Claire Hughes Johnson on being a “learning organism” during Stripe’s growth, and more scaling advice for leaders

Brett: ​ thank you for joining us.

Claire: Thank you, Brett. great to be with first round.

Brett: so I thought one interesting place to start is, you know, every startup when they get into this growth phase begins to, to build their executive bench.

Claire: Mm-hmm.

Brett: And in, in our experience in working with a lot of companies, this process often leads to sort of this rotating cast of characters where execs come and go, a CEO's incredibly excited about, exec X, and nine months later, they're no longer at the company.

Um, and I'm curious, when you reflect on this transition, you know, you, you, you had this big chapter of your career at Google and then went to Stripe. There's so many amazing people that were at Google and then take a big exec job, and it blows up in nine months, as I was saying. And so I, I'm curious, w what do you think when you reflect on your own, either ways that you behave or what's kind of going on for you that you were able to stick and have this many, many year career at Stripe?

Claire: A a lot of people have tried to ask me that question, but not so artfully Brett. Um, well, I appreciate the underlying thing, which is, yeah, it didn't blow up. Um, and I'm still involved with Stripe, but I don't know if I will ever not be, because I, I feel so tied to, 

To the company and the founders and everyone there and what we've built. I'll give you my assessment. I think there was an amalgamation, as you suggest, of some things that had to do with my sort of d n A and makeup. Some things that had to do with, uh, the hiring process, honestly, and how much time I spent with, uh, the founders of Stripe.

And then I think the third part is probably actually cultural, a little bit in Stripe. so yeah, in part one, I was, you know, pretty early. First of all, I, I, my career is not a very. Straight line. And I took a lot of different kinds of risks. I graduated from college without a job and started working on political campaigns.

Uh, I kept getting into law school and then saying no, and realizing I should try to go to business school, which based on my upbringing was like a very radical thing to do. Obviously not radical when you say it out loud, but, uh, but my parents were appalled. Anyway, uh, I go to business school, I end up, uh, working for like a startup consulting firm that was pretty scrappy and also had technical, had engineers, right?

So I started getting into technology. Um, but point is I think I'm pretty entrepreneurial. I think I'm a more of a risk taker, uh, than your average quote unquote executive. I've never been comfortable, even still today, once people call me an executive, I, I kind of start laughing. Uh, so I think that that spirit in me, I mean, it was just crazy to me when Google, Google was the biggest place I'd ever worked and I joined, it was about 1800 people.

Um, and then when I left, it was almost 60,000 people. And I was just flabbergasted that I worked at a company that was that big because it just wasn't my jam. Um, so I think I'm pretty entrepreneurial. I'm not afraid of risk. I saw the opportunity for Stripe, even though it was so early on, it was like 160 when I first started talking about Patrick.

It was like 80 people, barely. Um, so that's part one. Part two is, yeah, the hiring process. I mean, we just, the collisons, I mean, if you were gonna fault our hiring of leaders is that we always took way too long, uh, because there was a little bit of looking for that perfect candidate. And then you realize, of course there's no one perfect.

And I wasn't either. But we certainly, there's a lot of diligence done on both sides. Uh, a lot of conversations. We even sort of practiced working together. Like I drive to SF from Menlo Park and hang out in the office with them for a couple hours, a few nights, and we like wrote company goals together. So I think the hiring process was very thoughtful, lots of mutual diligence.

There were no surprises really. When I joined, um, I'd seen a lot of the data and written, again, I helped write the company goals before I joined. Um, so that, uh, was pretty critical. And I think, um, and I think the third part is, We really worked hard as a leadership team to be introspective about giving each other feedback, but also shifting our portfolios, thinking differently each year about what people's value would be and where they could have an impact, which was good for my development and my growth, but also I, I'd like to think I helped create some of that open environment and that willingness, at least I think early on, we didn't hire anyone whose ego got in the way of the right thing for the company. Um, and if we did hire that kind of person, we would part ways with them. And I really thrive in that kind of environment. And I think, so my cultural alignment, but also the fact that the culture, uh, kept, you know, the spirit that the founders had, we were just like all really in it for the long term. Uh, and that, that meant a lot.

I think there are some people who get a certain type of career success and they th they think like, well it means, you know, big money, big title, big company. Right? And, and to me, career success is big impact and I don't really care what seat I'm in.

Brett: There's a lot to kind of dive in on there. I, I'd be interested to, to hear at, in a more granular way what that hiring process looked like and when you were kind of getting together, even if it was more about time and less about structure, what was going on in that time, uh, when you were together, what are the types of things that you explored together?

Claire: Yeah. Um, as I say, you know, in the book, in Scaling people, I have, I have a little section on, um, me joining as coo cuz there's a lot of questions about that role and should you hire one and, and I'll give you what I think the context was at Stripe at the time because I think it, it is relevant to what you're, you're asking, which is the company had started to really, obviously had product market fit, was getting real traction.

Um, and my sense was that the investors were rightly and the one board, the one board member who is Mike Moritz from Sequoia, um, were starting to, to give a lot of strong, strongly worded advice to the founders. Like, you gotta grow a little faster, like you gotta invest. Um, strip's always been quite conservative, at least ally early on in, in sort of the p and l, but also just in adding people.

Um, and, and I think there was a real need acutely to really build out sort of sales in particular. And so Patrick and John Patrick in particular was on a journey, from what I could tell, meeting sales candidates and or COO candidates. And I will share a lesser known fact, which is Stripe had a coo. O uh, so Stripe, my colleague, who by the way was, has been at Stripe longer than I have, uh, is a guy named Billy Alvarado who was hired.

He's like a bd Jedi. I mean, the guy is a master and very strategic and also very smart about payments. And he, um, and, and in another story about doing work before you're hired, so I helped write the company goals. Billy helped do a deal with Wells Fargo before he was hired, which I love. Uh, he, and somehow the Collisons have that effect on people.

You just start working for them before you're working for them. Um, but anyway, Billy was the coo and Billy was, this is what I mean, I guess, about the culture, which is Billy was really aware that there were aspects of what the COO role needed to be for Stripe as it hit the scale moment that were not his favorite.

Like not, not only did he not love them, he, he, you know, often the things we aren't as passionate about, we're not as strong at. And um, he. Was part of my interview process, right? Like, that's a big deal. Like, he was like, look, I want you to take my job. Um, and, you know, he became the chief business officer. He, again, critical colleague, critical builder of Stripe, really needed to focus on our payments and our product partnerships on some of our sort of international payment infrastructure work.

Um, but point is he actively recruited me to be the coo o and then when I joined, there was this awkward thing where Patrick's like, well, we don't really feel like we should give you the COO title when you first start. This is after I'd been recruited for like six months as the coo, and I said, Uhhuh, and I'm, for a minute, I'm, I'm thinking, wow, I really trusted these guys.

Is this a bait and switch? But they, I think Patrick had a, a legit concern, which is the company didn't know how long I'd been talking to them and how we'd all gotten to know each other. And obviously Billy was an important figure. And they're like, Patrick's like, I think people might think you're taking his job.

You know, and that it, it reflects on him. And, and so we came up with chief of Business Operations. That was my initial title.

Brett: very fancy.

Claire: Very fancy and very kind of amorphous, which type likes either no titles or something really amorphous. So, um, and then we, like a few months in, actually not long, Patrick just sent a short note out to the company.

