EP 83: Silicon Valley Legend Claire Hughes Johnson (Advisor, Stripe) Unveils Her Best Operating Advice

26:52Like we had a dependency on Joe's team. His team didn't deliver. And that's why we missed the goal. And you kind of say to the person, wow, and was there nothing you could have done differently? Oh, no, Joe's total failure by Joe. You know, you're like, what? How are you even have a straight face? It's actually crazy if you ask someone like, what's a project you failed at in your last job? How quick they are to shun responsibility? Because it's an interview setting and you want to put yourself in a good light. Exactly. It's actually. But if they don't highlight any self-reflection, like you have no learning.

27:26By the way, this is also not a high learn person. It's like you really learn from mistakes. You know, like actually my son came home last night. He's like, we got a pop quiz in science. And I got one of the questions. Only three questions. I got one wrong. and I said I tried to like you as a parent you try to say oh well and what did that do for you like you know that's probably why it was a pop quiz he goes yeah now I really know that thing and I was like yeah you do because you screwed up and I mean I think the the people and so Logan to answer your own question you just did which is in an interview setting you're saying tell me about a time you failed tell me about one of the biggest lessons you learned describe the project?

28:05What was your role in it? And the victim people, again, they'll be less overt than, I mean, some of them just blame everyone and vent and you're like, okay, you're just a downer to interview with. But they'll be less overt, but it'll be a lot about other people involved. It'll be about constraints. It'll be about dependencies. The thing I learned is I was spread too thin. I didn't delegate. But they won't take responsibility. It'll be very hard to get them to say, it was my project and ultimately I was responsible. And yes, I should have delegated better, but that was on me. That's what you're waiting for is someone to say.

28:42Yeah, I look back. I mean, I could say I look back and say some of my worst hires were people that I just wanted to like and I didn't like hold them to a high enough bar in the interview process. Do you find the opposite to be a problem if someone tells you an accomplishment and there's too much like, well, I did this and I did that. Yes. Yeah. I mean, I think there's this balance. This is where having the pattern match of thousands. I think I've done, I have, I've done thousands of interviews and I wish I could totally distill this, but it's about balance. There's a lot of, the best candidate to me, the best interviews, there's a lot of we actually.

29:17There's a lot of, because that's the thing that the player, by the way, construct is not, it's all about me and I take all responsibility and I'm the the star of the show, because that's like a narcissist, right? It's someone who is all about understanding their role, understanding what they could have done differently, but also giving credit and collaborating and being like, oh, if I hadn't had this person on my team, I don't know if we would have made it. You know, I love, it's a self-awareness thing. It's like, it's going to be the combination of things, but when the chips are down and they did have a role to play, do they own what their role was and what they learned from it and were they accountable?

29:52And you want a little bit of I. And if they're not, if they're bringing a lot of we, you stop them and you say, I really appreciate actually that you're bringing a lot of the we to this conversation. You're giving examples of your whole team. Tell me what you specifically did. What was your role? And they'll kind of look at you like, yeah, you caught me out. And then they will, if they're good, they'll go there and they'll say, look, I, it was my idea. I did come up with that idea and, you know, but you kind of have to force them into it. And I like that. I like people like that. But if they don't go there, that's also a flag.

30:28Hi, I'm Logan Bartlett, the host of this podcast. This is not an ad. As you may know, we do not advertise or monetize this podcast in any way. I just wanted to take a quick second to tell you that we have a bunch of killer guests coming on over the course of the next few weeks. And so if you're enjoying these conversations behind the scenes with both entrepreneurs and investors, please do subscribe to our channel so you don't miss out. Now back to the episode. One of the things I've heard you also interview or use as an interview tactic is an org structure. Yeah. Oh, yes. That's one of my favorites.

31:00Their org structure, which I thought was so fascinating. Can you talk a little bit about why asking someone about their org structure, how it came to be, how that can be used as an interview tactic? On the good parts of my executive hiring, I want to say it wasn't all disasters. One of the best questions I found I came up with was, this is the days where ideally you're in person with the candidate, but you could do it over Zoom, which is let's get it a whiteboard. And just, can you just map out your current team for me? So there's you. And then like, tell me the roles. And, you know, you don't have to name all the names, but like, I'd love, you know, Joe, Teresa, you know, Mahak, whatever, give me the names.

31:36And then I'd love to walk through a couple of things like, well, one, why this org structure? Because one of the traps there is your org structure should really reflect your priorities and your strategy. And it should have clean accountability lines. And when you're in org structure, they're like, wow, this guy was going to leave. So I had to give him like two jobs, basically. You're like, hmm. So you didn't really have the hard conversation with that guy, did you? Or they'll be, well, I inherited that person and I don't love this structure, but I don't want to rock the boat. You're like, hmm.

32:11And why not? What are you afraid of? So one is why that org structure isn't logical based on what your objectives are and your strategy is within the broader company. The other is tell me about the individuals. And the trap there is people, leaders who come in. I'll put it in context. I'll say, well, how long you've been in the role? Say they've been in the role three years. It's the same team they got. I mean, maybe once in a while you inherit the perfect team. But I have never seen that happen. Like perfect, especially if you come in as a leader and reset the strategy. Like they can be great people, but do you have the right capabilities for that strategy?

32:49That's really the perfect team. So big red flag if they've made no changes. Also a red flag if everything is different. Like everyone is new. I'm like, did you just churn every single directory? Like did no one want to follow you. This goes back to followership, right? You want this mix. You want thoughtful, you want a story. By the way, my favorite is while there was this person in the org I found, incredibly talented, you developed them into a role. You didn't just hire from the outside, or you did change the team, but part of the team are people you identified who were talented, who were getting squelched in the org, and you lifted them up.

33:23And what will happen is also, you'll see how the person is, and this is the more nuanced part of this question. do they get energized talking about the people and their development and their stories the people under them as leaders or are they kind of a little dry about it they're like yeah she's been in you know at the company for 10 years i do wonder if she's gonna leave but you know if she does she does like right you're kind of like well what have you done about so some people are more energized as managers in that moment when they're describing their people and they almost get into it. And some people, you can tell that that's not how they lead.

34:01That doesn't mean they're a bad hire, by the way, but they're not leading with the people element of management. I heard you say some of the most successful hires you've made, I think they - Drove me crazy. Annoyed you. You knew exactly where I was going. Did they drive you crazy in the interview process? In the interview. And also closing. Closing, okay. Some of the hardest closes I've ever had, candidates who were driving me up a wall questioning every number of the business the role the jd what do i expect what am i like to work with like you're through the ringer and you're like do you even want a new job like what they were some of the best hires i ever made it is that they were just like hyper analytical different brain thing you know i'm very into that is that because it was a compliment to you.

34:50Yes, huge compliment. Yeah. Huge compliment. Brought out some stuff in me that needed to be brought out. It's not like I don't have it, but I don't lead with it. I'm much more intuitive. These are just like hyper data driven people. Some of them are actually a little bit risk averse. Some of the compliments to me, I'm not afraid of change. I'm not afraid to make a decision and like drive to action. And some of the compliments to me are people who are like, hey, wait a minute. Do you really have all the data you're going to want to make that decision? and sometimes they're right. Like I should stop.

35:21Like why, what's the rush? I mean, and so yes, they drove me crazy. They were hard to connect to in the interview but they did well on the questions but I had to sort of, this is where you have to check your biases. I'd be like, wow, this is like sort of annoying but actually when I read the answer back and I think about my frame, my rubric for what is a good answer, these were great answers. They just didn't deliver them in a connected way to me because they thought about it very differently than I did. And then in the process of answering their questions and closing them as candidates, that they're very different.

35:55Yeah, some of my best hires were completely the opposite of me. That's a compliment point to like, sometimes you need to hire to augment your own weaknesses. And we'll talk about self-awareness in a second. Yeah, all the time. Hiring the exact same profile that you have is going to lead to duplicity. Well, it's going to lead to a team with a giant amount of blind spots. I mean, I think diversity gets used as a word meaning certain things, but I actually think fundamentally a diverse team meaning in all the ways, whether that's gender and racial, but I'm talking about really work styles and preferences and what part of your brain do you lead with or even your socioeconomic background.

36:35How hard did you have to work to get to where you are? What's your perspective on our users? How have you experienced life? That kind of diversity is how you get a team that's going to outperform other teams. But it's not going to be as comfortable a team for you to hire and lead. And the minute you recognize that, the better. Like it will not be, it's easy to hire a bunch of your friends. Right? But you're just not going to be, you're going to be a team that can move pretty comfortably, quickly within a very narrow band. If you want a team that can outperform, you're going to have to dig. And there's empirical evidence, maybe the hospital story.

