LOGAN: Claire, thanks for doing
CLAIRE: Thank you for having me, Logan.
LOGAN: So you joined Google in what year
CLAIRE: 2004.
LOGAN: and how many people was that the
CLAIRE: Google 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. Yeah. Oh, absolutely.
LOGAN: mean there was so much value created after the I P O for Google that not
CLAIRE: It was. In retrospect, it was really early, but.
LOGAN: to say pre I P O is just like such a point of validation. It was like, yeah, I was there pre i p
CLAIRE: Yeah, it was funny though, because, I think rightly Google was super suspicious of hiring in that final sort of six months, right before, because, there was some probably mercenary behavior going on with candidates so I felt like a miracle to get hired, but I was so naive, I had no idea what I
was walking
LOGAN: in your hire at that point was your background prior to [00:02:00] that was very unusual.
CLAIRE: Yeah,
eclectic
No, I think, yes, I think eclectic. I worked in politics and government. I ended up going to business school instead of law school, ended up working in like a sort of a startup consulting firm that was actually one of those tech strategy mashups that happened in the pre bust early 2000, end of the 90s.
And so in fact, my work with some consulting engagements that were really about like CRM and doing data work and back in the days of data marts and data warehouses. And how do you get insights on your customer base? Anyway, so that was relevant. in that I was used to working with some, I think calling them engineers or developers would have been advanced then, some folks, it was more integration.
It was a lot of ETL stuff, but point is I worked at this consulting firm that had some technical aspects to the, to our work. So I was on the strategy side, obviously, but in the end I was running engagements. That was a mix of technical people and strategy
LOGAN: So [00:03:00] more relevant
CLAIRE: it was a little more relevant, but yeah, I get to the West Coast and.
LOGAN: And in.
CLAIRE: Sheryl Sandberg hired
Sheryl hired me and I knew some people who, this is how the world works. I went to business school with some folks who were friends of hers or 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.
And I thought I was doing a friendly call with one of them who was a friend of a friend, and she grilled me for 45 minutes. And I said, I was like, Laura, is this an interview? I'm driving in California with my husband going away for the weekend. He was then not my husband, but and she grilled me and she's if I'm going to refer you, I have to believe you're going to be good.
And I said, because Google, like it was very serious in a good way. Now, now I wrote about it in my book. I'm like, you got to take your hiring very So she didn't want to refer me if she didn't think I was
LOGAN: It's a good, interesting lesson that like, you're always being interviewed way.
CLAIRE: Oh yeah. I don't
LOGAN: cause
there's a microphone here. Yeah. [00:04:00] Yeah. It's just you're talking to your friend. That's what I tell founders as well is if you're talking to an investor you're fundraising,
you
CLAIRE: getting assessed, it
LOGAN: might not be a process of you fundraising in some way, but they are definitely putting inputs into how you assess things.
And I
CLAIRE: Yeah. Oh,
for
LOGAN: candidates as general. So then you were at Google for how long? Yeah.
CLAIRE: Almost 11 years. So I left in 2014.
LOGAN: And then joined Stripe 2014 and you did full
CLAIRE: Stripe. One week later.
LOGAN: is that right? week later and you were there for six and a half years full time
CLAIRE: I was, yeah, six and a half years full time as COO, and then now part time for the last few years.
LOGAN: and Stripe was 162
CLAIRE: 160. Yes, precisely.
LOGAN: No. Yeah. I
CLAIRE: I gonna say about 160.
LOGAN: I take
CLAIRE: It was 162.
LOGAN: When you when you look back on both Stripe and Google, what are one or two takeaways from the cultures themselves? Very
cultures,
but and I'm sure they involved, 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?[00:05:00]
CLAIRE: I think all companies should internalize. That there is a culture and to try to understand it, and some of it is intentional and some of it's not right. Young companies are mirrors of their founders, and so a lot of the culture that you is maybe less conscious is often that mirror of the founder and their.
LOGAN: behaviors
CLAIRE: More than behaviors, right? It's your actions, unless 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 ambitions, but not completely pie in the sky, like ambitious, but Realistic to a point, this, the thing that's amazing about both those companies is on the B2B side of the businesses, [00:06:00] obviously Stripe is all pretty much B2B and Google, everyone thinks it's a B2C because of the search.
But it's AdWords that it was the revenue business. And now, Google cloud and all of that, but To have millions of B2B customers, right? Multi segment from pretty early on, it's pretty astonishing. Like 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, and that was in common.
And it was not just this is the starting place and we're just gonna figure it out. It was like, no, 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 it.
Bring technology to the financial services world, which has 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 clear missions for both of them high value on individual [00:07:00] 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 had to share my college transcript when I was in that process for Google and I was 10 years out of college, right? Like that to me, it was like haven't I done something since then? But they were really, I was writing essays, but so not only was it where did I go to school and where did I go to business?
school and, actually business school was a knock on me at Google but Stripe much more open to really very different sources of talent. And I think Patrick and John themselves were such active, are such active participants in so many internet communities, which in Google's defense were not as active in the late nineties.
When they started, but whether that's IRC or hacker news or Twitter in the more of the heyday of Twitter, but Patrick especially would see someone who had interesting ideas or who seemed talented. Maybe [00:08:00] 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.
LOGAN: it's an interesting lesson
startups And
CLAIRE: we would hire them.
LOGAN: so that's the
thing. It's like Stripe did it. You need to take chances on the why this person would join 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 fit 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. 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? It's not just going to be the pedigreed person with the background that you're seeking out.
CLAIRE: Yeah. I would say early, 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 [00:09:00] 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 again We just talked about this the economy wasn't in great shape 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 and that sort of Turn of the 2000, 2001, 2002.
And I joined Google in early 04, right? Coming out of that, but Google was definitely the shining star in that moment. They had their pick. I would argue that Stripe less when I joined Stripe, So I feel like I look back now, I'm like, gosh, I felt like every Friday, if not multiple days of the week, I was taking Lyfts 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 yeah, because [00:10:00] Yes, we were, we had really nice growth rates.
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 an 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, Patrick, when he reached out to people, I think them taking the time to meet him was about him
LOGAN: more than
CLAIRE: Stripe, at least in those first years. And then Stripe started to get. More of a reputation, but for having, yeah, strong product market fit, strong trajectory, but it like a while.
like
doing things that don't scale on the candidate side for sure Do remember from the strike
LOGAN: strong trajectory. It took a while. Hey, here's a candidate and here's what we did that went above and beyond to convince them to join.
Oh yeah[00:11:00]
CLAIRE: 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 happen to need some security engineers and, but it was hard and it like took a lot of work to build, but [00:12:00] 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 have fun, but solve hard problems. So capture the flag was very big. Some of the comments that you would find from Stripe founders and Quora again, and Hacker News like that, their amount of activity communicating themselves directly in different channels was really high. And I think, and including directly to candidates.