He's like, Claire is no coo and Billy is now, you know, chief business officer. Goodbye. You know, like whatever. No big deal. Um, but I think that the interview process really, we spent a ton of time on the sales stuff, actually building sales, what would go to market build look like. Also internationalization, which was really happening at the same time.

And they're related of course, cuz you need to build, go to market in all those countries. And I think this is part of, they were talking to a lot of sales leaders and then talking to me and of course I've built sales teams and I've been a sales leader, but I actually didn't want a job as a head of sales.

And I was very clear about that. I was like, I know that I can do it and I will help build sales for Stripe, but I'm not gonna be the ultimate like revenue officer. Um, just because it's not everything that I care about. And, you know, I'm, I'm more operationally wide, I guess was what I was trying to say.

And they had a decision to make, which is, well do we go for, do we give this. You know, ostensibly bigger title COO to, uh, to this person and trust that they will be able to put the scaffolding and start to build this critical function. Again, at the time was sales. They were really fixated on, um, and then eventually that she or we will hire, you know, who is needed to help lead that function.

And, and I think what happened also, so one is I think they became convinced that I knew enough that I could in fact build it and I haven't built it before. Um, but then they also got some bonus topics essentially, which is one I had a lot of support and operations experience. And our support situation was a little bit of a tire fire at the time.

Uh, and I had some real opinions about what we'd have to do there. And then the third was that I cared so much about company building. you know, I care about the people side, the org side, the, the structures you needed to put in place to have a healthier company. And to their credit, they came back to me and they're like, you know, you kind of talk about some of this stuff on the company side and we just don't talk about it.

We don't, we haven't been thinking about that and we realized we have a blind spot and you care and you could fill it. Um, and that meant a lot to me cuz it meant they were really listening. They were paying attention to what I cared about. And they were looking for a way to put a portfolio together of what they needed, but what I cared about.

But also admitting that maybe the company needed some things they didn't know. Um, which shows that they're learners, right? They're curious, um, they're interested in, in changing how they think about the world. And so in the end, the portfolio I walked in with was sort of a combination of those things. Um, and as I said, and it evolved over the years.

Uh, I added, you know, marketing, I added at one point risk, um, our workplace and real estate stuff. But I also gave stuff up. You know, we, we've moved things around. Um, but it, it, it was that iterative process of what does the company need? What is my career aspiration and skillset? And then what might I bring that, that they didn't even know the company needed, and could I take responsibility for that?

So Billy ended up handing over some things to me, um, that were all in his, he was holding them as well, um, that we weren't sure would be in the COO remit, but it started to make more sense as we got to know each other.

Brett: What did you learn from Patrick about wooing exceptional talent that maybe is differential than, you know, you, you already had a big career coming in and you've recruited in that role. Lots of exceptional people. Were there net new insights in studying what he does That is part of your sort of, um, repertoire now.

Claire: Yeah, I, I mean that is a fantastic thing to try to package up. I mean I think the number one thing is I think he will relentlessly pursue until he can get the conversation with the person that he is heard great things about he'll relentlessly research, right?

Who are the best people? Um, in fact, I was talking to an engineering leader who worked for me at Google a month ago who I met up with cuz he was in Boston and he was describing Patrick's reference call for our current C t o David Singleton, who we both worked with at Google. David. Um, I was part of the reason David came into the Stripe orbit, but Patrick certainly really hired him and closed the deal and Patrick did a reference call with Richard and Richard said to me, this is, by the way, this reference call was years ago now.

And Richard was like, this reference call feels like it was yesterday. He is like, look, it was the hardest reference call I've ever experienced in my life. I was, felt so much pressure, not just cuz it was Patrick Coll and, and because I care about David and the right thing happening. He's like, but because it was like intense and he said that, um, Patrick at the end asked him, you know, a lot of very detailed questions about how David works, but then at the end said, who have you worked with?

And this is mostly at Google, right? Richard had been at Google for a while at Google, who David is better than, and who is better than David. Um, you know, engineering leader wise, right? But if you think about that as a research project, if you do enough of those calls, you're gonna be mapping a certain type of talent, uh, in a pretty interesting way, right?

Which is you're, you're interviewing these folks about other people, and then you're asking them who do you know? Um, and then these people are are, you know, one would think pretty talented themselves if they're being offered as references for executives, right? So there's this very interesting, but anyway, Patrick does the research.

He's relentless in the pursuit of getting the meeting with the person. He's incredibly persuasive in the initial meeting. Not in a take, take this job, you know, but in sort of, you know, his own manner. I mean, he's just a very, um, incredibly intelligent, but also curious and worldly. And, and he has a lot of ideas and he has a really nice mix of his own opinions and things he's curious and interested in that are not just Stripe, but also about any individual he meets.

You can just feel like he's just collecting knowledge. And I feel like, great, but you know, we have, you have these. Dynamic conversations and you learn about what he sees for Stripe, which is inevitably bigger than what you thought it could be. Um, and then I remember distinctly, like after one of our, our first conversations, he was talking, um, about Stewart Brand and the whole Earth Catalog and then computer lib this, this old sort of newsletter that was created that was really formative to his interest in technology.

And next thing I knew in my office at Google, a package shows up where he has tracked down cuz computer lib is like not published anymore. He's tracked down and paid for a vintage old book copy of this newsletter and sent it to me with, you know, a note about what he thought I might, I might enjoy in. Um, after our conversation and you know, that's like an old tactic in the world, but it felt very genuine. It felt really authentic and it really related to our conversation and to his ability to share his knowledge and his passion and then connect it with someone else's. So part of that is just being himself, honestly.

And so you have to figure out how do I beat myself in a way that is really persuasive to someone? Um, and, and I think I couldn't say no to another conversation because I just like loved talking to him and I didn't feel like he was pushing the hard sell. He was, he was doing his own investigations.

That's the other thing is he's not, You know, blindly selling, he's really trying to make a match. Um, so I think those tactics and then being diligent throughout the whole thing, really, you know, probably too many interviews. Um, you know, I famously ended up interviewing with everyone at the company in one, you know, massive all hands meeting where I had to answer questions.

Um, and then also the diligence on the references. Uh, there was a point where I had mentioned offhand to Patrick and John that I'd send video messages to my global team because I was just sensing that my email updates, cuz you know, you have a global team, they're in all time zones, you can't get them all together at once.

So I do these email updates and they were getting kind of long and I was sure the open rate was crap and that no one was really reading them. And I was like, well, why don't I, I know this seems very trite right now, but this was actually somewhat innovative at the time. Like, why don't I just send a quick video message, which is much more efficient, they can watch it in their own time.

And like literally I would be with like an iPhone in my office on a like, you know, tripod recording these three minute messages, uh, to email out. And I offhand mentioned that to Patrick and John and they were like, can you send us something? and can you send us an email update that you sent to your team?

And I think like, I don't know if it was just that they wanted to see what I was like as a leader or they didn't trust that I did this, or they wanted to see, I think it was both by the way. Um, and so yeah, I ended up, uh, I had to actually edit, I had to edit out some Google specific content. Don't worry, Google, I protected you. Um, but I, uh, you know, I had to x out the numbers for the quarterly goals cuz that was a sales team. But anyway, point is, I did send a couple examples to them, but they were relentless. They were like, if I didn't send them, they'd say, well, can you send those things? Like, they were not gonna hire me without seeing examples of my work.

Uh, so that was, and we did that. We, there's a form of, that we've done with a lot of candidates to strive is we would like look for either a work sample or do a workshop with a candidate. Like, let's just take a real topic and sit in a room with you and give you some pre-reads and have you talk to us.

