over and over again, which is we're like dying inside that we're disappointing someone, and I'm like, "No, just renegotiate the terms-

    8. TF

      Mm

    9. CJ

      ... of what expectations they should have of you."

    10. TF

      How else does this renegotiating show up? This has become [laughs] it's embarrassing to say, but I'd say maybe in the last two years has become such a, a revelation for me in a sense, because I always thought about negotiating as the thing you did in the beginning. [laughs] And I got, I think, pretty good at that.

    11. CJ

      I'm sure you did.

    12. TF

      At times, though, I would have, who knows, like maybe I've had two glasses of wine or I had too little sleep or whatever, and I would agree to these things, and then later I'd look at my calendar and my blood pressure would go up, you know, 30 points because I felt trapped by these commitments that I made when I was compromised or rushed or lazy, fill in the blank.

    13. CJ

      Mm-hmm.

    14. TF

      And this renegotiating has become an invisible option made visible for me in the last two years. Could you talk a little bit more about how you have used that in your life, personal or professional, how that shows up? Like, examples would be really helpful here-

    15. CJ

      Yeah

    16. TF

      ... so people can really get a grasp on it.

    17. CJ

      Yeah, I mean, I can really... I'm having like almost a physical reaction to relating to you about this calendar. It's like, it's like your past self. I used to say, "Oh my gosh, I just mailed myself a letter bomb." Like you're like-

    18. TF

      [laughs]

    19. CJ

      ... later I'm gonna, you know. So one is, of course, we all strive to improve, which is-

    20. TF

      Yeah

    21. CJ

      ... do not make a decision in the moment about a time or, or a, a commitment of resources or time without trying to project your future self.

    22. TF

      Mm.

    23. CJ

      You know? Like, but of course we all do, because you're right, we're rushed, we're trying to be responsive, we're trying to move through our inbox, by the way-

    24. TF

      Yeah

    25. CJ

      ... 'cause we've only got 30 minutes or we might fail-

    26. TF

      [laughs]

    27. CJ

      ... the corporate training test. [laughs]

    28. TF

      Or the Japanese TV show. Don't wanna come

  12. 1:03:28 – 1:06:02

    Listening for the quiet no.

    1. TF

      in last.

    2. CJ

      Yes. So one thing is trying to be better about projecting, and I also had a friend, ooh, who's like a very kind of spiritually in touch person and she said, "When you're... Something is requested of you," she said, "you need to sometimes listen for the quiet no."

    3. TF

      Hmm. Can you say that one more time?

    4. CJ

      She said, "When something's requested of you, a person..." I mean, she's like sort of like, "Sometimes your reaction is, 'Wow, yes.'" Right? You've had this. Someone-

    5. TF

      Mm. Yeah

    6. CJ

      ... I mean, hey, Tim Ferriss asked me to be on his podcast. I was like, "Yes," emphatically. That is something I wanna do, right?

    7. TF

      Mm.

    8. CJ

      That is easy. My past and future selves are very happy to be here. But often we get a request, you have this experience, and you're looking at it, and she says, "Listen for the quiet no."

    9. TF

      Mm-hmm.

    10. CJ

      Because we are often feel like we have to say yes. And so, and her trick is, and I know this wasn't the question you asked me, which I will answer, but her trick is-

    11. TF

      These are really closely related. I'm so interested in this, yeah

    12. CJ

      ... I think they are. You do not respond immediately, because we often feel, I mean, if you're someone who's prides yourself on being decisive and responsive and empathetic, as I do, I feel like, well, they asked me to be on this panel at this important conference or whatever. And I'm like, I've learned that my response in fact should be, "When do you need to know whether or not I can do be on this panel?" Or I'll even say, "I need two weeks to get back to you about whether I can be on this panel," because if I don't give myself some space, I will do yes instead of the quiet no, because I didn't give myself time to really think about, is this my priority? Should I spend my time? Oh my gosh, I have to fly to this city [laughs] and do... You know? Like, you have to really think. So when you are renegotiating, so I'm proud of you that you found this as a skill, and by the way, I have the same problem. Like, I had a delayed travel earlier this week, and I was looking at my next day and I was thinking-

    13. TF

      Mm

    14. CJ

      ... "Well, I am gonna get home, but I'm gonna get home at like now 2:00 in the morning." And then I looked at, and I was like, "I should not even be doing that stuff." I was like, "Why did I even agree to go into Boston and have lunch with this person and then talk to this other person when I'll be..." And so I was like, "I am going to renegotiate those commitments. I don't even have to say that I was delayed." I, you know? Like, it was a good, so it's a good skill, but what I look for is a pattern, a pattern of why am I-

    15. TF

      Mm

    16. CJ

      ... renegotiating this stuff? It means I'm not making the right decision in the first place. So I listen for the quiet

  13. 1:06:02 – 1:08:02

    Money versus time.

    1. CJ

      no. But if I find myself renegotiating, it is often about, yeah, commitments I've made. Commitments t- especially of time is the main thing. I mean, that is my mom, my mom was a very talented, apparently, mathematician in college, and my mom went to Harvard, well, Radcliffe then, but-

    2. TF

      Mm-hmm

    3. CJ

      ... you know. I think it was pretty rare for a woman to be like a, a star in the math department.

    4. TF

      Super rare.

    5. CJ

      And she decided to go get her PhD in history and to major in history, and I said, "Why did you switch? Like, why did you make this, the switch?" And she said, "I realized that there is a trade-off that most people find themselves making between money and time."

    6. TF

      Hmm.

