Silicon Valley Legend Unveils Her Best Operating Advice

[Music] Sometimes you give good advice, and you don't always take it, but that's being a VC. Welcome to the Logan Bartlett Show. On this episode, what you're going to hear is a conversation I had with Claire Hughes Johnson. Claire was the longtime COO of Stripe and, before that, a senior executive at Google. Claire and I have a conversation that goes in a bunch of different directions, including the distinction between leadership and management, how important self-awareness is as a leader, how to have difficult conversations with members of your team, lessons she's learned from hiring thousands of people over the years, and what makes the C-Suite brothers so special. Claire recently wrote a book on operating and is known as one of the top operators in all of Silicon Valley, which you'll hear in this discussion.

Now, giving out high-level titles in a young, smaller company is a little bit like eating junk food. It feels really good to eat that bag of Cheetos for about 10 minutes. If you are under 40 people, under 100 even, and you've got a bunch of C-levels—are those going to be your Chief Marketing Officer, your Chief Revenue Officer, and you're doing well as a company, by the way, in three years? Probably not.

[Music]

Claire, thanks for doing this.

Thank you for having me, Logan.

So, you joined Google in what year?

2004.

And how many people was that?

The company was like five or six months from the IPO and about 1,800 people.

Being pre-IPO, you get so much credit.

I had nothing to do with any of that.

Oh, absolutely. I mean, there was so much value created after the IPO for Google that not having it, in retrospect, was really early. But being able to say "pre-IPO" is just such a point of validation. I was like, "Yeah, I was there pre-IPO."

Yeah, it was funny though because, I mean, I think rightly so, Google was super suspicious of hiring in that final sort of six months right before because, you know, there was probably some mercenary behavior going on with candidates. So, I felt kind of like a miracle to get hired, but I was so naive. I had no idea what I was watching.

Your background prior to that was very unusual.

Yeah, maybe not unusual to go to Google. I think it was eclectic. I mean, I worked in politics and government. I ended up going to business school instead of law school. I ended up working in a sort of startup consulting firm that was actually one of those tech strategy mashups that happened in the pre-bust early 2000s, end of the '90s.

In fact, my work with some consulting engagements was really about CRM and doing data work, back in the days of data marts and data warehouses, and how do you get insights on your customer base. Anyway, so that was sort of relevant in that I was used to working with some—I think calling them engineers or developers would have been advanced then—but some folks. It was more integration; it was a lot of ETL stuff. The point is, I worked at this consulting firm that had some technical aspects to our work, though I was on the strategy side, obviously. But in the end, I was running engagements that were a mix of technical people and strategy people, so more relevant.

So, you get to the West Coast, and Cheryl Sandberg hired you?

Cheryl hired me. I knew some people who—I mean, you know this is how the world works. I went to business school with some folks who were friends of hers or friends of friends of hers from Harvard. She hired some folks from that time in her life as early operations managers essentially in her online sales and operations group. I thought I was doing a friendly call with one of them, who was a friend of a friend, and she grilled me for like 45 minutes. I said, "Laura, is this an interview?" I mean, I'm driving in California with my husband, going away for the weekend. He was then not my husband, but she grilled me, and she's like, "Well, if I'm going to refer you, I have to believe you're going to be good."

I said, "Because Google—" like, it was very serious in a good way. Now, you know, I wrote about it in my book. I'm like, "You got to take your hiring very seriously." Totally.

So, she didn't want to refer me if she didn't think I was good.

It's an interesting lesson that you're kind of always being interviewed in some way, right?

Oh, yeah. There's a microphone here.

Yeah, it's just like you're talking to your friend. That's what I tell founders as well. If you're talking to an investor, you're fundraising—like, you might not note it might not be a process of you fundraising in some way, but they are definitely putting inputs into how you assess things, and I think that's true for candidates in general.

So then you were at Google for how long?

Almost 11 years.

So, I left in 2014 and then joined Stripe in 2014.

I did, and you did full-time at Stripe, is that right?

One week later.

And you were there for six and a half years full-time?

I was, yeah. Six and a half years full-time as COO and then now part-time for the last few years.

And Stripe was about 160 people?

Yes, about precisely 160.

It was 162 when you—

When I look back on both Stripe and Google, what are one or two takeaways from the cultures themselves? Very distinct cultures, but I'm sure they evolved. But from the times that you were there, is there a thing or two that really stands out about the cultures that you think all companies should internalize?

I think all companies should internalize that there is a culture and to try to understand it. Some of it is intentional, and some of it's not, right? I mean, young companies are mirrors of their founders, and so a lot of the culture that you see is maybe less conscious. It's often that mirror of the founder and their behaviors—more their behaviors, right? It's your actions and less your words. You can be aspirational with your words, but it's what do you spend your time on? What do you value? What draws your attention in terms of decisions you're making?

But Google and Stripe have had some things in common that resonated for me and had some things that were quite different, actually. I would say in common, both sets of founders had very big ambition, but not completely pie-in-the-sky—like ambitious but realistic to a point. But you know this; I mean, the thing that's amazing about both those companies is on the B2B side of the businesses. Obviously, Stripe is all pretty much B2B, and Google—everyone thinks it's a B2C because of the search, right? But it's AdWords that was the revenue business, and now, you know, Google Cloud and all of that.

But to have millions of B2B customers, right? Multi-segment from pretty early on, it's pretty astonishing. You have to have a very big ambition, a global ambition—one where you believe you're building a product that appeals to millions of other businesses. That was in common. And it was not just, "This is the starting place, and we're just going to figure it out." It was like, "No, you know, this is commerce infrastructure in the case of Stripe. This is not just payment processing."

And there were credible details behind that on plans that the company had and things that Patrick and John saw that needed to be addressed, really to bring technology to the financial services world, which is a challenge because it's really pretty entrenched—not in every country, but in a lot of countries around the world. And Google similarly had clear missions for both of them, high value on individual talent.

But very different. Google was using a lot, as you probably remember, pedigree to filter out. So, what school did you go to? I mean, I had to share my college transcript.

