#724: Claire Hughes Johnson — How to Take Responsibility for Your Life, Create Rules That Work, Stop Being a Victim, Set Strong Boundaries, and More

24:18If they're later in their career, it's a little more ingrained and it's quite hard, especially because they tend to not be aware of it because they've somehow been successful operating in that mode. And so they're kind of like, what are you saying? You see leaders who, you know how they behave, Tim, is they say, well, if it's not under my direct control, then I am not responsible. And so they become empire builders. And some organizations let them get away with it. They're like, sure, you can have all the infrastructure teams then. It becomes this weird failing upward problem where people say, well, if I can control it, I'll take responsibility.

24:52If it's within my house, then I'll take responsibility. So people satisfy that checkbox by giving them more and more resources. What a nightmare. Exactly. And it becomes this weird expanded scope of this person who actually doesn't take responsibility. It's a pattern I've seen. For people earlier in their career, the easiest coaching move you do, which I'm sure you've heard, or someone's done it to you, I've certainly had it done to me. They're saying, Lucy didn't send me her notes. And you're saying, what could you have done differently? And you have to let uncomfortable silence then. And some people will then say, what do you mean?

25:25You're like, oh my gosh. But some people will say, well, I guess I could have helped Lucy write the notes. So what I try to do is stay in the discomfort, which is hard, and just sort of like, let's list out a few things you could have done differently. And not be judgmental, like not judge the things, just say what it was. So you could have helped Lucy write the notes. You could have set a deadline with her that was ahead of your deadline. Right. Put a deadline in a sauna where people can actually see it. You could use a productivity tool where you could see. I love those tools because that's sunshine.

25:55Sunshine is a great disinfectant, Tim. Like if everybody can see that Lucy has not done her action item, that is going to help Lucy be more accountable. But the point is you come up with this list and the person often is like, wow, you're right. Really what they're kind of going to have to admit to you is they're being a little lazy. They're not helping others do the work. They're not a good collaborator. And that's what I sometimes do with someone who's like, you know, if this is a pattern, I say, you know, I see this pattern. Do you see this pattern where you're waiting for other people all the time?

26:24Tell me more about why you think that's happening. Why are people not delivering for you? And the question is like, either it's because they haven't figured out how to do action items or accountability or be clear about deadlines, or there's someone people don't like to work with. I always call it like going meta, like you're looking from the balcony at the situation, which is a term from adaptive leadership. Are you on the balcony? Are you on the dance floor? And if you're on the balcony, you try to get the person up there with you and say, why do you have this pattern of people not helping you get your work done?

26:55And then I think of it as going to the basement. I know this is, I'm a very visual person. So we look down and they sort of, if they acknowledge it, they say, yeah, I guess I see that. And I say, well, let's talk about a few examples. And we come up with some examples. Then we go down and we're in the scenario. And I say, let's do the five whys. I mean, everyone loves the five whys. I'm like, why do you think Lucy didn't send you the notes? Well, she's not good at deadlines. Okay. And then this is a wonderful expression that I learned from some coach I had a million years ago. Be that as it may, which is not normal English language, but I don't know, it worked.

27:26Sort of like, be that as it may. Okay, maybe Lucy's terrible at deadlines. But why else? Well, I didn't ask her to get it to me at a specific time. Okay. So maybe there's a thing. Why else? You know, and you're sort of pushing them. And sometimes, not every time, they'll sort of say, well, I don't know, Lucy and I don't work that well together. Aha. And you're like, oh, say more about that. What do you think's going on? And of course, by the way, your left-hand column, Tim, is it's because Lucy doesn't like you. Because you blame her for all of your missed deadlines, right? But I can't say that because that person is going to go from learning to barely in learning mode.

28:07I'm trying to bring them along with me and they're going to just shut down. And by the way, they may never admit that Lucy doesn't like them because they blame her for missed deadlines, but they're going to realize that their manager, who's me, is not letting them off the hook. If they can't get into an agency, a player mindset, I'm a responsible party for my work and others, then they are going to be off my team. If I can't coach them out of it, to your point, there's two gaps that I think are really hard. One is people who can't stop being victims. And the other gap I call self-awareness gap, where they think they are the best in the world.

28:42I once worked with this BD person who was like, I can negotiate a deal better than anyone. And talk about not being in a learning mindset. I'm like, do you not think we should get any outside advice? I'm exaggerating a little bit, but really unaware that they had any potential blind spot or had never done a deal like this deal. And I'm like, how are we going to close this awareness gap? because the people around you are saying you are not the best person to negotiate this deal. And I'm trying to hand it to someone else. And you're like, what? You have no one better than me. And that's a very hard gap to close.

29:17Yeah, totally. And I promise we are going to spend some time on self-awareness. The book I've probably gifted most to my friends and house guests and so on in the last few years is actually a very short book called Awareness by Anthony DeMello, which is outstanding. I need to read it again. I read it probably once or twice a year. So we are going to spend some time there. I'm kind of tiptoeing around the edges of the dance floor, as it were, and tiptoeing and sidestepping on the balcony because I want to paint a picture of you also as a person, not just the concepts. So we are going to spend some time there.

29:52Also, just as a side note, if you decide to write another book, I think the toy is broken as the title, and then the subtitle could be like a high performer's guide to taking responsibility. Oh my God. So good. The toy is broken. Tim, you're hired for my marketing team. I got to tell you, we're not always the best at naming things at Stripe. So you're invited. That's the one thing that I'm good at. That's the one thing that I am good at. You're on the team. Congratulations. Thank you. That's a hell of a team. I'm in. My boss sucks. Oh wait, I'm my boss. Oh, you're the boss. Terrible. Terrible.

30:26You said you don't recommend a lot of business books. And I am going to come back to Cheryl and Excellent in a little bit, but 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. And that book is To the Lighthouse by Virginia Woolf. What is your history with this book and why do you recommend it? 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.

31:02And my mom was a college professor for a long time. And 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 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. Sort of like when you see a product. I think you love innovative products. When you see something, you're like, that is going to change my life. And so I think that To the Lighthouse represents, I mean, Virginia Woolf is a writer that resonated for me.

31:47And 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, 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, it's basically one of the earliest feminist manifestos that exist. 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.

32:34I mean, 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 worry that we started to not study certain artists because they've said some things or done some things, which I would disagree with. 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 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.

33:11I will be honest with you and say when I wrote my thesis in college, I was going to 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 love 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 this book, The Passion, and then a book called Sex and the Cherry. She's published now several books. But Jeanette Winterson, I think, is a descendant, in my opinion, of Virginia Woolf.

33:50And I was like, I'm going to examine these two novels. And I didn't choose To the Lighthouse. But I will say that, and To the Light is not an easy read. And I want to own that. Also, I think it's very, To 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 the 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. You're like, the points of view are shifting. Who's the real narrator here? What is the story?

34:20There's not like, you're not being driven by your classic plot or character driven story. It is much more internal. It's like John Wick in some sense. I'm kidding. I'm kidding. I feel like the plot of John Wick is pretty clear. You know, I am going to take vengeance. Excuse me now. I'm going to come out of retirement and kill everyone. Oh, what a great work of art. I'll be the first one to tell you. I read a lot of mysteries and thrillers and I like movies like that, actually. So I'm very multidimensional. But I think for To The Lighthouse, you find something new every time you read it. You think about life, death, the human condition.

34:55What 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 lighthouse and they go out in the boat. Like you literally feel like you're surfing in a boat. Like that feeling when you're like, I'm not really connected to firm land, but I'm in this inner sanctum of people's heads. So I think that it changed me because of the way it felt to read it. 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.

35:29I should go read To the Lighthouse again because now that I am a mother and a wife of a certain age, I'm like, this book is going to resonate a lot more for me. But what's amazing is Virginia Woolf was never that. She didn't have children, and she unfortunately did kill herself. She had a lot of demons, and actually the way that she killed herself, brutal. Which she did. She filled her pockets with rocks and drowned herself. And I think that a lot of artists are tortured, but the fact that she could project into this Mrs. Ramsey and this woman, this very maternal figure, was a sign of true artistry.

36:04Sorry, that was very long. That's why I have a long podcast.

36:10Just a quick thanks to one of our sponsors, and we'll be right back to the show.

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37:18That is linkedin.com slash TFS as in Tim Ferriss show. One more time, linkedin.com slash TFS. Terms and conditions apply.

37:30So I'm not going to let it go. I'm going to continue to chew on this bone a little bit. And for the record, I actually love John Wick. But I don't want to dwell on John Wick. I was going to say, first, if you like dream state evoking novels, the one that blew my mind, and nine out of 10 people hate this book, so it's a very strong caveat, but it's Little Big by John Crowley, who's actually a poet by training. It is so unbelievably good. You have to We've slogged through the first 150 pages, but beyond that, it's absolutely stunning. So what are the reasons to read fiction aside from the, as I think you put earlier, the insight into the human condition?