So that was the main thing was that bespoke. There were also some instances of aqua hires that were really again, targeted, like a really talented young designer. So young.
LOGAN: that
CLAIRE: How did we hire him? I wonder and relocate him from his
Scandinavian home as an example. Yeah, just Logan, but like that kind of a situation where we're like, Oh, we acquired a company.
A kid who was amazing. You have to take some risk. That's a risk,
LOGAN: It's
an interesting lesson of like, when [00:13:00] 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, X company that has hundreds of, 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 right? What can
CLAIRE: Same with early
LOGAN: same with early sales. What can you do to beat Stripe in a sales you can reach out to that person individually and Patrick and John,
CLAIRE: It's
LOGAN: they're doing a of other things and they probably can't spend all
time they did
in the early days of reaching out.
First cold to individuals, right? so using those things, if Stripe had to do it, I guarantee you should probably be doing
CLAIRE: I think you would still find it, Stripe, senior members of the executive team and the founders helping to close candidates, but you're right. Not anymore. Like they're not doing cold.
They're not doing a lot of cold DMs on Twitter.
LOGAN: Yeah, it
CLAIRE: Now, I guess you have to pay for[00:14:00]
LOGAN: Yeah, knows the old twitter.
LOGAN: One of the things you said was that you were rated at different times at google of holding people to a high standard that you're rating like would be variable.
CLAIRE: Me, individually.
LOGAN: personally
sometimes you good ratings and sometimes you get at
CLAIRE: No, generally not that
LOGAN: Okay
CLAIRE: had very positive manager feedback. For every Google Geist, which is our sort of survey engagement survey, but also had a manager 360 component. However, me as a manager. However, there was 1 question was about consistently holds my work to a high standard where that was not my highest scoring
LOGAN: But at Stripe you were scored
on it Yes.
And what do you think you changed in between the two?
CLAIRE: Yeah I really, I think part of it was having the revelation and the maturity, the process of maturation at Google where I went from being, and this happens to a lot of folks in high growth companies, which is elevated from, I started as a manager, not as an IC, but I was like a entry level manager.
I got pretty quickly moved into like more of a senior [00:15:00] 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 I don't want to change a lot here.
I, they're my peers, like we're going to collaborate. I'm going to be their partner. I'm not going to, I'm not going to, you 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 also you just don't want people to be turned off by your behavior when you all suddenly become their boss. And then I 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 [00:16:00] me, not just in the feedback I was getting, but in our performance or in, I would see my team with another executive kind of bringing their a game and with me 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 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 strike So one I matured out of that and I started to drive more At the end of my career at Google, 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 a caveat, when I first joined the company, management was a [00:17:00] fairly new concept. And there were a couple of people who had been hired, one in a sort of engineering leadership role.
LOGAN: who seemed to have
CLAIRE: Who seemed to have this construct in his mind that there was like. Almost like the tech lead and that 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, and I would say Patrick and John certainly had the leader element of holding the bar. They hadn't thought as much about what, who they were as managers, right? Which makes sense. They 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 [00:18:00] think it's going to have to change. And I also talked to the founders about it and they were totally on board. Patrick being Patrick was like, I started to read up and look at some research studies. He's turns out management matter like this is actually one of the things the United States on like economic indicators.
We outperform other countries because we have, we value management and have management structures that we use and have so for,
LOGAN: hundreds of
CLAIRE: And it does create some output advantage again, if done well, ideally, but
That's funny. Now, talking little bit about hiring. I heard you be fairly self critical about your executive
Oh, yeah.
your team member I know Yes can you articulate that. And then also, what you think that is exactly?
That's a great segue because it's the same problem.
It
LOGAN: same problem. It sounds
CLAIRE: the same
LOGAN: the
likability
thing
CLAIRE: So the,
LOGAN: the
CLAIRE: yeah, the
LOGAN: likeability,
CLAIRE: likeability slash, like if anyone, if you asked anyone on any [00:19:00] team, either a team of colleagues or a team under me, they would call me, I think, a very collaborative leader.
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 idea. I don't think, part of the value of, look, I've worked with some really smart people, Logan. I'm like, am I the smartest person in the room?
No. Am I good at some things? Yeah. But I need all of you and so I think part of it is the likeability that 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 if I like I want to like them I want to be like let's you 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 yeah leads me to has led you
LOGAN: to some
CLAIRE: It's, I think I just have better Matt pattern match on hiring teammates and hiring executives is hard because there's also how they show up with you [00:20:00] versus how do they show up with, whether they're, if 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 we're falling down on some of their own leadership stuff for the people below them, right? Which I wasn't assessing very well.
Making the hire
LOGAN: Do you think you, 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
CLAIRE: think that's also, I think that it's always a tricky balance, you know this, because you're selling them to get them into the process.
LOGAN: That's the hardest part of venture is like it's this buying and selling
we're selling to get them in Because
CLAIRE: That's 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 [00:21:00] 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 percent right. If you aren't really intentional about, wait a minute, I am going to really assess. Now, I would say, yes, that was part of my mistakes. But actually, Stripe, we are, if anything, a little over rigorous on hiring and process, like I wasn't hiring alone.
Patrick and John are meeting these candidates, multiple people are meeting them, we do reference calls. 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 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, these folks had track records. And I'm looking at the track record, I'm thinking, I'm believing it. Which sometimes [00:22:00] people fail up.
Sometimes also, people get lucky they're in the right place at the right time.
LOGAN: lucky
they're in the right place at the right time. Cheryl did this well. She had someone who was really opposite.
CLAIRE: I think one is, Cheryl did this well. She had someone who was really opposite to her, who she had on basically every hiring committee with her who I, by the way, was my scariest interview for Google. And I was like, geez, this guy's poker face. So
LOGAN: like
CLAIRE: all in the details, very analytical, high pressure interview.
And Cheryl's so charismatic. And let's talk about you, and he was like, the opposite. And I think she was smart. She's this person is going to pull stuff out of the candidates that I'm not. And I need that foil. 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've got to [00:23:00] find someone who's going to get at it. And I think that what I did is I maybe over trusted Stripe, some of my executive colleagues to be that. But if I really thought about it now, I'm like there's 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, that's one. I think another was, I did a lot of reference calls. Did I talk to people who'd 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, pretty selectively people they provided. I wish I'd gotten more of that view of them as leaders. That'd be another tactic.
Player vs Victim
LOGAN: 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 used or
victim.
Can you elaborate on what that [00:24:00] difference is and how you were maybe able to tease that out Popkin.
CLAIRE: like questions lead to being player versus a victim
Yeah, so credit where credit's due. So Fred Kaufman wrote this book, conscious Business, which is one of the. I don't read that many business books, like, all the way through.
LOGAN: here you write
CLAIRE: 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. That's why it's so detailed and read what you want to read. But Fred's book is really strong and he has a few frameworks. Fred founded this company, Axcellent.