Wow.

When I was in that process for Google, and I was now 10 years out of college, right? To me, it was like, "Well, haven't I done something since then?" But they were really—I was writing essays.

So, not only was it where did I go to school and where did I go to business school, and you know, actually, business school was a knock on me at Google. But Stripe was much more open to really very different sources of talent. And I think Patrick and John themselves were such active participants in so many internet communities, which in Google's defense were not as active in the late '90s, right, when they started.

But whether that's IRC or Hacker News or Twitter—in the more heyday of Twitter—but Patrick especially would see someone who had interesting ideas or who seemed talented—maybe that's a designer, maybe it's an engineer—who's like shouting some stuff out into the Twitter sphere and contact them and be like, "Hey, let's meet."

It's an interesting lesson for startups.

And then we would hire them.

Well, so that's the thing. If Stripe did it, you sort of need to take chances on why this person would join your company because Google maybe is on a short list of best businesses of all time, at least in terms of Google search and the product-market fit around that. And Stripe's on a very short list of like best product-market fit of all time as well.

And if they're going to join your startup as a Mr. or Mrs. startup company CEO, you probably need to evaluate what's the reason for them picking you. Are you taking a chance on them in some way? Like, it's not just going to be the pedigreed person with the background that you're seeking out.

Well, yeah. I mean, I would say early Google, it was like, "Let's find some smart people from Stanford," essentially, because Larry and Sergey had dropped out of there, and that was their network. And then fairly quickly, you're right. I think the product-market fit for the search side of the business and then AdWords got built—not immediately, but soon enough that they did have their pick.

They also were in a—I mean, again, we just talked about this—the economy wasn't in great shape. I mean, Google was founded at a time where there wasn't so much traffic in San Francisco, as people pointed out to me when I moved there, because there were a lot of businesses that were suffering in that sort of turn of the 2001-2002.

And I joined Google in early '04, right? So, coming out of that. But Google was definitely the shining star in that moment, so they had their pick. I would argue that Stripe less so when I joined Stripe.

So, I feel like I look back now, and I'm like, "Gosh, I felt like every Friday, if not multiple days of the week, I was taking lifts or Ubers either down back into the South Bay or around San Francisco, having coffee with everyone I could meet and selling them and convincing them."

Because, yes, we had really nice growth rates. I mean, it was an API through which you could wire up your payment acceptance and a little bit of paying out. But at that time, that was very compelling to developers, but it wasn't understood by a broader set of potential candidates you'd hire necessarily, and even engineers beyond people who were having to wire up payments for a startup.

And so it was a lot of education. It was more—I mean, Patrick, when he reached out to people, I think them taking the time to meet him was about him more than Stripe, at least in those first years. And then Stripe started to get more of a reputation for having strong product-market fit, strong trajectory. But it was like a while.

Is there anything about doing things that don't scale on the candidate side that you remember from the Stripe days of like, "Hey, here's a candidate, and here's what we did that went above and beyond to convince them to join?"

Oh, yes. I mean, I think so many things come into my mind. I think it was really that bespoke outreach personally from executives or from the founders was the number one thing. But being willing to travel and even meet people—or we had some really active early users, some of those developers who were integrating Stripe, who were giving a lot of good feedback.

And Patrick and John just turned around and were like, "Why don't you come in the office and sit with us, and maybe work with us?" And then they hired a few of those people. We had this role called support engineer early on, and a bunch of those folks were just early users who were just really smart about, "Here's the bugs, here's the things we need to change," and they came in and started changing it from the inside.

Stripe also ran this Capture the Flag contest that some early engineers built. They did it twice, but it was basically this sort of buzzy set of problems to solve. One was very security-oriented, and yeah, we happened to need some security engineers, and it was hard.

And it took a lot of work to build, but it also said a lot about the kind of company it was, which is true—like incredibly smart people willing to use their technical prowess to sort of have fun but solve hard problems. So, Capture the Flag was very big.

Some of the comments that you would find from Stripe founders in Quora, again in Hacker News, like their amount of activity communicating themselves directly in different channels was really high, and I think—including directly to candidates. So, that was the main thing was that bespoke.

There were also some instances of, you know, acquihires that were really, again, targeted—like a really talented young designer, so young that how did we hire him? I wonder. And relocate him from his Scandinavian home, from his parents' house.

Yeah, just Logan, like that kind of a situation where we're like, "Oh, we acquired a company that is really a kid who was amazing."

I mean, you have to take some risks.

Totally. It's an interesting lesson of like when you're competing against—today, if you're a startup with 20 people, 25 people, and you're competing against Stripe or Google or whoever it is—like ex-company that has hundreds or thousands of people, and everyone's parents and their friends and their family will pat you on the back for joining that company, you have to use what you have to your advantage.

And CEO outreach can be one of those things, right? Like, what can—early sales, same with early sales. What can you do to beat Stripe in a sales cycle? Well, you can reach out to that person individually.

And Patrick and John, I mean, they're doing a bunch of other things, and they probably can't spend all the time they did in the early days of reaching out first cold call to individuals, right? And so using those things—if Stripe had to do it, I guarantee you, you should probably be doing it.

You would still find senior members of the executive team and the founders helping to close candidates.

Sure, totally. But you're right, not anymore. Like, they're not doing a lot of cold DMs on Twitter.

Yeah, it works now, I guess you have to pay for it anyway.

Yeah, exactly. Who knows? The old Twitter.

One of the things you said was that you were rated at different times at Google for holding people to a high standard—that your rating would be variable sometimes, sometimes individually, you personally sometimes you get good ratings and sometimes you get—

Not that good.

Okay, well, I had very positive manager feedback for every Google Guist, which is our sort of survey engagement survey, but also had a manager 360 component. So, you manage as a manager. However, there was one question about consistently holding my work to a high standard where that was not my highest scoring C.

But at Stripe, you were scored well, highly.

Yes.

And what do you think you changed in between the two?