    7. CJ

      And she said, "I knew that if I prioritized math, it would likely lead to a more lucrative career," which, I mean, by the way, my mom was like out there. She was gonna work, and she did, and she was gonna have kids and work, but she was like, "It would lead to a more lucrative career, but I would not have time." So I decided to become... She became an academic, she got her PhD, she became a professor. And why? Because professors have more control over their time, and they have the summers off-

    8. TF

      Right

    9. CJ

      ... and they have time to think and write, and that's what she knew she wanted. Which by the way is pretty aware for like a 19 or 20-year-old-

    10. TF

      That's incredible

    11. CJ

      ... to realize you're gonna trade money and time.

    12. TF

      Wow.

    13. CJ

      And I, I think it's Peter Thiel, or is it E- who says, like, people don't value their time highly enough, right?

    14. TF

      Mm-hmm.

    15. CJ

      Like, they just like don't get, like every hour is costing you something, and I've taken me so long to come to this point where I'm like, oh my gosh, I just threw away and said, "Sure, I'll meet with you to give you advice about that thing," and I'm like, "Oh." So I've become less responsive on email because I am trying to stop myself from, I don't know, mortgaging my time.

    16. TF

      [laughs]

    17. CJ

      So I... I mean, you, you may or may not have had the same

  14. 1:08:02 – 1:11:12

    Good rules can be liberating.

    1. CJ

      experience, but I renegotiate... All right, here's an example. You were looking for concrete. I have a woman who I highly value personally in my life. She's a founder, and she asked me to be on her board, and I had made a rule. I make ru- by the way, to, to stop myself from saying yes to stuff, I make rules. So I, I, I made a rule. I was like, "No more boards." I also had a rule, I have a rule about travel right now. I'm like, "My daughter's going to college soon. No more travel unless it meets these criteria, because I wanna be home." Of course, she doesn't wanna hang out with me, but I wanna hang out with her.

    2. TF

      What are the criteria? Just out of curiosity. Could be just a few examples.

    3. CJ

      Really important to Stripe. I still actually work-

    4. TF

      Mm

    5. CJ

      ... part-time for Stripe, and they are s- you know, they get bids on my time.

    6. TF

      Mm-hmm.

    7. CJ

      And if Stripe said, "The most important thing you can do for Stripe is go to," this happened to me recently, "go to Helsinki to Slush, to this conference," I was like, "Fine. I will do it. I will go to Helsinki for Stripe," right? 'Cause I... And by the way, I had a great time, and I met a great number of founders, and it was actually a blast, but... So is it important to Stripe? Is it a personal connection that is meaningful to me that is asking, you know, of my time treasure talents? I will at least... But my criteria is not to say yes to default, but it is to, number one, I'm s- I've gotten... I'm like number one, is there a way I could do it that is less friction, as in am I flying to California anyway, therefore I can do that commitment if I bundle it? So can I control when it is?

    8. TF

      Mm-hmm.

    9. CJ

      And if I can control when it is and it's a personal connection that's meaningful to me, I will s- make it happen, but it will not happen quickly. But if it's not something I can control where and when it is, then I have a subset [laughs] of criteria of like, like can I do... But I often will say like, could this thing, maybe it's a conference, can I do this next year and get back to you later so I can actually think for a minute about my... A lot of it is buying time. But anyway, I have these rules about things 'cause it stops me. So I said to her, I said, "I have made a commitment to myself that I will not join another board." And then I said... And she, because she's a talented founder, she's persistent, and she said, "Why don't you just come and be an observer? Why don't you just come to-"

    10. TF

      No. Tricky.

    11. CJ

      I know. I know.

    12. TF

      [laughs]

    13. CJ

      Come to the board meeting, and then she told me why she really needed help in this particular moment, and there was a s- situation where having someone who was sort of a friendly, who was neutral in the room was gonna be valuable. So I said, "Okay, I will come, but I will not... Like, I really wanna set your expectations," right? But I was like, "I am not... This is not gonna reel me in. I'm not gonna join the board." And I did go, and she actually convinced someone else, and the two of us went, and we actually, I think, helped her through a particular moment by being sort of board participants. But then she said, "I'd like you to come to every bo- you know, of course, every board meeting."

    14. TF

      [laughs]

    15. CJ

      And I said, "I don't think I can commit to that, but I can try when it's virtual. And if it's in person, I'm pretty sure I won't, but like, you can invite me."

    16. TF

      Mm.

    17. CJ

      And I went to a couple, I did pretty well, and then I started to look at my calendar and I was like, "I can't do this. I can't even take three, four hours. Like, I can't..." And so I needed to renegotiate it.

  15. 1:11:12 – 1:16:39

    Leadership and disappointment.

    1. TF

      Mm-hmm.

    2. CJ

      There's a quote that I have in my book that people find, I think, the most compelling line in the book-

    3. TF

      Hmm

    4. CJ

      ... and I keep having to remind them it is not my line.

    5. TF

      [laughs]

    6. CJ

      And-

    7. TF

      Yeah, I, I know this problem, where I'm like-

    8. CJ

      Do you know this problem?

    9. TF

      ... "No, no, no, don't attribute it to me. That was Mark Twain," or whatever.

    10. CJ

      Exactly.

    11. TF

      Yeah. [laughs]

    12. CJ

      Exactly. So the line is from Ron Heifetz or Marty Linsky, these are the adaptive leadership guys who do the balcony-

    13. TF

      Mm-hmm

    14. CJ

      ... and the dance floor analogy.

    15. TF

      Mm-hmm.

    16. CJ

      And it is, "Leadership is disappointing people at a rate that they can absorb."

    17. TF

      Yeah. I had that line underlined. It's very catchy.

    18. CJ

      It's very com- 'cause it really makes you think.

    19. TF

      Yeah.

    20. CJ

      And it's kinda dark, too. You're like, "Wow, leaders-"

    21. TF

      What does that mean in, like, concrete terms? And then I'm not gonna let go of the renegotiating, 'cause I'm gonna come back to that. I wanna ask you about phrasing and wording that you use, but-

    22. CJ

      Oh, okay. All right

    23. TF

      ... let's talk, let's, let's talk about-

    24. CJ

      All right

    25. TF

      ... leadership and disappointing people.