That was 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, like 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 at all levels, not just executives, anyone in a company, basically any of your friends too. Like we have, [00:25:00] I have friends who are victims and who are players. I tend to like the players better, but we, and the victim is.
Either the example Fred would give is when your kid comes home from school with some, they lost something, 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 the toy is broken or the, they imply it broke itself. And it's, and it does happen early in your life where you 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've become, are programmed to 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 the no, Joe didn't deliver, like we had a dependency on Joe's team, his team didn't deliver, and that's why we [00:26:00] missed the goal. And you say to the person, wow.
And was there nothing you could have done differently? Oh, no. Joe's total failure by Joe. You're like, what?
LOGAN: you
CLAIRE: How are you even
LOGAN: if you
CLAIRE: have
straight
LOGAN: it's actually crazy. If you ask someone like, what's a project you failed at in your job, how quick they are to shun responsibility.
Cause it's an interview setting and you want to put yourself a
light
but if they don't highlight any self reflection, like you, you
CLAIRE: no learning, by the way, this is also not a high learn person. It's like you really learn from mistakes
I actually my son came home last night He's like we got a pop quiz in science and I got one of the questions only three questions I got one wrong and I said I tried to like you as a parent you try to say Oh
LOGAN: and what
CLAIRE: did that do for you?
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 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 [00:27:00] 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 you.
Some of them just blame everyone and vent and you're like, okay you're just a downer to interview with, but there'll be less overt, but it'll be a lot about other people involved. It'll be about constraints. It'll be about dependencies of the, the thing I learned is I was spread too thin.
I didn't delegate but they won't take responsibility. It'd be very hard to get them to say it was my project. And ultimately I, and 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. 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.
LOGAN: do, you find the opposite to be a problem? If someone tells you an accomplishment and there's too much I did this and I,
that.
CLAIRE: Yeah. I think there's this balance. This is where having the [00:28:00] pattern match of thousands, I think I've done, I have, I've done thousands of interviews and I wish I could totally distill this, but it's about balance.
There's a lot of, the best candidate to me, the best interviews, there's a lot of, we actually, there's a lot of, cause 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. I love, it's a self awareness thing. It's 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 eye. 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 [00:29:00] your role? And they'll look at you like, yeah, you caught me out. And then they will, if they're good, they'll go there and they'll say, look, I, it was my idea. I did come up with that idea and but you have to force them into it. And I like that. I like people like that. But if they don't Go there.
That's also a flag.
LOGAN: one of the things I've heard you also interview or use as an interview tactic is an org structure
CLAIRE: Yeah. Oh, yes.
LOGAN: on their org structure, which I thought was so fascinating. Can you talk a bit about why asking someone about their org structure, how it came to be, how that can [00:30:00] be used as an tactic?
CLAIRE: wasn't all disasters. One of the best questions I found I came up with was, this is the days where ideally you're in person with the candidate, but you could do it over zoom, which is let's get it a whiteboard and just, can you just map out your current team for me? So there's you and then tell me the roles and You don't have to name all the names, but I'd love, Joe, Teresa, Mahak, whatever.
Give me the names. And then I'd love to walk through a couple things like 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, Wow, this guy was going to leave.
So I had to give him two jobs, basically. And you're like, so you didn't really have the hard conversation with that guy, did you? Or, there'll be a I inherited that person, and I don't love this structure, but I don't want to rock the boat. You're like and why not? What are you afraid of, right?
So one is why that org structure, is [00:31:00] it logical based on what you are, 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 how long have you been in the role?
Say they've been in the role three years. It's the same team they got. 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. They could be great people, but do you have the right capabilities for that strategy?
That's really the perfect team. Big red flag if they've made no changes. Also, a red flag if everything is different. Everyone is new. I'm like, did you just churn every single director? 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 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 are people you identified who [00:32:00] were talented, who were getting squelched in the org and you wrote, lifted them up.
And what will happen is also, you'll see. 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 a little dry about it? They're like, yeah, she's been in, at the company for 10 years.
I do wonder if she's going to leave, if she does you're what have you done about the, so some people are more energized as managers in that moment when they're describing their people and they almost get into it. And some people you can tell that'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
LOGAN: I heard you say some of the most successful hires you've made.
I think
CLAIRE: drove
me
LOGAN: annoyed you. You knew exactly where
was going Did
they drive you crazy in the
process
Hey but
CLAIRE: And also closing, okay.
Some of the hardest closes I've ever had. [00:33:00] Candidates who were driving me up a wall questioning every number of the business, the role, the JD, what do I expect? What am I like to work with? Like you're through the ringer and you're like, do you even want a new job? What? They were some of the best hires I ever made.
They were just like hyper analytical, cool.
LOGAN: Different
CLAIRE: thing. I'm
very
LOGAN: And is that because it was at a compliment to and so drove you
CLAIRE: Yeah. Huge compliment. Brought out some stuff in me. That needed to be brought out. It's not like I don't have it, but I don't lead with it. I'm much more intuitive.
These are just like hyper data driven people. Some of them are actually a little bit risk averse. Some of the compliments to me, I'm not afraid of change. I'm not afraid to make a decision and like drive to action. And some of the compliments to me are people who are like, hey, wait a minute. Do you really have all the data you're going to want to make that decision and sometimes they're right.
Like I should stop. Like why? What's the rush? And so yes, they drove me crazy. They were hard to connect to in the interview.[00:34:00] And, but they did well on the questions, but I had to this is where you have to check your biases. I'd be like, wow, this is like annoying, but actually when I read the answer back and I think about my frame, my rubric for what is a good answer, these were great answers.
They just didn't deliver them in a connected way to me because they thought about it very differently than I did. And then in the process of answering their questions and closing them as candidates that they're very different. Yeah. Some of my best hires. or completely the opposite of me.
LOGAN: That's a compliment point to sometimes you need to hire to augment your own weaknesses, and talk about self
CLAIRE: the time. Yeah, the time.
LOGAN: hiring the exact same profile that you have is going to lead to duplicity.
CLAIRE: Going to lead to a team with a giant amount of blind spots. I think diversity gets used As a word meaning certain things, but I actually think fundamentally a diverse team, meaning in all the ways, whether that's, gender and racial, but I'm talking about, really work styles and preferences and what part of your brain do you [00:35:00] lead with or what, 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 what, how have you experienced life like that kind of diversity? Thank you. Is how you get a perform 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
LOGAN: Totally.
CLAIRE: 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.
LOGAN: outperform.
CLAIRE: is. There is. Yeah. No. I think one of the interesting things to look at is if you have inclusive, this is a big gift.
If you lead a team with inclusive practices. You can get a three to five X return on that team. So they're diverse and there's inclusive practices. If there's not inclusive practices, we can talk about a homogenous team can actually get pretty far pretty fast, just not [00:36:00] outperform. But yeah, I thought Amy Edmondson, who's the psychological safety researcher and writer, which she now wishes she hadn't called it psychological safety, because I think it's a term that.