It's very effective. Um, you really do get a sense for not just the interview person, but the worker person.

Brett: Yeah, you're touching on this a little bit, but sort of given what you shared h how did it map to some of the changes you made when it came to recruiting exceptional talent and, and you sort of mentioned this point about authenticity, which I think is really important. You often, I think one of the weird things is you see there are certain people who are around incredibly charismatic people and then they try to behave in that way.

Claire: And it doesn't

Brett: really, you know, somebody trying to be charismatic is probably from a hierarchy perspective, one of the worst things you can do. And so I'm curious maybe how did you adapt some of those insights that you picked up into what it looked like when you were going after talent?

Claire: Yeah. Yeah. I, I would say, I think definitely being more patient and being more willing to pursue and being more willing to, I'm not someone who asks for help very easily, but I really, you need to use your network. You need to ask for introductions. So I learned that I, and in terms of the authentically showing up, I think that has always been a strength of mine, if I'm gonna be honest.

But what I will say is I learned pretty quickly, uh, Brett, that I needed to pitch Stripe in my own way, right? like if you put me in front of a candidate and I was parroting out Patrick's vision or John's vision, it was not as effective. And I, you know, there's one version of the story where you think, well, I've gotta say what the founders would say.

No, actually, it's not authentic to me. I had a reason I joined Stripe. I had a vision for Stripe, and that was much more compelling to candidates. I have this like whiteboard drawing that I would draw for what I thought was possible for Stripe. And I tried to draw it for Patrick and John once, and they were kind of like, yeah, okay.

You know, I mean, it wasn't the, just the way they tell the story. but I had to get comfortable that it's, it, that's my version of the story. And, and none of us are wrong, by the way. We hadn't built the thing yet. Um, and it was working. Like, I, I think that version of authentically talking about what the company could be, um, true to my own version of it was, was really important.

Um, I'd say that. And then I think just never stop the diligence, do the reference calls. I will say though, I don't think my leader hiring track record is as strong as my other hiring track record, and I don't know why that is. I think that I can, I'm very care, I care a lot about collaboration and if I'm hiring an executive, I think I'm thinking of them like, you're my team.

You know, you're kind of like my teammate and we're gonna work together. And I, I maybe didn't push hard enough on some of those and that, and Patrick would've, Patrick would've pushed harder.

Brett: What else? When you. That sort of self-reflection comes to mind for you And and when you say hiring for other, you mean non-executives or something else? Specifically

Claire: managers. Anyone else? Like I'm, I have a high hiring bar. I think I have a pretty good eye for talent. I will tell you that if I've worked with someone ever in my career, I have a very good eye for talent. Um, you know, it's a little different when you're in an interview process. But for example, we have this stripe, you know, in our applicant tracking system.

You can sort of say strong. Yes. And I have rarely ever used the strong. Yes. But when I used it on any candidate, let's say there were 10 maybe, so I'm not talking about a lot. They all ended up being top performers like I knew immediately. Right? But if you gave me an executive, I don't, I don't for some reason have that same insight.

Um, here's my theory. My theory is that in the same way that early in my management career, I had a thing about sort of wanting to be liked by my team and I was too nice, let's be honest, and not setting a high enough standard, uh, which I got over. And actually being at Stripe, I really got over it. I think I got a good balance between, I think I'm a very empathetic leader.

Um, but I have, I think my teams felt I had really high expectations of them, and I would give them the feedback if they weren't being met, right? I, I wanted results. Um, and I would think, I think in some of my errors at Google, that was not as true. Um, I certainly did well, but. You know, Google was on its own momentum.

Um, the point is, I think what happens to me in some of the executive hiring, or certainly earlier on at Stripe where I was, you know, at Google, I wasn't really hiring executives. Maybe at the very end I was actually, but, um, at Stripe, it was a new skill for me. It's a little bit of a different motion as, as they say, in sales.

Um, and I was trying to be liked, I was trying to recruit the whole time, right? I wasn't, I wasn't pushing hard enough on really getting underneath how they would work and how, and frankly, the other thing I wasn't pushing hard enough is I was making the assumption, okay, if you got to be this successful in your career, you're gonna adapt and be successful in our environment.

And guess what? As you said, Brett, a lot of those things blow up. You know, I adapted and was very successful in Stripes environment, but I am, apparently, I'm not the norm necessarily. Right? And I was doing that thing. This is another management lesson that I would share, which is you have to manage different people differently.

And too many managers have grown up being told the golden rule, right? Treat others as you want to be treated. in fact, the golden rule is not a great rule for management. You need to study those people and figure out what gets the best out of them and what gets the best out of them is not what gets the best out of you usually, especially if you've hired a diverse team, which I hope you have.

And so I think on executive hiring, I was making assumptions about my executive skills, um, and my personal skills and grafting them onto people who had, you know, great track records and saying, well, they'll, they'll have those same skills, you know, they can handle this environment, they can adapt. And that was wrong.

That was wrong. Some people, uh, no, the answer was no. Um, just flat out just being successful. You know, I think one of the, the most telling things, by the way, as a side note, but because we're on this topic, um, as you said, you can have this leader that you hired that you're really excited about, and then they flame out in, you know, six to nine months.

The biggest indicator that I could find in our time at Stripe when we had that issue was, uh, people who joined as leaders, as a, you know, executives and didn't hire anyone good in their first three to six months, that's an indicator that there's a problem.

Brett: and so what's going on there?

Claire: Yeah,

Brett: assume when you think about your directs, or even given the scale that you are operating, the directs of the directs, I would assume, and correct me if I'm wrong, an enormous percentage of their job is who's on the team, who's off the team, and how they're managing it.

So obviously you're sitting down and you're thinking very critically about this person's ability to evaluate and recruit talent ahead of the process. And so you're hiring them with some level of conviction they can do it, and then it doesn't happen. So what's going on there?

Claire: And actually Brett, one of my favorite executive interview questions, I now have like convinced people, I'm not credible on executive interviewing, but let's say I'm not that bad at it.

Brett: Maybe relative to other people, your,

Claire: but anyway, one of my favorite executive interview questions is tell me about your current team and why you chose the structure that you have everyone in, and then each team member, how they got in that role.

Right? You learn a lot. You learn, and because what happens is they say, well, I came into the job and here's what I had, and then here's the choices I made. And there was this person and I elevated them, and there was this person and I, you know, maybe fired them. And there was this like, and it's a real red flag if someone's like, well, this is the team I got, right?

Like, I would never hire someone, especially in a scale environment, like who said, I just took what I got, you know? Um, and also that means they're not developing people, et cetera, et cetera. So, so I'm really on the watch out for that. Um, so yeah, what happened? So why were those people who passed that interview test with me then not bringing in talent to Stripe?

I think that the answer is one, they, well, first of all, as you know, well, you, even if you ha, I mean Stripe, when I first started, barely just had a couple of recruiters. So I was the

Brett: Mm-hmm.

Claire: for all of my early hiring. So one is some executives, if you're pretty early on, have never had to actually do the recruiting process.

Brett: Mm-hmm.

Claire: They do not know, and Like they're used to showing up in a conference room and there's a candidate sitting there. Yeah. So that's number one is maybe they don't know how to recruit, which of course I talk to them about and teach, try to teach them. Uh, number two is that's just because they've been in a more scaled environment.

Uh, number two issue may be that we just read them completely wrong and they have no followership. Right? And followership is a sign of strong leadership. There are people who want to come work with you. If you've had a long enough career, you should be able to pick up them. I'm not saying they should all get hired, by the way, Stripe.