    26. CJ

      Disappoint people.

    27. TF

      [laughs]

    28. CJ

      Well, I think one of the ways that leaders disappoint people is their time, right? They can't give... Like, you can't, you don't have unlimited time. You're the CEO of a company, right?

    29. TF

      Mm.

    30. CJ

      There's no way you're gonna be at all the things or do all the things. But the key is how do you create enough leadership buy-in that people understand and they kind of... And also you get a little bit of forgiveness when you're the CEO, I think. But-

  16. 1:16:39 – 1:37:34

    Renegotiating past disappointment.

    1. TF

      tellers. So this ties into the, the renegotiating actually pretty well because there are many different species of renegotiating. One was, uh, you gave an example very early on in the conversation when Lucy was getting thrown under the bus. [laughs] The dog ate my homework-

    2. CJ

      Yeah

    3. TF

      ... situation, and then we segued from that to the player versus victim.

    4. CJ

      Yeah.

    5. TF

      And the player would say, "You know what? You're right. I committed to get this to you by 5:00 PM. I didn't, and because this emergency popped up and I da, da, da, I didn't let you know, I should've let you know. How about 5:00 PM tomorrow?" Or whatever the example was.

    6. CJ

      Mm-hmm. Renegotiation.

    7. TF

      Renegotiation. So in this particular example, when it becomes clear to you that by whatever deadline had been agreed, you are not gonna be able to deliver what you were going to hope to deliver, what does that conversation look like? I mean, it's not exactly semiotics, but I know you like language, and I know you consume a lot of language.

    8. CJ

      Yeah.

    9. TF

      So what is the language that you use to have that conversation, whether it's verbal or in email?

    10. CJ

      You made the connection, and then you didn't finish making the connection, but it is so easy to sound like a victim-

    11. TF

      Mm-hmm

    12. CJ

      ... right, when you are facing this kind of a situation. And if you're someone who prides themselves on being a player, on taking ownership, and you've made this commitment and you're like, "Oh my gosh, there's no way I'm either coming to that meeting or delivering 24/7 global support in six months," you know. And so what does it look like? The first thing I did that was probably the smartest thing I did when I joined Stripe was I listened and I did my first 90 days and I talked to everybody and I heard sort of here's the priorities, here's what people need, here's what might n- need my attention. And then I sat down with Patrick and I said, "I'm hearing these four things that," one of them was the support thing, by the way, "that really need my attention, and I am gonna rank them, and then I want you to see my ranking, and I wanna agree on my level of priority of," I said, " 'cause I can't make meaningful progress on four things at once. I can maybe keep..." And I actually predicted, in that moment I said, "I don't..." 'Cause we had to build sales. We had to build recruiting. We had some internal, like, operational stuff that needed to be fixed, and then we had this support sort of smoldering fire. And I said, "I think I actually need to build sales and recruiting ahead of fixing support, but I predict support is gonna implode within the next six months."

    13. TF

      And at that point you were COO. Is that right?

    14. CJ

      I was COO-

    15. TF

      Yeah

    16. CJ

      I was actually hired as chief of business operations, and then I became... We just swapped titles with someone else, but it's a long story. But yes-

    17. TF

      Mm-hmm

    18. CJ

      ... I was basically COO, and he was like... And r- remember, we're users first. We gotta like... This was a painful, because we were also not getting back to sales leads though, Tim. I was like, you know, "I just wanna-

    19. TF

      Oof

    20. CJ

      ... I'm also here to build some revenue."

    21. TF

      Oof. Yeah, yeah.

    22. CJ

      Like, "I'm here to build go to market, and I'm here to deliver some revenue for this company." And I'm like, "We have this other thing where we're not, we're not getting back to our prospects," right? And so it was a very Sophie's choice kind of moment, honestly. Oh, and then we couldn't hire people to build the company, so we couldn't get back to sales leads. [laughs] Or get... Like, like you know, this is normal, by the way. This happens, especially for, for people like me coming into that kind of opportunity. But what I loved about that conversation was Patrick was, one, first of all, supportive. He was like, "Great. This is good for us to talk out now." And then he had to admit, he's like, "I can't believe I'm doing this, but I agree you're not gonna fix support in the first six months." Like, really.

    23. TF

      Mm.

    24. CJ

      We made an agreement. And then, by the way, Tim, four months in, complete explosion.

    25. TF

      [laughs]

    26. CJ

      And I was thinking in my head, "Thank goodness." This goes back to expectation setting. I'm like, "Thank goodness," I said out loud, "that I thought it was gonna explode." And then, I mean, by the way, still terrible. I was still sad. I was like, "Oh my gosh." I had to go then put it at the top of the priority list, basically. But I had at least four months to build some other things.

    27. TF

      Mm.

    28. CJ

      Point is, when you're renegotiating, so one is try to set the priorities, align on them, and set expectations ahead of time. Even if you haven't done that, you're gonna reach a moment where you're like, "There's no way we're getting to the top of this mountain." And so what you try to do is not come up and make a bunch of excuses. So what I, I think I did in those moments, and we were, you know, we had written public goals in the company. We had plans. We had... And I just wanna be clear, none of the plans, this is where when you're working with founders, maybe this is a side, what do you call them? Side quests. This is a little bit of a side quest.

    29. TF

      [laughs] Love side quests.

    30. CJ

      But when you're working with founders, people describe this reality distortion experience, which often is more that they have a version of reality and they're like, "No, no, no, we can ship the iPhone in five minutes," or whatever, you know.

  17. 1:37:34 – 1:41:17

    Asking a question versus stating an opinion.

    1. TF

      X, Y, and Z.

    2. CJ

      Yeah.

    3. TF

      What are some of the other rules that you have for yourself around what you will or will not do?