Doesn't really mean anything anymore. 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 ICU. So in intensive care units and 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 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 I don't have to describe them, but, 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 [00:37:00] 18 percent fewer deaths, like people died when there was a lack, when there was a diverse team and lack of inclusive practices.
LOGAN: was inclusivity
this
CLAIRE: inclusivity in this case is comfortable, 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? 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 these doctors are buzzing through and this is a team where you stop and you say, I think I see a problem.
It's like the Japanese pull the Kanban cord. right? But this is the equivalent in day to day operations around people who are very sick. And I think that, so how do you create that? It's how do you create [00:38:00] 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 do well. And it's hard to do well, but it is about how do I make sure, 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.
If you lead with, here's what I think we're going to do, we're going to launch product X next week, 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, you just started with the punchline. Like you should instead say, we've got this decision in front of us.
I want all of your opinions. I want to go around the room and hear them all or even better. Let's all write them down. So we don't group think. Everyone write them down on a piece of paper in front of you or in the doc or in your own [00:39:00] 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, we're animals. It's about status. It's about how comfortable we are. It's about group, group think is real and it has really good reasons behind it, but you got to prevent it.
LOGAN: Totally. I want to talk about your operating principles in so number one, build self awareness to build mutual awareness. Can self awareness be
CLAIRE: learned?
Oh, a hundred percent. Yeah. 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,
LOGAN: know
CLAIRE: for me is like breathing. I have no, I, my actual best strength, I had no knowledge of for most of my career.
Because I was like doesn't everybody? experience things this way? No, not everybody experiences [00:40:00] information, data, communication, whatever it is that way. But it's like breathing. So one, don't forget self awareness is about your strength as much. The other is blind spots are blind spots because they're blind.
You do not know the thing that you don't know, right? And so that feels easy to say, but hard to admit and actually see because you're blind. So how do you learn it? 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 and other models, right?
And can reveal, Hey, by the way, the other models have this thing that you don't have but let's say these tools. So I'm talking about Myers Briggs, DISC there's this insights discovery tool that I really like. Enneagram, some people use in a professional setting the big five personality test is one that has a more proven track record and research to, to actually determine some outcomes [00:41:00] in terms of you as an individual.
I don't really care. I've actually taken Hogan assessment is this like really long, intensive questionnaire that you can take. I don't really care which one I take them all. I think pretty much, but every single time I take one, the point of the exercise is to 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'd you think of that decision?
What do you think of me? Of course the people are going to be like, that was great. That was great. You have to say things like, what could I have [00:42:00] done differently to make that thing better? Or what do you wish I'd done? Now that we looked, look back and we made that decision, what do you wish I'd done that would have made it better?
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 do I think those things went well, but, or didn't really go well. And if you've done some work on your default settings, I bet you'll find, by the way, most of the time I'll find I was under stress. And I went to my default settings and I screwed that thing up.
LOGAN: that thing up.
CLAIRE: But if you don't sit and think about it for a minute, you're not learning.
LOGAN: I would encourage people if they want to build self awareness as well.
If you have a podcast, YouTube commenters will make you
self
CLAIRE: they sure will.
LOGAN: give you any insecurities you have. They're very quick
point
CLAIRE: I don't know.
LOGAN: Yeah. So that's another[00:43:00]
CLAIRE: your...
LOGAN: Yeah Myers
Briggs,
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
can?
CLAIRE: That's a great, 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
LOGAN: instance, which
CLAIRE: instincts, which is, I think people who are fundamentally curious and learning oriented,
LOGAN: you
CLAIRE: want to hire. And
LOGAN: I
CLAIRE: how you ask that question Or get to that
Yeah, I think you ask, I have some sections in the book where I have a bunch of like interview questions, suggestions, but I think there's one, tell me something that you learned about recently that.
Surprised you or that you're passionate about? Or, like there are people who just are like, I don't even know what to do with that question. And you're like do they not read? Do they not talk to people? Do they not study something new in there? [00:44:00] Look, we're in tech. I've worked in tech.
There is something new happening in literally the underpinnings of technology. There is a new AI model with significant advancements Improvements every 18 months right now, and it's getting faster if you're not aware. And then if you think about compute power and cost of that you're not thinking about what are the underpinnings of the capabilities we have to deliver the product, even if you are a 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 does that mean for my company? company, my product, my team, right? I better be curious. I better be educating myself. And by the way, bonus points, if I'm also doing that and something else that's outside of tech that I'm passionate about, maybe it's a gardening, maybe it's, Taekwondo.
I don't really care, but 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 [00:45:00] if they're not curious, if they're not a learner. And one of the things in the.
LOGAN: book that I talk about
CLAIRE: 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 trying to give them feedback and they don't see it.
They're like, no, I'm pretty great at that actually. Yeah. I don't know what you're talking about. I'm 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'd 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. 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.
LOGAN: Interesting.
LOGAN: [00:46:00] Operating principle number two, say the thing you cannot
CLAIRE: think you cannot
say.
LOGAN: can you share an example of ways in which you can approach difficult conversations in a slightly more comfortable way?
It's human nature try to be agreeable, I
CLAIRE: it is. it is. And it's also human nature to not feel confident about an intuition or a hypothesis you have, especially if you're more data driven, especially if you're, in an engineering or finance mindset.
But what say the thing you think you cannot say is really about is taking some. risk in putting out an observation, an 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. 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? Why are we talking about [00:47:00] this when the real problem is that right? But if you don't say that there's no breakthrough.
And so as a manager, you get nervous. Cause 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 that the safest to your question The safest thing to do is just ask a question
Now maybe that's in a meeting which is like maybe in the meeting It's 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 the, if I'm a good leader in that room, I jump all over that.
I'm like, yeah, I should have said that, 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. [00:48:00] Why are we not? Be the person who creates that breakthrough conversation.
Or with the individual, by the way, yes, you're taking a risk. It's a one on one, you're giving someone feedback. They might get to a breakthrough, they might get defensive, and that is okay. They might say, what do you mean you thought I was nervous? You say, I'm sorry, like totally my perception. I just experienced you in that meeting not as confidently as I normally see you with that material.
And they're saying I don't know. I don't know. You say, great. If that's, totally could have been just my, again, you're just a mirror holding up to someone. You say, that's just going to be my perception. But what I do find is people will then think for a minute. They'll sit on it. The next day they'll be like.
Maybe I was nervous. Like, why do you think I was? And I'll say why do you think, you'll still, the breakthrough might not happen quickly. And you can be wrong. 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 that are like, oh, and then I'll look around the room.