38:11If you were trying to get someone to take that first bite of the forbidden apple of fiction, are there any other points that you would make? How do you build empathy? How do you understand everybody has a story? 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. You want to 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. So I think it's a very cheap way.

38:46And there's also to build like emotional intelligence. 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 going to struggle. You are going to 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.

39:24Or, you know, I'm saying, no, you yourself as the reader, if the book is really good, start to feel the feelings. You start to feel like, oh, I lost a child. Emotional exercise is hard. It's either happening to you. 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 going to get emotional exercise from, in my experience, a lot of people get it from film. They get it from video content. 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.

40:08And then that guy rescued the dog. And you're sort of like 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, I like to see people rescue animals who are drowning. But like, no, I really want, I think it's a serious film. Maybe it's John Wick. John Wick might be a way to detoxify your left hand collar. I almost cried. I said to my friend who'd seen it before, I was like, if they touch that dog, I'm going to lose it. And he just stayed silent. I was like, oh no, here it comes. Yeah, anyway. But anyway, point is, I think it's emotional workout.

40:42Literature, great films. Yeah. The other thing I would say is fiction is often much more efficient and elegant in delivering truths than nonfiction. And that's speaking as someone who is a militant nonfiction purist for decades. And I really wish I'd started earlier with reading very, very high quality fiction. So what was your gateway fiction? What got you? I'm so glad to hear you're a convert. Oh, gateway fiction. I mean, I would say that early on, I was an avid fiction reader. So as a kid, there were books like The NeverEnding Story, and then later Dune, for instance, science fiction, A Stranger in a Strange Land by Heinlein, which were also very condensed thought experiments.

41:31This is part of the reason why I like sci-fi quite a lot. So for folks who are male, also female, but if they're male tech on the spectrum over performers, I'll usually steer them to say Ted Chiang short stories like Exhalation is his second collection. Then I stopped for a long time because it was time to get serious and follow the rules and be a business guy and so on and so forth. So I read all the nonfiction stuff. And then I would say later on, now that I'm reflecting on it, because I'm trying to pinpoint, and maybe it's because you seeded me with the Argentina. I used to live in Argentina for about nine months in 2004.

42:11And in an effort, this is going to sound ridiculous to people who are familiar with his work, but I wanted to read fiction in an effort to get better at Spanish. So I found side-by-side Jorge Luis Borges, which is incredibly challenging in Spanish, I will say right up front. But that ethereal kind of magic realism, fever dream type of conjuring that he was able to accomplish was intoxicating to me because it's effectively mind control, right? Like language on some level is mind control. If you said to me, like, what's the other to the lighthouse? I would say a hundred years of solitude. Gabriel Garcia Marquez and my introduction to magical realism.

43:01And what's interesting is you went to this because a lot of guys I talked to, they're like Neil Stevenson, three body problem. Like, it's like there's a sci-fi dune is always in there. Contact, you know, like whatever. It depends on when they were born. But like you get this sort of sci-fi. But what you just did, I love, which is where else is there sci-fi? In a lot of Latin American literature. Isabella Allende, Borges, Marquez. And that's where like maybe the genders can meet, which is like really emotional, gripping, multi-era stories, but really wild stuff. It's like Dream State is happening.

43:37And you're wondering, were they on drugs? What's happening here? Of course they were on drugs. I 100 % love that you went there. Because I think it's when you're pushing the sci-fi into a different realm. It's magical realism. The most creative people I know, this includes business for sure. The most creative, if they're the most creative dealmakers, they read and consume very widely. They're not going to this huge buffet and always eating the shredded carrots. Okay, fine. Shredded carrots. Yeah, they're healthy for you, easy to eat. I get it. There's a whole buffet. And they end up being able to connect disparate fields and ideas in a way that end up being ultimately incredibly interesting and sometimes very profitable.

44:20And I would say, who was it? He worked with Daniel Kahneman. I want to say it was Amos Tversky, something like that. But he said something along the lines of researchers waste years not being able to waste hours. I'm butchering the quote, but it's like, if you feel so rushed that you cannot read a short fiction book, that is a symptom of a much larger problem, I would say. And so proving to yourself, like creating the slack in the system to do that has its own benefits. All right. Fiction conversation check. We believe in it. Yeah, we believe. We believe. All right. So let's come back to, I'm going to take a further, not digression, because this is just a natural conversation, but we are going to come back to feedback for direct reports.

45:05But I feel like we needed a smoother off-ramp. So what might make a nice off-ramp from the fiction is something that is highly, highly, highly personal and nonfiction, and that is a working with me document. So I want to 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 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? A working with me document is basically trying to write your own user manual.

45:42And 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 going to 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 I 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?

46:14And one of the panelists said, well, I copied this thing that Urs, and this is Urs Hulzl, 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 like a lot of what really makes your Google results come very quickly. You can thank yours. 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.

46:45I 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, 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. So I invited a comment. I said, for those who actually have had me as a manager, please tell me how on base I am or not. And then I gave it actually, I at the time had this really amazing woman who had been a manager in my organization.

47:20And then she went on maternity leave and came back and asked to be my assistant. She said, I want to 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, she was actually, she's Irish, which is a theme somehow in my life. Like I really bond with the Irish. And she said, well, I feel like at the end, you know, you don't even acknowledge that you like good crack and crack, which I'm saying wrong in Irish is like sort of fun joke humor.

47:55Yeah. She's like, you know, your meetings, she said, I've never been in a meeting with you where we didn't laugh at least once. That's the kind of thing, by the way, that you don't know because you're never not in a meeting with you. Right. And so I was like, oh, that was super helpful. But I feel embarrassed that I'm like, I said, am I saying I'm funny? She's like, no, you like a good laugh. It's true. I'm not particularly that funny, but I really enjoy humor. Anyway, 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.

48:21But what's amazing, Tim, is that document has not changed markedly. Since 2009 or whenever it was. Like 2009. It has not changed very much. And we can decide how we feel about that. But I think 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 kind of 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. In today's world, you know that, I literally have people that I work with, actually.

48:57I think I work with Patrick and John Collison, the Stripe co-founders. Of course. They contact me on every channel. How is it that you're texting me, Whatsapping me, calling me, slacking me, rarely emailing me? Actually, emailing is probably the least interesting channel to them. So 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 this kind of decision, how long will I need? What kind of data might I like? I have a section in my doc, which is I tend to be intuitive.

49:28So I've taken a lot of different personality assessments and I actually don't really spike in a lot of areas, but I spike as highly intuitive. Meaning you come to me with something, I intuitively have an opinion. I'm like, oh, I think this is going to be the right thing to do. Or I think I say I'm intuitive. And then I write dot, dot, dot, don't worry, but data driven. So I'll tell you my intuition. And then I'll say, 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 just get out there and start operating without any basis. But I think that you're trying to reflect that, but I think it's important to reflect that.

50:04Like, for example, in my first version, one thing that did change when my team read it was, I said, I'm not a mic. By the way, every manager is like, I'm not a micromanager. It's like a common, everyone's like, 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'm concerned, you're going to 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 because it means I'm having an issue with trust, which means I'm not sure I'm happy with the product.

50:34So this guy who worked for me, he said, I'm not sure that you're accurate about this. And I said, well, 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 that was, 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 sales compensation scheme. I was like, that's the first time I'd ever built one. And I was really like wanting to learn.

51:06And he said, well, you never told me that. So as far as he was concerned, I showed up in every damn thing, this poor guy had scheduled and he's supposed to be leading and he's supposed to make a recommendation to me. And I'm like reading all the same stuff, participating. I mean, I was, it was looking back, I'm really embarrassed. I was like, I can't believe I didn't tell you because I had full confidence in this. He was probably, by the way, better positioned than I was to build this thing. And I was counting on him, but then I went and undermined him. And so that's why, by the way, the working with me document is also helpful is because if you have good relationships with people you work with, they will tell you, yeah, you think you act this way, but you really don't.

51:43So then I had to add a section about, sometimes when it feels like I'm micromanaging you, it's because I'm trying to learn. The first time I've ever done a thing, you are going to see me hyper-involved. But what we should do is establish that ahead of time. And if I don't, please call me on it. Anyway, the point is, yeah, the working with me document became something I just shared today with anyone who starts to work with me closely. And what happens in high growth environments like Google and Stripe is like your team changes a lot. There's new people. People's managers change. It's hard. You don't love that.

52:12But like I've had people come to me and say, you're my fourth manager in a year. So what are you trying to do? You're trying to create a shortcut because there's anxiety when we first work with someone. Well, should I call you if I have some kind of crisis? When you're at night and Slack looks like you're available, should I Slack you stuff? Or should I wait till the next morning? Or like you're looking for guidance, you're looking to read the person. I'm like, just tell them, tell them how to work with you. And then that reduces the anxiety. And ideally, they write their own manual. And then you've both sort of shortcut some of the get to know you stuff.