    4. CJ

      Well, I have a rule, this is more of just a self-awareness. I do get intuitive and I do jump to sort of judgments, conclusions, solutions quickly, so I have a rule that, like especially if I'm in a position of leadership and I'm in a meeting and there's other people, like instead of stating my opinion, I have to ask a question. [laughs] Because if you're the senior person and you state your opinion, like the whole thing is over, like you're not really gonna get-

    5. TF

      Yeah. Right. Yes, Steve, we can ship it in five minutes.

    6. CJ

      Exactly.

    7. TF

      [laughs]

    8. CJ

      Here's an iPhone.

    9. TF

      [laughs]

    10. CJ

      So that, that's a rule.

    11. TF

      Could you give an example of what that would... Because you could also ask a question in a way that makes it clear [laughs] it's your strong opinion.

    12. CJ

      No, you could. You could. Yeah.

    13. TF

      Right?

    14. CJ

      You could.

    15. TF

      So what might that look like?

    16. CJ

      They're kind of looking to you. Like they say, you know, "I think we need to X," and you're like looking at you, and you say, "I have a thought. I do. I'll, I'll share it, but actually I'm interested in, in what you all think we should do."

    17. TF

      Mm-hmm. Got it.

    18. CJ

      Like I want to learn from your thought before I share mine, you know? And that's, by the way, the benefit of seniority is you can be like, "No, I'm not gonna, like-"

    19. TF

      I appreciate and refuse to answer your question.

    20. CJ

      I'm not gonna perform right now.

    21. TF

      [laughs]

    22. CJ

      I will perform later, like because I actually want you to participate.

    23. TF

      Mm-hmm.

    24. CJ

      I'm often now in a position of sort of coaching leaders, and because I'm more of an operator, not a professional coach, I have the same problem. I'll be like, "Oh my God, this is obvious," like, "Here's what you're gonna do," and then I think, "No, no, no. No, no, no." So I'll say to them, "All right, give me the bones of the situation," and then I'll start to tell them what I think, and I'm like, "No." And then I'll say, "You know what? I'm a ba-" And I totally commentate. I'm like a sports color commentator. I'm like, "I was about to jump in and tell you exactly what I would do if I were you." And they're at the edge of their seat, 'cause that's what they came for, like that's what they want. And then I say, "We're not gonna learn from that. What I want you to do is tell me your instinct. What is it you think you're doing next?"

    25. TF

      Mm-hmm.

    26. CJ

      And I don't even say, "Give me the whole answer." I'm like, "What do y- what would you do next?" 'Cause it's often a situation. There's an executive they think is underperforming. There's a team off the rails, whatever. I'm like, "Well, what are you gonna do next?" Then I get them talking, and then I sort of get out from them, and I'll tell you, Tim, most of this... I mean, there's a reason these people are leaders. Most of the time they're like 80% of the way there, they're just not-

    27. TF

      Mm.

    28. CJ

      -confident in their instinct.

    29. TF

      Mm.

    30. CJ

      And so my job is not to tell them what to do or how to do it. It is to build their confidence in their instinct, and then yeah, we can brainstorm the last 20%.

  18. 1:41:17 – 1:42:54

    Training wheels for a “no.”

    1. TF

      How often do you say, "I have to get back to you next week," versus, "I'm not sure. Can you get back to me next week?" Versus... In other words, like where does the ball fall in whose court?

    2. CJ

      By the way, good feedback for me, Tim, and I take it. Thank you.

    3. TF

      [laughs]

    4. CJ

      No, I think that is actually a really good tactic that I don't do enough of, is to say, "I think this is unlikely that I'm gonna be able to do this. I'm willing to consider it, but what I'd like you to do is go look at your other options and if you're, you know, not finding something, feel free to get back to me by the end of the month and I will consider it," but it's, you know, like basically telegraphing, like, "I kind of want to try to help you, but I can't."

    5. TF

      Yeah.

    6. CJ

      Like, I really... You gotta go to your plan B. I'm not gonna be your keynote speaker. And that's a great feedback. I mean, if you find yourself doing that, you should be asking yourself, why is it just not a no?

    7. TF

      It's a no. Yeah.

    8. CJ

      It's a no for me. [laughs]

    9. TF

      It's a no.

    10. CJ

      You know? But maybe it's a way to trial yourself into realizing, oh, this is a no.

    11. TF

      This is the training wheels. Yeah.

    12. CJ

      But I like your idea, which is like put the ball in their court. Maybe, again, it's back to some donation request or something. Like, you know, "Why don't you get in touch? This is not for me now. Feel free to get in touch in the future."

    13. TF

      Mm-hmm.

    14. CJ

      A lot of those people might just not ever, and I mean, sorry for them 'cause they're not persistent, but, but is that, like is that being a player? Is that being a player enough? I don't know.

    15. TF

      Yeah, hitting the snooze button can lead to like a delayed 24-car pileup later in my experience.

    16. CJ

      Good analogy.

  19. 1:42:54 – 1:47:29

    Time, talent, treasure, and testimony.

    1. TF

      I was chatting with a friend of mine about this, 'cause I'm fascinated by rules for folks who handle a lot of inbound of any type.

    2. CJ

      Yeah.

    3. TF

      And his rule for the charitable stuff specifically, like, "Oh, here's my GoFundMe," or this or this, he's like, well, look... He's done very, very well professionally, and he's like, "Okay, look, if it's a friend," and it's basically any cause that's not going to entail reputational risk.

    4. CJ

      Yeah.

    5. TF

      If it's like, "Ah, my buddy's doing a, climbing Kilimanjaro for prostate cancer, and he has a GoFundMe," they'll basically give 5K to anything sight unseen, because the universe of possible acquaintances or friends who's going to come to them with that is, is pretty limited, right?

    6. CJ

      Yep.