By the way, you got to read the body language and the faces. This is not usually a verbal exchange when [00:49:00] there's look. And I'll say, Hey. From the look on all of your faces, it looks like I'm wrong about that theory. And there'll be some nodding and someone though will then jump in and say no. What it 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
LOGAN: in close proximity to when it occurred or giving a little bit time so that there's less defensiveness. But if you give too much time, then it seems like it's more of a affront to them. Better to do it closer or further away
CLAIRE: 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 one of my strengths, that's like breathing is I have like fast processing speed in moments and [00:50:00] 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 that everyone starts lobbying you so good if you also lay out a process.
And you say, if anyone has opinions, and you clearly do, please send me an email, or send it to the group by the end of the day, but right but try to, it's totally legitimate to say, you know what, the thing I think I cannot say, I'm not going to say right now [00:51:00] because there's a lot of emotion in the room, but I am going to commit to saying,
LOGAN: to say
CLAIRE: and that, again, is a risk because you might not be ready.
LOGAN: not be ready.
LOGAN: Operating principle number three, distinguish between management and leadership. Can you expound on that
CLAIRE: 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 he, I interviewed him for the book and he talks about it.
I actually believe you do need both ultimately in your career. Often I think people lead with one or the other. I probably led my career as a great manager and then became a leader. And I'd say probably the opposite for some, a lot of founders that I work with. 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. A lot of what's in my book is just me saying here's some basics, here's some checklists, here's some things like you, they happen behind closed doors, but they're very learnable.
It, management is about I, how do I get from [00:52:00] point A to point B? Look at my talent, make a roadmap, milestones, metrics. Like I it's like very doable. I think leadership is actually harder to learn. And very different. Cause 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. It's 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 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 [00:53:00] situation was a tire fire for good reasons. We were growing quickly, et cetera, et cetera. The team was small. We didn't have our processes. We didn't have good tooling, all the things.
And at some point, but admittedly under pressure from Patrick, the CEO and co founder of Stripe, I ended up having to say to the whole company. This is going to be fixed, we are going to have 24 7 chat, phone, and email support in seven languages by the end of next year, whatever. And I'm sitting there going, how the hell, 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, you have some idea, but it seems impossible. 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 can I do that confidently? And by the way, when you do and your team, [00:54:00] 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. Like I, I articulated a vision and people colored in the lines, people figured out how to get there. I didn't have to figure it all out. I just had to articulate where we were going roughly. That is so rewarding. Such a payoff.
But I say you need to distinguish between those things because there's moments when your team needs you to manage them. 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.
Like you are man, I'm managing, I'm making it clear who the owner is. I'm making it clear what the goal is and I'm tracking your progress. And then there are other times where I'm saying, Logan. What your team is delivering is just not good enough right now.
LOGAN: What? Tell me what
CLAIRE: And you're like what, tell me what to do.
I'm like, no, [00:55:00] you got, cause 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. 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.
LOGAN: But I thought that there are innate leaders or that can come naturally management's much more of a learned over time. I never really thought about learning leadership as something that you can do. It's
interesting
CLAIRE: can do. And the other thing I think a lot of leadership is storytelling.
And that's another thing you can learn, right? People don't remember all the substance of the plan you articulated as a manager. They remember, yes. Maya Angelou how they felt, but they remember the stories you told them.
LOGAN: told them.
CLAIRE: And I feel like that's also very learnable.
LOGAN: learnable.
LOGAN: Golden rule, treat others the way you want to be treated.
Not a great tactic for a manager a leader. why, is that[00:56:00]
CLAIRE: It's too bad because I'm a big believer in the golden rule generally for humans.
Let's treat, yeah, let's treat people the same way we'd like to be treated all around the world. For management and leadership, not a good role because you as an individual, are motivated quite differently than I am, Logan, I bet.
If you and I sat down and say, what really motivates us? How, what is our, how does our ambition show up? What does success look like for you versus me? Our answers would be pretty different. And so your job, if I'm the manager of these two different people, my job is to interview them. I call it the career conversation, but it's really the, I need to get to know your motivators conversation.
Tell me why you made these choices in your career, maybe even in your life. Why did you major in that thing in college? Why did you choose that first job out of college? Why? What are you trying to get out? What are they trying to do? What are they trying to accomplish? What are they trying to learn about themselves?
And you're taking that data and you're saying, okay, this is someone, and by the way, this is a very real thing. I have Worked with people and including [00:57:00] a child of mine, like some people are motivated by being recognized by positive feedback. Like you're basically cheer for all the good stuff and actually there's a lot of human behavior change.
That positive feedback highlighting, these are the things I want more of, is way more effective than nitpicking and the negative. But there are people who I've worked with who are like, Tell me the thing I did wrong, because I'm they're so self directed, they're, unfortunately, they're probably a little bit perfectionist, which is not an easy problem to have.
It's not an easy burden, but they're so perfectionist that you're like, I thought that, that work you did last year was like, excellent. Like you hit every goal except for that one. And they're like, I know I'm obsessed. I'm obsessed with that one goal. And there are people like that.
They're like trying to get the brass ring all the time. And all you're doing is being like, all right, let's talk about how we get the brass ring. But that may not. There was another person who spends the rest of the year demoralized that you pointed out that they didn't get that one goal out of eight, right?
You've got to know what you're dealing with or else you could completely [00:58:00] undermine them. So it's about interviewing them, observing them, collecting data, and managing them differently than you would like. to be managed. What drives me crazy is I manage, there's some people you manage who are obsessed with compensation and they're really obsessed with compensation because they're keeping score because they want, they're very competitive and that's how they score points.
And I'm like, Oh my gosh, I do not want to talk about compensation with people all the time and you should try to restrict it. But I've come to get Zen about it. I'm like, Oh, this is just them keeping score and this is a way they're looking for feedback and this motivates them. It motivates them to know that yes, there are compensation outcomes for good work.
And so we will now talk through that yet again, because that is what they want and it helps them and it is not for me.
LOGAN: We did away with bonuses and then there was no way recognizing out So we put bonuses back and were upset about not getting 150 percent of the bonus target. And I was like, this whole thing is [00:59:00] very circular. It just, some people though, they even, it doesn't matter the dollar amount.
It's just the recognition
that. Like that they are doing that of a job that it, the dollars could be totally
CLAIRE: This is, like a worker segment. The scorekeepers. And it is really about that. And they also have their own score in their head.
And what they're really checking with you is, do you and I see the same score? This actually goes almost to the self awareness gap. Sometimes, yeah, we see the same score, and I will celebrate it with you. Yes, you got 150%. But sometimes it's about, okay, why do you think you should get 150%? Are we looking at the same performance?
It can be actually a really rich conversation if you can flip their sort of, like, why are you so obsessed with that score? What's going on there? I, especially for high performers, actually, they sometimes need to be challenged. Even harder than they've been. And they're telling you that in a weird way when they're score keeping.
But yeah, compensation, headaches on the bonus. Bonus In, bonus Out is a whole other book.
LOGAN: yeah, it's
yeah
CLAIRE: it's a, it's fascinating.