Yeah, I really—I mean, I think part of it was having the revelation and the maturity, the process of maturation at Google where I went from being, you know—and this happens to a lot of folks in high-growth companies—which is elevated from—I mean, I started as a manager, not as an IC, but I was like an entry-level manager. I got pretty quickly moved into like more of a senior-level manager, which actually I did have some management experience, which was unusual at the time for people.

And then was made a few times in my career at Google the manager of my peers, and that's a hard thing to navigate. And the first thing you think was, "Well, I don't want to change a lot here. They're my peers. We're going to collaborate. I'm going to be their partner."

I'm not going to—you sort of, unfortunately, you don't consciously say, "I'm not going to hold a high bar," but you do consciously say, "I want to be friends," which unfortunately I don't think managers are friends with their team—not in the way that I think I was picturing. Like, nothing's going to change; it's all going to be fine.

And you just don't want people to be turned off by your behavior when you all suddenly become their boss. And then I sort of had that happen a few times, and I don't think I learned the lesson quickly enough, which is actually now I am the one responsible for holding the bar, driving the work product.

And then the other—and there were some instances where I started to see that my team wasn't stepping up, and it was a wake-up call for me—not just in the feedback I was getting, but in our performance. Or I would see my team with another executive kind of bringing their A-game, and with me sort of taking it easy and having a laugh.

And yeah, I was well-liked, but guess what? It's not a popularity contest. So, it took me some time to just get out of that mode. And also, people like to be challenged. People want to be on winning teams. By the way, our teams did fine, but like, was I driving results at the right level? I think I was driving more the process.

And I think the thing that clicked as I went to Stripe—so one, I matured out of that, and I started to drive more. At the end of my career, I would say I was more comfortable being that leader and setting the bar and focusing on results. But at Stripe, I stepped into a culture that was also more dialed into that.

John and Patrick are very clear about that being critical for any manager and leader.

With the caveat, when I first joined the company, management was a fairly new concept, and there were a couple of people who had been hired—one in a sort of engineering leadership role—who seemed to have this construct in his mind that there was almost like the tech lead, and you see this at some companies—the tech lead who was driving the work product and work plan and work results, and then the manager was more of this one-on-one coach buddy.

And I took him aside, and I was like, "I just want you to know we disagree on this." It took me a moment to first of all unravel what I think. I was like, "What is culturally going on here where the managers seem like a side job?"

And also more of a coach, not holding the bar. And I, of course, had just gone through my own learning process where I was like, "This is what leadership and management is."

And I would say Patrick and John certainly had the leader element of holding the bar. They hadn't thought as much about who they were as managers, right? Which makes sense; they'd barely been managing people that long.

But anyway, I took this guy aside, and I said, "I think I've diagnosed what's going on here, and I want to just voice to you that I think it's going to have to change." And I also talked to the founders about it, and they were totally on board.

I mean, Patrick being Patrick was like, you know, started to read up and look at some research studies. He's like, "Turns out management matters. This is actually one of the things in the United States on economic indicators. We outperform other countries because we value management and have management structures that we use and have for hundreds of years, and it does create some output advantage, again, if done well."

Ideally, totally.

But that's funny now. Talking a little bit about hiring, I've heard you be fairly self-critical about your executive hiring versus your team member hiring. I guess, can you articulate that? And then also, what do you think that is exactly?

That's a great segue because it's the same problem. It sounds like the likeability thing.

So, the likeability slash—like if anyone, if you asked anyone on any team, either a team of colleagues or a team under me, they would call me, I think, a very collaborative leader. Like, I am not out front. I will set the pace in some of my behaviors, but I am all about the sum of the parts. I'm like, "Give me your ideas, give me your ideas."

Like, I don't think—I mean, part of the value—look, I've worked with some really, really smart people, Logan. I'm like, "Am I the smartest person in the room? No. Am I good at some things? Yeah." But like, I need all of you.

And so I think part of it is the likeability, though I think I've gotten over more of that. But there's a big part of it, which is I want to collaborate with someone. I want their ideas, and I'm an optimist. I want to like them, right? I want to be like, "Let's give each other energy, and we're going to be better."

And so I think my optimism combined with the collaborative instinct and default leads me to—has led me to some—it's—I mean, I think I just have better pattern match on hiring teammates, and hiring executives is hard because there's also how they show up with you versus how do they show up with, you know, whether they're a sales leader with prospects, how they show up with their team.

Like, how do you get at them inspiring followership? And I think I hadn't got my tools built well enough on some of the hires I made where, in fact, they were actually decent colleagues—like great to have a one-on-one with—but were falling down on some of their own leadership stuff for the people below them, right? Which I wasn't assessing very well.

Do you think you determined at some point too early in the process to make the hire and that you liked the person, and you moved into selling mode?

And I think that's also—I think that's—it's always a tricky balance. You know this because you're selling them to get them into the process. That's the hardest part of venture is like it's this buying and selling relationship—selling to get them in because, again, at the point that Stripe was, we were looking around the corner and saying we need some really experienced leaders.

So, I'm trying to pull people who've got pretty nice jobs at pretty great companies, and so you're selling. And then you try to flip into assessing and being discerning, which is a hard flip after you've been selling.

And then at the end of the process, you're selling again. And you're 100% right. If you aren't really intentional about, "Wait a minute, wait a minute, I am going to really assess now," I would say yes, that was part of my mistakes.

But actually, at Stripe, we were, if anything, a little over-rigorous on hiring in process. Like, I wasn't hiring alone. Patrick and John were meeting these candidates. Multiple people were meeting them. We do do reference calls.

So, I didn't feel like I didn't have some of the risk mitigators in place. I think I did, but this does come down to me. Like, ultimately, I think my opinion became too favorable too quickly. To your point, I didn't rush to hire them too quickly, but my opinion became favorable too quickly, and it was often based on, again, a good chemistry one-to-one, but also, you know, these folks had track records, and I'm looking at the track record, and I'm thinking I'm believing it, right?

Yeah, which sometimes people fail up. Totally. Sometimes also, you know, people get lucky; they're in the right place at the right time.