You know, even if I had someone, I was like, they're the best person I've ever worked with. We put 'em through the ringer. But, you know, I brought people into the company. And by the way, not just for my function, I brought them in in, in a lot of different places. And I think that's because Stripe is great, but I also would like to think it's because people wanted to keep working with me, right?

So did they somehow not inspire followership? And did we miss a flag that they're just not a compelling leader? Right? The third thing is a little like almost. A variant of that, which is, are they not happy at Stripe? Like, do they not know how to, uh, sell the opportunity or convince people on the company?

Is it because they don't see it, they don't get it? Is it because they're not thriving? And often I think that was what was going on is they weren't adapting, um, in, into Stripe effectively. And therefore we're unable to sort of call someone and be enthusiastic. Um, I don't know. I don't know. Believe me, if I had the answer, it would be a chapter and the hiring chapter in the book is actually quite long.

But, but I didn't do enough introspection in the book on sort of what goes wrong when you're, um, trying to hire, it's like the, the initial leader onboarding is so fraught, right? And how do you handle that? I do talk a lot about leader on onboarding, but the, the reality is you can do a great onboarding process that it's probably gonna last about, you know, three months maybe.

And most of the problems happen after that. Three months.

Brett: So a bunch of things to sort of. Dig in on one is when you think about what you're looking in terms of foreign talent from raw ingredients, so not like the difference between you're hiring a revenue leader versus an ops leader and the differential skill sets, but like when you get down to sort of the threads that tie the very, very best people that you've ever hired, are there, are there sort of common traits?

And then if I were to talk to you after an interview and you thought that someone had those, like what is going through your brain and like what are you pulling at to get at that outside of the obvious, really important sort of functional area expertise that somebody needs to have.

Claire: Yeah. Yeah. I mean, I think at the highest level, I mean, I, I have this expression where I say, is the person a learning organism? But like, are they curious? Are they a learner? Are they interested in getting better? Um, which is different than by the way, a certain type of ambition is like, are they interested in success?

But some people sort of seek others' version of success and then achieve it and then aren't continuing to learn. And I don't find those people Very interesting. So curious learner seeking, um, I guess a more self-actualized version of success in their life. Um, another is, do they care about, I think it can be people who are very high level, who are very good at their jobs, but like aren't actually tracking outcomes.

Brett, it's very interesting to me, but like, maybe they're too into the process or they're too sometimes into the people. And I say that as a very people person. Um, but you know, my whole book is, is in the interest of great results. It's not in the interest just of,

Brett: Feel

Claire: I, I mean I like a healthy org, but the reason you do it is cuz you're gonna get outsized results anyway.

So are they interested in results? Are they a learner? Um, I, I think there's a element of resilience and adaptation, which is sort of related to learning, but a little bit different, which is like what happens to them under pressure and under stress. oh, I, there's actually a section in the hiring chapter, there's an appendix on sample interview questions and, um, in the book and, asking questions like, you know, tell me about a time you worked on something that you knew you wouldn't enjoy, but it was important to the success of, you know, your team or the company.

Um, a project where you've had to pull out, ev all the stops to get it done, a project that failed and what role you played in it. Like, that's a huge one for do they learn, did they take feedback? Um, how do they recover from failure? Um, you know, a lot of people like the question like, what would you change in your current sort of company or job, which gets to the final thing I would look for, which is a sense of ownership and agency. you'd be shocked at how many people you say, what would you change? And they dump, and these are leaders, right? They dump a litany of complaints on you of where they currently work, and you're sitting there thinking, wait a minute, you are a leader in that environment. What are you doing about those things?

And I get it that they're not the c e o, but, but I find that sort of, frankly v victim behavior, um, a real flag. Um, so, you know, those are some of the questions. And, and, and I often then go into, like, again to the point about hiring talent, you know, them to talk about the people who work with them and see if they're really, cuz there's some people who are really jazzed about results, but they're not jazzed about the people who got the results.

And I want the person who, who cares about both those things, like when they're getting jazzed describing one of their direct reports and their impact in their career. I'm really happy to hear that because most leaders, look, we don't do the work ourselves very often. Um, it needs to be through, through the people around you that you're coaching, that you're empowering. 

Brett: when you think about those few base traits, uh, orientation around results, resilience, curiosity, ownership and agency in the world, h how much of that do you think is, is set and inculcated in someone's childhood?

Claire: Um, I, I mean, if you were talking to me as a parent, I would say the parenting lesson I have, uh, a 17 year old and an almost 15 year old and is like, it is way more nature than nurtured. I really thought nurture mattered more. Um, that said, so, so my off the top of my head answer would be, I think it, a lot of it is Inculcated fairly early But I think that, I say that, and then I think about myself, right? And I would say that I am better on all of the dimensions that I just gave you at this point in my life and career than I was in the beginning or even maybe the middle. Um, maybe that comes down to being a learner.

My parents are educators, right? So if I'm not someone who's constantly learning, you know, like that, but, but I think I'm, you know, I'm just a little more confident, um, and more confident in what I don't know. And being okay knitting that and operating that way. And so I would like to think that you can work on all of those dimensions.

Um, I do, I do worry though, for folks who've never in particular learned to, to take ownership, right? There's something about that, you know, are you, there's a framework in Fred Kaufman's book Conscious Business, which is, are you a victim or a player?

Brett: Yeah, there's a great 10 minute talk that gets at the idea that we can link in the show notes that

Claire: Yeah. We should

Brett: minutes or something. Yeah.

Claire: we should link those because of all the things I described, like I'm more

Brett: that, by the way. I shared it like a few months ago to our, our whole company in, in an email.

Claire: Yeah. Great. Good. So you and I are in the same place, because if you think about it, am I, I think I'm actually more curious now, thank you to all the engineers I've worked with for 20 years.

I'm more resilient. Uh, I know I've overcome a lot and I know I can do it. I'm way more resilient. Um, I think I actually take more ownership. That was some of the feedback I got in my early time at Stripe that I needed to be even more of an owner. And, and I've seen what founders really look like as owners.

And the part that I would say I, I'm the least confident that people could change is the victim player thing. I have always been a player, Brett. I have always felt that I owned the outcome and it was on me. And yeah, some crappy thing happened. I'm not blaming anybody else. And I think that was partly my parents is partly my nature, but I think that is a thing that I think people have trouble getting over.

Brett: Do you remember what your parents, how they behaved with you that might have nudged you in that direction?

Claire: Um, well, one, I had one boyfriend who's like, you were kind of raised by wolves. Um, so, I was raised to be quite independent. Um, and my, it's interesting, right? My parents were teachers, they were both working, you know, they're busy. And I think because they were educators, like I think educators can go one of two ways.

They can sort of be over-involved or they can be under involved. And my parents were under involved because they wanted to leave the educating to the educators. I don't know. But anyway, I was raised to be very independent and, um, in particular my father, uh, which I think is important to the dads out there, like really wasn't bought into gender stuff at all.

And I think at the time, this is a little more radical, but like, he made me shingle a roof with him. He made me learn how to repair my own car and how is to have like an emergency kit in my car. He made me, I expressed interest in riding a motorcycle and he put me on a motorcycle and I promptly burned the crap outta my thigh, by the way.