LOGAN: [01:00:00] hole to go yeah, and how people are incentivized and all
stuff
LOGAN: What about titles? There's two concepts in Silicon Valley. that titles are free, cheap, give them away.
And the other one is titles are very expensive because it leads to a lot of complications. I get the feeling Stripe was much more on the are very expensive. Like that costs a lot of internal damage dealing with different promotions and hierarchies and all this stuff, or at least that's what it was in the early days.
CLAIRE: Yeah, Patrick and I really, this was one of the things we aligned on pretty early, which was titles.
It's like a little, to me, I'm really gonna display my opinion here, giving out pretty 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. You're like, I love those flavoids, and then you're like, oh my god.
I just mailed myself a letter bomb,
Because if you are [01:01:00] Sub 40 people, sub a hundred even, and you've got a bunch of C Levels. Are those going to be your Chief Marketing Officer, your Chief Revenue Officer, your COO even, in three, and you're doing well as a company, by the way, in three years, three to five years? Probably not. Maybe a few will scale with you. So you will then have a conversation in front of you, where you're saying, actually, You're no longer the CMO. I'm hiring a CMO. And you are a lot more likely to lose that person then who might be a really good employee, by the way, but not the CMO. Then if you had just called, called them marketing lead, maybe head of marketing, but, and now I'm bringing, so I think for C level titles, like the.
The more you can wait, like it's also, you look at a small company, you're like, how can you have that many VPs? It's silly looking now. I totally get, sometimes you need a title because that's important for your sales process, but it's stripe. We would try to come up with a [01:02:00] title, a growth lead or something that was hard for the prospect to.
They'd be like I don't, it sounds important. You're like, exactly. It sounds important, but you can't pin me down on exactly what the job is. But I think titles back you into a future corner, essentially. As you evolve your architecture and it'd be nice not to back yourself into it. I do think we took it too far at Stripe.
I'm going to be honest and own that. For example, we got a lot of feedback, which I thought was really legitimate that a lot of the engineer, it was just like engineer, right? And we did have job levels on the back end. We had level four or five really senior engineers. But no one knew that except for, the people who were leading those teams.
And. A bunch of the less experienced engineers were like, who are our mentors? Who are we supposed to look to? Who do we listen to in code review? And we realized, oh, we need to actually, when someone achieves the staff engineer level, which for us is level four, we should really tell people because one, it's, it is an accomplishment.
It is recognition for them, but also [01:03:00] it's a signal. This is someone you should watch their work, listen to their feedback, use them as a mentor. So that was a miss. And I think there's a similar miss we had on the sales equivalent of that. And so I think there's different, there's one thing we're talking about mailing yourself the letter bomb on sort of senior titles of leaders.
There's another, which is how do you think about organizational structures? And there's a. We were trying to avoid basically hierarchy. We're trying to do the inclusive thing right in the room. If you don't know who's the most senior, everybody's gonna show up pretty equally. It's almost a cheat code for inclusivity in a way.
You still have to do the work to get that meeting, to get everyone participating, engaging in that meeting. Let's say it's a meeting, but there's a time when the org starts to get big enough that it's just confusing. You're like, I don't even know who to go to. I don't even work with that team.
And who do I even call? Or who's the best example? But we were trying to avoid also some hierarchical behavior, which just is not what Stripe is about.
LOGAN: we're talking about it from the company side.
It's also tough from an employee side as [01:04:00] well. It feels to get called the C level of whatever company you're at. But then weirdly, you might have to take a step back. Let's say you get moved out of that job and you decide to move on to a different company. Now, are you addicted to being the CMO or the CRO or the COO, right?
But actually, if it were apples to apples versus the next company, you're not C level. And from the employee
Can be problematic as
CLAIRE: It
do you a disservice. It's a great point.
LOGAN: Yeah
CLAIRE: won't want to hire you because they're like they're going to
want that
LOGAN: they're want to see love or happened in your career where you went from to that right, actually, I've told the story but one of the I took a step back when I joined battery From where I was title wise at investment banking And I thought, I was like, what am I, what is this?
Why would I do this? And it was actually the best thing in the world. Cause I got comped against everyone else at this level. And I was a little bit older and a little bit more experienced. And so the apples to apples comparison, I just looked so much
CLAIRE: better
really
LOGAN: Actually a [01:05:00] good thing starting over.
CLAIRE: You were in a slightly different field.
LOGAN: different
field. And but perceptions are defined early. And if you if. If I had that slight the higher level, I probably wasn't quite there. And so people would have questioned if I was of that caliber versus I was really good at that level. And it allowed me to accelerate.
CLAIRE: the way, this is another example of like inclusive choices, which is actually you would rather someone, especially moving into a new company, a new kind of role for them to be exactly in your situation, which is slightly more experienced than the others, but In a learning mode and, much more likely to succeed.
LOGAN: what was your title when you joined Stripe?
CLAIRE: Oh, my title was Chief of Business Operations. Yes.
LOGAN: Which was because of a similar
CLAIRE: Yes, there was a, the reason was... We had a lot of conversations about being the COO and the current that Stripe had a COO at the time, which people forget. And it's funny how companies rewrite their history.
People [01:06:00] forget that. But my colleague, Billy, who's amazing, who is also still with Stripe, but he was a COO and he helped recruit me, which says a lot, by the way, about him and the company and the parts of the role where he was like, this is not my. Talk about self awareness. He's I'm not a scale, big operations guy.
I'm not going to build the sales team. He was really like, he's a brilliant payment strategist, brilliant at BD and that kind of work, partnerships work. But point is, Billy helped recruit me. But then Patrick and John were like two things happened. I think one is a true founder moment. Two things happened.
One was They realized that they'd not told anyone internally that this was a decision they'd made, that I was going to be the COO. And they felt if I came in and it looked like I'd taken Billy's job from him, and Billy was very popular, that it would have been, that I would have been unpopular. They were like, we were not setting you up for success.
If you walked in the door and being like, and I'll just take that title. Thank you very much. And so we made this other innocuous title. And then after about, I don't know, not even that [01:07:00] many months in the job, Patrick, just People have gotten to know me though, and seen my work. Patrick sent out this note by the way, Billy's going to be chief of business and Claire's going to be COO and isn't that great?
We all sometimes switch titles and switch responsibilities and everyone's great, it was nothing. The other reason was more, I think John and Patrick had a title because they were very in, in the camp of titles. You got to be stingy with that. They were like, maybe if you could just come in as head of business operations cause I think they got nervous.
They're like, this is a, it's a big deal to bring someone in as basically COO. And you're trusting. Now I look back, I'm like, that was a big decision for them. I was going to have a big impact on the culture and the results and outcomes for Stripe. And I think they wanted an out. And, but I said to them, I was like, guys, I was like, I think in this case, if you look at my career and where I'm at in my career and my track record and the conversations we've had, I was like, you do need to give me a title.