If you're looking back on all the lessons you've learned, is there a point to take away from all of that? Like, if someone were to hear that and say maybe they have a bias to all the things you just said, is there anything you would encourage them to think about?

Yeah, I think one is—I mean, Cheryl did this well. She had someone who was really opposite to her who she had on basically every hiring committee with her, who, by the way, was my scariest interview for Google. And I was like, "Geez, this guy is poker-faced, so like all in the details, very analytical, high-pressure interview."

And Cheryl's so charismatic and so, you know, like, "Let's talk about you," you know? And he was like the opposite. And I think she was smart. She's like, "This person is going to pull stuff out of the candidates that I'm not, and I need that foil."

I mean, my book talks a lot about self-awareness. Like, you got to know your blind spots. You got to know what you're not going to do in the interview and what you're not going to get at, and you got to find someone who's going to get at it.

And I think that what I did is I maybe over-trusted some of my executive colleagues to be that. But if I really thought about it now, I'm like, there was probably someone I worked with in a different part of the company who could have been my buddy in that way.

So, that's one tactical thing that I probably should have done differently and more consistently, frankly. So, that's one. I think another was I did a lot of reference calls. Did I talk to people who worked for the person? Not enough. Maybe not at all.

I talked to their manager; I talked to former colleagues. But I think—and occasionally, I would talk to former team members, but you know, pretty selectively people they provided. I wish I'd gotten more of that view of them as leaders. That would be another tactic.

It's interesting. One of the things I heard you say is that the hardest mindset thing to overcome as an employee or with an employee is if they're a player, I think was the term you used, or a victim.

Yes. Can you elaborate on that difference and how you were maybe able to tease that out in an interview process? Or like what questions kind of lead to being a player versus a victim?

Yeah, so credit where credit's due, Fred Kaufman wrote this book, "Conscious Business," which is one of the—like, I don't read that many business books all the way through.

You write business books.

I now write them, but even my book is written more as a reference manual. I'm like, I don't expect you to read all the way through; just look in the table of contents and read what you want to read.

But Fred's book is really strong, and he has a few frameworks. Fred founded this company, Excellent, that was sort of a consulting. He had been an MIT—he'd been an accountant, then he was an MIT professor, then he founded this consulting company working with leaders, and then he ended up as like the in-house leadership coach at LinkedIn. I think he's still there.

And Fred had this—a bunch of frameworks. The book has some great frameworks, but one of them is victim-player, and it is, I think, a very common framework you see at all levels—not just executives, anyone in a company, basically any of your friends too.

Like, I have friends who are victims and who are players. I tend to like the players better. But the victim is either—the example Fred would give is when your kid, you know, comes home from school with some, you know, they lost something. You know, they left their sweater at school, or they had a toy they brought to school for show-and-tell, and it's broken.

And they don't say—they don't take responsibility. They don't say, "I left my jacket at school." They say, "The jacket is at school," or they say, "Well, the toy is broken," or they kind of imply it broke itself.

And it does happen early in your life where you kind of don't—it's embarrassing to fail; it's hard to make a mistake. And pretty early on, kids and adults, like the adults we become, are programmed to sort of not want to say, "I failed."

And the victim part of that framework is people who blame others or who have trouble taking responsibility or accountability. And the really overt version of it is, "No, no, no, Joe didn't deliver. Like, 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."

And you're like, "What? How are you even—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. But if they don't highlight any self-reflection, like, you have no learning. By 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 wrong. There were only three questions; I got one wrong."

And I said, "I tried to, like, you as a parent, I 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 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. What 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. You know, 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 someone to say.

Yeah, I look back, and 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 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," and—

Yeah, I mean, I think there's this balance. This is where having the pattern match of thousands—I think I've done thousands of interviews, and I wish I could totally distill this, but it's about balance.

There's a lot of "we." The best candidate, to me, the best interview, there's a lot of "we." Actually, there's a lot of "I," 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 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?

And 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 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 fail.

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One of the things I've heard you also interview or use as an interview tactic is an org structure and people on their 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 a whiteboard, and can you just map out your current team for me?"

So there's you, and then like tell me the roles. And you don't have to name all the names, but I'd love—you know, Joe, Teresa, you know, Mahaw, whatever. Give me the names, and 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 hear an org structure, they're like, "Well, this guy was going to leave, so I had to give him like two jobs, basically." You're like, "So he 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." And you're like, "And why not? What are you afraid of?"

Right? So one is why that org structure is—it is 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, and I'll put it in context. I'll say, "Well, how long have you 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 could be great people, but do you have the right capabilities for that strategy? That's really the perfect team.

So, big red flag if they've made no changes. Also a red flag if everything is different. Like, did you just churn every single director? 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, "Well, there was this person in the org I found incredibly talented. You developed them into a role."

Like, you didn't just hire from the outside, or you did change the team, but part of the team were people you identified who were talented, who were getting squelched in the org, and you lifted them up.

And 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 the company for 10 years. I do wonder if she's going to leave, but you know, if she does, she does."

You're kind of like, "Well, what have you done about that?" So, some people are more energized as managers in that moment when they're just describing their people, and they almost get into it.

And some people, you can tell that that's not how they lead. That 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 you said, drove you crazy.

Yeah, annoyed you.

You knew exactly where I was going.

Did they drive you crazy in the interview process?

Interview, but also closing.

Okay, some of the hardest closes I've ever had—candidates who were driving me up a wall, questioning every number, 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. They were just like hyper-analytical, different brain thing. You know, I'm very—

Is that because it was a compliment to you?

Yeah, huge. 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 am not afraid to make a decision and go and drive to action.

And some of the compliments to me are people 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. Like, 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, you know, 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, they're very different.

Yeah, some of my best hires were completely the opposite of me.

That's a compliment point too. Like, sometimes you need a hire to augment your own weaknesses.

And we'll talk about self-awareness in a second, but 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, you know, gender and racial—but I'm talking about, you know, really work styles and preferences and what part of your brain do you lead with or even your socioeconomic background.

How hard did you have to work to get to where you are? What's your perspective on our users? Like, how have you experienced life?