37:13No, I mean, I think one of the interesting things to look at is if you have inclusive, this is a big if, if you lead a team with inclusive practices, you can get a three to five X return on that team. So they're diverse, and there's inclusive practices. If there's not inclusive practices, we can talk about a homogenous team can actually get pretty far pretty fast, just not outperform. But yeah, I thought Amy Edmondson, who is the psychological safety researcher and writer, which she now wishes she hadn't called it psychological safety, because I think it's a term that doesn't really mean anything anymore.

37:45But Amy Edmondson has been part of some research studies. There's a whole field now that looks at this. And one of them that I thought was fascinating was about ICUs, so intensive care units in hospitals, which are actually all pretty similar. They'll run quite similarly. And intensive care is essentially the patient is monitored 24 hours a day. And there is a team of care. There is like a nurse, a physician's assistant. There's often the person in charge of anesthesia or drug administration. There's the doctors, multiple doctors. And there's power dynamics in that team. You can all imagine them.

38:18Like, I don't have to describe them. But, you know, the people who see the patient the most, though, are more the nurses, the medical assistants, and less the doctors, right? That's just the way it is. they're sitting in the room practically with these patients. And the ICUs that had high inclusion, there were 18 % fewer deaths. Like people died when there was a lack of, when there was a diverse team and lack of inclusive practices. What was inclusivity in this? So inclusivity in this case is comfortable. Like think about this, comfortable speaking up to power, comfortable sharing ideas like the nurse saying actually i don't know if that drug agrees with that patient or i saw you come through yesterday and make this observation what happened like this is a team that is putting it on the table to each other and is actually doing it to get the best outcomes as opposed to not rock the boat with egos and power dynamics and by the way these are people under a lot of stress and pressure um and you know these doctors are buzzing through and this is a team where you stop and you say, I think I see a problem.

39:28I mean, it's like the Japanese pull the Kanban cord, right? But this is the equivalent in day-to-day operations around people who are very sick. And I think that, so how do you create that? It's how do you create an environment where people are unafraid, no matter what, where they feel they fall in the status stack to speak up? Ideally, obviously with a great idea or with an observation or a question. and that is a thing that is very important tactically day to day to do well and it's hard to do well but it is about how do I make sure you know the right people are in the meeting that they're all participating you can use check-ins and check-outs which I talk about in my book that if you're the leader it's probably going to be a killer if you give your opinion first like if you lead with here's what I think we're going to do we're going to launch product acts next week.

40:17You know, like, are you really, you've got to have a pretty great team environment for someone to say, I don't agree with you, boss. You just started with the punchline. Like you should instead say, we've got this decision in front of us. I want all of your opinions. I want to go around the room and hear them all or even better. Let's all write them down. So we don't group think like everyone, write them down on a piece of paper in front of you or in the doc or in your own doc. And then let's all at once load them in and see what we think, How do you build these ways to prevent human behavior?

40:49Human behavior is about, we're animals. It's about status. It's about how comfortable we are. It's about group think is real. And it has really good reasons behind it, but you've got to prevent it. Totally. I want to talk about your operating principles in your book. So number one, build self-awareness to build mutual awareness. Can self-awareness be learned? Oh, 100%. Yeah. I mean, I think that, look, the thing that, so true, I've observed this. First of all, the thing that you, Logan, are probably really the most amazing at as a human, I know for me, is like breathing. Like I have no, my actual best strength, I had no knowledge of for most of my career.

41:37Because I was like, well, doesn't everybody experience things this way? No, not everybody experiences information, data, communication, whatever it is that way. Like, but it's like breathing. So one, don't forget self-awareness is about your strength as much. The other is blind spots are blind spots because they're blind. Like you do not know the thing that you don't know, right? And so that feels easy to say, but hard to admit and actually see because you're blind. So how do you learn it? I mean, there's a ton of different assessment tools. They're not all perfect. And they're not all specifically custom.

42:18I know in the world of AI, actually, maybe we'll have a tool that is much more built and trained on your model that can reveal these and other models, right? And can reveal, hey, by the way, the other models have this thing that you don't have. But let's say these tools. So I'm talking about Myers-Briggs, DISC. There's this insights discovery tool that I really like. Enneagram some people use in a professional setting. The big five personality test is one that has a more proven track record in research to actually determine some outcomes in terms of you as an individual. I don't really care. I've actually taken Hogan assessment as this like really long, intensive questionnaire that you can take.

42:57I don't really care which one. I take them all, I think pretty much. but every single time I take one, the point of the exercise is to like one, listen to it. And ideally someone who has some experience with the tool is giving you some readout on your results, but you can also read it yourself. You're listening and self-reflecting and you're like, huh, what did I learn that I didn't really know about my, it's really about preferences. It's about your defaults. Like all humans have some default settings. Like what are my default settings? And if those are my default settings, what are my not default settings?

43:29What do I not do naturally. And I think, so yes, you can learn, you can take the tools, you can be better even when it's not fun asking for feedback. And actually, instead of saying, especially if you're the leader, you can't end a meeting or make a decision and be like, hey, what'd you think of that decision? Like, what do you think of me? Like, of course the people are going to be like, that was great. That's great. You have to say things like, what could I have done differently to make that thing better? Or what do you wish I'd done? Now that we looked, look back and we made that decision what do you wish i'd done that would have made it better right like you have to get pretty specific but asking for feedback and then by the way listening to it writing it down self self-reflection is underrated like why don't people at the end of the week like sit down for 15 minutes and just write what do i think went well this week what didn't go well and why why do i think those things went well but or didn't really go well and if you've done some work on your default settings.

44:27I bet you'll find, by the way, most of the time I'll find I was under stress and I went to my default settings and I screwed that thing up. But if you don't sit and think about it for a minute, you're not learning. I would encourage people if they want to build self-awareness as well. If you have a podcast, YouTube commenters will make you very self-aware. Oh, they sure will. They give you any insecurities you have. They're very quick to point out. Yeah, I don't know. Like issues. Yeah. So that's another way. Always dangerous to read. Yeah, Myers-Briggs, Enneagram, YouTube commenters. Yeah, you can each find your own.

44:58Do you try to hire for self-awareness or do you understand then that you can develop that over time? How much of that do you think you can? That's a great, I mean, I think earlier in the career, the less you're going to expect that someone's really developed that. But I do hire for it in that I think people, this goes to kind of core instincts, which is I think people who are fundamentally curious and learning oriented, you want to hire. And I mean, tease that out. Like, how do you ask that question or get to that? Yeah, I think you ask. I mean, I have some sections in the book where I have a bunch of like interview questions, suggestions, but I think there's one, you know, tell me something that you learned about recently that surprised you or that you're passionate about.

45:47Or, You know, like there are people who just are like, I don't even know what to do with that question. And you're like, hmm, do they not read? Do they not talk to people? Do they not study something new in their look? We're in tech. I mean, I've worked in tech, like there is something new happening in literally the underpinnings of technology. Like there is a new AI model with significant improvements every like 18 months right now. And it's getting faster. And if you're not aware, and then if you think about compute power and cost of that, you're not thinking about what are the underpinnings of the capabilities we have to deliver the product.

46:24Even if you are an English major who has not ever, I've written some HTML, but not a lot of code. I think a lot about the macro environment of the underpinnings of technology and how it's changing and what does that mean for my company, my product, my team. I better be curious. I better be educating myself. And by the way, bonus points if I'm also doing that in something else that's outside of tech that I'm passionate about. Maybe it's gardening. Maybe it's taekwondo. I don't really care. But are you curious? Do you care? Are you a developing human? So self-awareness, I think, can be learned. But it's very hard for someone to learn if they're not curious, if they're not a learner.

47:05And one of the things in the book that I talk about, I think the hardest employee situation I faced is someone who is a good performer, but could be great, but they have what I call a self-awareness gap where you're sort of trying to give them feedback and they don't see it. They're like, no, I'm pretty great at that actually. Yeah. Like, I mean, I don't know what you're talking about. Like what, what are we talking about the same thing? And most people I find when you give them the feedback and you have to be direct are totally with you. They're like, wow, yes. If only I'd communicated more crisply in that moment, or if only we'd done the analysis and scoped the problem in the way that made that analysis more helpful.

47:47They totally get it. But then there are people who are saying, yeah, no, I feel pretty good. I don't know what you're talking about. It's so hard to close that gap. So I think to a point it's learnable if they're curious and they're a learner, but there are some individuals who cannot get at the blind spot. Interesting. Operating principle number two, say the thing you cannot or you think you cannot say. Can you share an example of ways in which you can approach difficult conversations in a slightly more comfortable way? It's human nature to try to be agreeable, I think. It is. And it's also human nature to not feel confident about an intuition or a hypothesis you have, especially if you're more data driven, especially if you're, you know, sort of in an engineering or finance mindset.