Um, but like he, he just, Really didn't take, oh, and he has a another thing, like you carry your own luggage. Like, I don't care. He's like, you pack, you carry it. And there's like a weird thing that still happens to me today. I mean, I travel a lot for business. A lot of men try to like lift my bag for me, and I get super skied out and I'm like, I gotta get over it.

They're just trying to be nice. But my dad is like, really, really was like, you carry your own freaking luggage, you know? And, and I think that, and that is a metaphor too, right? It's, it's not just being strong. Uh, I think, uh, and being independent, but I really give him a lot of credit. And my mom, by the way, I'm fantastic example of a woman balancing somehow everything working and kids and, and frankly, the more active parent of my two parents.

But, um, I think my dad did not buy into gender norms. I'll just say that. Uh, and that was helpful. And himself, their own behavior. Actually, you know what? Parents, it's like leaders.

Brett: Yeah. Model it.

Claire: It's, it's what they do more than what they say. I mean, they never complained my parents, like, it was never like shit happened to us.

Actually, I remember we were on a family trip, which was very rare for us. We went to Europe together and my dad got robbed in the subway in Paris. And it was like, it was, it wasn't like, it's all my fault, but he was like, all right, this sucks. Like, what are we gonna do? You know? What, what's our action plan? It was not, whoa is me. Um, and I think you wanna see those examples?

Brett: I, I, I wanted to, I had a couple follow up questions about the, the sort of four base traits, but while we're sort of on this theme of wiring and orientation, you mentioned at the start of the conversation, this, this sort of insider realization that, that maybe you were more focused on, on being liked by people you worked with.

What, what was the, the phase shift that happened for you? how did you move to a, a different point where maybe you dialed that down in some way?

Claire: Yeah. Um, I think that I can point to a couple specific things that happened. So I was at Google and I, I hadn't had a lot of performance reviews in my earlier career. I was just working at these sort of startup e operations kind of things, campaigns and a, a very young consulting firm. And so I really had my first kind of review, uh, with a guy named David Fi at Google early in my time there.

And he, first of all, the review was a revelation cuz there was a lot of positive. And I was like, oh, I turns out I am okay. Like, I had never known, like I was, I was a good performer. So I do remind people that reviews have a role actually, not just in negative feedback, but, um, but the other part was like, he, he, he made a comment that he saw me put nets under my team.

Too much meaning like protecting them. from failure, but also a little bit micromanaging. Right. and being overly involved, which isn't the same as like wanting to be liked, but I do think part of my calculus on the liking thing was like, well, if they fail, they're not gonna like me.

You know? And, and I really had to look at that feedback, uh, for a while and think, okay, how do I stop doing that cuz my team is not growing and I have to like, let them fail and maybe be unhappy with me. Um, and then the next was also at Google. A few years later I ended up in a situation as one often does, where my parts of my team were kind of reporting to me and to this other person, right?

And I, they were solid line to me, but they were dotted line. Um, and we just happened to have this occasion where I was holding like an offsite and they were presenting plans to me. And a few days later I happened to see a few of them presenting to this other person who happened to be a guy who is definitely a high bar kind of a guy at Google.

And I watched their second run, like them presenting to him. And I just have to tell you, Brett, I was like, oh my gosh, my team members are bringing their A game to this other leader and not to me. And I was really upset with myself. I was like, so I am running this really collegial offsite and my team is great and they love each other and I think they're like me, but we are not bringing our A game.

Like what kind of leader am I? I'm not setting the bar high enough. My expectations, my standards aren't high enough and maybe I'm less scary than that guy, but I don't care. It was just very demoralizing. Um, and I felt lucky that I got to see it because I then could really examine it and even talk to them and say, what is it that I'm doing?

And the other was actually also a Google, there was like a employee engagement question, something related to like, does my manager set, you know, the highest standards for my work? Something like that. And it wasn't, you know, in my top scoring, I, I did pretty well as a manager. I had a lot of very strong positive feedback.

Um, and sometimes that's a bad sign, right? You don't want too much positive feedback. Um, anyway, that data. So I'd like to think I listened to that feedback. and then what I also got much more comfortable with was just giving people constructive feedback and pushing them.

And I started really practicing that in my later stage at Google. But at Stripe, I think I was known actually in the company as someone who would be very, you know, Supportive and empathetic, but would set a high bar and tell you pretty damn quickly if like, if I wasn't happy with the work or if I didn't think someone was performing.

Um, and that wasn't happening a lot at Stripe, you know, or young companies. You're not, you're not always verbalizing the constructive feedback. Right. Um, so I, it started to feel like something that I was known for. I also think I just got over the fact like, you're not gonna be friends with your team. You can be friends with them later, which I am, but I, I, I, part of my com compartmentalization psychological sort of resilience training was to just get over that. Like, people do not have to be my friend. They do not have to like me. And by the way, I think they all like me better once I got to be more like real about results. But that took about 10 years to get there, you

Brett: Yeah, can you talk more about the shift? So, you know, you did such a great job of explaining. How you sort of, the self-awareness piece, how you became aware of this, and I find that that the type of thing that you're talking about, it's not a three step program and, and it's this type of stuff that I think when you check in on people six months later, two years later, five years later, they're still not exceptional at because it's so squishy.

Is there anything that you kind of did that, that, that tangibly moved you in the direction?

Claire: Yeah, I, I tried to, to outline some of this in, there's a sort of performance chapter, um, individual management chapter in the book. I tried to outline some of this, and, and I would say that, the thing that helped me was a mindset shift, which was, part of realizing, like too often when we're about to give feedback to someone or a team, like you're in a room and the data doesn't look good, right?

Is that you feel like you're judging a person. You know, I, like I'm saying, Brett, Brett, you're, you're a bad communicator, but no, you're not. You're judging the work. You're judging the task. And so even, you know, in the team meeting, and I'm looking at the chart and the chart doesn't look great, and I, and I say, wow, you know what?

The data does not look good. What is, you know, what do we think is happening here? But like, I'm not criticizing a particular person. Um, even maybe if it's one members of the team's data, but especially in a one-to-one feedback, I'm saying not you're a bad communicator. I'm saying, Hey, I didn't know if that communication was effective as it could have been.

What do you think? You know, the next is what I just showed you, which is, I also realize I just need to start with more curiosity and questions. But what happens is managers sort of don't even ask the question. You know, they don't say, well, how did you think that went? I mean, I was sitting, I was sitting in a board meeting last week and a, a guy presented to the board who was a report to one of the executive team.

And, um, it wasn't a particularly great presentation and I, and I could immediately see things that would've been made it more effective. And I worried, and by the way, I mean this is terrible, but I looked to my, I looked and the, uh, after he finished presenting, the executive who happened to be sitting next to me was slacking the guy and said, great job.

Which is of course the supportive thing to do. Like it's scary to get up and present to the board. Um, and I was sitting there, I really almost intervened, which is terrible, but I was like, oh my God, this is a huge missed opportunity for that guy. Like, you gotta say, how did you think that went? Right? And then let them self-assess. And so, and I actually, in my estimation, more people are better at this than you think. What, what, well, what didn't, you know, what do you think? And then reinforce, well, either they have a massive gap and they don't actually give you the right answer, but most of the time they do. And you say, yeah, I kind of agree.

When I think about that presentation, again, I'm not talking about you specifically. I'm not saying you are bad. I'm saying I think some of those things didn't go as well as they could have. And I have this framework in my book, which is be an explorer, not a lecturer. You know, your job is not to tell somebody what to do or what was good or bad.