    7. TF

      So but, but the rule is, like 5K, that's it. That's our rule. And then for anything l- large, it's just like we focus on this and this and this, and outside of that, we are not involved. That's it.

    8. CJ

      Yeah. No, I think that is so powerful. That would be another rule is like for something that's a major commitment of my time or my resources, someone said to me it's time, treasure-

    9. TF

      Talent

    10. CJ

      ... talent, but there's another one that's like testimony.

    11. TF

      Ooh, okay. All right.

    12. CJ

      Which I loved.

    13. TF

      So time, treasure is like capital.

    14. CJ

      Treasure, talent, and testimony. And testimony is interesting, right? 'Cause you could, Tim, care about something that you can't give time to, and you could say, "If you need a quote from me..." I mean, again, now we're like in this weird rarefied air where someone might want a quote from not, probably not me, but I think that that's another thing you could do. But, but the thing that for any of those categories, you need some criteria.

    15. TF

      Yeah.

    16. CJ

      Which is like, you know, some people it's about climate. If it's not related to climate and working on the climate crisis, it's a no. And I think those people actually make more friends than I probably make because I'm like, "I'm not sure. That sounds so important." [laughs]

    17. TF

      [laughs] Just to ask a clarifying question on one. Time I get. That seems pretty straightforward.

    18. CJ

      Yeah.

    19. TF

      Hours, minutes. Treasure, it's like financial resources.

    20. CJ

      Yeah.

    21. TF

      Things of that type. Testimony, okay, like endorsing something-

    22. CJ

      Yes

    23. TF

      ... or some version of that.

    24. CJ

      By the way, a version of that might be like, "Can I introduce you to someone and, and endorse you?"

    25. TF

      Yeah.

    26. CJ

      You know, like-

    27. TF

      Yeah, totally. What is talent? I mean, I understand the word, but I think of talent as u- if they're utilizing your talent, wouldn't that kind of fall into the time bucket or is it a separate thing?

    28. CJ

      I had a similar question because this was a friend of mine who was like facilitating this workshop with people trying to think about what their criteria were for like-

    29. TF

      Mm-hmm

    30. CJ

      ... what am I gonna spend my time on. I think that the version of it is you say to someone, "I agree with you. Like, I can't really deploy my particular talent [laughs] without-

  20. 1:47:29 – 1:49:34

    Spotting bad apples while hiring.

    1. TF

      you know, you've, you've done so much hiring and developed so much talent. I'm so curious how you spot bad apples or elicit negative feedback or infer negative feedback, when in the US it is so incredibly difficult to get honest negative feedback from anyone because they're so concerned about liability.

    2. CJ

      You're talking about like references or something?

    3. TF

      Hiring. Yes, references.

    4. CJ

      Yeah.

    5. TF

      Exactly.

    6. CJ

      The non-dissertation answer is-

    7. TF

      [laughs]

    8. CJ

      ... this is like people have trouble giving hard feedback. People have trouble asking this question, which is I think a, a question you just asked, which is like is this someone in the top 20% of people you've ever worked with?

    9. TF

      Mm-hmm.

    10. CJ

      And then they say yes. You say, "Top 10?" And then if they say yes, "Oh, so is it top five?" And then they're like... 'Cause what happens is when people are asked for a very specific quantifiable w- ranking of something, they don't like lying.

    11. TF

      Mm.

    12. CJ

      And so what I think happens is we don't, we're not comfortable asking for ranking questions sometimes about humans, and I don't love them actually in most contexts. But in this case, I'm like, "I'm gonna pin you down on how good this person really is."

    13. TF

      Mm-hmm.

    14. CJ

      And how they handle... And you could go just to top five.

    15. TF

      Mm-hmm.

    16. CJ

      I think that's the short answer. I think the other answer is you say to someone, you put them, again, in the role of you say, "Look, I'm gonna be their manager. You were their manager. What's the thing I could do that's most important to help them?"

    17. TF

      That's a good question.

    18. CJ

      And people will say some very revealing things. 'Cause all of a sudden they're back being the manager of the person, and they're like, "Well, I'll tell them to really be more truthful when things are off the rails."

    19. TF

      [laughs]

    20. CJ

      And you're like, "What?"

    21. TF

      Yeah.

    22. CJ

      And then you'll sort of get going and you're like, "Tell me a situation where you had to use that advice. Like what..." You know. Anyway, so those are two, one very specific-

    23. TF

      Excellent

    24. CJ

      ... pin them down, and one a little more tricky.

    25. TF

      So good. Oh, deft. Very, very elegant.

  21. 1:49:34 – 1:52:34

    If you’re not self-aware, how would you know?

    1. TF

      All right. As promised, the garage of self-awareness. [laughs]

    2. CJ

      [laughs]

    3. TF

      That is the, the very strained analogy that I used. And tell me if this ties in. I'm curious what good answers to this question might be-

    4. CJ

      Mm-hmm

    5. TF

      ... but I do wanna talk about self-awareness, so we can go into it however you would like. 'Cause this is sort of the foundational layer for everything that is built upon it, or it seems that way to me.

    6. CJ

      Yep. That's my hypothesis [laughs] so-

    7. TF

      Yeah. So actually, I, I was gonna ask you about the question, when have you seen me do my best and worst work, but-

    8. CJ

      Mm

    9. TF

      ... we can come back to that. We can come back to that. I'm gonna bookmark that. Maybe we'll get to it, maybe we won't. But how should people think about self-awareness? And I'm just going to share something that I found in the course of doing homework, and you can certainly fact-check this, but I, I thought it was quite thought-provoking. This is from CNBC, and I think it was an interview with you. So this is, you know, if you're not self-aware, how would you know, right? That's a hell of a question. It's kinda like [laughs] you know, the tree falling in the forest and no one to hear it kind of question.

    10. CJ

      Yeah.