52:42So you can just jump right into working together. This is something I wanted to explore because jumping, I suppose, to something you explore at some length in your book, which I definitely recommend people check out. 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. Make the implicit explicit. And that shows up in so many different ways. It can manifest in so many different ways. And I want to stick with the Working With Me document for a minute. This first came to my attention because I had Dustin Moskovitz on the podcast from Facebook fame and then certainly of Asana.

53:29And he shared his Working With Me document. And I've since seen a few versions of this. But I wanted to get your take on what might be worth adding to this list of questions. Here are a few. 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? Are there other questions that you have found helpful to address or topic areas worth including? Having seen these letters, having crafted your own Working With Me document. My Working With Me document was published in Elad Gill's book, High Growth Handbook, and went like a little bit viral, like viral for Claire, not for Tim Ferriss.

54:14But like, still, I was like shocked at how many people that I've never met had like seen it. And I also got some criticisms on the interwebs that was like very egotistical in some way. It was sort of like, here's how you make me happy, which I was like, okay, that's like a totally fair criticism and not the intention. By the way, I'm like pretty highly empathetic. I'm like, I'm trying to reduce anxiety and help people feel comfortable being honest with me, whatever. But I get it. It seems very self-absorbed. So one of the things that I'm reacting to is like, the question, I guess, if I were going to phrase it as a question, it would be, how do I help you make great decisions?

54:51Or how do you like to make decisions? But I think in my document, I just sort of have headers, like decision-making. Because I'm not, that's why yours called it user manual, which is a very technical, like an engineer is going to be like, I'm going to write a user manual to me. And I just called it working with me. There's a section on what types of information do you like to see? Because that's different than how do I want to 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 like someone on your team is having a major life event, I'd like to know about it.

55:27I'd like to send them a note. I'd like to say, I'm sorry, or celebrate their child. Or, you know, I think, 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. 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, I'm like, Like, if you send me FYI. That means no response. That means, well, it means, yeah, like I can read it later and it's interesting, but I don't need to respond.

56:05And I'm like, I can't believe this, but I think I have to, back to, I think you asked your guests a question of like, if you were going to have a billboard. Yeah. I think the fight for me and my billboard would be, is it make the implicit explicit or is it undermine the superstructure from within? I'm not sure, but one of those, one of those is my billboard. But the first one, I think I get the first one. Making the implicit explicit is so valuable. By the way, a lot of people are like, I love that your book is so humanistic about people and how to care for. I was like, folks, my book is about getting results.

56:40I do appreciate other humans and I love working with them, even though sometimes Patrick calls and I would be like, oh my gosh, this is the hardest problem. And we'd go, oh, if there were no humans involved, it'd be so much easier. but point is I love humans and the human condition, but I really am talking about how do you get results and how do you get results? You get super clear and transparent about anything implicit. You make it explicit and you're like clear, like this is a process we're going to go through it to get to this outcome. And what is the outcome we want? Make it explicit. I mean, Tim, you, I think are the master of this.

57:13What are we measuring? Why are we measuring it? How will we know if we won? And I would add to that. And what process will we go through together to get there so that no one is guessing or reading the tea leaves or wondering why another team is doing the same project. Put it all on the table so that we can get to the end faster and frankly, more inclusively. And why do I care about inclusion? Yes, inclusion is a good thing for people to feel better and included, but actually because if you've hired a bunch of smart people and yet they don't feel included, they will not share their opinion. And the reason you hired them is because they're smart people who bring diverse opinions.

57:51And if they won't say them, then you're not really benefiting from all that work hiring them because you want a better outcome. This is all about results. But I think it's a little windy to get there sometimes. Yeah, totally. Until you make it explicit. 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 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.

58:29Based on the little that I feel like I've sort of felt out with our Fiction Love Fest, I think you would really enjoy this. It is one of the better short films I've ever seen. It's really good. It's really, really good. So An Irish Goodbye. I've got, what is it? Little Big and Irish Goodbye. Start with an Irish goodbye, because 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. Okay. All right. That's fair. I'll do it. It's like the amuse-bouche before you try to chew on the fever dream. And I'd also say, also, I'd love a good Irish goodbye.

59:02I used to find it a little offensive, but now I'm like, gosh, there's some real beauty in just disappearing. 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. 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 slash rules, systems, anything that they have ended up using that they have found helpful.

59:39And I will say in advance, 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 and it's hard. So I understand that. Being that as it may. See, it's a beautiful experience. There we go. Be that as it may. Be that as it may. You are still going to have to enter this. Yeah. Are there any sort of email policies, systems, rules, implicit things that you make explicitly that you found helpful? I actually worked on Gmail right after it launched at Google.

1:00:15And you should think I would be a power email organizer. And I'm okay, but I'm not great. But one thing that just stuck out in my mind as you brought this up is I had a good friend who was an 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. Honestly, whenever I look at my inbox, I think of this training where they gave them some 30 minutes, some window. They gave them an inbox and they were like, you need to process all this and kind of do the right things, right?

1:00:50Okay. And so in this inbox of like a hundred 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. Sounds like an anxiety dream. It'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? Yeah. And I kind of was like feeling like Japanese game show. I'm like, would this be a show that people might want to watch? And I think there is a sector of people who might find that like really interesting to watch.

1:01:22So sometimes I look at my inbox and I'm like, oh my gosh, I have 30 minutes and I need to find all of the legal time bombs. but one of the things that I think I'm very good at on email is it's a set of people in my both professional and personal life like they get opened immediately and I'll open it and if it's by the way read FYI I'll read it later I really want to make sure I mean it's easy some of these people it's like easy it's like your kids by the way my kids are 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.

1:01:57If the founders of Stripe emailed me directly, I'm going to open the email pretty freaking quickly just to make sure. So it's sort of like your boss. But I do think that some people have a methodology, which is either LIFO or FIFO, last in, first out, whatever. Yeah. And I think that that's tempting. My husband does this a little bit. It bothers me. I'm like, you have cues, which is who is it from? And is it a group or is it direct to you? and use those cues to prioritize. And so if you only have 30 minutes, you know where to start. That's one of the things, and it is a combination of the people and what's being sent to you directly.

1:02:36So I think that's like a number one rule I have that I'm pretty actually good at. So there's certain people who feel I'm very responsive on email because I am very responsive to them. I'm not maybe responsive to everyone as consistently. The other is I have, this is like more of a cheat, but you're an investor, I think, right? So I've invested in some companies and a lot of them send these investor newsletters or investor updates. And of course, because I do have some Gmail skills, I label them. I know there's a folder full of them and I have every intention, Tim, that on Friday for like two hours, I'm going to read those investor updates, okay?

1:03:18You know what? That is not correct. Sometimes when I'm on an airplane and I'm trapped. I like open and start reading them, but like, I am not reading them in a timely fashion and I'm sorry, all the founders I've invested in. I'm sorry. I'm not reading your investor updates in a timely fashion, but what I've learned to do, and this goes back to making the implicit explicit and also to another rule I have, which is strive to set expectations with people. So now when I invest in a company, I say to them, I say, look, you may email me. I'll give you my email. I said, I'll give you my cell phone. I'm quite good on text, but please don't abuse it.

1:03:54And if you want to WhatsApp me and not text, whatever, either of those is going to work. And then I say to them, I want you to know, I really appreciate getting the investor updates. I will not read them in a timely fashion. I may not read them at all. If you need something from me directly, like you need help me interview this person, or I have a, you should get in touch with me directly. Not as like at the end of an investor email, it says, please help us hire some data a scientist. And cognitive load wise, I'm like, phew, I have been feeling so much guilt about not reading their, by the way, they spend so much time on them and it's terrible sometimes, but I no longer feel guilt.

1:04:32I've told them you must contact me directly. 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 of ignoring this kind of thing. And if you need my attention, please, 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. 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 of what expectations they should have of you.

1:05:08How else does this renegotiating show up? This has become, it's embarrassing to say, but I'd say maybe in the last two years has become such a revelation for me in a sense, because I always thought about negotiating as the thing you did in the beginning. And I got, I think, pretty good at that. And at times though, I would have, who knows, maybe I 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, 30 points because I felt trapped by these commitments that I made when I was compromised or rushed or lazy, fill in the blank.

1:05:47And 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? Examples would be really helpful here so people can really get a grasp on it. I'm having like almost a physical reaction to relating to you about this calendar. It's like your past self. I used to say, oh my gosh, I just mailed myself a letter bomb. So one is, of course, we all strive to improve, which is do not make a decision in the moment about a time or a commitment of resources or time without trying to project your future self.

1:06:27But 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, because we've only got 30 minutes or we might fail the corporate training test. Or the Japanese TV show, I don't want to come in last. Yeah. So one thing is trying to be better about projecting. And I also had a friend who's like a very kind of spiritually in touch person. And she said, when something is requested of you, she said, you need to sometimes listen for the quiet no. Can you say that one more time? So she said, when something's requested of you, a person, I mean, she's like sort of like, sometimes your reaction is, wow, yes.