48:35But what say the thing you think you cannot say is really about is taking some risk in putting out an observation idea you have a question you have. And I think doing so as a manager is part of what I talk about in the book. But I actually I don't care what your job is. like this is how breakthroughs happen for individuals like whether it's out to dinner with someone or in a meeting or in a project which is the person who like pokes at but wait a minute did we think about this all wrong or why haven't we thought about x you know why are we talking about this when the real problem is that right but if you don't say that there's no breakthrough uh and so as a manager you get nervous because like i think i'm issuing some kind of judgment on someone when I say the thing I think I shouldn't say.

49:22And you have to, I think, step back from that and say, no, what you're doing is sharing a hypothesis you have and asking someone to react to it. And then you can refine the hypothesis. And I think that the safest to your question, the safest thing to do is just ask a question. Now, maybe that's in a meeting, which is like, maybe in the meeting, it's like, well, why aren't we talking about the fact that we have missed this milestone on our roadmap for three quarters in a row. And everyone's like, awkward. But hey, if I'm a good leader in that room, I jump all over that. I'm like, yeah, I should have said that.

50:00I'm like, why did we? And then you're having a really rich conversation about a huge blind spot, probably, by the way, that your team has, which is we keep saying we're going to prioritize that thing. And then we're not. Why are we not? Be the person who creates that breakthrough conversation. Or with the individual, by the way, yes, you're taking a risk. It's a one-on-one. You're giving someone feedback. They might get to a breakthrough. They might get defensive. And that is okay. They might say, what do you mean you thought I was nervous? You say, I'm sorry. Totally my perception. I just experienced you in that meeting not as confidently as I normally see you with that material.

50:37And they're saying, well, I don't know. I say, great. If that's, you know, totally could have been just my, again, you're just a mirror holding up to someone. You say, that's just could be my perception. But what I do find is people will then think for a minute, they'll sit on it. The next day, they'll be like, maybe I was nervous. Like, why do you think I was? I'll say, well, why do you think, you know, you're still, the breakthrough might not happen quickly. And you can be wrong. Like, believe me, I've been in the meeting where I've put a theory out on what's not being said. And I've gotten looks of horror from people.

51:08They're like, oh. And then I'll look around the room. By the way, you got to read the body language and the faces. This is not usually a verbal exchange when there's look. And I'll say, hey, from the look on all of your faces, it looks like I'm wrong about that theory. And there'll be some nodding. And someone, though, will then jump in and say, no, no, no, what it is, is this. Because so what I've done is I've provoked opinion. And ultimately saying the thing you think you cannot say is trying to provoke someone to share an opinion or some data that backs up an opinion, ideally, that wasn't out on the table.

51:41Do you find it's easiest to do that in close proximity to when it occurred or giving a little bit of time so that there's less defensiveness. But if you give too much time, then it seems like it's more of a affront to them. Is it better to do it closer or further away? If I had to give one answer, I'd say closer in the same way that like giving feedback to someone, ideally pulling them aside immediately and saying, hey, how do you think that went? Here's some like ideally closer, but I'll like one of my one of my strengths that's like breathing is I kind of have like fast processing speed in moments and I'm like unafraid to go there real time.

52:24And that is not the case for a lot of people and that is totally normal. And so I would say you have to read the context, read the individual, maybe close proximity is the next day. And to your point, sometimes things are heated, right? Sometimes you're in an executive team meeting, maybe you're the founder, they're all disagreeing. Everyone's looking at you, I want a decision right now, right? You feel like I've got to call peace. And the best thing you can say, because you need some space is say, wow, a lot of disagreement, appreciate all the opinions. It's looking to me like I'm going to be the one who has to make this decision and I'm going to take some time and gather my own data and think about it and I will make it by Friday.

53:02Now, the danger of doing that, by the way, is everyone starts lobbying you. So good if you also lay out a process and you say, if anyone has opinions and you clearly do, please send me an email or send it to the group by the end of the day. But try to, it's totally legitimate to say, you know what, the thing I think I cannot say, I'm not going to say right now because there's a lot of emotion in the room, but I am going to commit to saying it. And that, you know, again, is a risk because you might not be ready. Operating principle number three, distinguish between management and leadership. Can you expound on that?

53:35Oh, yeah. So I think there are some schools of thought that you can be a great leader and you don't need a lot of management skills. I think Reid Hoffman would cop to believing that. And I interview him for the book and he talks about it. I actually believe you do need both ultimately in your career. Often I think people lead with one or the other. I probably led my career as a great manager and then became a leader. And I'd say probably the opposite for a lot of founders that I work with. But ultimately, if you're a founder who's the CEO, you're going to have to manage executives and an executive team.

54:11And that's going to take some skills in that area. Here's the good news. Management is really knowable. It's learnable. I mean, a lot of what's in my book is just me sort of saying like, here's some basics. Here's some checklists. Here's some things like you, they happen behind closed doors, but they're very learnable. You know, management is about like, how do I get from point A to point B? Like, look at my talent, make a roadmap, milestones, metrics. It's very doable. I think leadership is actually harder to learn and very different because I think management is a lot about moving people through time and space to accomplishments, whereas leadership is making people pretty uncomfortable.

54:54Fundamentally, I think great leadership is setting a vision that doesn't seem possible often or setting a bar that doesn't seem achievable. And as we talked about, like one of my, I guess, areas for development or blind spots is like, I'm pretty empathetic. I'm pretty collaborative. I look at a group of people and to say to them, and now we are going to do a thing we have never done before without any real knowledge of how we're going to do it. And we're going to do it by December. is very uncomfortable for me because I am so empathetic to the people in that room. I'm like, how the hell are we going to figure this out?

55:30I remember when I started at Stripe and our support situation was kind of a tire fire for good reasons. We were growing quickly, et cetera, et cetera. The team was small. We didn't have our processes. We didn't have good tooling, all the things. And at some point, but admittedly under pressure from Patrick, the CEO and co-founder of Stripe, I ended up having to say to the whole company, this is going to be fixed. We are going to have 24-7 chat, phone, and email support in seven languages by the end of next year, you know, whatever. And I'm sitting there going, how the hell are like, you're putting out a vision and you're putting people on the line.

56:08You're putting people who report to you on the line and saying, we're going to deliver this thing. And you have no idea how it's going to, I mean, you have some idea, but it seems impossible. Like leadership is uncomfortable. And it's also turning up the heat on some people who are often very good. You're like, you know what? That still isn't good enough. So you can learn it, but it's much more psychological. It's much more about can I feel comfortable? Like, can I do that confidently? And by the way, when you do and your team, maybe you don't hit like the crazy goal you set for December, but they're going to do better than you expected.

56:41and that's when you start to get this virtuous cycle of wow, leadership actually works. Like I articulated a vision and people colored in the lines. People figured out how to get there. I didn't have to figure it all out. I just had to articulate where we were going roughly. That is so rewarding, such a payoff. But I say you need to distinguish between those things because there's moments when your team needs you to manage them. Like do the work assignment. like Logan you are accountable for this goal and I will hold you accountable please come back to me with the underlying metrics that we are going to track you know like you are man I'm managing I'm making it clear who the owner is I'm making it clear what the goal is and I'm tracking your progress and then there are other times where I'm saying Logan what your team is delivering is just not good enough right now and you're like well what tell me what to do I'm like no you got because I'm treating you in this case as a leader.

57:39I'm like, I'm a leader managing a leader. And I'm like, you're not leading hard enough. Right. And that's very amorphous. I'm not defining it for you, but I just know that it could be better. And I'm challenging you to push your team to make it better. Yeah. I've always thought that like there are innate leaders or that can come naturally. Management's much more of like a learned skill over time. I never really thought about learning leadership as something that you can do. It's an interesting - You can do. And the other thing, I think a lot of leadership is storytelling. And that's another thing you can learn, right?

58:14People don't remember all the substance of the plan you articulated as a manager. They remember, yes, Maya Angelou, how they felt, but they remember the stories you told them. And I feel like that's also very learnable. So golden rule, treat others the way that you want to be treated. Not a great tactic for a manager or a leader. Not a great golden rule. Why is that? Yeah. It's too bad because I'm a big believer in the golden rule generally for humans. Just in humanity. Yeah. Let's treat people the same way we'd like to be treated all around the world. For management and leadership, not a good rule because you as an individual are motivated quite differently than I am, Logan, I bet.

58:57Like if you and I sat down and say, what really motivates us? How does our ambition show up? What does success look like for you versus me? Our answers would be pretty different. And so your job, if I'm the manager of these two different people, my job is to kind of interview them. I call it the career conversation, but it's really the I need to get to know your motivators conversation. Tell me why you made these choices in your career, maybe even in your life. Why did you major in that thing in college? Why did you choose that first job out of college? Why, why, why? what are you you're trying to get out what are they trying to do what are they trying to accomplish what are they trying to learn about themselves and you're taking that data and you're saying okay this is someone and by the way this is a very real thing i have um worked with people and including a child of mine like some people are motivated by being recognized by positive feedback like you're basically cheer cheer cheer for all the good stuff and and actually there's a lot of human behavior change that positive feedback highlighting these are the things I want more of is way more effective than nitpicking and the negative.