    11. TF

      Here are some telltale signs: You consistently get feedback that you disagree with. This doesn't mean the feedback is correct, but it does mean how others perceive you differs from how you perceive yourself. Interesting. I added the interesting. Uh, you often feel [laughs] frustrated and annoyed because you don't agree with your team's direction or decisions. You feel drained at the end of a workday and can't pinpoint why. You can't describe what kinds of work you do and don't enjoy doing. So that's setting the table or maybe just piquing people's curiosity.

    12. CJ

      Yep.

    13. TF

      How would you suggest people think about self-awareness? Why is this important in the worlds in which you operate?

    14. CJ

      I spend a lot of time thinking about how do you get results through people, through teams. Like, I'm not actually the one building the product, so I gotta do it-

    15. TF

      Mm-hmm

    16. CJ

      ... through kinda brute force human brain power and human time. And I think that most people who think that way start with the individuals you're managing or the team or the organization, and my argument is where you started this, this section of the garage, is it's-

    17. TF

      [laughs]

    18. CJ

      ... the foundation is self-awareness. This actually has to start with you. You're not gonna get great results from the people around you until you understand yourself.

    19. TF

      Mm-hmm.

    20. CJ

      And, I mean, I think it, there's some obvious reasons why, which is like, look, I alone can't move the mountain. I need you, and I need to complement myself. How am I gonna complement myself with other capabilities and skills if I don't understand what I'm bringing to the table? By the way, a lot of people think they're the director in every scene. No, you're not. You're often an extra, and just knowing that will make you more effective. Uh, so that's a, a side piece of advice for you. But a lot of self-awareness building, to me, a lot of these work style assessments you can take are just trying to help you figure out your defaults. Like, what's-

    21. TF

      Mm-hmm

    22. CJ

      ... my default setting? So a lot of them are asking you, you know, are you more introverted

  22. 1:52:34 – 2:00:10

    Work style assessments for self-awareness building.

    1. CJ

      or extroverted, right? And so I-

    2. TF

      So you're talking about s- I guess for maybe lack of a better descriptor, almost like personality typing tests-

    3. CJ

      Yeah

    4. TF

      ... like Myers-Briggs.

    5. CJ

      Like Myers-Briggs, DiSC, Enneagram. I mean, there's a mill- there's Discovery Insights. I've taken, there's the Hogan Assessment, like whatever. There's, that's like 170 questions. Like, there's a r- all these different, there's the Big Five personality test.

    6. TF

      There's a lot of them. StrengthsFinder. It goes on and on.

    7. CJ

      StrengthsFinder, good one.

    8. TF

      Mm-hmm.

    9. CJ

      There's so many, but to me they all boil down to on one axis, let's call it the horizontal axis, you've got are you more introverted or extroverted? And the litmus test is sort of introverts think to talk and extroverts talk to think, right?

    10. TF

      Hmm.

    11. CJ

      So where do you fall on that continuum? And then the other thing is the vertical axis, which is are you more task-oriented or people-oriented? Which, by the way, doesn't mean you can't get a task done, and my litmus test for this is, like, if someone comes to you with, like, a massive problem in some organization, is the first thing you think of the first task that has to get done or, oh my God, the people? And it's just what do you lead with? For me, I'll be like, oh my gosh, someone's getting fired. [laughs]

    12. TF

      [laughs]

    13. CJ

      Which is sort of a task and a person answer. Anyway, but, but I would say... Sorry, I'm being very negative today.

    14. TF

      You're so negative.

    15. CJ

      I would say it sort of boils down then, and then you think, okay, what quadrant am I in? Am I a more extroverted task-oriented type person or extroverted people? By the way, a lot of extroverted people-oriented people are excellent at sales. Makes sense, right?

    16. TF

      Mm-hmm.

    17. CJ

      Their, their default is, "I love getting stuff done talking to you. Like, let's, yay," be a sal- And then you've got your introverted task-oriented people. Where do a lot of those people work, Tim, do you think, introverted task-oriented people?

    18. TF

      Engineering, programming.

    19. CJ

      Engineering, finance. Give me a spreadsheet and I will rule the world.

    20. TF

      [laughs]

    21. CJ

      I do not need to talk to you to finish this model, right?

    22. TF

      Mm-hmm.

    23. CJ

      In fact, you often do, and I know that. And so that's the other thing, is you have to be really careful not to stereotype with any of this, and not to generalize, but I think it helps any human... Frameworks are useful for a reason, which is I am comfortable sorta saying, okay, where can I place myself in these quadrants, and then what does that mean my default setting is? And by the way, the people around me have different default settings. This is such a dumb tactical lesson, but I'm one of those people where if I trust who I'm meeting with, I don't need the agenda ahead of time.

    24. TF

      Mm-hmm.

    25. CJ

      I'll be like, let's meet, and then at the very beginning of the meeting, bang out the agenda, make sure we know what we're gonna get done. You know, like I, I, I still like to run it well-

    26. TF

      Mm

    27. CJ

      ... but I'm kinda loose with the prep.

    28. TF

      Mm-hmm.

    29. CJ

      I have people who have worked for me who are, like, frozen. If they're like, "I don't have time to think ahead of this meeting what we're gonna talk about," and I'm thinking there's something wrong with them. I'm like, "Well, come on. We trust each other. We've worked together. We're just gonna spitball about this." And they're like, "No, I don't wanna meet with you." Like, I had to learn-

    30. TF

      [laughs]

  23. 2:00:10 – 2:02:36

    Paragons of no.

    1. TF

      Yeah. So going to the kind of black belts of no, people who... I'm wondering if there are people who stand out outside of the Collisons as people who are sort of paragons of no, people who are really good at saying no or defending their time, where you're like, "Wow, that person's really good at, like, keeping their eye on the one puck that matters."

    2. CJ

      Yeah.