1:07:04Right? You've had this. I mean, hey, Tim Ferriss asked me to be on his podcast. I was like, yes, emphatically. That is something I want to do. That is easy. My future self is very happy to be, 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, because we are often feel like we have to say yes. And her trick is, and I know this wasn't the question you asked me, which I will answer, but her trick is - These are really closely related. I'm so interested in this. Yeah. I think they are.

1:07:40Do not respond immediately. Because we often feel, I mean, if you're someone who 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 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?

1:08:18Should I spend my time? Oh my gosh, I have to fly to the city. Like you have to really think. So I think 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. I had a delayed travel earlier this week and I was looking at my next day and I was thinking, well, I am going to get home, but I'm going to get home at like now two 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?

1:08:48And so I was like, I am going to renegotiate those commitments. I don't even have to say that I was delayed. So it's a good skill. But what I look for is a pattern, a pattern of why am I renegotiating this stuff? It means I'm not making the right decision in the first place. So I listen for the quiet no. But if I find myself renegotiating, it is often about, yeah, commitments I've made. Commitments, especially of time. My mom was a very talented, apparently, mathematician in college. And my mom went to Harvard, well, Radcliffe then. But I think it was pretty rare for a woman to be a star in the math department.

1:09:23Super rare. and she decided to go get her PhD in history and to major in history. And I said, why did you switch? Why did you make the switch? And she said, I realized that there is a trade-off that most people find themselves making between money and time. And she said, I knew that if I prioritized math, it would likely lead to a more lucrative career. By the way, my mom was like out there, she was going to work and she did, and she was going to 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.

1:10:05And why? Because professors have more control over their time and they have the summers off 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 to realize you're going to trade money and time. I think it's Peter Thiel who says like, people don't value their time highly enough. They just like, don't get 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.

1:10:37So I've become less responsive on email because I am trying to stop myself from mortgaging my time. You may or may not have had the same experience, but all right, here's an example. You're 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. By the way, to stop myself from saying yes to stuff, I make rules. I made a rule. I was like, no more boards. I also 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 want to be home. Of course, she doesn't want to hang out with me, but I want to hang out with her.

1:11:17What are the criteria to study curiosity? Could be just a few examples. Really important to Stripe. I still actually work part-time for Stripe and they get bids on my time. 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. And by the way, I had a great time and I met a great number of founders and it was actually a blast. So is it important to Stripe? Is it a personal connection that is meaningful to me that is asking of my time treasure talents?

1:11:50My criteria is not to say yes to default, but it is to, 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? And if I can control when it is, and it's a personal connection that's meaningful to me, I will 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 of criteria of like, but I often will say 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?

1:12:27A lot of it is buying time. But I have these rules about things because 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 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 the board meeting? And then she told me why she really needed help in this particular moment. And there was a situation where having someone who was sort of a friendly, who was neutral in the room was going to be valuable. So I said, okay, I will come, but I will not, like, I really want to set your expectations right back.

1:13:00I was like, I am not, this is not going to reel me in. I'm not going to 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, you know, of course, every board me. 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 you can invite me. 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.

1:13:33I can't even take three, four hours. And so I needed to renegotiate it. There's a quote that I have in my book that people find, I think the most compelling line in the book, and I keep having to remind them, it is not my line. Yeah, I know this problem where I'm like, no, no, no, no, don't attribute it to me. That was Mark Twain or whatever. Exactly, exactly. The line is from Ron Heifetz or Marty Linsky. These are the adaptive leadership guys who do the balcony and the dance floor analogy. And it is leadership is disappointing people at a rate that they can absorb. Yeah, I had that line underlined.

1:14:07It's very catchy. Because it really makes you think and it's kind of dark too. Yeah. What does that mean in concrete terms? And then I'm not going to let go of the renegotiating because I'm going to come back to that. I want to ask you about phrasing and wording that you use, but let's talk about leadership and disappointing people. Well, I think one of the ways that leaders disappoint people is their time. You don't have unlimited time. You're the CEO of a company. There's no way you're going to 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.

1:14:40And also you get a little bit of forgiveness when you're the CEO, I think. But leadership is disappointing people at a rate they can absorb. To me is about, you know, management is very knowable. It's like, how do I get from point A to point B? What people do I need? What's the scope? How are we going to measure it? Here's the project plan. Here's the milestones. Here's the talents I need. And now I'm going to deploy and delegate. And I think leadership is very unknowable because it is essentially having a vision, an idea, a goal that you haven't even fully understood yourself, right? Often. Yeah.

1:15:15It's like, we're going to climb this mountain that no one has ever climbed before, by the way. And you have to be really convincing to build followership. You're painting a picture of the top of that mountain, man, and it is awesome. And the climb is going to be like really challenging, but really rewarding. And you are going to get on that journey with those people. And you are going to be wrong about a lot of what you just said, right? No, actually, it wasn't as easy up the south face as we thought it was. Yes, we did actually need special equipment. I mean, come on. You don't even know how you're going to get up there.

1:15:54The analogy that's more concrete that I use is I came into Stripe and look, it's a product that has people's money. And you need to have good support experiences when something is wrong with any kind of payment. I'm expecting money. I'm trying to take money. I'm moving money. There's a high expectation. And Patrick is like, we need to build 24-7 global support. We had really good ambitions. And by the way, I want to be clear. One of the things that Stripe has as a value is to be users first. It is always our most important operating principle. It is actually deeply in the culture of the company.

1:16:31So much so, Tim, that when the support team would get behind, the entire company would stop and answer support emails. And so this was becoming an existential problem because we had to do engineering work and other work to build the company. But we were like ending up on Fridays before the weekend because you want to get back to people quickly, answering support tickets. By the way, you hit product market fit, you get traction. This is a super normal problem. But it is not great because the product is people's money. It's a quality problem, but it's a problem nonetheless. And so Patrick is like, look, we need to have this 24-7.

1:17:07And I had to get up as the leader and say, I will build this. And I had built similar things for Google. So I wasn't completely describing a mountain I'd never seen. but I certainly didn't join Google when it was only like 160 people with 21 support people. And I was like, we are now going to do a set of things to solve this. And it took me a few years and it's not perfect and involved hiring very talented people. I don't get credit for what we built, but I still look back on that and I say, I can't believe I declared that I would get it done. And I didn't have a plan because I'm more of a manager.

1:17:42I'm more of like, I need to have a clear plan on how I'm going to get this done. And instead I was like, yep, we're going to have it. Public announcement. And I mean, Patrick kind of pushed me there, but I was like, this is uncomfortable. And I'll tell you, I did disappoint. Did I deliver it by the end of that year? Oh no, Tim, I did not deliver it by the end of that first year. Like, let's not kid ourselves. I disappointed, but I did figure out a way to do it. And I think people followed me. They kept following me. They kept believing we were going to do it, which is some combination of me being authentic, I think, me being honest about where we were, me having a plan eventually, me demonstrating that it mattered, whatever.

1:18:21So I think that's what it means, is like, you will not live up to everything you said, all the expectations of you, with your time, with your ideas. We're all humans. We're not perfect. And we're not fortune tellers. I'm not a fortune teller. So this ties into the renegotiating, actually, pretty well, because there are many different species of renegotiating. One was, you gave an example very early on in the conversation when Lucy was getting thrown under the bus, the dog ate my homework situation. And then we segued from that to the player versus victim. And the player would say, you know what, you're right.

1:18:59I committed to get this to you by 5 p.m. I didn't. And because this emergency popped up and I didn't let you know, I should let you know. How about 5 p.m. tomorrow or whatever the example was? renegotiation. So in this particular example, when it becomes clear to you that by whatever deadline had been agreed, you were not going to 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. So what is the language that you use to have that conversation, whether it's verbal or in email?

1:19:36I think you made the connection and then you didn't finish making the connection, But it is so easy to sound like a victim 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 is no way I'm either coming to that meeting or delivering 24-7 global support in six months. And so what does it look like? I think what it looks 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 priorities, here's what people need, here's what need my attention.

1:20:14And then I sat down with Patrick and I said, I'm hearing these four things. One of them was the support thing, by the way, that really need my attention. And I am going to rank them. And then I want you to see my ranking. And I want to agree on my level of priority. I said, because I can't make meaningful progress on four things at once. I can maybe keep, and I actually predicted in that moment, I said, because we had to build sales. We had to build recruiting. We had some internal operational stuff that needed to be fixed. And then we had this support smoldering fire. And I said, I think I actually need to build sales and recruiting ahead of fixing support.

1:20:54But I predict support is going to implode within the next six months. And at that point, you were COO. Is that right? I was COO. I was actually hired as chief of business operations. We just swapped titles with someone else, but it's a long story. But yes, I was basically COO. And remember, we're users first. This was a painful, because we were also not getting back to sales leads, though, Tim. I was like, you know, I'm also here to build some revenue. 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 getting back to our prospects.

1:21:26And 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. This is normal, by the way, this happens, especially 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 going to fix support in the first six months. We made an agreement. And then, by the way, Tim, four months in, complete explosion.