1:00:03But there are people who I've worked with who are like, tell me the thing I did wrong because they're so self-directed. Unfortunately, they're probably a little bit perfectionist, which is not an easy problem to have. It's not an easy burden. But they're so perfectionist that you're like, you know, I thought that, you know, that work you did last year was like, excellent. Like you hit every goal except for that one. And they're like, I know, I'm obsessed. I'm obsessed with that one goal. And like there are people like that. They're like trying to get the brass ring all the time. And all you're doing is being like, all right, let's talk about how we get the brass ring.

1:00:37Right. But that that may not there was another person who spends the rest of the year demoralized that you pointed out that they didn't get that one goal out of eight. Right. You got to know what you're dealing with or else you could completely undermine in them. So it's about interviewing them, observing them, collecting data, and managing them differently than you would like to be managed. I mean, what drives me crazy is I manage, there's some people you manage who are obsessed with compensation. And they're really obsessed with compensation because they're keeping score. Because they're very competitive and that's how they score points, right?

1:01:11And I'm like, oh my gosh, I do not want to talk about compensation with people all the time. And you should try to restrict it. But I've come to sort of get zen about it. I'm like, oh, this is just them keeping score. And this is a way they're looking for feedback. And this motivates them. It motivates them to know that yes, there are compensation outcomes for good work. And so we will now talk through that yet again, because that is what they want. And it helps them. And it is not for me. Yeah, we did away with bonuses. And then there There was no way of recognizing out performance. So we put bonuses back.

1:01:47And then people were upset about not getting 150 % of the bonus target. And I was like, this whole thing is very circular. It's just some people, though, they even it doesn't matter the dollar amount. It's just the recognition that that's exactly right, like that they are doing that good of a job and that the dollars could be totally nominal. This is like a worker segment, the scorekeepers. And it is really about that. And they also have their own score in their head. and what they're really checking with you is, do you and I see the same score? I mean, this actually goes almost to the self-awareness gap.

1:02:17Sometimes, yeah, we see the same score and I will celebrate it with you. Yes, you got 150%. But sometimes it's about, okay, why do you think you should get 150 %? Are we looking at the same performance? Like, it can be actually a really rich conversation if you can flip their sort of, like, why are you so obsessed with that score? What's going on there? I mean, especially for high performers, actually. They sometimes need to be challenged even harder than they've been. And they're kind of telling you that in a weird way when they're scorekeeping. But yeah, Compensation Headaches on the bonus in, bonus out is a whole other book.

1:02:55It's fascinating. Infinite rabbit hole to go down. Yeah, and how people are incentivized and motivated and all that stuff. What about titles? There's kind of two concepts in Silicon Valley. One is that titles are free, cheap, give them away. And the other one is titles are very, very expensive because it leads to a lot of complications. I get the feeling Stripe was much more on the titles are very expensive. Like that costs a lot of internal damage dealing with different promotions and hierarchies and all this stuff. Or at least that's what it was in the early days. Yeah, I mean, Patrick and I really, this was one of the things we aligned on pretty early, which was titles.

1:03:33it's like a little to me, I'm really going to display my opinion here. Giving out pretty high level titles in a young, smaller company is a little bit like eating junk food. Feels really good to eat that bag of Cheetos for about 10 minutes. You're like, I love those flavoyeds. And then you're like, oh my God, I just mailed myself a letter bomb. Because if you are sub 40 people sub 100 even and you've got a bunch of sea levels Are those going to be your chief marketing officer, your chief revenue officer, your COO even in three and you're doing well as a company by the way in three years, three to five years, probably not maybe a few, maybe a few, you're going to three, you're going to three, you're going to three, you're going to three, person, who might be a really good employee, by the way, but not the CMO, than if you had just called them marketing lead.

1:04:43Maybe head of marketing, but now I'm bringing... So I think for C-level titles, the more you can wait... It's also you look at a small company, you're like, how can you have that many VPs? I mean, it's sort of silly looking. Now, I totally get sometimes you need a title because that's important for your sales process. But at Stripe, we would sort of try to come up with a title like growth lead or something that was hard for the prospect to grok. They'd be like, well, it sounds important. You're like, exactly. It sounds important, but you can't pin me down on exactly what the job is. But I think titles back you into a future corner essentially as you evolve your work structure and it'd be nice not to back yourself into it.

1:05:26I do think we took it too far at Stripe. I'm going to be honest and own that. For example, we got a lot of feedback, which I thought was really legitimate, that a lot of the engineer, I mean, it was just like engineer, right? And we did have job levels on the back end, we had sort of level four or five really senior engineers. But no one knew that except for, you know, the people who were leading those teams. And a bunch of the less experienced engineers were like, who are our mentors? Like, who are we supposed to look to? Who do we listen to in code review? and we realized, oh, we need to actually, when someone achieves the staff engineer level, which for us is level four, we should really tell people.

1:06:05Because one, it is an accomplishment. It is recognition for them, but also it's a signal. This is someone you should watch their work, listen to their feedback, use them as a mentor. So that was a miss. And I think there's a similar miss we had on the sales equivalent of that. And so I think there's different, like there's one thing we're talking about, mailing yourself the letter bomb on sort of senior titles of leaders. There's another, which is how do you think about organizational structures? And we were trying to avoid basically hierarchy. We're trying to do the inclusive thing, right? In the room, if you don't know who's the most senior, everybody's going to show up pretty equally.

1:06:41It's almost a cheat code for inclusivity in a way. You still have to do the work to get that meeting, to get everyone participating, engaging in that meeting. Let's say it's a meeting. But there's a time when the org starts to get big enough that it's just confusing. Like you're like, I don't even know who to go to. Like I don't even work with that team. And who do I even call? Right? Or who's the best example? But we were trying to avoid also some hierarchical behavior, which just is not what Stripe is about. We're talking about it from the company side. It's also tough from an employee side as well.

1:07:12It feels good to get called the C-level of whatever company you're at. But then weirdly, you might have to take a step back. Let's say you get moved out of that job and you decide to move on to a different company. Now, are you addicted to being the CMO or the CRO or the COO, right? But actually, if it were apples to apples versus the next company, you're not C-level. And so from the employee side, it actually can be problematic as well. It can do you a disservice at the wrong moment in your career. It's actually a great point. Yeah. People almost won't want to hire you because they're like, well, they're going to want that title.

1:07:49Yeah, they're going to want to C-level. Or what happened in your career where you went from this to that, right? Actually, I've told the story, but I took a step back when I joined Battery from where I was title-wise in investment banking. And I thought, I was like, what is this? Why would I do this? And it was actually the best thing in the world because I got comped against everyone else at this level. And I was a little bit older and a little bit more experienced. And so the apples-to-apples comparison, I just looked so much better. You really stood out. And it was actually a good thing with starting over, right?

1:08:19And you were in a slightly different field. A slightly different field. But perceptions are defined early. And if I had had the higher level, I probably wasn't quite there. And so people would have questioned if I was of that caliber versus I was really good at that level. And it allowed me to accelerate. By the way, this is another example of inclusive choices, which is like, actually, you would rather someone, especially moving into a new company, a new kind of role for them to be exactly in your situation, which is slightly more experienced than the others, but in a learning mode and much more likely to succeed.

1:08:55Well, what was your title when you joined Stripe? Oh, my title was Chief of Business Operations. Yes. Which was because of a similar issue. reason, right? Yes. The reason was we had a lot of conversations about being the COO and the current, Stripe had a COO at the time, which people forget. And it's funny how companies rewrite their history. People forget that. But my colleague, Billy, who's amazing, who is also still with Stripe, but he was a COO and he helped recruit me, which says a lot, by the way, about him and the company. And there were parts of the role where he was like, this is not my talk about self-awareness.

1:09:34He's like, I'm not a scale big operations guy. I'm not going to build the sales team. He was really like, he's a brilliant payment strategist, brilliant at like BD and that kind of work, partnerships work. But point is, Billy helped recruit me. But then Patrick and John were like, well, two things happened. I think one is a true founder moment. Two things happened. One was, they realized that they'd not told anyone internally that this was a decision they'd me, that I was going to be the COO. And they felt if I came in and it looked like I'd taken Billy's job from him, and Billy was very popular, that I would have been unpopular.