    3. TF

      Anybody come to mind?

    4. CJ

      Well, I mentioned to you, I think Sheryl's very good at getting back, being very accessible and fast and sort of-

    5. TF

      Mm-hmm

    6. CJ

      ... decisive, like no. Efficient. She's very efficient. She's, she's someone... And, and sometimes that efficiency is a no, right?

    7. TF

      Yeah.

    8. CJ

      Who else have I worked with that are... I mean, my version of it is someone who I think is at least doing it carefully with others' feelings. Like, I don't love the person who has an assistant, for example, who cancels everything, right?

    9. TF

      [laughs]

    10. CJ

      There's a mo- no. There's a model here, Tim. You've seen it.

    11. TF

      Yeah.

    12. CJ

      Where they agree to everything, and then they have a cleanup crew.

    13. TF

      Yeah, it's lame.

    14. CJ

      They have a cleanup crew.

    15. TF

      Like the wolf from Pulp Fiction. They send it out to, like, do the dirty work.

    16. CJ

      Yeah. And I think what's happening is I'm doing left-hand column filtering names of people right now in my mind, where I'm like, "Nope, can't mention them," because I think they actually have a cleanup crew.

    17. TF

      They use the cleanup crew. [laughs]

    18. CJ

      They use the cleanup crew. Like, like, there aren't that many who seem... I mean, I think you have some good, I think it's in 4-Hour Workweek, you have some good models of pushing people on-

    19. TF

      Mm

    20. CJ

      ... not just being busy, but being productive.

    21. TF

      Yeah.

    22. CJ

      And I think the people actually that I... There's some engineering leaders I worked with at Google who I thought was very bold, but it of course makes sense. They would look at what were we planning in a meeting, and they'd be like-

    23. TF

      Mm

    24. CJ

      ... "Mm, I don't need to be here," or, "This meeting doesn't seem important."

    25. TF

      [laughs]

    26. CJ

      You know? And to me, those are paragons of no, though, 'cause it was very-

    27. TF

      Yeah

    28. CJ

      ... open, very direct, very honest. It was like, "I see what you're trying to do with this one hour, and I am not giving you my hour." [laughs]

    29. TF

      Yeah.

    30. CJ

      And, and I think that-

  24. 2:02:36 – 2:06:50

    No more boards.

    1. TF

      uh, the board, why no more boards? Uh, just the thinking behind it.

    2. CJ

      There are different motivations for being on boards. I don't know if you are, serve on boards.

    3. TF

      No. I've, I basically from the beginning, having run into a lot of people, I don't even... I have a number of friends who have policies that they won't join any more boards, and I took that as a-

    4. CJ

      As a sign

    5. TF

      ... an indicator.

    6. CJ

      And you should.

    7. TF

      And so I've only done advising. I've never been on boards.

    8. CJ

      Yeah. So I would say there's a sector of the world that feels it is a service, and I do think it's a valuable service. By the way, I serve on some boards with some people who are like Jedi Master board members, and I'm like, wow, you are serving, like, these companies 'cause you are, like, awesome at governance and, you know, proxy statements, politics, and you, like, get it, you know? But I think there's a service motivation. There's a motivation that has to do with maybe a personal, CEO really trusts you, you wanna help them. Like, that's mostly what happens with me. I'm like, "I wanna be there for that person." But it is a big commitment, and if you're someone who's realized that time is your most precious resource, which is, my mom realized somehow when she was 19, but I did not, you know, boards can stomp all over your calendar. They can just say, "You know what? All day Friday, we got, you know, someone just made an acquisition offer," and you're like, "Goodbye." You realize, like, you think you're controlling your time-

    9. TF

      Mm-hmm

    10. CJ

      ... because they don't meet that often, but no, no, no, no.

    11. TF

      Yeah.

    12. CJ

      So really what I've decided is I need to go on a board diet and then rebuild b- I'm not gonna say no-

    13. TF

      Yeah

    14. CJ

      ... ever to, like, I'm never doing it again, but I've realized the bar has to be, like, extremely high. I mean, I'm on the board, one of my favorite boards, and I would do it forever if they... I don't know if I'm adding that much value, but is The Atlantic.

    15. TF

      Mm-hmm.

    16. CJ

      Which is private, so it's easier, but the quality of the people involved, it's a very different part of my br- I mean, it, we're doing the business brain stuff, but there's also, like, you get to meet these amazing writers, and you get to-

    17. TF

      Yeah

    18. CJ

      ... be part of, like, exchange of ideas about the future of democracy. Yes. You know, that's enriching me, right?

    19. TF

      Mm-hmm.

    20. CJ

      That's the other thing, is making sure there's an exchange in the board of you're learning, you're getting enriched, they're benefiting, and I don't think it's easy to always get that balance right, and so you just have to be careful. I think you just have to be. And I, I, I think I just didn't realize the level of commitment, not just time, but sort of to do it well.

    21. TF

      Mm-hmm.

    22. CJ

      I mean, it's goes back to renegotiating.

    23. TF

      Yeah.

    24. CJ

      So what I'm doing is I'm saying no more boards until I've renegotiated some of my current commitments, and then we'll see.

    25. TF

      That's also very powerful language right there, right? Like categorically, "I have a policy of saying no to X until-

    26. CJ

      Yeah

    27. TF

      ... I have A, B, and C."

    28. CJ

      That's right.

    29. TF

      Done deal.

    30. CJ

      And by the way, people can't argue with that because they're like, "That does sound-

  25. 2:06:50 – 2:14:20

    Pushers and pullers.

    1. CJ

      broken.

    2. TF

      The t- I'm telling you, that's, that's your next book. The [laughs] I really think it could do well. So I have to ask this 'cause it's of acute interest for me personally, also because it might help me individually, but also with employees of mine. Managing high performers. How do you get extraordinary output from extraordinary people without burning them out or letting them burn themselves out?