Like, 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.

Totally.

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.

Yeah, no, I mean, I think one of the interesting things to look at is if you have inclusive—this is a biggie—if you lead a team with inclusive practices, you can get a 3 to 5x return on that team.

So, they're diverse, and there's inclusive practices. If there's not inclusive practices, we can talk about a homogeneous 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 like doesn't really mean anything anymore.

But 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. Like, 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—when there was a diverse team and a 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. 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." I mean, it's like the Japanese pull the 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 checkouts, 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 X next week," you 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 groupthink." 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."

Right? Like, how do you build these ways to prevent human behavior? Human behavior is about, you know, we're animals. It's about status; it's about how comfortable we are. It's about group—you know, groupthink 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. The first one is "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—I—my actual best strength, I had no knowledge of for most of my career because 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 strengths 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?

Like, 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. I 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 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.

Any of 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 the Hogan assessment. It's this like really long, intensive question that you can take. I don't really care which one. I've taken 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? What 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 do 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. It was 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 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—like writing it down.

Self-reflection is underrated. Like, why don't people at the end of the week 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 or didn't really go well?"

And if you've done some work on your default settings, I bet you'll find, by the way, most of the time, I will 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.

They give you any insecurities you have; they're very quick to point out issues.

Yeah, so that's another way.

Dangerous to read.

Yeah, Myers-Briggs and YouTube commenters.

Yeah, you can each find your own.

Do 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, can you 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 question 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."

Or, 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, like if you're not thinking about like what are the underpinnings of the capabilities we have to deliver the product—even if you are an English major who has not ever—like 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 do that mean for my company, my product, my team, right?

Like, 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.

You know, maybe it's gardening, maybe it's, you know, Taekwondo. I don't really care, but like are you curious? Do you care? Are you like a developing human?

So, self-awareness may, 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.

And 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 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 had done the analysis and scoped the problem in the way that made that analysis more helpful."

Like, they totally get it. But then there are people who are saying, "Yeah, no, I feel pretty good."

Like, I don't know what you're talking about.

It's so hard to close that gap.

Like, I 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 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, for most. It is, and it's also human nature not to 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.

But "say the thing you think you cannot say" is really about 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?"

But if you don't say that, there's no breakthrough.

And so as a manager, you get nervous because you're like, "I think I'm issuing some kind of judgment on someone when I say the thing I think I shouldn't say."

And 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 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."

You know, I'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?

Like, 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. Like, totally my perception. I just experienced you in that meeting like not as confidently as I normally see you with that material."

And they're saying, "Well, I don't know. I don't know."

You 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 could be my perception, but what I do find is people 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 say, "Well, why do you think?" You know, you'll still—the breakthrough might not happen quickly, and you can be wrong.

Like, oh, 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.

They're like, "Oh."

And then I'll look around the room, by the way. You've got to read the body language and the faces. This is not usually a verbal exchange when there's a 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.

Do 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—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 did you think that went? Here's some—"

Like, ideally closer.

But I'll—like 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.

And 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."

Now, 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," you know, or send it to the group by the end of the day.

But right, like—but try to—it's totally legitimate to say, "You know what? The thing I think I cannot say, I am 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?

Oh, yeah. So, I think there are some schools of thought that man—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 interviewed him for the book, and he talks about it.

I actually believe you do need both ultimately in your career. Often 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, and 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, "Here's some basics. Here's some checklists. Here's some things."

Like, 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? Look at my talent, make a roadmap, milestones met, metrics."

Like, it's very, 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 fundamentally.

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?"

I remember when I started at Stripe, and our support situation was kind of a tire fire for good reasons. We were growing quickly, etc., etc. 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?"

Or like you're putting out a vision, and you're putting people on the line. You'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 happen.

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—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.

And that's when you start to get this virtuous cycle of, "Wow, leadership actually works. 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 are 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 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, "Nope."

You got—because I'm treating you in this case as a leader. I'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.

Culture and the results and the outcomes for Stripe—I think they wanted an out, but I said to them, "Guys, 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, you do need to give me a title. I'm not going to walk in; I'm not going to leave the job I have at Google for an AE of business operations job at your company." They were like, "Yeah, right, okay." It's a balance; it's a balance.

Now, one of the things I heard you say is that 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 to balance tangibility with idealism?

Yeah, so we're talking about Stripe; they call them operating principles; some companies call them values. 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 survive; surviving is your long-term goal.

Then, though, as you start to get traction, you should check if it's real. This is where it's good to have investors and advisers. It feels like this is real, and all of a sudden, whoa, you have to think about it. I think I might be building a company here because we have a product, and people are buying it, and the ARR is X or whatever metric you want to start to see.

As the leader, you're thinking, "Alright, for company building, I think there's a set of things you want to start to put in place." This is where a lot of the early chapters of my book discuss operating structures. One of them that I argue is really important at this point is these founding documents, including articulating what your company values are. If I was going to simplify it, I'd say, look, start with what's your mission, your vision—which is the why. Why do we exist? 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 it's time to start thinking about it because it's going to matter to the people that you bring on board.

So, why are we in the world today? Employees care about this. Why do we exist? What's our mission? Then the next thing is the how—how do we want to work together? This is where the values come in: what do we value? When the chips are down, are we going to choose the user, or are we going to choose our growth? Sometimes you'll have those choices, and you really want to have established what values we're using when we make hard decisions. Sometimes you can inductively get there; you can look at some hard decisions you've made and say, "Oh, it's interesting; what we really valued, by the way, was speed, maybe over quality." There's no judgment from me, but the thing that I see too often, which you alluded to, is that some executive team, a founder, or even a focus group in a company sits down and writes a bunch of values that are really aspirational.

"Customers first" is a common value. I'll be honest: 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; we're actually about the technology first and the customers later." No judgment; I actually think just own it. 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 undermine you. It would be better to have none, in my opinion.