1:10:12They're like, we were not setting you up for success. If you walked in the door, I'm being like, and I'll just take that title. Thank you very much. And so we kind of made this other innocuous title. And then after about, I don't know, not even that many months in the job, Patrick just, people had gotten to know me though, and seen my work. And Patrick sent out this note, like, by the way, Billy's going to be chief of business and Claire's going to be a COO and isn't that great? We all sometimes switch titles and switch responsibilities. And everyone's like, great. It was nothing. The other reason was more, I think John and Patrick had a title because they were very in the camp of titles.

1:10:47You got to be stingy with that. They were like, maybe if you could just come in as head of business operations, because I think they got nervous. They're like, this is it's a big deal to bring someone in as basically COO and you're trusting I mean now I look back I'm like that was a big decision for them I was gonna have a big impact on the culture and the results and the outcomes for Stripe and I think they wanted an out and but I said to them I was like guys I was like I think in this case if you look at my career and where I'm at in my career and my track record and the conversations we've had I was like you do need to give me a title.

1:11:24Like, I'm not going to walk in. I'm not going to leave the job I have at Google for a head of business operations job at your company. And they're like, yeah, right. Okay. Yeah. It's a balance. It's a balance. Now, one of the things I heard you say, too many companies make their principles so idealistic that they don't resonate with employees because they have no connection to how the company actually operates. How do you think about principles in general for companies and how how to make them balance tangibility with the idealism. Yeah, so we're talking about Stripe calls them operating principles.

1:11:57Some companies call them values. I mean, the first thing I'll say is there's a lot of work that needs to be done. Before you get to some of the content in my book, you're just trying to stay alive. You're looking for product market fit. There's a lot of stuff you could start to build for that. It's product building more than company building. And really, that's the right place to focus. You shouldn't have long-term goals because you're just trying to make it the next few months. Surviving is your long-term goal. Surviving, right? And so then, though, you start to get traction. You should gut check.

1:12:27Is it real? And this is where it's good to have investors and advisors. And it feels like this is real. And all of a sudden, whoa, you got to think about, I think I might be building a company here because we have a product and people are buying it. And ARR is X or whatever metric. You can be the expert, Logan, on what benchmarks you want to start to see. And so then as the leader, you're thinking, all right, so for company building, I think there's a set of things you want to start to put in place. And this is where a lot of the early chapters of my book, the operating structures. But one of them that I argue is really important, again, at this point more, are these founding documents, including articulating what are your company values.

1:13:05And if I was going to simplify it, I'd say, look, start with what's your mission slash vision, which is the why. Why do we exist? And by the way, why you exist is probably beyond that initial product that you've built, it's a bigger vision that you have. And you may not exactly know it all, but this is time to start thinking about it because it's going to matter to people that you bring on board, right? So, you know, why are we in the world today? Employees care about this. So why do we exist? What's our mission? And then the next thing is the how. How do we want to work together? And this is where the values are.

1:13:37Like, what do we value when the chips are down? Are we going to choose the user or are we going to choose our growth. By the way, sometimes you'll have those choices and you really want to have established when we make hard decisions, what are the values we're using? And sometimes you can inductively get that. You can look at some hard decisions you made and say, oh, it's interesting what we really valued, by the way, with speed maybe over quality. There's no judgment from me. But the thing that I see too often, which you alluded to, Logan, is that someone, executive team, a founder, even a focus group in a company sits down and writes a bunch of values that are really aspirational, like customers first is a common value.

1:14:21I'll be honest, like Google was not a particularly customer oriented company and would sometimes talk about being one. And I would be like, but we're not really like we're actually about the technology first and the customers later. And so no judgment, like I actually think, but just kind of own it, like own what your actual values are. And if they're too aspirational, and they don't resonate with employees or with your customers, by the way, eventually, it's going to actually undermine you. It'd be better to have none, in my opinion. So, you know, this is the sort of there's the motherhood and apple pie version of this, which is like they're so abstracted up that you're like, yes, we collaborate well.

1:15:06I mean, yeah, everyone wants to collaborate well. If they can be kind of specific and kind of true and even stack rank, like what do we value? It's a really good exercise. I wouldn't overdo it or overthink it, but try one thing we did at Stripe when we wrote the initial draft was we came up with stories and examples of those values in practice. And there were a few where we were like, hmm, we don't of a lot of examples. Maybe this isn't a value. Maybe it's something we want it to be true. And then we actually had to think about how do we make this more true, right? Or some that we put out there got misinterpreted.

1:15:39And sometimes weaponized, right? Yes. Oh, yes. There's a few. I feel like I've suppressed them at this point. But we had some around trust. And people were really interpreting something along the lines of trust but verify. There was a lot of verification going on, not as much trust. Or we had the, does it pass the front page test, which is really about integrity and ethics. But people, I think, kind of turned it into a more broad application of, oh, we can't do that. What if it was on the front page? And it's like, well, no, you can still be bold. You want to be on the front page sometimes. I'm just saying the thing - You don't want to be arrested.

1:16:21I'm just saying the thing you think I cannot say. It's like, you're being an asshole. Yeah, exactly. You're being a jerk, actually, is what you're doing. So really try to apply the values and see if they stick. It's interesting because everything does have, there's two sides of every coin, right? And if we were to say we're founders first, right? And Founders Fund does a great job. They say they're founders first. Now, that comes at times at the expense of limited partners, right? That is a, there's two sides to these. You can't just say platitudes without thinking through the other side of that, right?

1:16:54And there's everything. It's not hollow. It sounds hollow to say, oh, we're founders first. Or like Google, we're customers first. Are you though? Are you actually customers first? When push comes to shove and you have to make a technological trade-off of what the future roadmap is going to be and it's going to piss off a bunch of customers, are you actually a customer first, right? And there's no real platitudes. All these things have another side of the coin. And then that's when you know you have a good one because it has an edge. You're like, this is going to have a downside at some point.

1:17:22We are going to have a decision we have to make that it's going to hurt. I say a strategy should hurt. So should some of your values should feel pretty painful, but it should be. I mean, Patrick, in a different context than I talked about this, I talked to him a lot about expectations of leaders and how they should they should be higher. And this is a sort of behavioral expectations, leaders, you know, ethics expectations. And I said, there's going to be a time when a leader who we highly value, who's incredibly talented and incredibly impactful does something humanly with poor judgment. And you all can color in whatever story that is.

1:17:57And I said, and I will tell you, it is going to hurt like hell, but we should, they should, there's, if it's bad enough, they should leave. Even if they're the best person at that job. And he was like, and we actually like went pretty deep on examples I'd seen and what I thought, because culturally you've then taken someone who you've elevated to a leadership role and they've done something like with horribly bad judgment and said it's okay. And even if it's private, it still gets known. In my opinion, a big enough company, it still gets known. And we kind of locked arms on it and we had to act on it.

1:18:30Occasionally, you know, there's times when you're like, oh my goodness. And now we're like, it feels like you're stabbing yourself, but you're not in the longterm. You're live, you're honoring the culture you're trying to set. Yeah. Which is we hold leaders to a higher bar. Sometimes you need to have surgery to tear your ACL. You have to have surgery to rehab yourself forward, right? And it can be painful. It's not like the payoff is tomorrow. No. It actually hurts soon. It's a long time in the future. Don't let perfect be the enemy of good. I know that's something you believe and I happen to share.

1:19:02How do you think that manifests itself in startup and high output companies? Yeah, I think there's this continuum that is so interesting and you probably see you see more companies than i do where the sort of uh move fast and break things facebook whatever and then there's the perfect is the is is actually starting to kill the good and i think that some companies and it's really about the founders and and their uh their proclivities or their instincts their defaults which is our get i'm not saying analysis paralysis but like are so intelligent often they think of so many angles they're trying to preserve of optionality and they're like, how do I get more data?

1:19:44How do I know? Who do I also check with? And they're making some decisions or choices for the first time in their lives and they're waiting or they're waiting for this candidate who's perfect, right? And you can be too far on that continuum. And you can also be too far on the outcome be damned. I am running up the mountain and I don't care who I hurt. And that could be a user, a partner. You could have bad behavior, but you're getting the goal, you know, like that's also not good. That is, you know, not even the good being the enemy of, of the, you know, I don't know the bad winning in that case.

1:20:17So I think on that continuum, being aware of where you fall, this is self-awareness actually in the end, be aware of where you fall. It's like in your defaults as a founding team, as an executive team. And then think about how do I push myself? How do I make sure I don't fall on the wrong side of that? That I'm way often for the perfect being the enemy of the good. It's like taking too long to make a decision, to make a hire, to sign a partnership. There's this quote from either Hewlett or Packard, which is after a certain point, there are some companies that die more of indigestion than starvation.