1:22:00And 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 going to explode. And then, I mean, by the way, it's 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. Point is, 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 going to reach a moment where you're like, there's no way we're getting to the top of this mountain.

1:22:28And so what you try to do is not come up and make a bunch of excuses. So what I think I did in those moments, we had written public goals in the company. We had plans. And I just want to 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. Love side quests. 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?

1:23:03And like, everyone's like, yes, Steve, yes, we can. Right. There's another version of reality distortion, I find, which is you can fix that thing in five minutes. It's now a joke between Patrick and I, because he'll be like, yeah, we could just like code that up. And I say in five minutes, it's not five minutes. So we had a consistent conflict where I would say to him, no, that mountain is not going to be climbed by the end of this year. I never actually said I was going to build that thing by the end of the year. And he refused to hear it. He was like, no, it really needs to be the goal. This actually needs to be the goal.

1:23:40Be that as it may, Claire. Yeah, be that as it may, Claire, I'm making it your goal. And I was like, okay, under duress, I am going to take this goal and try to put some language in it. I mean, I'm going to get a red, right? Whatever on your, I mean, that doesn't feel good. This is the other thing. It's beneficial to walk into a situation like that after some amount of career success so that you have some amount of self-actualization. So I was like, luckily, my whole identity is not tied up in this goal because I would have been destroyed. I would have really lost confidence. By the way, a lot of leaders you hire into a startup environment end up losing confidence just because you're getting pummeled, totally pummeled.

1:24:22And like, you need to sort of be like, no, no, no, I have identity outside of the success of this moment. But I was like, all right, I'm going to publicly get up in front of the company and have failed on this goal. But we disagree. We agreed to disagree that this is possible. What's also funny, though, is I I was like, I think he really believed it was possible. And he's very smart. And of course, then I'm going home. I'm like driving home at night. I'm like, has he ever built anything like this? No. Why am I even listening to him? But they reality distort you into thinking, yes, it's completely possible.

1:24:51Like, I don't know how. I got fooled. But what I did sort of commit to myself is like, I have to make meaningful progress. So what are some of the milestones we can point to? So what you do is you go in and you say, well, I was not convinced this was the right goal, but I agreed to it. Here are the milestones. that I'm glad we hit. So you kind of don't forget to point out you made progress. I think sometimes people get defensive. They're like, I don't want to be defensive. But you have to be like, look, it's like nothing happened. And then you try to be data-driven. And what I think, because this is where the context matters, Stripe's founders and Stripe's culture is very learning-oriented.

1:25:25Very, very. More so than almost maybe any startup I've come across. Yes. At an early stage, too. Yes. So think about the cultural context you're in. What did we learn? What did we not know and what did we learn trying to get there on this goal? What did I learn? By the way, some of them are mistakes I made. And so try to be humble. Stripe is also a very humble culture. Say, here's some things I thought I knew. By the way, I thought I did know. I was like, we were going to outsource certain things that I thought was going to be easier than it was. And that is true. And here's what I learned. Here's what I thought.

1:25:57Here's what the truth was. Here's what I learned. Here's now what we're going to do differently. And by the way, everyone's nodding in the room because they're like, cool, cool. We had a plan. We tried it. I mean, they're engineers. They know it did not work the way we thought it was going to work. We're going to try this other thing. So you basically do a retro postmortem, whatever you want to call it, sort of publicly in front of everyone in the language they like speaking. So the language Stripe likes speaking is learning. I made mistakes. What am I doing differently? What do I see next? How are we going to get there now?

1:26:29You know what I mean? I'm confident but humbled by this experience, and I've learned a lot. and here's some data that shows we have made some progress because that also people want to make sure like are we actually know what we're doing so that's what you do and I think depends on your context and sort of what language do you speak so that is a big example and that is I think a very effective way to as a player offer a mea culpa in a way yeah yeah at that point then and this may be if this is going to require a dissertation, then tell me and I can rejig. But how did you decide to scope the thing and then make a counteroffer effectively?

1:27:08Or was that even your decision to make? I don't know. In terms of like, okay, we've learned these things. These were some assumptions and then leading into the kind of now what? I won't do the dissertation version, Tim, but I will tell you one bind I found myself in consistently that I'm sure you have also is it's a talent bind, which is I can only do so many things at once individually, me alone. And I did feel like a victim. I'm going to be honest, because I had been trying to hire someone. I had hired someone. They hadn't worked out. Partly my fault, partly not my fault. And I'm in a meeting.

1:27:42This happened so many times, but I'm talking to Patrick and I'm like, look, we know so-and-so didn't work out. Here's what happened with that. We now have face a choice, which is you have Claire as a resource, me alone. Am I going to go lead support directly? Like, am I going to go start building this thing with most of my time? And what is the opportunity cost of that? What is the trade-off of me not leading sales, by the way, at that moment, which I was also leading? And this is where I fell into a trap because I had like a few too many needing to clone myself problems. And this happens when you're growing quickly, but it's still, I got into an egregious case of needing cloning.

1:28:19Then we're having a renegotiation conversation. Not even a reasonable case of needing cloning. Egregious. No, it was egregious. It was egregious. There was one point where, I mean, I think it's important that people, especially because they seem to think I have some like storied career. I'm like, there was a moment where I had taken a former colleague from Google who I was admittedly, I'll be honest, was trying to recruit to Stripe out for a coffee. You're just going to be a board observer. Just come once. Yeah, right. Exactly. Exactly. And he says to me, he used to actually work for me, and he knew how much I pride myself on good management practices.

1:28:53And he asked me, how many direct reports do you have? And I told him, and he almost, like, I had to peel him off the ground. He's like, I can't believe you let that happen to you. He was like, what happened to the Claire Johnson that I know? I'm like, I know, I'm so sorry. Like, I had so many direct reports. How many direct reports? It was a crime. At peak. I think the peak, I want to say the peak to you is 23, but it might have been 27. And I just like lost control. I really don't. Tim, I didn't want to go here. That's a lot of one-on-ones. I didn't want to go here. It's so many one-on-ones. And of course, I do actually make one-on-ones happen.

1:29:28So point is, I got schooled by my former direct report for violating my own rules in the need for cloning. But the point is the negotiation turns from we're negotiating you getting this massive goal done to what's the cost of me getting that goal done for the other priorities. And then you're making a joint decision. By the way, the outcome of that negotiation could have been let's not build out sales any further. Let's not keep internationalizing. Let's not open new markets. Let's wait on those other things because we decided you should just go and be the directly the head of support. Honestly, that was not where the conversation went.

1:30:10It was like, okay, what creative ideas do we have to somehow do both? Because we're reality distorting. That's fine. But actually, you know, you got to push yourself. And so I think in that exact moment, if I'm remembering the scenario, we talked about some talented people. I had hired some people into the org. who we're like, could we lean on them? Could we put some newer leaders, managers into the deep end and get them to take on more of this plan? And in the end, that was part of the solution, which is let's take some risks with some people we have, give them more than they probably are ready for and see if they can swim, which I'm not always a fan of because I have seen people not make it out of the pool.

1:30:53By the way, a lot of young companies find themselves in that situation. and if you have great hiring, which we did, I'm proud to say that, actually that's where opportunities and magic can happen for people. Like I'm going to get to build out the global support org. But anyway, so we ended up sort of compromising, but we weren't going to trade off my other responsibilities. And that became a more important discussion about how do I deploy anyone who's the CEO has got to be thinking, well, who are my most important resources and how am I deploying them against the most important priorities? So take the negotiation up to that level would be my advice.

1:31:28That's a great macro renegotiation example. And we're not going to stay on this forever, but I want to spend a little, little, little more time on it. When you're renegotiating the next day, so we're moving down to the micro here, what language do you use? Like you have a meeting booked, you got a lunch booked in Boston, you got this, you got that, and the other thing. When you reach out to these folks, what do you say? I think you want to, again, be a player, not a victim, and you got to take responsibility. So I think there is a version of saying, I don't love if it's the next day. That's rough.

1:32:04Yeah, it could be the next week too, right? It's just broadly speaking. I do actually tend to look at my calendar at least a week ahead and sort of start renegotiating because I don't like to be the one who's like the morning of or the day before. But I think you sort of own it, whether this is an email, it's probably an email, but it might be a text and you say, first of all, I am very sorry. I know we had time tomorrow on the calendar. I am staring at a list of priorities and I've realized you're saying something that doesn't hopefully make them feel diminished. I mean, I often will tell them there's this thing.

1:32:37I am on this board in the middle of a transaction and I have to be on a phone call for four hours tomorrow. And unfortunately, I think I need some time to prep. I need some time to prep. And I booked our lunch and it's not realistic. I'm not gonna be able to be present at that lunch. It's not great. I try to give, like, I'm probably over context people, but I think it makes you more human. It's like, look, I did this thing. I'm sorry. What if you don't have like a house fire to point to? What if you just look at it and you're like, oh. You're like, you're not important. Yeah. I mean, you get it.