There's the motherhood and apple pie version of this, which is so abstracted that you're like, "Yes, we collaborate." Well, I mean, yeah, everyone wants to collaborate well. If they can be kind of specific and kind of true, and even stack-ranked what 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. There were a few where we were like, "Hey, we don't have a lot of examples; maybe this isn't a value; maybe it's something we want it to be true." Then we actually had to think about how to make this more true.

Some that we put out there got misinterpreted and sometimes weaponized. Yes, oh yes. There were a few I feel like I've suppressed at this point, but we had some around trust, and people were really interpreting it as 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 "We can't do that; what if it was on the front page?" I was like, "Well, no, you can still be bold; you want to be on the front page sometimes." I'm just saying you don't want to be arrested.

The thing you think, "I cannot say," you're being a jerk. Really try to apply the values and see if they stick. It's interesting because everything has two sides to every coin, right? If we were to say we're founders first—Founders Fund does a great job; they say they're founders—now that comes at times at the expense of limited partners. There's two sides to these; you can't just say platitudes without thinking through the other side.

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 tradeoff of what the future roadmap's going to be, and it's going to piss off a bunch of customers? Are you actually customer first? There's no real platitudes; all these things have another side.

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; we are going to have a decision we have to make that is going to hurt." I say a strategy should hurt; some of your values should feel pretty painful. Patrick, in a different context, and I talked about this. I talked to him a lot about expectations of leaders and how they should be higher. This is a sort of behavioral expectation for leaders, ethics expectations. I said there's going to be a time when a leader who we highly value, who's incredibly talented and impactful, does something humanly with poor judgment. You all can color in whatever story that is, and I said, "I will tell you it is going to hurt like hell, but if it's bad enough, they should leave, even if they're the best person at that job."

We actually went pretty deep on examples I'd seen and what I thought because culturally you've then taken someone you've elevated to a leadership role, and they've done something with horribly bad judgment and said it's okay. Even if it's private, it still gets known, in my opinion, in a big enough company; it still gets known. We kind of locked arms on it, and we had to act on it. There are times when you're like, "Oh my goodness," and now it feels like you're stabbing yourself, but you're not. In the long term, you're honoring the culture you're trying to set, which is we hold leaders to a higher bar.

Sometimes you need to have surgery. If you tear your ACL, you have to have surgery to rehab yourself forward, right? It could be painful; the payoff is tomorrow. No, it actually hurts soon; it's a long time in the future. But now, don't let perfect be the enemy of good. I know that's something you believe, and I happen to share it. How do you think that manifests itself in startup and high-output companies?

I think there's this continuum that is so interesting, and you probably see more companies than I do, where the sort of "move fast and break things" Facebook mentality exists, and then there's the "perfect is the enemy of the good" mentality, which is actually starting to kill the good. I think that some companies—and it's really about the founders and their proclivities or their instincts, their defaults—are not saying analysis paralysis, but they are so intelligent, often thinking of so many angles. They're trying to preserve optionality, and they're like, "How do I get more data? How do I know? Who do I also check with?" They're making some decisions or choices for the first time in their lives, and they're waiting for this candidate who's perfect.

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." That could be a user, a partner; you could have bad behavior, but you're getting the goal. That's also not good. That is not even the good being the enemy of the bad winning in that case.

So I think on that continuum, being aware of where you fall—this is self-awareness, actually, in the end—being aware of where you fall 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? Too often, the perfect being the enemy of the good is 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." I think perfect being the enemy of the good is like you've gotten 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're just examining every damn thing too closely.

It's important to analyze yourself and where you fall, and then not every market is going to be the same either, right? I'd be glad self-driving cars take a little bit of time to be perfect.

It does depend on your market and who your customers are and what they... I mean, gosh, Stripe's dealing with payments; we better be on that side of the continuum, and we are. But sometimes we flip too far over to like, "Oh, if you're CEO, you can get by a little bit more."

I was in this funny situation; I was at a conference running a roundtable discussion as a breakout. This was with another venture capital firm that sponsored this, but it was all founders. We were all talking, 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. There is no question.

If you think about it, we're dealing with people's money with payments. Even if it works, but we don't like the quality and the craftsmanship—that's also what we like to be known for—we'll delay the launch. This guy across the room from another company starts laughing. He's like, "Are you kidding?" 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." He named a city in Canada. He's like, "If you live in Canada, you have seen some crazy stuff from our product." I was like, "Are you serious?" He was like, "Oh yeah, we'll move it up because we're trying to understand why it's 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 watching us like we were playing a tennis match, and I think it was 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. It really depends on your product, your market, but also your appetite for risk, who you are, your value system.

By the way, good on them that they have some test markets that they learn from, right? I was kind of jealous, but sorry, Canada.

I think 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.

To the point we talked about earlier, have some people around you who will call it when they think you're dying of indigestion. You said leadership is disappointing people at the rate that they can absorb. I guess it's an interesting line; I actually didn't know what you meant by it. What does that mean?

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 think is worth checking out. Some of Heifetz and Linsky's work on adaptive leadership is worth checking out because it's about distinguishing between the fact that there are technical problems—this is almost management versus leadership.

There 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 are answers. Adaptive problems never stop. Something is happening in the competitive landscape always. Is your go-to-market product interlock perfect? No, it is never perfect. You'll be adapting constantly, right?

Getting comfortable as a leader with adaptive problems, 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? 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 to work this problem forever. It's like infinite systems, essentially.

So, "Leadership is disappointing people at a rate they can absorb" is one of their quotes. I didn't have it in the original book, and then someone who used to work with me at Google was an early reader. He was giving me 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've been reading and learning about adaptive leadership."

He said, "It stunned me, and I've thought about it the rest of my life since then." 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." 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?

Actually, leadership is often disappointing people. You do become a little bit mythic, especially founders; they become bigger than who you are as a human, and you aren't perfect. If you start thinking you are, you're going to have other problems.

I think one of the biggest ways leaders aren't perfect is, as we talked about, you set a vision. You don't even know how you're going to get there. You're like, "We're going to completely pivot our company to this brand new product line and launch it in the next six months." You'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.