[01:08:00] Like I'm not going to walk in. I'm not going to leave the job I have at Google for a head of business operations job at your company. And they're like, yeah, okay.
LOGAN: Yeah it's balance It's
CLAIRE: That's a balance
LOGAN: Now, one of the things I heard you say too many companies make their principles so idealistic that they don't resonate
employees
because they have no connection to how the company actually operates. How do you think about principles in general for companies and like how to make them balance tangibility with
the
CLAIRE: So we're talking about Stripe calls 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, like, 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.
LOGAN: There's
CLAIRE: lot of stuff you could start to build for the it's product building more than company building. And really, that's the right place to focus. You shouldn't have long term goals because you're just trying to make it the next
three months Surviving is your long goal
And so then, though, you start to get traction. You should gut check. Is it real? And this is [01:09:00] where it's good to have investors and advisors and it feels like this is real. And all of a sudden, whoa, you got to think about, I think I might be building a company here because we have a product and people are buying it and ARR is X or whatever metric you can be the expert, Logan, on, on what benchmarks you want to start to see.
And so then as the leader, you're thinking, all right, so for company building, I think there's a set of things you want to start to put in place. And this is where a lot of the early chapters of my book, the operating structures, but one of them that I argue is really important again, at this point, more are these founding documents, including articulating.
What are your company values? And if I was going to simplify it, I'd say, look start with what's your mission slash vision, which is the why do we exist? And by the way, why you exist is probably beyond that initial product that you've built. It's a bigger vision that you have, and you may not exactly know it all, but this is, it's time to start thinking about it because it's going to matter to people that you bring on board, right?
Why are we in the world today? Employees care about this. So why do we exist? What's our mission? [01:10:00] And then the next thing is the how do we want to work together? And this is where the values are like, what do we value when the chips are down? Are we going to choose the user or are we going to choose our growth?
By the way, sometimes you'll have those choices and you really want to have established when we make hard decisions, what are the values we're using? And sometimes you can inductively get there. You can look at some hard decisions you made and say, Oh, it's interesting what we really valued. By the way, with speed, maybe over quality.
I don't, there's no judgment from me, but the thing that I see too often, which you alluded to Logan, is that someone executive team, a founder, even a focus group in a company sits down and writes a bunch of values that are really. Aspirational, like customers first is a common value. I'll be honest, like Google.
With 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 [01:11:00] and the customers later. And so no judgment, like I actually think, but 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 actually undermine you. It would be better to have none in my opinion. This is the sort of there's the mother had an apple pie version of this, which is they're so abstracted up that you're like, yes, we collaborate.
Yeah, everyone wants to collaborate. If they can be specific and true and even stack rank, like what do we value? It's a really good exercise. I wouldn't overdo it or overthink it, but try, one thing we did at Stripe when we wrote the initial draft was we came up with stories and examples of those values and practice, and there were a few where we were like we don't have a lot of examples.
Maybe this isn't a value. Maybe it's something we want it to be true. And then we actually had to think about how do we make this more true, right? Or some that we put out there got misinterpreted.
LOGAN: And sometimes [01:12:00] weaponized, right?
CLAIRE: Yes. Oh, yes. There was, there's few. I feel like I've suppress them at this point, but we had some around trust and people were really interpreting with something along the lines of like trust, but verify.
There's 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 turned it into a more broad application of we can't do that. What if it was on the front page? And it's no, it's you can still be bold.
Like you want to be on the page sometimes.
LOGAN: I'm just
the thing
CLAIRE: arrested.
LOGAN: I'm just
saying the thing that you think I cannot say it. It's an asshole. That's you're
being a jerk
CLAIRE: yeah. Exactly. So really try to apply the values and see if they stick.
LOGAN: It's interesting because everything does have, there's two sides of every coin. And if we were to say we're founders first, founders fund does a great job. They say they're
CLAIRE: yes
LOGAN: Now that comes. At times at the expense of limited partners, That [01:13:00] is a there's two sides to these.
can't just say platitudes without thinking through the other
CLAIRE: the hardest decision
LOGAN: And there's everything. It's not hollow. It sounds hollow to say, Oh, we're founders first or like Google. We're customers first. Are you though? Are you actually customers first when push comes to shove and you have to make a technological trade off?
Of what the future roadmaps going to be, and going to piss off a bunch of customers. Are you actually a customer first? And there's no real platitudes. All these things have another side
the coin
CLAIRE: then that's when you know you have a good one because it has an edge. You're like, this is going to have a downside at some point. We are going to have a decision we have to make that it's going to hurt.
I say a strategy should hurt, so should some of your values.
LOGAN: have a
CLAIRE: should feel pretty painful, but it should be, Patrick in a different context. And I talked about this. I talked to him a lot about leaders and how they should be higher. And this is a sort of behavioral expectations, leaders, ethics, expertise expectations.
And I said, there's going to be a time when a leader who we highly value, who's incredibly [01:14:00] impactful does something humanly with poor judgment. And you all can color in whatever story that is. And I said, and I will tell you. It is going to hurt like hell, but we should, they should, there's, if it's bad enough, they should leave.
Even if they're the best person at that job. And he was like, and we actually went pretty deep on examples I'd seen and what I thought, because culturally you've then taken someone who you've elevated to a leadership role and they've done something like with horribly bad judgment and said, it's okay.
And even if it's private, it still gets known in my opinion, in a big enough company, it still gets known. And. We locked arms on it and we had to act on it. Okay. There's times when you're like, Oh my goodness. And now we're like, it feels like you're stabbing yourself, but you're not in the longterm you're live, you're honoring the culture you're trying to set.
Which is we hold leaders to a higher bar.
LOGAN: sometimes you need to have surgery to if you tear your ACL, you have to have surgery to rehab yourself forward. [01:15:00] And it could be painful.
CLAIRE: it can It's not like the payoff is tomorrow. It actually hurts
LOGAN: a long time in the future, now
LOGAN: don't let perfect be the enemy of good. I know that's something you believe.
I happen to share. How do you think that manifests itself in like startup and high output companies
CLAIRE: interesting. And you probably see, more companies than I do where the sort of move fast and break things, Facebook, whatever.
And then there's the perfect is the is is actually starting to kill the good. And I think that some companies, and it's really about the founders and they're,
Their proclivities or their instincts, their defaults, which is our get, I'm not saying analysis paralysis, but are so intelligent.
Often they think 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? And they're making some decisions or choices for the first time in their lives and they're waiting or they're waiting for this candidate who's perfect.
And you can be too far on that continuum. [01:16:00] And you can also be too far on the, Outcome be damned. I am running up the mountain and I don't care who I hurt. And that could be a user, a partner. You could have bad behavior, but you're getting the goal. Like that's also not good.
That is, not even the good being the enemy of the, I don't know 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, be aware of where you fall. It's like in your defaults as a founding team as an executive team and then think about how do I push myself?