1:33:10Like, you're like, why did I agree to? Why did I mail myself the letter bomb? Yeah. The ghost of Christmas past is coming to scratch my door. And I'm realizing I don't want to moderate this panel in Tuscaloosa. No offense to Tuscaloosa, but you get the idea. because I've got all this other stuff going on and I just don't want to spend the energy. What do you do in a case like that? So again, I try not to be the day before. Sure. No, let's say you look out and you're like, okay, this thing is in two weeks. I'm not doing this thing. Yeah. So my instinct is always to offer context and be a little bit vulnerable, which maybe is not expected.

1:33:41I think you also know there's a, I think women will get judged more for certain things. And in particular, like not being conscientious is the thing that gets a little more beaten into you, is my feeling as a woman. And so you have to also watch out for creating some reputational issue that I think maybe not everyone has to watch out for. So maybe some of my instinct to offer more information is to try to avoid that hit. But I've been saying to people recently, actually, that I have reworked my personal priorities and the demands of my time are higher than I've actually seen in my professional life, which is true.

1:34:22And I've realized that I cannot do a good job of some of the commitments I've made. And unfortunately, I can't travel and be on this panel and be effective for you. And this is where I feel sometimes I'm a little weak. I'll try to offer, I mean, I try to think, do I know anyone locally who could do this? I'll be like, I think I have an idea if you want an idea on someone who could sub in. I'll try to find some solution for them if I'm really leaving them in a lurch, right? Because I don't love that. But I kind of am just honest about like, I can't do this well. And I think you want someone at their best.

1:34:58It's not going to be my best. Yeah. That's good language. That's really good language. I'm not going to drag us back into the swamp of selling literature, but it's good language. That's good wordsmithing, right? Right. And I think you're showing, look, I looked at priorities. I realized, And also you're showing context, which is, this is a true statement. I'm like, I have more demands on my time than I've ever had in my life. And I'm learning to cope with it. And I'm learning that I can't perform at the level I'd like to perform. And I don't want you to suffer for that. You want to show respect for people.

1:35:28They want a good panel. They want your best. You know, you're saying like, please just, you have to trust me. I'm not going to be great. And they'll be disappointed. One thing that I do think, I think Cheryl's an example of this. They're people I've come to respect. They're the people who protect their time like demons, right? The other people I've come to respect are the people who are like very comfortable just saying no. Like, you know what? No, I'm sorry. I can't do that. My hope for myself, my future self is I am not in the situation where I'm doing that renegotiation. Again, it goes back to being honest, taking time before you make the commitment to say no.

1:36:03But it's also with investments. Like a lot of founders will be like, or even nonprofits, they come and they're like, I want to tell you about our organization. and you're like, oh, that organization sounds amazing. But then do you want to waste an hour of your time and their time learning about it when you realize, I don't have time to commit a lot to this organization. What they would rather have is one, no, it's not on my list of causes that I support. Or by the way, two, I will give you X amount of money. You never have to meet with me. I don't actually have time, but it sounds good. Here's some money, goodbye.

1:36:33And they'll say, well, can you make that commitment for multiple years in a row? Maybe, maybe not. But I think getting faster at like, there's a pattern here, which is you want my money and my time. Am I willing to give any money or time? Yes, no. If I'm willing to get a little bit, just tell them and get out. Don't have a dog and pony show about it. Or investments. I just don't really invest in a lot of B2C. I'll just write back and say, this is not for me. I don't really do B2C. Good luck. And they're like, thank you. Because they didn't waste their time sending you a deck, sending you, you know.

1:37:03Yeah, they're not chasing the Glengarry beads forever. And so you think you're being an empath by saying, oh, let me hear your story. This is my trap. My personal trap is I think I'm being an empath, giving them 30 minutes. Let me hear your story. And in fact, the empathic thing to do is to say, I'm going to do a probability assessment. The chance that I'm going to invest slash make a donation are sub 5%. No. No for you. No for me. And you don't have to think about it ever again. You don't have to email me tomorrow and ask me again, right? Like they're going to keep coming back. Yeah. Yeah. Absolutely.

1:37:37I love that. So glad I asked. And a great answer. Also, very useful, useful answer. What are some other rules we are going to back the car into the garage of self-awareness? Because a lot of this pulls at the hem of self-awareness from a bunch of different directions. But you mentioned that there are certain rules you have because your kid has gone off to college and therefore X, Y, and Z. What are some of the other rules that you have for yourself around what you will or will not do? 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.

1:38:17So I have a rule that, especially if I'm in a position of leadership and I'm in a meeting and there's other people, instead of stating my opinion, I have to ask a question. Because if you're the senior person and you state your opinion, the whole thing is over. Yeah, right. Yes, Steve, we can ship it in five minutes. Uh-huh, exactly. Exactly. Here's an iPhone. So that's a rule. Could you give an example of what that would, because you could also ask a question in a way that makes it clear. It's your strong opinion. So what might that look like? So what it looks like is they're kind of looking to you, you know, I think we need to X and you're like looking at you and you say, I have a thought.

1:38:58I do. I'll share it. But actually, I'm interested in what you all think we should do. Got it. You know, 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 going to like, I appreciate and refuse to answer your question. I'm not going to perform right now. I will perform later because I actually want you to participate. 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.

1:39:28Like, here's what you're going to do. And then I think, 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'll say, you know what? 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 because that's what they came for. Like, that's what they want. And I say, we're not going to learn from that. What I want you to do is tell me your instinct. What is it you think you're doing next?

1:39:57And I don't even say, give me the whole answer. I'm like, what would you do next? Because it's often a situation. There's an executive they think is underperforming. There's a team off the rails, whatever. I'm like, what are you going to 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 confident in their instinct. 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.

1:40:27And then, yeah, we can brainstorm the last 20%. And I mean, it's just like, this is a total digression, but good pedagogy, right? Like how do people learn? People do not learn by being told answers. We all know this, but yet we get some amount of experience in our life and we think, I'm going to go tell some people some answers. No, what you're going to do if you're a good leader, good teacher, is you're going to lead them through learning with you, and they are going to get to the answer, and you are going to celebrate them doing that. But I cannot tell you how many times I myself have to create a rule to shut my own mouth, because I love helping people.

1:41:09Luckily, I don't think it's the know-it-all version of this. I think it's the, I can help you. Oh my God, I see how to help you. And I just want to tell them the answer. And I got to zip it, zip it. So one rule is like, yeah, I'd make a travel rule. Another rule I make is, as I already told you, which is don't say yes immediately. It has to be very rare for me to say yes immediately. And as a pleaser, that's very hard to be like, no, I'm sorry. I have to get back to you next week. 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?

1:41:47Good feedback for me, Tim. And I take it. Thank you. Now, 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 going to 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 not finding something, feel free to get back to me by the end of the month and I will consider it. But it's basically telegraphing. I kind of want to try to help you, but I can't. You got to go to your plan B. I'm not going to be your keynote speaker. And that's a great feedback. I think that's a good, maybe even it's just, if you find yourself doing that, you should be asking yourself, why is it just not a no?

1:42:27It's a no. Yeah. It's a no for me. It's a no. Tim, right? But maybe it's a way to trial yourself into realizing, oh, this is a no. This is the training wheels. Yeah. 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, Like, this is not for me now. Feel free to get in touch in the future. A lot of those people might just not ever. And I mean, sorry for them because they're not persistent. But is that being a player? Is that being a player enough? I don't know. Yeah, hitting the snooze button can lead to like a delayed 24-car pileup later in my experience, right?

1:43:02Good analogy. I was chatting with a friend of mine about this because I'm fascinated by rules for folks who handle a lot of inbound of any type. 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, if it's like, oh, 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 pretty limited.

1:43:42But the rule is like 5k, that's it. That's our rule. And then for anything large, it's just like we focus on this and this and this and outside of that, we are not involved. That's it. 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, talent, but there's another one that's like testimony. Ooh, okay. So time, treasure is capital. Talent and testimony. And testimony is interesting, right? Because you could, Tim, care about something that you can't give time to. And you could say, if you need a quote from me, again, now we're like in this weird, rarefied air where someone might want to quote from probably not me.

1:44:27But I think that that's another thing you could do. But the thing that for any of those categories, you need some criteria. 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. Just to ask a clarifying question on one time I get, that seems pretty straightforward. Hours, minutes, treasure, it's like financial resources, things of that type. Testimony, okay, like endorsing something or some version of that.

1:45:02By the way, a version of that might be like, can I introduce you to someone and endorse you? Yeah. Yeah, totally. What is talent? I mean, I understand the word, but I think of talent as if they're utilizing your talent, wouldn't that kind of fall into the time bucket or is it a separate thing? You know, 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, what am I going to 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 without putting some time in.