You've told a customer, by the way. Leaders often do that; they announce things. It's like burning the boats. You know, Alexander the Great just burned the freaking boats so you can't go back, right?

So that is leadership, and leadership is uncomfortable. It makes people uncomfortable, and by the way, it's not perfect. Guess what? I bet that pivot to that new product line took 12 months or 18. 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. Another way 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.

A lot of it is about learning to be a better leader. Some 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.

One woman I mentored at Stripe, who went on to a pretty senior role in a very successful sort of younger company, called me not that long after she took her role. She was like, "Oh my God, how did you live with the fact that everything is broken all the time, every day?" She had elevated to a point where she saw what the equivalent of me saw in early Stripe, and I was like, "Oh yeah, welcome to the terror dome. Everything is broken; nothing is perfect."

If you are motivated as a leader by fixing everything quickly and it being perfect, you will die. This is not the next three years of your life. The next three years are living with a lot of discomfort and imperfection.

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 Seagal Barade, and she was trying to teach that change management is a hard, hard thing to teach. It's actually a thing you need to spend energy on and think about and plan and build processes.

You 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.

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 at 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 finding out which flavor people want, and you leave it, and it gets a little melty and kind of looks a little gross. Then you put it back in the freezer, and it's never quite the same because it got weirdly... I'm sure some food chemist is listening to this; 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."

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! Ice cream's on the counter! We got to finish; we got to see the change through." I think it's just a good watch out.

So you wrote this book; it was published in March of 2023. 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. I think it ties to this ice cream on the table; it's a different version of that. Can you expound on that concept and thought?

Yes, it's a great connection you're making. You know, I think what I've gained more conviction in—I knew Patrick and John read the book, the earliest manuscript version I had they could read. A few, 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 thing."

This is an interlude: you wrote a section of a book for Elad Gil, who's been on the podcast before, "High Growth Handbook." You wrote a chapter in that, and it was well received.

Yes, I did this chapter in Elad Gil's book, "High Growth Handbook," which was our bestselling Stripe Press book because I think it's a great book, by the way, and I highly recommend it. 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; management leadership advice is often abstract. You're like, "How do I actually do the thing?"

I did some of that discussion in Elad's chapter; it got some traction. I also... there's a YouTube video of me on how to run an effective meeting that's got so many millions of views, which I find scary and fascinating.

I did it at a CEO conference, and that got a lot of traction. I went once to a wedding, and I got introduced to this guy who's a prominent academic, and he was like, "Oh, I know you from your meetings video." I was like, "Weird, okay, nice to meet you."

The point is Patrick observed those things, but also John and Patrick observed that a lot of Stripe customers are really interesting companies that are growing quickly around the world and wanted to spend time with me on their scaling stuff, 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."

Patrick's like, "You just have to write the stuff down." I said, "I don't know that I'm the right person to write this book, but yes, I wrote it." It came out in March. I knew that he was cringing; there's a section on managing people out and firing people, and I talk about how long it can take.

I say, "Look, it's not going to be one conversation, and the more senior the person is, by the way, the longer it can take." I think that makes sense to everyone; it's like they've got a whole team, they've got an org, you spent all this time hiring them, they've had a successful career. Can they course-correct? There's a high cost.

I talk about 30 days, 60 days, and Patrick and I joked because 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's of the mind like the faster, the better.

Now that he's managed more senior people for longer, he realizes it's not always the fastest path. But I sit on a lot of boards now; you probably sit on a lot of boards. When you get 10,000 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, it feels like someone is painting neon paint on this person for me now.

"Oh my gosh, this is holding the whole company back! Holy crap, we have got to move!" It's really interesting; you get much more clarity on how critical it is to address when you've got some separation from it.

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. I'm like, "Having an issue in... 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, but no one ever says, "I wish I'd moved 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.

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 will cost you money, usually. But I just think if you're not talking directly to the person about, "We have a problem," you are doing them a disservice.

As I see now, you are killing yourself on your strategy, and probably the people under that.

Great people hate mediocrity, and if they're seeing, saying, "Hey, this is acceptable," it kills their perspective on it. The people thing—people will delude themselves into thinking 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... it's supremely unfair, right?

That person should be given an opportunity to go to a business that doesn't have all the questions, inevitably ready to get rid of them. 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, "The 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 if you 100% know someone needs to leave, then you're moving them out. But 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.

Maybe my conviction is more... you know in your heart of hearts if it's going to work or not. You've got to start trusting your gut and moving. The hardest part about that is if they were the right person four to six months ago in the company, but the company's grown out of them, that's when it's particularly hard.

You've started to have that... a lot of this is stuff—I mean, I 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. You'll be like six months; you feel it in you.

You feel it. No, but you're like in the room, and you're a little uncomfortable, and you're like, "Six months ago, I was fine; our executive team meeting was fine." That's probably true, by the way, and then all of a sudden, you're not feeling it.

You've got to listen to the feelings.

Now, you referenced being on a bunch of boards. You're on Hallmark's board. I was on Hallmark. That was a purposeful decision; it's an unusual... it was a personal development decision. Can you talk a little bit about being on a board of a company that has been built to last—over a hundred-year-old company? What did you learn from being on something that is that endurable?

Hallmark was interesting to me because, 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 is competitive in any way to any of Google's products, which eliminates a lot of companies—a 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 Massie—it's like a soap company. We should study them because that is a sustainable—not just business; you built a business that has sustained and had revenue and had growth for a hundred years, but often also the culture through multiple generations of leaders and well-passed founders. By the way, that's astonishing.

How do we harness what's happening in those companies? 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 a meaningful amount of revenue, which is private but in the billions of dollars of revenue.

They owned a media company, Crown Media, that 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. Then obviously the core Hallmark cards business, which you would say, "Oh, well, isn't that a dying thing?" That'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 interesting greeting cards, weirdly. I learned, but I was most interested in how they had structured succession planning, multigenerational strategy planning.

Actually sitting in the moment where technology was disrupting elements of their business, what were they going to do with that? One of the big things we did is that Crown Media, the media properties, which is the content—and I think you know what Elad—that content is very fragmented, but it's at a premium good content.