Your job is to explore with them what happened, why did it happen, what do you wanna do differently the next time? And so I think using Quest, so one mindset shift, you're, you're, you're offering feedback on the task, on the work, not the person. Two, start with curiosity. Give them a chance to assess. And three, which by the way is a pedagogical thing, students do better when they self-assess before the teacher assesses because we have to learn.

That's where you get a growth mindset, right? And the third thing is to absolutely, you know, be supportive, but be really specific with them about like, what is their plan? They're empower them. To, to work on the thing. But for me, um, I just had a mindset shift in like what I, because I, you know, the feedback is a gift is sort of a trite cliche, but I think I also just shifted my attitude on like, this is my job.

 and if I'm not doing it and people aren't getting better and having more impact, thanks to what I say to them, uh, than I am failing. So that would be the other thing. But I think it was mindset and then it was practicing. And honestly, Brett, it was being uncomfortable, being uncomfortable practicing, uh, meaning in the room with someone and saying like, look, here's my observation by the, that's the other thing.

You really need to own your feedback. You say, this is my observation. This is me holding up the mirror. I'm not telling you who you are, but here's what I thought. I thought you seemed nervous in the meeting. What do you think? But I, I, I definitely had some misfires. I definitely said some things that I think people reacted to, but I wouldn't take that back.

I mean, I, I, um, if I look at my early career, like I think everyone manages on a continuum. I was way too far on the continuum of like sort of coding any feedback in the niceties and being indirect and not taking risks. And now I think I'm more likely to take risks. And if I had to tell my younger self any lesson, I would say, um, in my book I have an operating principle, which is say the thing you think you cannot say, which is a version of Fred Kaufman's sort of detoxify the left-hand column.

But it is really, i, I, I cannot emphasize enough that I wish I had taken more risks with sharing my observations and asking questions of people on their performance.

Brett: I think you explained how you sort of figured out that balance where you both sort of share the feedback or the observation and also create this dynamic where it seems like people feel supportive and actually to your point in, in knowing people that have worked with you, they're just enormous fans of yours.

 is there anything outside of what you just shared that if I was watching you in meetings with your team or directs that you do sort of differential or allows you to create this dynamic that's high standards, high expectations and also

Claire: High devotion. Yeah, high devotion too. Um, if there was anyone watching me, I mean, I think first of all, I really do care and I think people feel that I care about them being better, uh, and them as people. Um, I think that you'd, you'd have to ask them. I will say that John Coon once said to me, he's like, you are amazing.

You, you say the most critical things to me, and somehow I feel like inspired. Um, but I think part of it is, again, at the end of that, when I said like leaving people feeling with that they've come up with something they can do differently. you know, it's really in their hands. I think that's, that's part of it is you would see me being more inquisitive about like, well, what do you think you can do?

Or What is the plan? And then me adding some special sauce in like, well, here's one thought. React to it. Tell me, you know, it's much more of an exploration with my team, with the people, but it is not, there are like very few undiscussables, like we are talking about the real stuff. I mean, I think that's the reality is people gravitate toward.

 honesty, authenticity, transparency. Um, I provide my teams people. I work with a lot of context and then a lot of expectations. And I say, I'm giving you everything I can give you. And now, you know, you have to own it. Um, but, but I do think that the other thing that maybe distinguishes me is that I think I do multi-level feedback, which is tactical on the work and the thing, but also developmental feedback, Brett.

And that's why I think when people say they like working with me is that I really pride myself on studying people and li like, have the career conver, what are their aspirations? What do they wanna be good at? What do they wanna learn? Keep those in my mind over like multiple years of working with them and bring it back and say, okay, if you really wanna found a company someday, here's some thoughts for you.

Like, do you think you're working on the right things, et cetera, or help them change their aspirations. But I, I pride myself on having some, at least one breakthrough moment with anyone who's worked with me where they've been like, oh yeah, that's the thing that really holds me back. Right. Or that's the thing I read.

And in the same way, you, you, you very nicely said to me that I became self-aware. I'm a real believer in self-awareness. Like I heard feedback and data and I changed myself. But what I'd like to think is I'm providing the data and the feedback to the people who work with me, but I'm also their partner in that change.

Um, whether that's my team or that's the person, and I know this doesn't seem super tangible, but I think it's this combination of really pushing at the same time that you're really supporting, um, and offering your help, offering your advice, offering your resources, and at the same time saying, and, and, you know, better, faster, stronger, please.

Um, and, and people respond to that by the way, right? We all like that. We, I mean, anyone I liked working with wants to be challenged, but then they want to learn. Um, so, so I think that's, that's part of it. And then I think there is a thing you're getting at, which is there's a little bit of, this is hard in a virtual world, but you know, are you really present?

Are you making eye contact? Are you energized? Right? Are you showing up in the way you want them to show up? And you can deliver the same words and your body language, your tone, your energy can dramatically change how those words are received. And I think that's particularly important in moments when you're giving feedback or trying to like motivate.

Brett: I wanted to loop back on a couple topics that we talked about and, and get some quick hit tactics that hopefully will give a lot of folks a sense of, of what's in the book. Um, and so I wanted to go back to first reference checking With the hundreds of references that you've done, when you get on the phone, what are you doing with that time?

What's super high signal? , what might be net new other than the obvious things that most people do references as some sort of confirmation bias exercise at the end. It's high level, it's, they've already made up their mind. They're hoping it's not a skeleton as in the closet. Um, how do you approach it?

Claire: Yeah, I mean, the number one thing is if you are delegating the references, uh, you're making a mistake. Like we're talking now about pretty high level hires, you gotta do them yourself. Um, so that's number one. Number two is they are not just a box checking exercise. They are part of the diligence. You never wanna be making an offer until you've done those calls.

And by the way, if the candidate gives you kind of crappy references, you wanna really push and say, is there someone else I could, you know, meaning they just seem like softballs or people they worked with five years ago. Um, you really wanna push and say, I wanna meet someone who's worked with you more recently.

You know, is there someone who left your company recently who could talk about you without exposing, you know, something confidential? Um, so you wanna push for the right people. Um, and then the reference call, like is, should not be a softball conversation. And I suggest some questions you can ask in the call, but the one that I never.

And I get when recruiters are doing reference calls at Stripe and, and doing them maybe for, uh, earlier career hires. I'll read the interview, I'll read the notes When I, before I approve a hire, which I used to do for a lot of, I, I would read the reference call notes, and if the recruiters did not ask the following question, I would basically say, you have to go and like get this information from me before I can approve this hire.

So it's the classic, I mean, there's variance of this question, which is like, you know, on a scale of one to 10 is this person, you know, where are they? But you know, the version that Stripe we like to ask is like, you know, are they sort of top 50%, top 20%, um, top 10? And like people when you ask for data tend to not lie, right?

Like people will easily say that they're one of the best people I've ever worked with, right? And then you say, oh, does that mean like they're the top 5% of people that you've ever worked with? And they'll be like, oh God no. Right, right. And, and, and so I really, you really wanna pin down some specifics. So that's that, that one.

And the other one I ask that I'm a big fan of is, you know, you're gonna become the manager of this person, presumably that you're hiring and this person, you're doing the reference call. Let's say they are their manager or have been, I say, look, I'm gonna be their manager. What can I do to help them be success? It is extremely revealing because they go immediately into manager mode and they think about performance, feedback, and development and the blind spots the person has, and they start describing to you, um, those things and what you could do as a manager to support them. But it's also highly helpful information, so.