1:45:38But the example was, say you are very good at some specific thing and the thing takes you less than 30 minutes. They're like, all right, I don't want you to join my board, but can you read this press release and tell me is it good or not? I think it's like, you know what? I can't give you my time. I can't join a board. I can't commit to a regular meeting. It's almost what I say to some of the founders I work with. I'm like, don't expect me to read the newsletter and try to volunteer for all the things you need. But if you think my particular talent is going to be useful, and here's what it often looks like, Tim, is they send me profiles of people they're thinking of hiring, and I give them a five-minute Claire assessment.

1:46:20And so that is my time, but I don't get on the phone. I'm just like, here's the questions. Usually how it comes back, because I'm all about questions is, here's the three to five questions I'd have about this background. If I'm you and I'm hiring for this role, why did they move around five times? Why did they stop doing that job? I would just give them interview questions and then I would back away. So you're right. It takes me a minute. You probably have a version of that. I've heard people like text you with very specific, which supplement should I take? Or which, you know, should I intermittent fast?

1:46:54Yeah, I get that kind of stuff. You could probably like text back this one, no, this one, you know, that's probably still time and you probably should count how much time it is, but it's a way to stay connected. It's compressed because of the expertise slash exposure. Right. You already know the answer. You have the talent. You don't have to go do extra work and you can answer quickly. quick add-on because I realize 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.

1:47:40You're talking about like references. Hiring yes references. Exactly. The non-dissertation answer is one, people have trouble giving hard feedback. People have trouble asking this question, which is, I think, a question you just asked, which is like, is this someone in the top 20 % of people you've ever worked with? And then they say, yes. You say top 10. And then they say, yes. Oh, so is it top five? Because what happens is when people are asked for a very specific quantifiable ranking of something, they don't like lying. And so what I think happens is we're not comfortable asking for ranking questions sometimes about humans, and I don't love them, actually, in most contexts.

1:48:17But in this case, I'm like, I'm going to pin you down on how good this person really is and how they handle. And you could go just to top five, but 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 going to be their manager. You are their manager. what's the thing I can do that's most important to help them? That's a good question. And people will say some very revealing things because 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.

1:48:57And you're like, what? And then you'll sort of get going. You're like, tell me a situation where you had to use that advice. Like what? Anyway, so those are two. One very specific, pin them down, and one a little more tricky. So good. Oh, deft. Very, very elegant. All right. As promised, the garage of self-awareness, that is the very strained analogy that I used. And tell me if this ties in. And I'm curious what good answers to this question might be, but I do want to talk about self-awareness so we can go into it however you would like. Because it's sort of the foundational layer for everything that is built upon it, or it seems that way to me.

1:49:36Yeah, that's my hypothesis. Yeah. So actually, I was going to ask you about the question, when have you seen me do my best and worst work? But we can come back to that. We can come back to that. I'm going to 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 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?

1:50:07That's a hell of a question. It's kind of like, you know, the tree falling in the forest, no one to hear it kind of question. 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. You often feel 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.

1:50:36So that's setting the table or maybe just piquing people's curiosity. How would you suggest people think about self-awareness? Why is this important in the worlds in which you operate? 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 got to do it through kind of 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 section of the garage is it's the foundation is self-awareness.

1:51:12It actually has to start with you. You're not going to get great results from the people around you until you understand yourself. And I mean, I think there's some obvious reasons why, which is like, look, I alone can't move the mountain. I need you and I need to compliment myself. How am I going to 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. So that's a side piece of advice for you.

1:51:45But 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 my default setting? A lot of them are asking you, are you more introverted or extroverted? So you're talking about, I guess for maybe lack of a better descriptor, almost like personality typing tests, like Myers-Briggs. Yeah, like Myers-Briggs, DISC, Enneagram. I mean, there's Discovery Insights. There's the Hogan assessment, like whatever. That's like 170 questions. Like there's all these different, there's the big five personality test.

1:52:18There's a lot of them. Strengths Finder, it goes on and on. Strengths Finder, good one. Like there's so many. 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. 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.

1:53:00And it's just, what do you lead with? For me, I'll be like, oh my gosh, someone's getting fired, which is sort of a task and a person answer, but you're kind of, anyway, but I would say, sorry, I'm being very negative today. But 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. Their default is, I love getting stuff done, talking to you. Like, that's, yay, be a salesman. And then you've got your introverted, task-oriented people.

1:53:36Where do a lot of those people work, Tim, do you think, introverted, task-oriented people? Engineering, programming. Engineering, finance. Finance. Give me a spreadsheet and I will rule the world. I do not need to talk to you to finish this model. 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 sort of saying, okay, where can I place myself in these quadrants? And then what does that mean my default setting is?

1:54:12And by the way, the people around me have different default settings. One of my big, 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. I'll be like, let's meet. And then at the very beginning of the meeting, bang out the agenda, make sure we know we're going to get done. I still like to run it well, but I'm kind of loose with the prep. I have people who've 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 going to talk about. And I'm thinking there's something wrong with them.

1:54:44I'm like, well, come on. We trust each other. We've worked together. We're just going to spitball about this. And they're like, no, I had to learn that there are humans in the world who, if they don't have time to think before a meeting, will not be effective in the meeting and will be uncomfortable. Because my water is really different than that. Really different. But you, if you're trying to create an environment that's conducive to different styles, different defaults, you got to be aware of your own and then realize, and I have to operate aware of others because I want that meeting to be really effective.

1:55:17And I've got to email Richard the day before and tell him we're going to spitball ideas for this new marketing campaign. That's what it all boils down to. And it's really cultivating awareness, but starting at home in the sense. Start at home and then start to map other people. Guinea pig is always in the cage right next to you in that case, right? It's just easier to, some cases a little easier to study. Coming back to the personality test for a second, where are these, I'm not sure if that's the right way to categorize them, Myers-Briggs, work style assessments. If you could only choose one or two that have been most helpful to you personally, what would you choose?

1:55:53I would say there's one that's called, I think if you just Google, it's insights discovery, which is sort of, to me, more effective than Myers-Briggs. Myers-Briggs has a lot of interpretive work you have to do on your results. Like, understand what sensing is, understand what the decision-making process of a sensing judger or whatever. Insights maps you more and they have some shading and colors, but it's sort of like more straightforward. That is one I'm a fan of. The other is more of a simple one, but Patrick Collison, obviously who I've worked with, I think I brought him around. He felt like these things are like horoscopes.

1:56:30He's like, they're just going to give you a report and it's going to sound like a plausible prediction of you. And I said, I get it. I get the skepticism. And I really do, by the way, for anyone. And actually, I think there's value in getting a horoscope. How does it actually make me feel? Like, do I agree with it or not? What am I really? Like, it actually is part of a process, in my opinion. Yeah, as a prompt, like a Rorschach prompt. It's a prompt. And how you react to it is interesting, right? Like, you're like, I really, yes, I am finding love this year, you know, or am I not? But so point is, he then did some research and there is the big five personality test is very simple.

1:57:06It's available for free online, as far as I can tell, or I've seen. And it's just these five factors like neuroticism, agreeableness, conscientiousness. There's one that's sort of entrepreneurial comfort with ambiguity, like whatever. And you can tell a lot from, well, one, the research supports that they're pretty indicative of certain human behaviors. You and I have had a lot of conversations in this discussion about things like saying yes too easily. But if you're like very high agreeableness and very high conscientiousness, guess what? You're going to end up committing to too much stuff. Yeah, for sure.

1:57:45And so when I'm saying, oh, I'm jealous of those people who protect their time, you know what? They're pretty comfortable being disagreeable. They're pretty comfortable being like, no, or frankly, canceling at the last minute, saying, sorry, I don't have time today for you. And if they're not very conscientious, they're like, I don't even feel bad. But by the way, no judgment. A lot of founders are really good about being like, look, I'm doing the most important thing that I got to be doing today. And I'm the operator. I'm like, oh, but we made a bunch of commitments and we made a plan and we got to stick to the plan, right?

1:58:17And that meeting of those styles is very powerful. That's why you want a diverse team. But anyway, I would say those two. Yeah, Patrick is endlessly fascinating. He's been on the show. It's probably a couple of years ago. But boy, oh boy, does that man read. He really is a voracious consumer of knowledge. He is. He puts the rest of us to shame. You know what though, Tim? I bet he's never seen John Wick. So we have that. We have that going for us. We do. One zero, Ferris Coulson. Put Wick on the scoreboard. Yeah, we were actually in a meeting and he said something about Greg Popovich and two of us looked at each other and were like, do you really know who Greg Popovich is?

1:59:01It was like amazing because Patrick also is not super up on sports, popular culture, you know, we all have our strengths. Popovich, also incredible. Somebody I would love to have on the show at some point. Oh yeah, absolutely. Yeah, well, that's why he knew. So going to the kind of black belts of no, I'm wondering if there are people who stand out outside of the Collinsons 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 keeping their eye on the one puck that matters. Anybody come to mind?