Crown Media was public, and so we took it private. We owned like 96% of it, but that was one of the biggest decisions as a board: 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?

It was like the media business actually matters quite a lot, but only if you can control it. So it was just 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.

You realize how these are smart... that's another thing. Silicon Valley is like, "What's wrong with these leaders, these executives of these companies? Why don't they get themselves to just rip up your stack, put in... you know, move it to the cloud, you idiots?"

We all think that. We're like, "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."

They are fighting a war with like two hands and one leg tied behind their back because ripping out those systems is so disruptive and it's just like... it's a total Jenga game that is way more complicated than you realize.

It really hurts your head when you think about it, but it's very instructive when you're trying to sell B2B and sell SaaS, and you're like, "Oh, I see. You just explained why IBM is still in business."

Why they don't get that? Yes, 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. Actually, I'm on the board of The Atlantic, which used to be The Atlantic Monthly. It's a 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.

I think it's really... I will say, as a development thing, Patrick and I talk about this. It's really good to try to be on... I mean, it's hard because it's time-consuming; it's a commitment. But to see, 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."

Yes, I 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 if you're talking about a lot of tactics, a lot of operational detail, something's wrong."

There are better places to get there, better places for the board. You're also inviting, by the way—you don't want to invite me, an operator, into the how details because I'll be like, "Oh, what about this? Have you tried this?" Then you're not talking about the stuff that removes the needle for the business right now.

I think we both have places to be at some point here in the next couple of hours. So, as succinctly as you can, what makes the Collison brothers so special?

Patrick and John Collison are really multi-dimensional humans, and they're very different from each other, I think, but they have a sort of Venn diagram where they're very complementary in certain ways. I think they obviously have some shared values, which is a good foundation to have, but high IQ, high EQ, with different kinds of EQ, but really curious learners—very ambitious but humble—comfortable that they don't know everything and really excited about others teaching them and giving them feedback.

A lot of vision—I think the amount of energy they both bring, but in different ways, to discover problems. You discover a problem space, and I'll say this as someone who's had a few years under my belt, I'm like, "Oh my gosh, I'm exhausted. Am I really going to go fix that?"

I think the energy level for tackling really horrifically painful problem spaces is amazing to see, and they both sustain it—the level of commitment to that. I don't know; I think there's an element of solving problems they themselves faced as engineers and doing that at a scale.

I think they have not gotten cynical about that. That feels like an important responsibility that they have, and I really appreciate that too. Just flat-out super intelligent people—I mean, let's not kid ourselves; they're rare.

But you could 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.

I thought it was all SATs and GPAs 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—a value of autonomy. He had you shingle your roof, taught you how to fix a car, a point never had you build a car, never helped you with your luggage or suitcase—a family rule: you pack it, you carry it.

Can you talk about how those little things impacted who you are today?

I think, I mean, 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. You better add some value, especially if you went to business school and you were the black sheep in the family.

I know I was very unpopular when I went to business school. It's 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: 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 someone; your kids can do a lot for themselves, but a lot of parents don't ask them to or don't expect them to.

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. I had to figure my own stuff out. I planned my whole college application process. 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. I'm looking at it like, "Am I an enabler?" 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, but that's being a VC.

That's your secret tagline: we give great advice; we just don't take our own advice. Right, right.

But I really value, you know, my father's not with us anymore, but he talked about people who had no biases. He believed that every human could do something interesting with their life, and he expected it of us. I think that's one of the best things you can do for other people.

To the point of... he also, back to the victim mindset, right? You've 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.

Totally. In retrospect, I'm like, "How horrible would that have been to lose your wallet, your ID? You're in a foreign country." He was just like, "I should have been smarter." He 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. I remember 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, 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 amazing. Again, 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.

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. We 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... I think 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 super attuned to boundaries and balance, and more than we were."

I have to sit and examine that because the story I'm about to tell is more in the vein of what I experience with most of the successful people I know, which is we've worked our asses off for a lot of our careers. 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.

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. Sheryl had left; I had taken part of her responsibilities and ended up then being more after this period. I had come back from maternity leave with my second child, and it was 2008. Lehman Brothers collapses literally like the week I'm back from maternity leave.

I had come back early because things were shaky, and in a very not well-known action—because I think the recent layoffs Google did, people think it's the first time Google's ever done layoffs—actually, no, I laid people off in 2008 in my division. I came back from leave and made that call.

The day that I had to do that, the layoff announcements were happening, and I personally spoke to some of the affected employees—meaning laid them off—in a conference room with HR. I talked to my mom and said, "I really want you to come to New York; we're going to surprise your father for his birthday." I was like, "Oh, I just don't think I can. I've got to do this. I'm under so much pressure as a leader; I've got to deliver this message. It's going to be brutal."

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. You've got to do this." I sort of thought about it, 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 in Boston, in Cambridge, actually—I could meet that team, which would actually be a good thing to do, do back-to-back Google visits, and then I could fly to New York, and I could be there in time."

He said to me, "If you think you can do that and the red-eye isn't going to affect you, and you know I've got to deliver messages in Cambridge, then yeah, go for it." To his credit—and this is for all the managers out there—he was like, "If you can make it work, then align."

It's never... you can't always choose one or the other; you're balancing your professional obligation and 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 on the way to the airport.

I called my best friend, and I was sobbing, and I was like, "What if I hadn't gone? What if I hadn't gone?" She was like, "But you did; you did." But really, it was me saying to myself, "Oh my God, I really had a high chance that I had not gone," because I was just in that mode professionally and my ambition and my sort of priorities, honestly.

I think that's the lesson that when I share that story sticks with people because now for sure, you know, I'm a certain age; I've had a certain amount of success. Of course, I'm going to go to my parents' surprise birthday party. But then it was not so obvious.

I guess I would just ask everybody, 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.

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 turns out we're all humans. There's important stuff outside of it.

Well, Claire, thanks for doing this.

Thank you, Logan. It was a great conversation. I really appreciate it.