1:20:51I think perfect being the enemy of the good is like you've gotten to product market fit, you're starting to steam ahead, and then all of a sudden you're starting to die of indigestion. You cannot get stuff through the system because you are just examining every damn thing too closely. And it's important to analyze yourself and where you fall. And then And not every M market is going to be the same either. That's true. That's true. I would be glad self-driving cars take a little bit time to be perfect or and roll. I was just going to bring that up. Yeah, it does depend on your market and who your customers are and what they, I mean, gosh, Stripe's dealing with payments.

1:21:23We better be on that side of the continuum. Yes. And we are. Yeah. But sometimes we flip too far over to like, ooh. Yeah. If you're a Kanban board or workflow software, you can get by a little bit more. But I was actually, I was in this funny, I was at a conference running a roundtable discussion as a breakout. This was with another venture capital firm sponsored this, but it was all founders. We were all talking. And it was me and a couple of leaders from some other companies talking to a group of founders. And I was saying how when the chips are down at Stripe, if we are doing a launch review for something, we may have even publicly said we're launching, maybe at least to some customers, and we don't think the quality is there, we will delay the launch.

1:22:02like there is no question and if you think about it yeah we're dealing with people's money with payments if we don't like and even if it works but we don't like the quality and the craftsmanship that's also what we like to be known for right we'll delay the launch and this guy across the room from another i'm not going to name the company starts laughing he's like are you kidding and i was like yeah he's like we would do the opposite if we weren't liking something we would move the launch date up i was like excuse me he's like well we have this whole idea of these test markets. And he named a city in Canada.

1:22:32He's like, if you live in Canada, you have seen some crazy stuff from our product. I was like, are you serious? And he was like, oh yeah, we'll move it up because we're trying to understand like, why is it not working the way it should? Hopefully this business isn't healthcare or self-driving. It's not a safety critical system. But the founders were like watching us, we were playing tennis match. And I think it was actually probably the best thing that could have happened because it was like, these are equally reasonable choices that you make in the face of something that you're not happy about launching.

1:23:05And it really depends on your product, your market, but also your appetite, your appetite for risk, who you are, your value system. And by the way, good on them that they have some test markets that they learn from, right? Like I was kind of jealous, but like this, sorry to that one city in Canada. But you know, I think that that's, that's what's kind of fun about working with different companies in different markets. But the key is self-awareness. Know where you fall. And then to the point we talked about earlier, have some people around you who will call it when they think you're dying of indigestion.

1:23:38You had said leadership is disappointing people at the rate that they can absorb. And I guess it's an interesting line. I actually didn't know what you meant by it. What does that This is a quote from Ron Heifetz and also probably Marty Linsky. These are some researchers, academics, and I guess sort of leadership gurus at this point who've written about adaptive leadership, which I actually, back to books that are worth checking out. I think some of Heifetz and Linsky's work on adaptive leadership is worth checking out because it's about like distinguishing between the fact there's technical, this is almost management versus leadership.

1:24:14There are technical problems, like we can't meet our SLAs. You can work your way to fixing that problem. There is not a right or perfect answer, but there's answers. Adaptive problems never stop. Something is happening in the competitive landscape always. It is adaptive. Or is your go-to-market product interlock perfect? No, it is never perfect. You'll be adapting constantly, right? And getting comfortable as a leader with adaptive problems, and they talk about various tactics. One of their favorite ones is how do you get up on the balcony and observe the problem and then get on the dance floor and interact with it.

1:24:51But being able to do both of those things at different times really helps you as a leader to adapt because you are going to have to keep iterating, right, to work this problem forever. It's like infinite systems, essentially, right? So leadership is disappointing people at a rate they can absorb is one of their quotes. And I didn't have it in the original book. And then someone who used to work with me at Google was an early reader. And he and I were, he was giving me you my feedback, which was great. And he said, you know, it's funny. I remember we were in this meeting where you shared that quote because I'd been reading.

1:25:22I'd been a learner about adaptive leadership. And he said, and it stunned me. And I thought about it the rest of my life since then. And it's interesting because in the book, a lot of people have picked up on this and they're like, I really want to talk about that. And I think it's because we think of leaders as superheroes, right? We think of them as these people who don't disappoint us. They inspire us, don't they? and actually leadership is is often disappointing people you do become a little bit mythic especially the founders right you become bigger than who you are as a human and you aren't perfect and if you start thinking you are you're gonna have the other problems and I think one of the biggest ways leaders aren't perfect is we talked about this you set a vision you don't even know how you're gonna get there you're like we're gonna completely pivot our company to this brand new product line and launch it in the next six months, right?

1:26:14You're setting this vision. You don't have all the details. You're expecting your team to, one, follow you, which you better have some skills to get that to happen. And two, to color in the lines to get that whole pivot to that new product line done in the next six months. And you've told a customer, by the way, leaders often do that. They announce things. It's like burning the boats. And, you know, Alexander Gray, just burn the freaking boat. So you can't go back, right? So that is leadership. And leadership is uncomfortable and it makes people uncomfortable. And by the way, it's not perfect.

1:26:44Guess what? I bet that pivot to that new product line took 12 months or 18. Right. And people are sitting there thinking, hey, we didn't get it done. But actually, as a leader, you're like, oh, my God, but we are doing it. Totally. But you are a little disappointed. Or another way is you disappoint people is you get them really excited about following you and spending time with you. And then guess what? You can't spend time with everyone. You're going to disappoint them with your time because you cannot give it to everybody. You are still a human being. And I think that's what I mean about living with that discomfort is a lot about learning to be a better leader.

1:27:21Some of it is setting the bar and the inspiration and some of that is not showing up perfectly and giving yourself permission to realize that's okay. It's going to happen. I mean, one woman who I'd mentored at Stripe and who went on to a pretty senior role in a very successful sort of younger company that's in a growth stage called me not that long after she took a role. And she was like, oh my God, how did you live with the fact that everything is broken all the time, every day? Because she had elevated to a point where she saw what the equivalent of me saw an early stripe. And I was like, oh yeah, welcome to the tarot dome.

1:27:59Everything is broken. Nothing is perfect. And if you are motivated as a leader by fixing everything quickly and it being perfect, you will die. Like this is not, this is not the next three years of your life. The next three years are, are, are living with a lot of discomfort and imperfection. But never, never releasing the bar, right? Keep holding the bar. What does don't leave ice cream on the counter for too long mean? Oh, I think this is such a great analogy. And this is from a business school professor of mine who sadly died last year at a pretty young age. Her name was Segal Barsade. And she was trying to teach like change management is a hard thing to teach.

1:28:36It's actually a thing you need to spend energy on and think about and plan and build processes. Like I can't just pivot to the new product line. You can't just reorg the whole company. You have to think about the change management, not just to propose the change, but who to tell and then how to cement the change. And so her analogy was this, the minute you start the change and that start could be just telling a few people about it is like, you know, your house, when you take the ice cream out and you put it on the counter because you're going to scoop some ice cream. Then you get distracted and you're like finding out which flavor people want and you leave it and it gets like a little melty and kind of looks a little gross.

1:29:13And then you put it back in the freezer and it's never quite the same because it got weirdly like the consistent. I mean, there's so I'm sure some food chemist is listening to this like there's a reason for that. Anyway, she's like, if you start the change and you leave that out hanging in the wind without all the decisions or the communications or you haven't started to cement it, you could irreparably affect some things culturally or in your team stability. And so I actually introduced that analogy to the Stripe leadership team early on in my tenure. I don't know. It always stuck with me. And a few people still to this day will be like, oh my gosh, ice cream's on the counter.

1:29:53Ice cream's on the counter. We got to finish. We got to see this change through. And I think it's just a good watch out. So you wrote this book. It was published in April? March of, yeah, 2023. And I heard you say one of the things that you've only gained conviction in since doing it was to manage people out of seats earlier. Once you sort of have that conviction. And I think it ties to this ice cream on the table thing. Yeah, it does. It's a different version of that. A different version of it. Can you expound on that concept and thought? Yes. So it's a great connection you're making. You know, I think what I've gained more conviction, I mean, I knew Patrick and John read the book, the earliest manuscript version I had they could read.

1:30:46And I mean, phew, Patrick's like, yes, this is what I was picturing. Because he really wanted me to write the book. And I was like, I don't even know if we're talking about the same. So maybe use this as an interlude of, so you wrote a section of a book for Eli Gill, who's been on the podcast before, High Growth Handbook. You wrote a chapter in that, and it was well-received. Yes. So I did this chapter in Eli Gill's book, High Growth Handbook, which was our best-selling Stripe Press book, because I think it's a great book, by the way, and highly recommend it. And my chapter, even though I was definitely one of the lesser known contributors to that book, in terms of tech luminary types, got a lot of traction because I think it was very tactical and concrete in a way that's maybe, you know, it's hard.