1:59:37Well, I mentioned to you, I think Cheryl's very good at getting back, being very accessible and fast and sort of decisive, like no, efficient. She's very efficient. And sometimes that efficiency is a no, right? I mean, my version of it is someone who I think at least doing it carefully with others, others like feelings. Like I think that I don't love the person who has an assistant, for example, who cancels everything. No, there's a model here, Tim, you've seen it where they agree to everything. And then they have a cleanup crew. They have a cleanup crew. Like the wolf from Pulp Fiction. They send it out to like do the dirty work.

2:00:12Yeah. Yeah. 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. They use the cleanup crew. They use the cleanup crew. There aren't that many who seem, I mean, I think you have some good, I think it's in four-hour work week, you have some good models of pushing people on not just being busy, but being productive. 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, I don't need to be here.

2:00:48Or this meeting doesn't seem important. You know, and to me, those are paragons of no, though, because it was very 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. Why can't more people just call it, you know? Yeah, uncomfortable. There's a finance guy that I'm on a board with, and he'll be like, what are we trying to accomplish in this, and how long do we need? And like, he'll set his, I'm here for that objective, and I'm only here for this long. and I admire it because he's like, don't be chatting away about other stuff.

2:01:22I want to be productive. Don't hear about your fishing trip right now, Ralph. Exactly. So just because you mentioned the board, why no more boards? Just the thinking behind it. I think there are different motivations for being on boards. I don't know if you serve on boards. No, I basically, from the beginning, I have a number of friends who have policies that they won't join any more boards and I took that as an indicator. And so So I've only done advising. I've never been on boards. 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.

2:01:55By 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 these companies because you are like awesome at governance and 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 like CEO really trusts you. you want to help them. That's mostly what happens to me. I'm like, I want to 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, boards can stomp all over your calendar.

2:02:33They can just say, you know what? All day Friday, someone just made an acquisition offer. And you're like, goodbye. You realize you think you're controlling your time because they don't meet that often, but no, no, no, no. So really what I've decided is I need to like go on a board diet and then rebuild. I'm not going to say no ever, 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. I don't know if I'm adding that much value, but it's the Atlantic, which is private, so it's easier.

2:03:09But the quality of the people involved, we're doing the business brain stuff, but there's also like you get to meet these amazing writers and you get to be part of exchange of ideas about the future of democracy. Yes. You know, that's enriching me. That's the other thing is making sure there's an exchange in the board of your 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 think I just didn't realize the level of commitment, not just time, but sort of to do it well.

2:03:43I mean, it goes back to renegotiating. 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. That's also a very powerful language right there. Categorically, I'm saying I have a policy of saying no to X until I have A, B, and C. That's right. Done deal. And by the way, people can't argue with that because they're like, that does sound like a very sane thing to do. But I have a lot of appreciation, more than I did before, of folks who do this in service. Governance matters, right? It matters for institutions, not just companies.

2:04:15And it should be done well. But gosh, it's a big commitment. Be careful with those big commitments, folks. They sneak up on you. Yeah. Anything that has multiple years attached to it. Yeah. Oh, boy. It's kind of like the scope creep, time evaporating version of the best business model of all time, which is being a venture capitalist, where you have these stacked funds. That's great if you're taking your two and 20, but if it's a commitment of your time over multiple years and then they start to stack and oh my God, then you're like 27 snow layers deep in the avalanche of time requests. That's right.

2:04:53That's right. And you get like a 10-year horizon. Yeah. I mean, at minimum. And that seems exciting at the beginning. And then you stack another 10 and another 10, and you're like, wait a minute. All of a sudden, I'm like 65 years old. And anyway, I think it's, yes, some funds have closed, and hopefully you've done well. But you made commitments before those things happened to another set of them. Yeah. So it's like a rolling avalanche. The avalanche is not ending. Do not say yes right away, folks. Yeah, especially to multi-year commitments. That's probably the headline. That and the toy is broken.

2:05:31I'm telling you, that's your next book. I really think you could do well. I have to ask this because 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? If I was like, what are the pantheon of management lessons? So one of them is you got to manage different people differently. Another pantheon lesson is spend disproportionate amount of time with your high performers. Because instead, what we all do is get all of our time sucked by the folks who are struggling.

2:06:10And 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 going to go get investment somewhere else. 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? In my book, I steal. I mean, I don't steal. I credit. I source a lot of frameworks.

2:06:39The book, Skilling People, Tactics for Management and Company Building. Oh, yes. Thank you. Just to throw it in there. 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 Kaufman's in there. One framework, I think, I mean, as far as I can tell, I made up myself, was a top talent framework, 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.

2:07:16I want responsibility. I want scope. I want to 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 because they're like going for it, grabbing it, grabbing it. But it's fun because you load them up and they're just like carrying the whole thing up the hill without you. 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? Because they're all keeping score, but they're keeping score in the sort of maybe early in his life, Tim Ferriss version.

2:07:56I don't know. 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. It can be a huge superpower and it can be a huge liability. 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. Because in the case of the pusher, yeah, they might burn themselves out, but they actually like burn out the people around them.

2:08:30So that's the pusher. So the puller, it's funny, this happened to me in a couple of conversations I've had is 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 it. They're not pushing, but they're highly competent. They're very organized. They're very consistent, reliable, 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, you whatever it is.

2:09:04And you just start loading them and they don't renegotiate. They don't know how to say no. And then they explode. They basically implode or explode. That's what I've run into with past employees. Yep. And there's some, I went through a period of my own development where I was like, I think of it as my martyr period where I literally, I don't know who I thought I was martering myself for like everyone else. I would be doing all this stuff for my colleagues, for my team. And I was like, no one appreciates. I don't know. And I eventually had a really good open conversation with a guy, not my boss, who worked with me.

2:09:43And he's like, did I ask you to take that on? You just started running that project. Or you run our planning process. Or did someone ask you? And I'm like, well, no, no one was doing it. So I'm doing it. And I was like, And why do you feel like you have to do that? I was martyring myself for nothing. I think martyrs at least are celebrating like a god. I was sacrificing myself on the altar of someone didn't do the work, so I'll do it. It was very bad. Very bad. And I was resenting the hell out of my colleagues. For sure. I'm like, I mean, this happens in relationships. I mean, it's like the who's going to take out the garbage thing.

2:10:20I designated myself the garbage collector for a whole set of things, partly because I thought it was that was part of my job, but still it was not good. Not good. Anyway, the polar will implode slash explode and you might not be able to save them if it gets too far. So your job with them is like, look, let's work on delegation skills. Let's work on saying no. Let's work on boundary. Like, look at me. Let's work on rules, boundaries. How do you not be the person carrying everything and doing three jobs? And I think that once you know those two archetypes, you can sort of look for the signs of them.

2:10:54And then you can think, well, what's their classic development area? And then your job is to be all over them on that development area because they will collapse if you don't get them to see that part of their job, like the pusher, especially part of your job is to stop creating friction for everyone. And like, for me, I really started to take exercise seriously when I decided it's part of my job to be like a better leader. I need to get a certain amount of exercise and now I will make time for it. And I think a lot of these types are like, I'm going to do everything to win these pushers. And you're like, you know what?

2:11:29Part of winning is like avoiding a Pyrrhic victory, avoiding one where everyone wins but dies on the field, right? Like that. And they're like, oh, well, then how do I do that? Because it doesn't come naturally to them. They're like, how do I? And then they'll say, I don't want to work with low performers. And this is the problem. They're so good that, I mean, now we're going deeper on this. They're so good that you can't quite say back to them, no, those people are the same as you. So instead, you're like, yeah, okay, we all have different strengths and weaknesses. What I feel like you're doing is not even appreciating what anyone else is bringing to the table.

2:12:04Why do you think that is? And it's like they don't stay up all night like I do getting the thing done. You're like, no, they don't. And I actually don't think sometimes you should stay up all night getting the thing done. But what do they do well? And then you get them trying to think about assets. You're like, how can you use that asset to get the things done? And they're like, hmm. But they really don't think that way because it's all on their own shoulders. Takes practice, like so many things. Claire, this has been a fantastic conversation. Thank you so much. I've had so much fun. I've taken copious notes.

2:12:36I'm going to be following up on a million side quests, as we call them. 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. I'm trying to also health first, sort of foundational along with the awareness, having the vehicle to do the things you want to 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.

2:13:11people can find you, correct me if I'm getting this wrong, but on Twitter at C. Hughes Johnson. We'll link to LinkedIn as well. Are there any other websites or anything else that you'd like to point people to? 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, which we can give you all the link to that. But no, thank you, Tim. This has been wide ranging as promised and stimulating. And I've got some recommendations I'm walking with. So thank you. Thank you so much, Claire. And for everybody listening, we will link to everything in the show notes.

2:13:46This will be encyclopedic. And you can find that at tim.blog slash podcast. And you just search for Claire and this will pop right up and you'll find everything that we discussed. And so 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. Hey guys, this is Tim again. Just one more thing before you take off. And that is five bullet Friday. Would you enjoy getting a short email from me every Friday that provides a little fun before the weekend between one and a half and 2 million people subscribe to my free newsletter, my super short newsletter called five bullet Friday, easy to sign up easy to cancel.

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