    3. CJ

      So if I was like, what are the pantheon of management lessons? So one of them is you gotta manage different people differently.

    4. TF

      Mm-hmm.

    5. CJ

      Another pantheon lesson is spend disproportionate amount of time with your high performers because-

    6. TF

      Mm-hmm

    7. CJ

      ... instead what we all do is get all of our time sucked by the folks who are struggling, and then we don't invest in the high performers, and then they're either burning themselves out or finding a new opportunity because they're not realizing they're high performers and benefiting, or they know they are, and they're not getting investment, and they're like, "I'm gonna go get investment somewhere else."

    8. TF

      Yeah.

    9. CJ

      So number one is how do you manage them, is you make sure that they are a priority of yours, even though they are perfectly good on their own, which is the sort of dilemma, right? Like, how do I help them?

    10. TF

      Yeah.

    11. CJ

      I came up with, in my book, I steal... I mean, I don't steal, I ... credit. I source a- a lot of frameworks

    12. TF

      The book Scaling People: Tactics for Management and Company Building-

    13. CJ

      Oh, yes. Thank you

    14. TF

      ... just to throw it in there.

    15. CJ

      So there are a lot of QR codes. You can scan and look at the sites where I reference a lot of materials and books. Conscious Business, Fred Kofman's in there. One framework I think, I, I mean, as far as I can tell I made up myself, [laughs] was a top talent framework.

    16. TF

      Hmm.

    17. CJ

      Which is, again, I try to, like, simplify things, but I think high performers fall into two categories, and I call them pushers and pullers. And so the pusher is the one who's like, "Give me more, give me more." They're often wanting to get more comp too, but they're like, "I want recognition, I want responsibility, I want scope, I wanna move the needle, I'm high impact." They're very impatient with themselves, with other people. They can be a little high friction for the team, 'cause they're, like, going for it, grabbing it, grabbing it. But, you know, it's fun 'cause you load 'em up and they're just, like, carrying the whole thing up, you know, like, up the hill without you.

    18. TF

      [laughs]

    19. CJ

      But they can be tough. My main coaching often ends up with them is saying, "Until I believe that the people working with you love working with you, I don't think you're succeeding." And they're like, "What? What?" 'Cause they're all keeping score, but they're keeping score in the sort of maybe early-in-his-life Tim Ferriss version, I don't know. [laughs]

    20. TF

      Oh, no, that's a fair assessment. I mean, I think I am a pusher as an entrepreneur for sure, and that I've learned how that can be a liability, right? It can be a huge superpower and it can be a huge liability.

    21. CJ

      Right, and your job is to sort of, like I say, you know, giving direct feedback is holding up a mirror and just being like, "Here's the beauty of you and here's the liability part, and if you can't show me that you can work on the liability part, I can't keep loading you up."

    22. TF

      Mm.

    23. CJ

      Because in the case of the pusher, yeah, they might burn themselves out, but they actually, like, burn out the people around them. So that's the pusher. The puller, it's funny, this happened to me in a couple of conversations I've had. I'm usually being interviewed by someone who's, like, the pusher and I'm the puller, but anyway, I'm the puller, is someone who, no complaints, you load them up and they're like, "Yep, yep, I got it," but they're not asking for it. They're not grabbing-

    24. TF

      Mm-hmm

    25. CJ

      ... it. They're not pushing, but they're highly competent, they're very organized, they're, they're very consistent, reliable, and you just... And they have good judgment. And you're like, "Okay, I know that person won't screw that up. I know that person will get the people to the party and the, the..." You know, whatever it is, and you just start loading them. And they don't renegotiate. They don't know how to say no, and then they explode. Like, they basically implode or explode.

    26. TF

      That's what I've run into with past employees.

    27. CJ

      Yep. Yep.

    28. TF

      Mm-hmm.

    29. CJ

      And there's some, like, I went through a period of my own development where I was like, I think of it as my martyr period-

    30. TF

      [laughs]

  26. 2:14:20 – 2:16:01

    Parting thoughts.

    1. TF

      this has been a fantastic conversation. Thank you so much. I've had so much fun. I've taken copious notes. I'm gonna be following up on a million side quests, as we call them.

    2. CJ

      [laughs]

    3. TF

      But important side quests. I've taken notes of phrasing that you've used, all sorts of things. So I am looking forward to actually digging into my homework. I will not stay up all night, for the record.

    4. CJ

      [laughs]

    5. TF

      I'm trying to also, health first, sort of foundational along with the awareness.

    6. CJ

      Yes.

    7. TF

      Having the vehicle to do the things you wanna do. Your book, which I highly recommend to folks, it's incredibly tactical. Scaling People: Tactics for Management and Company Building. Tons of templates, tons of frameworks, lots of specifics that you can apply immediately. People can find you, correct me if I'm getting this wrong, but on Twitter @CHughesJohnson. We'll link to LinkedIn as well. Are there any other websites or anything else that you'd like to point people to?

    8. CJ

      The Stripe Press website you can find Scaling People, and you can find... Actually, I did interviews with a bunch of leaders that there's digital-only content, uh, which we can give you all the link to that. But-

    9. TF

      Beautiful

    10. CJ

      ... but no, thank you, Tim. This has been wide-ranging, as promised-

    11. TF

      [laughs]

    12. CJ

      ... and stimulating, and I've got some recommendations I'm walking away with, so thank you.

    13. TF

      Oh, thank you so much, Claire. And for everybody listening, we will link to everything in the show notes. This will be, uh, encyclopedic, and you can find that at tim.blog/podcast, and you can just search for Claire, and this will pop right up, and you'll find everything that we discussed. And until next time, be a little bit kinder than is necessary, not only to others, but also to yourself. And as always, thanks for tuning in.

Episode duration: 2:16:12

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