1:31:27Management leadership advice is often abstract. You're like, how do I actually do the thing? And so I did some of that discussion in Elad's chapter. It got some traction. I also there's like a YouTube video of me how to run an effective meeting that's got some many millions of views, which I find scary and fascinating. Yes, I did it at a COSLA conference. Yes. And that got a lot of traction. I mean, I went once to a wedding and I got introduced to this guy who's a prominent academic. And he's like, oh, I know you from your meetings video. I was like, weird. OK, nice to meet you. But point is, Patrick observed those things.

1:32:01But also John and Patrick observed that a lot of Stripe customers are really interesting companies that are growing quickly around the world. Wanted to spend time with me on their scaling stuff and less on payments and Stripe's products, which would drive us a little crazy. But I was like, hey, I'm happy to have dinner with them. I'm happy to talk about it. And Patrick's like, you just have to write stuff down. And I said, I don't know that I'm the right person to write this book. But yes, wrote it. And it came out in March. I knew that he was cringing. there's a section on managing people out and firing people.

1:32:33And I talk about how long it can take. And I say, look, it's not gonna be one conversation. And the more senior the person is, by the way, the longer it can take. And I think that makes sense to everyone. It's like, they've got a whole team, they've got an org, you spend all this time hiring them, they've had a successful career, can they course correct? There's costs, there's a high cost. And so I talk about, you know, 30 days, 60 days. And Patrick and I joked, because I said, I got in front of it. I said, I know you're cringing at the section on how long it can take to get someone out. And he's like, yeah, you know, I am because he he's of the mind, like the faster, the better.

1:33:08And I think now that he's managed more senior people for longer, he realizes is not always the fastest path. But I sit on a lot of boards now. I mean, you probably sit on a lot of boards. But when you get 30 ,000, 10, I mean, 10 to 20 ,000 feet away from a company, and you're talking to the CEO, the founder, you're sitting with the executive team and there's clearly a leadership issue in one department. And it's like, so it feels like someone is painting neon paint on this person for me now. I'm like, oh my gosh, this is holding the whole company back. Holy crap. We have got to move. You know, it's really interesting.

1:33:50You get much more clarity on how critical it is to address when you've got some separation from it. So that's why I really have more conviction. It's because since writing the book and since I changed my role at Stripe, I've gotten involved with a lot more organizations, not just companies, you know, nonprofits, schools, you name it. And I'm like, having an issue in, and I don't care if it's your team of individual contributors or it is your executive team, but I'm talking about in the executive level, having a performance issue is a killer. I've never seen it come back around. I'm sure it has.

1:34:22No one ever says, I wish I'd move more slowly. It's never happened, which means our bias, we need to overcome our bias to keep someone around and give them a chance. And by the way, the key is, I still think, and I talk in the book, you can do this with empathy. You can do this with good, honest, direct, open conversations. In most circumstances, some of these go sideways and it will cost you money usually. But I just think if you're not talking directly to the person about, I'm worried, we have a problem. You are doing them a disservice. And as I see now, you are killing yourself on your strategy.

1:34:59And probably the people under them. Well, I was just about to say, great people hate mediocrity. And if they're saying, hey, this is acceptable here, it kills their perspective on it. And the thing people will delude themselves into thinking is that you're being fair to the person that you've made the decision on. I'll give them more time so that they can get settled. And that's actually... Or that you're keeping things stable for their team. It's supremely unfair, right? It's actually that person should be given an opportunity to go to a business that doesn't have all the questions and are inevitably ready to get rid of them.

1:35:34And their team will be happier with a leader who's got, by the way, the confidence of the CEO. That is a real problem. If you're on a team where you're like, person managing you isn't trusted, you may not know it, but you feel it unconsciously. I will say we're talking about, I mean, I don't know, maybe, obviously, if you've 100 % know someone needs to leave, then you're moving them out. But we're talking to the upper. It's always a gradient. Yeah, we're talking about a gradient here. I do think it's hard when there's someone who's clearly not the best. And those are the ones that actually drag out more.

1:36:06And maybe my conviction is more, you know, in your heart of hearts, if it's going to work or not. And you've got to start trusting your gut and moving. And the hardest part about that is if they were the right person for six months ago in the company, but the company's growth is outpaced where they are, that's when it's particular. And you've started to have that. A lot of this is stuff. I mean, I'm sound like a weird Californian and I'm now back on the East coast. So I want to say I'm not a weird Californian, but you know, in your body, like it's a weird thing. Like you'll be like six months ago.

1:36:38You feel it in your lumbar. No, but you're like in the room and you're a little uncomfortable. And you're like, six months ago, I was fine. Like our executive team meeting was fine. And that's probably true, by the way. And then all of a sudden you're not feeling it. And you got to like, listen to the feelings. Now you referenced being on a bunch of boards. You're on Hallmark's board. I was on Hallmark's board. I was on Hallmark's board. I was. Now I'm on - But that was a purposeful decision. It's an unusual - It was a personal development decision. uh and can you talk a little bit about like being on a board of a company that has been built to last over a hundred year old company yeah what did you learn from being on something that has been that endurable yeah i mean hallmark was interesting to me because uh well one if you're at google as an executive google is supportive of you joining boards not every big company is actually which i appreciate however you can't join a board that as a competitor a competitive in any way to any of Google products, which eliminates a lack of companies.

1:37:35A high percentage of the world. So I want to own that, first of all. But Hallmark was interesting because I don't think there's enough respect paid, especially in Silicon Valley, but in tech generally. Some people are the exception to this. But to look at companies that have existed for 80, 100, 120 years, there actually aren't that many in the world. There's like a soy sauce company. There's Caswell and Massey. It's like a soap company. Like, we should study them because that is a sustainable, not just business, like you built a business that has sustained and had revenue and had growth for 100 years, but often also the culture through multiple generations of leaders and well-passed founders, by the way.

1:38:17That's astonishing. Like, how do we harness what's happening in those companies? So Hallmark became really interesting to me. It was also interesting because it runs like a public company, but it was private, which meant less time commitment. but actually has a meaningful amount of revenue, which is private, but in the billions of dollars of revenue, owned a media company, Crown Media, I think we all love our Hallmark movies, and the Hallmark Channel, owned Crayola, which is actually a very interesting company they bought in the 1980s. And then obviously the core Hallmark cards business, which you would say, oh, well, isn't that a dying thing, right?

1:38:51That's an interesting thing to think about. It's like a very, there's only a few players, it's kind of an oligopoly. So it's actually competitively really interested in creating cards, weirdly, I learned. But I was most interested in how had they structured succession planning, multi-generational strategy planning, actually sitting in the moment where technology was disrupting elements of their business, what were they going to do with that? And one of the big things we did is that Crown Media, the media properties, which is the content, and I think you know well, but content is fragmented, but it's at a premium, good content.

1:39:29Crown Media was public. And so we took it private. So we owned like 96 % of it. But that was one of the biggest decisions as a board was like, we have to own our own destiny and our content is going to matter to us more than, whereas the greeting card business sort of mattered more, right? Like it was like the media business actually matters quite a lot, but only if you can control it. so it was really good to take me out of Silicon Valley put me in a situation by the way also oh my gosh the legacy systems have a stranglehold on these companies that have been around a long time and you realize these are smart Silicon Valley is like what's wrong with these leaders these executives of these companies why don't they get themselves just rip up your stack move it to the cloud you idiots we all think that what's wrong with them they must not be smart guess what really smart really competent people a bunch of amazing leaders I would work with at Hallmark and I was like geez I was really judgmental I was not being open-minded and they are like fighting a war with like two hands and one leg tied behind their back because ripping out those systems so disruptive and tear like it's just like really existential threat to the business, especially if you've got physical goods.

1:40:47I mean, it's a total Jenga game that is way more complicated than you realize. And it was really like hurts your head when you think about it, but very instructive when you're trying to sell B2B and sell SaaS. And you're like, oh, I see. You just explained why IBM's still in business. Why they don't get that. Yeah, exactly. They get that they need a different solution. It's how they get to there that is brutal. So that was really, really helpful. But yeah, I sit on a bunch of boards of actually different stage companies and some not companies. I'm actually spending time on, I'm on the board of the Atlantic, which is used to be the Atlantic monthly.

1:41:22It's publication. It's won the national magazine award the last two years. I had nothing to do with that. I'm on more of the business side of things, but I'm going to visit with them tomorrow. But yeah, I think it's really, I mean, I will say as a development thing, Patrick and I talk about this, like it's really good to try to be on. I mean, it's hard because it's time consuming. It's a commitment. But for me, being on the Hallmark board and being on the other side of the table from the executive, from the operators, I immediately was like, oh my gosh, when I'm presenting to the board, I'm going into way too much detail.