Brett: are there any bugs you've noticed in this process of reference, checking in, in the sense of you've, you, you get a higher wrong and you revisit like, wow, that was a strong reference. What did I miss?

Claire: Um, I think that the bug when I've gone back and looked is, we have a theme here, Brett, is I did not tell the person I was doing the reference call with enough about what success looks like in the

Brett: Mm-hmm.

Claire: right? So you make an as like, you know, a lot of our mistakes in life are because we haven't set expectations or we've made assumptions.

And so, you know, the role has a title, but the titles don't tell you everything. And I've made the mistake of going into reference call and being like, well, head of sales is an understandable job, right? I don't need to describe my version of it to this referee. And in fact, that was a. I should have described this is the current, like not, I'm not telling them any secrets, but I'm like, here's our current context.

Here's what success probably looks like in the first year. Here's what I think the capabilities are that the candidate is really gonna need to succeed. You know, give them enough flavor and ask them to react. Especially if you've built some rapport with the person that is doing the reference and say like, do you think so and so will thrive in that ask, you know, in that context with the, do they have those capabilities?

Um, and I think that's where I've failed is sometimes I just assumed they would understand what was needed in the role.

Brett: Do you, what about timing? Do you always back load it or are you doing references along the way?

Claire: oh, that's a, I am more of a, this is a, a a point of discussion sometimes in Stripe because you wanna be careful here, right? Because there's a, a very, especially in Silicon Valley, there's a very hot back channel, set of behaviors, right? And that I think can really destroy trust with candidates if all of a sudden, especially if they're like in a job and they think the interview process is confidential and then all of a sudden they get a text from a friend who's like, Hey, so-and-so from Stripe texted me about

Brett: You're in process. Yeah.

Claire: Like, that's a disaster. So I think you have to be super careful. I say this in the book about back channels. And I'm not saying you don't do them, but I, I, what I would do is say to a candidate, Hey, by the way, I think I worked with this head of product that you worked with. Is there, you know, would you be comfortable if I talked to them very confidentially? So I would, earlier in the process, if I see a potential connection, I would ask their permission to make that connection and even to introduce me, you know what I mean? Like to, to emphasize confidentiality. And sometimes people will say no. They'll say, not until I'm at the end of this process and I have to respect that.

Um, so mostly you're gonna end up in a back loaded situation unless they are not in a current role. Um, or maybe you're talking to someone from their, their past. Right? Um, but, but I think if you, if if you give them awareness that you would like to talk to certain people that you know in their network and they say, that's fine, then great.

You could do it along the way. Otherwise you're ending up toward the end of the process. And then you just have to make sure you bake it into your timeline. Um, and, and the problem is you've been exhausted by the whole process. So then you rush the

Brett: That's, that's it. You have just tremendous confirmation bias. It's like, please do not say anything now. I spent 20 hours.

Claire: yeah, which by the way is an argument. I know I've just said do your own references, but at Stripe we often divide them up, like maybe the recruiter does one, but like if it's a really important leadership hire. It's not, I mean, we're lucky we've got two founders, right? But if someone's super invested in the hire, like asking someone else to do at least one of the references or, or maybe they had a role, like a very technical role, let's say, having our C t O do that reference, uh, I think could be a great practice.

I don't, I wouldn't say we've done that a ton, but as I say that to you, I, I can think of some occasions when we have, and I can think, and I think we did not regret it. Cause also those people tended to be in the interview loop. So they're, they, they know, you know, they've talked to some candidates, they know why we like this particular candidate, but they're maybe not the hiring manager who is very invested.

Right?

Brett: So before we get in into the, the sort of last few topics, you, you talked about these base traits of results oriented resilience, curiosity, and um, sense of ownership for those. Can you talk a little bit, just kind of maybe go a couple minutes and turn on each w what are you doing in an interview process to, to accurately forecast someone's level of curiosity, resilience, et cetera.

Claire: one of my favorite ways to start an interview, I tend to like behavioral interviewing more than resume based interviewing. However, I wish I could explain, but I, I, um, tend to start an interview picking something off their resume often, by the way, not a recent thing, and asking a kind of curious question about, wow, this looks interesting.

you took, you know, that sort of mid-market sales team from 20 people to 250. Uh, tell me like, what was, you know, what was the biggest learning for you? Or What would you have done differently? You know, and try to get them talking in the first few minutes about something, one, they know they're comfortable.

They should be, they should know it, they should be comfortable with it. And then I kind of, I don't quite do the five why's, but I sort of try to peel the onion pretty far with them. I'll be like, well, why did, why was that such a learning or why would you have done, you know, like, just ask them. And, and the thing that I find people will relieve is like, One, if they're not super curious, they can't really go deeper.

Well, it also means they might not have been as involved as they claim to be, but if they can't go deeper, and they also can't really introspect if they can't be like, yeah, in hindsight we learned that that segment was the wrong segment for us to be pursuing. And I'd be like, well, how did you figure that out?

And you know, and then they're like, well, I started to look at the data and I was looking at, you know, time and process in the pipeline and you know what I mean? Like, I'm like, great, this is someone who is data driven, who cares about, you know, having the right strategy and who, um, learned who changed, who changed trajectory of what they were doing.

Um, so I usually start with something they know, but then I really try to get them to go deep on that one thing before I go to some more behavioral, um, and behavioral can also, you know, tell me about a challenge you overcame or tell me about the worst work assignment you ever had. You know, but you're looking for the resilience then.

Um, but the curiosity and the learning, I usually start with, I also am a big fan of the question. Um, this is more of a self-awareness question, but it's also a learning one, uh, which is if I, you, you sort of talk to them about their current, either colleagues or their team members that report to them, and they say they're talking about somebody named Peter.

And, and you say, oh, well, like if I interviewed Peter next and asked what it's like to work with you, what would Peter say? Um, that's a very successful tactic because again, people. Try to be more truthful when they're representing other people's opinion. Uh, but it also shows if they will be self-aware and sort of balanced in their response.

Um, which to me is a little bit of a combination of the curiosity, but also the ownership version. Like if they say, well, Peter would probably say I'm a very good big picture thinker, but that I can sometimes, you know, be slower on the execution of the details. I'm like, perfect answer. Right? Like, because you're being honest about what Peter would say.

You've clearly heard feedback from Peter and you realize you have a thing to work on, which is your execution in the details. Um, and and I, you know, and I'm not getting hung up on the fact that they might not be per, you know, unless the job is all about execution in the details, but, but that's the kind of thing I'm looking for on the combination of learning and self-awareness.

Uh, for sure. You want me to go through the resilience

Brett: Yeah, that would be awesome.

Claire: Yeah, I think our resilience, Amanda mentioned this, you know, I really wanna get at hard times. They've. Um, and sometimes it puts people off to go immediately to the word failure, right? Because they're nervous, they wanna interview, well, they don't wanna talk about failure.

And so, you know, asking about like, tell me about your hardest assignment, basically is a good start point. And then again, really dive in on like, well, what was the challenge? What was their role in it? But what I really care more about is less about that story and you kind of have to cut them off cuz they'll start telling you the story, but you're like, okay, then what happened?

Right? You had this like, really hard thing happen. I wanna know what they did about it, which is a bridge between resilience and the agency, the ownership, right? Some terrible hard thing. My, you know, my top client, uh, churned, whatever it is. And I wanna say, okay, so this happened. What did you do? Did they take ownership?

Did they have an action plan? Did they think, what can I do differently? And did they also dust themselves off? Were they resilient? How did they recover? Um, and I, and you know, too many people in that particular moment in an interview, Brett will inadvertently reveal that they blamed another team. Um, and that's a real flag to me.