1:41:56I was like, I am not. Brian Halligan, we were talking about Brian at the beginning of this, who's the founder and the chair of the HubSpot board, previously CEO. we have a new board member who's like, you really shouldn't be talking about so much how in your meeting, right? You should be talking about the why and maybe the what to a point. But like, if you're talking about a lot of tactics, a lot of operational detail, something's wrong. There's better places to get feedback. There's better places, yeah, for the board. Like you're also inviting, by the way, you don't want to invite me, an operator, into the how details.

1:42:30Because I'll be like, oh, what about this? Have you tried that? And then you're not talking about the stuff moves the needle for the business, right? Now, I think we both have places to be at some point here in the next couple hours. So as succinctly as you can, what makes the Collisons so special? Patrick and John Collison are really multi-dimensional humans. And they're very different from each other, I think, but they're sort of like a Venn diagram where they're very complimentary in certain ways. And I think obviously have some shared values, which is a good foundation to have. But high IQ, high EQ, different kinds of EQ, but really curious.

1:43:16Learners, very ambitious, but humble, comfortable that they don't know everything and really excited about others teaching them and giving them feedback. And a lot of vision. I think the amount of energy they both bring, but in different ways to, they discover a problem. You know, you discover a problem space and I'll say this as someone who's like had a few years under my belt. I'm like, oh my gosh, I'm exhausted. Like, am I really going to go fix that? I just, I think the energy level for tackling really horrifically heinous problem spaces is amazing to see and sustained they both sustain it the level of commitment to that um and and i don't know i think there's an element of you know solving problems they themselves faced as engineers and doing that at a scale i i think they have not gotten cynical about that that that feels like an important responsibility that they have and i really appreciate that too uh and just just flat out super intelligent people.

1:44:24I mean, let's not kid ourselves. But you can be really intelligent and not respect others and others' contributions at intelligence, and they are the opposite. There's a lot of different types of intelligence, which is something I've found more and more. Absolutely. I thought it was all SATs and GPA once upon a time, and that is not just intelligence. I want to back up and talk about, I guess, your parents, but your dad in particular, instilling in a value of autonomy to you at a young age. So he had you shingle your roof, taught you how to fix a car. To a point. Never had you, yeah, build a car.

1:45:03Yes. Never helped you with your luggage or suitcase. Yes. There's a family rule. You pack it, you carry it. Can you talk about how those little things impacted who you are today? Yeah, I think, I mean, and my parents are both teachers. And I think another thing is, if you aren't contributing to the conversation, this goes to the sort of say the thing you think you cannot say, or just confidence generally, you kind of can't leave the dinner table. Like, you better add some value. And that's true. Especially if you went to business school and you were the black sheep in the family. I know, I know.

1:45:36It was very unpopular when I went to business school. It was not very intellectually deep of me. But at the dinner table conversation, I had to carry my weight. And I think that taught me from a young age to think about what I'm saying and have ideas and share them, which helps when your parents are teachers because that's what they're doing. It's bringing that out of young people, which is what you hope teachers are doing. But how do you... Yeah, it's sort of a combination of confidence, interest in learning and sharing ideas, and feeling comfortable being independent. I do think as a parent, I fail some on this, which is your kids can do a lot for themselves, but a lot of parents don't ask them to or don't expect them to.

1:46:24And I think my parents were busy with their lives and their careers. That's one of the benefits of having two working parents, I think, and I had to figure my own stuff out. Like I planned my whole, I'm laughing now because I've just been working with my daughter on her college visits. And I planned my whole thing. I scheduled my visits. I scheduled at the time there used to be interviews for colleges. There's not as much anymore. And I'm looking at like, hmm, am I an enabler? I am. Oh, no, I'm not listening to my own advice. You and I were talking about sometimes you give good advice and you don't always take it.

1:46:57That's being a VC. That's being a VC. That's your secret tagline. We give great advice. We just don't take our own advice, right? That's right. But I really value, you know, my father's not with us anymore, but he talked about people who had no biases. Like he believed that every human, you could do something interesting with your life. And he expected it of us. And I think that's one of the best things you can do for other people. And to the point of he also back to the victim mindset, right? you told the story of him being robbed at gunpoint in Paris, was it? I don't think it was a gun. I think he was just mugged, but like meaning jostled in the metro.

1:47:43And yeah, totally like in retrospect, I'm like, how horrible would that have been to lose like your wallet, your ID, you're in a foreign country. And he was just like, yeah, should have been smarter. He like totally took responsibility and just dealt with it. And somehow we got home. I guess I think he didn't lose his passport, but I was young. But I remember, like, if you think about how you react to something like that and watching your parent react to what is one might view as a failure, at least something really bad happening, such resilience, like such, I'm going to take responsibility. I'm going to do what I can do, what I can control, control what I can control is it's amazing.

1:48:24Again, I think leading, especially young companies is a lot like parenting, which is it's not so much what you say, right? You try to say the right things, of course. It's your behaviors, your actions, and even your emotional reactions when under stress. That is what people are really watching and they're taking their cues from. And I would say both my parents really had a lot of resilience and personal accountability and believed in sort of independence. And I watched that from a young age and I experienced it. The story that you've shared, I think is an important one, if you're comfortable sharing it, of the Google layoffs and just balancing work.

1:49:09We spent a ton of time talking about operating practices and all this, but when you zoom out, what actually is important in life, if you're comfortable telling the story of the Google layoffs and your father's birthday party? The thing to think about is, and there's some, like, I think there, I was at a dinner on Sunday night with a bunch of educators who were talking about how they've had a set of employees that they've hired who are sort of of the latest generation. Every generation is criticizing the younger generation, but they're like, they're really like super attuned to boundaries and balance and like more than we were.

1:49:47And I I have to sit and examine that because the story I'm about to tell is more in the vein of what I think what I experienced with most of the successful people I know, which is we've worked our asses off for a lot of our careers. And yeah, we've been successful. And some of that was luck. But someone told me luck is when preparation meets opportunity. I really believe that. And I think I was really driven. I was driven even despite, you know, I had young kids. I was at a point in my Google career where I had an opportunity to be in a really, I was in the most senior role. Cheryl had left. I had taken part of her responsibilities.

1:50:28It ended up then being more after this period. I'd come back from maternity leave with my second child. And it was 2008 Lehman Brothers collapse is literally like the week I'm back from maternity leave. And I'd come back early because things were shaky. And in the end, that 08 sort of mini recession was not as impactful to tech. But at the time, it did not look like it was going to be an easy one. And in a very not well known action, because I think the recent layoffs Google did people, it's the first time Google's ever done layoffs. Actually, no, I laid people off in 2008 in my division. And I came back from leave and made that call.

1:51:05And the day that I had to do that the layoff announcements were happening, and I personally spoke to some of the infected employees, meaning laid them off in a conference room with HR. um I talked to my my mom said I really want you to come to New York we're going to surprise your father for his birthday and I was like oh I just don't think I like I gotta do this like I'm under so much pressure as a leader I've got to deliver this message it's going to be brutal and I talked to my manager who at the time I mean kudos to him could have said yeah no way you're going to New York like you got to do this and I sort of thought about and I was like you know what I think if I did the Mountain View stuff for Google and took a red eye and went to, we had a team, I had a team in Boston, in Cambridge, actually, I could meet that team, which would actually be a good thing to do, do back to back geo visits.

1:51:59And then I could fly to New York, and I could be there in time. And he said to me, he's like, if you think you can do that, and the red eye isn't going to affect you enough, you know, I can deliver messages in Cambridge, then yeah, go for it. So to his credit, and this is for all the managers out there, he was like, if you can make it work in a line, because you can't always choose one or the other. You're balancing your professional obligations, your personal life. But yeah, I got there. I surprised my father. I saw him the next day, too, which ended up being really important because just a few weeks later, I got a call during the day in California from my mom, and my dad had died of a heart attack.

1:52:38on the way to the airport, I called my best friend and I was like sobbing. And I was like, what if I hadn't gone? What if I hadn't gone? And she was like, but you did, you did. But really, it was me saying to myself, oh my God, I really high chance that I had not gone. Like, because I was just in that mode professionally and my ambition and my sort of priorities, honestly. uh and I think that's the lesson that when I share that story I think sticks with people because now for sure you know I'm a certain age like I've had a certain amount of success of course I'm going to go to my parents surprise birthday party uh but then it was not so obvious and so I guess I would just ask everybody just you can't be there for everything but having an eye on what's really important earlier in your life than you're developmentally ready to ends up being maybe the biggest lesson of all.

1:53:39Yeah. Well, I appreciate you sharing that. It's a powerful story and I think it's a good lesson. We spend a lot of time talking about operating tactics and philosophies around hiring and managing and all that stuff. But at the end of the day we're all people with lives and family members and uh turns out we're all humans there's important stuff outside of it well claire thanks for doing this thank you no thanks logan it's great conversation really appreciate it