I, I'm not a fan of. They'll be like, well, the reason they churned was that the integration team totally dropped the. you're like, Hmm. They say, wow, that's unfortunate. Yeah. Well, what did you do then? And if they just keep, if they're like, well, I mean, I told my manager like, the integration team really needs to change.

Right? But like, that's not gonna be a popular answer with me. I wanna know, did you go give the feedback? Did you dive in yourself? Did you change it for the future? Like, and that's again, a combination of resilience and ownership. Like, are you acting like it's someone else's fault or are you, you're someone who, who's gonna make the outcome better the next time?

Um, or even save the customer. So, so that does that. I think that covers almost like all three of them. But, um, you know, and I think anytime you just ask the question, like, what, what could you have done differently on almost anything they say, people will reveal a lot in the curiosity learning department and also in the agency department. Um, and, and they get, you know, bonus points with me if they then describe a subsequent situation where they demonstrated they took the learning and acted differently and had better results.

Brett: So I wanted to end, by talking a little bit about the interviews in the book. And one of the interesting parts is that you spent time with people like Eric at Zoom in the world of technology, but also people building non-technology businesses like Dominique cre. And, I'd be interested in real, tactics cuz so much of the book is, is about taking something squishy like management, leadership and scaling and then turning it into a series of implementable ideas, frameworks, um, et cetera.

And so I, I'm curious what sort of sticks out of those conversations, 

Claire: Yeah. I really talked to a huge range of people, and not every one of them made it into our, our microsite or into the book. actually the really motivating thing was, how common a lot of the answers were across different fields.

Um, but I would say some of the newer information, well, one that's that's in technology, I, you know, interviewed, uh, Reid Hoffman and my fav, one of my favorite moments is he was talking about, how he had hired a head of operations for an earlier startup in his career before LinkedIn. And the guy started to get really frustrated with Reid and said, I wouldn't hire you to manage a McDonald's.

 which we both were laughing, and I, by the way, I think managing McDonald's is hard, but, but Reid, um, immediately responded with like, kind of gratitude and Great, you're right. Tell me like what we should do differently. But what Reid and I ended up talking about was that one of what Reed's superpowers is, is creating a really active feedback culture, right?

People are unafraid to tell him what they think and that that's something that he's really held onto. And I, I liked that idea of like, you have a personal value and that what makes you strong is like really healing to that value and walking that walk no matter what size company you're in. So I, I really like that takeaway, but that one's one I probably could have predicted more.

I think one that I didn't predict is I interviewed the guy who's the c e O of the Metropolitan Museum of Art, who's been the president of also a few colleges. Um, obviously very different roles in terms of stakeholder management than your average c e o role. And he had a lot to say about what that takes, um, by the way, including a version of, you know, you can't be seeking to be liked all the time.

He said, my job is to actively listen to all the stakeholders and then say to them, here's what I heard from you. And sometimes say to them, and we're not doing that and here's why. And I think that kind of courage to push back on, you know, an influential group is leader. But what the part that Dan really shared that inspired me, his was one of my favorite interviews, um, was he is a passionate, writer and teacher and he has a creative pursuits in his life.

And I'm like, yeah, but you're like the c e o of one of the largest museums in the wor in the world, I think. And, and I said, what do you mean you, you make space for these things that are your side projects, right? And he said, oh, well, you know, every Saturday morning I work on my own work separate from my c e o job.

And that is part of how I do good work as a C E O, is I feed my other needs. And he said, I spent too long, and I think we all learned this a little bit. You know, you, it's hard to have a job that satisfies all of your interests and your passions. And he just added into his schedule, dedicated time to pursue his other interests.

And he's written and published like a couple of books completely unrelated to his day job. And I mean, that's someone I just really impressed me. Cuz that's a, it's kind of a discipline, but it's also a form of self-care and awareness that he's like, I would be terrible as a CEO if I didn't get to do my own work.

Um, so that, that was a good one. Dominique Cre, who's a Michelin star, chef you know, the restaurant industry has this reputation that the chefs are in the kitchen yelling, right?

That they're sort of abusive. And I talked to her about that cuz she does not have that reputation. And she said, I don't believe in that management style. And she said, look, I'm strict, but I'm also kind. but I never, she's like, I never hold back. I just don't raise my voice. Uh, and I think that that is a, a thing that goes back to our conversation about sort of being very devoted to people, but having very high standards.

And I think she really cares and she's empathetic, but she does not hold back on what she expects. And she's very strict. You have to be, and I think if you're gonna produce these fantastic dishes like night after night, um, so those were like, those were some examples. Actually. Zani Mitten Betos, who's the, the, uh, editor of the Economist had this expression that she ga crashes meetings.

But you know, when you think about skip levels, right? She does a form of skip level where she doesn't like really ask permission, she just shows up and listen. Um, and look, it's not a very big org. So she knows when they are and she's, uh, they must have some system where she can be invited to all of them, but she just shows up and listens.

And I think that's a really interesting form of skip level. Anyway, I could go on and on, but those, those are some of the the things that really stuck out to me as I think about the interviews. But above all, that everyone really, um, Sam Hagood, who's a chancellor of U C S F, said to me, he's like, look, there's too much leadership stuff where people think it's you walking around sort of telling people what to do.

And he's like, more and more all I can do is influence and me being a good influencer, I don't care what power I have is, is really how I do my job. And I think that's so true, uh, especially when you're thinking about that kind of a role, a very, you know, big organization, complex organization, um, being an influencer instead of being the power center, that that mental model is one that I think more people could adopt.

Brett: as any good interviewer, I tried to ask some of the same questions to everyone, but I really asked them to talk about the difference between leadership and management. And they all pretty much felt there was a difference.

Claire: And their general descriptions of what good management and good leadership is, we're all fairly consistent. So that's like every single industry you can think of. and then I asked them to reflect on sort of their own strengths and weaknesses. And again, I would say they all showed an ability to be self-aware and to have learned from feedback and to have sort of changed over time how they lead.

Which again, I think a, a really great leader has the ability to do that, to be curious and to adapt. I mean, I wasn't actually really surprised that a lot of what was consistent about what sort of great looked like in their minds or how did they learn or how did they listen, how did they, you know, inculcate the culture.

All of those things are kind of universal things cuz we're all working with humans, right? I don't care what industry, I mean, there's maybe a few where you're like pretty solitary, but, um, In the same way that management is not a very new concept, right? It's been around for hundreds of years and, and management structures have these truths about management and leadership or things that people in, you know, a 40, 30 year career learn are very common.

And I think my book ultimately, um, I hope can apply beyond a high growth tech company. Um, and, and I felt like those interviews reinforced that to me, you know, maybe the tactics of how you, I mean, my book is very tactical in how, you know, Dominique CRE might do something in a restaurant than the way that I might recommend you do it in a technology company are different, but actually fundamentally similar.

And they have to do with, uh, respect and trust of the people you work with. and an ability to be self-aware, about your own role and your own learnings and need to learn. And I think we're all humans in the end, and we have a lot in common. And that's what inspires me actually, is, you know, if we have all this in common and we really wanna be treated fairly similarly, uh, it it means that, that we can all be better managers and leaders no matter where we work.

Brett: What a perfect place to end. Thanks so much for spending all this time with me. This was so wonderful.

Claire: Brett, it was fantastic as usual, talk about people who dive deep in the interview. you get the prize today.