How do I make sure I don't fall on the wrong side of that I'm way often for the perfect being the enemy of the good. It's like taking too long to make a decision to make a hire to sign a partnership like you're gonna. 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 you've gotten to product market fit. You're starting to steam ahead. And then all of a sudden you're starting to die of indigestion. You cannot get stuff through the [01:17:00] system because you're just examining every damn thing too
LOGAN: thing. And it's important to analyze yourself and where you fall. Yeah. And then not every end market is gonna be the same
CLAIRE: That's true. That's true.
LOGAN: I would be glad self-driving cars take a bit time to be perfect or, and roll
CLAIRE: was
going to, I was just going to bring that up. Yeah. It does depend on your market and who your customers are and what they, gosh, stripes dealing with payments.
We better be on that side of the continuum. And we are, but sometimes we flip too far over to Ooh,
LOGAN: If
you're a Kanban board, a workflow
CLAIRE: long.
LOGAN: By a little bit
CLAIRE: But I was actually, I was in this funny I was at a conference running a round table discussion as a breakout. This was with another venture capital firm sponsored this, but it was all founders.
We were all talking and it was me and a couple of leaders from some other companies talking to a group of founders. And I was saying how, when the chips are down at Stripe. If we are doing a launch review for something, we may have even publicly said we're launching maybe at least to some customers and we don't think the quality is there, we will [01:18:00] delay the launch.
There is no question. And if you think about it, yeah, we're dealing with people's money, with payments. If we don't like, and even if it works, but we don't like the quality and the craftsmanship, that's also what we like to be known for, right? We'll delay the launch. And this guy across the room from another company, I'm not going to name the company, starts laughing.
He's are you kidding? And I was like, yeah. He's 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 we have this whole idea of these test markets. He's, and he named a city in Canada. He's if you live in Canada, you have seen some crazy stuff from our product.
I was like, are you serious? And he was like, oh yeah, we'll move it up. Cause we're trying to understand like, why is it not working the way it should?
LOGAN: this business isn't
healthcare
CLAIRE: not
LOGAN: or,
CLAIRE: a Safety critical system, but I, we, but the founders were like watching us, like we were playing tennis match. And I think it was actually probably the best thing that could have happened because it was like, these are equally reasonable choices that you make the face of something that you're not [01:19:00] happy about launching.
And it really depends on your product, your market, but also your appetite for
risk
who you are, your value system. And by the way, good on them that they have some test markets that they learn from, right? I was jealous. Yeah. Sorry yeah, sorry to that one city in Canada. I think that's that's what's fun about working with different companies in different markets.
But the key is self awareness. Know where you fall and then, to the point we talked about earlier, have some people around you. Who will call it when they think you're dying of indigestion.
LOGAN: the is disappointing people at the rate that they can absorb. And it's an interesting line. actually didn't know what you meant by it. What?
CLAIRE: Yeah. This is a quote from Ron Heifetz and also probably Marty Linsky. These are some. Some researchers, academics, and I guess sort of leadership gurus at this point who've written about adaptive leadership, which I actually, back to books that are worth checking out.
I think some of Heifetz and Linsky's work on adaptive leadership is worth checking out [01:20:00] because it's about distinguishing between the fact there's technical, 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 like not a right or perfect answer, but there's answers. Adaptive problems never stop. Like you are never, like something is happening in the competitive landscape, always. It is adaptive. Or is your go to market Product interlock. Perfect. No, it is never perfect. You'll be adapting constantly, right?
And getting comfortable as a leader with adaptive problems. And they talk about various tactics. Like 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. But 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. Leadership is disappointing people at a rate they can absorb is one of their quotes. And I didn't have it in the original book. And then someone who used to work [01:21:00] with me at Google was an early reader. And he and I were, he was giving me my feedback, which was great.
And he said, it's funny, I remember we were in this meeting where you shared that quote because you'd been, I'd been reading, I'd been a learner about adaptive leadership. And he said, and it. He's it stunned me and I thought about it the rest of my life since then. And it's interesting because in the book, a lot of people have picked up on this and they're like, I really want to talk about that.
And I think it's because we think of leaders as superheroes, right? We think of them as these people who don't disappoint us. They inspire us, don't they? And actually leadership. Is often disappointing people. You do become a little bit mythic, especially the founders, right? You become bigger than who you are as a human.
And you aren't perfect. And if you start thinking you are, you're gonna have other problems. And I think one of the biggest ways leaders aren't perfect is, we talked about this, you set a vision. You don't even know how you're going to get there. You're like, we're going to completely pivot our company to this brand new product [01:22:00] 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. And you've told a customer, by the way, leaders often do that.
They announce things. It's like burning the boats and, Alexander grade, just burn the fricking boat so you can't go back. So that is leadership and leadership is uncomfortable and 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.
And people are sitting there thinking, Hey, we didn't get it done. But actually, as a leader, you're like, Oh my God, but we are doing it. But you are a little disappointed. Or another way is you disappoint people is you get them really excited about following you and spending time with you. And then guess what?
You can't spend time with everyone. You're going to disappoint them with your time because you cannot give it to everybody. You are still a human being. And I think that's what [01:23:00] I mean about living with that discomfort is a lot 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, one woman who I'd mentored at Stripe and who went on to a pretty senior role in a very successful sort of younger company that's in a growth stage called me not that long after she took her role and she was like, Oh my God, how did you live? with the fact that everything is broken all the time, every day.
Because she had elevated to a point where she saw what the equivalent of me saw in early stripe. And I was like, oh yeah, welcome to the terror dome. Everything is broken, nothing is perfect. And 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.
LOGAN: what is don't
CLAIRE: Never releasing the bar, right? [01:24:00] Keep holding the bar.
LOGAN: leave ice cream on the counter for too long mean?
CLAIRE: 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 Barsade and she was trying to teach like change management is a hard thing to teach. It's actually a thing you need to spend energy on and think about and plan and build processes. Like I can't just. pivot to the new product line. You can't just reorg the whole company. You have to think about the change management, not just to propose the change, but who to tell, and then how to cement the change.
And so her analogy was this. The minute you start the change, and that start could be just telling a few people about it. It's 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 like finding out which flavor people want and you leave it, and it gets like a little melty,
LOGAN: And
CLAIRE: Looks a little gross, and then you put it back in the freezer and it's never quite the same because it got weirdly the consi I mean there's, I'm sure some food chemist is listening this there's a reason for that, Claire.[01:25:00]
Anyway, she's if you start the change and you leave that out hanging in the wind without all the decisions or the communications or the, you haven't started to cement it, you will, you could irreparably affect some things culturally or in your team stability. And so I, 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. Like we got to see this change through. And I think it's just, it's a good watch out.
LOGAN: and
You wrote this book. It was published in April?
CLAIRE: of 2023. Yep.
LOGAN: And I heard you say one of the things that you've only gained conviction in since doing was to manage people out of seats earlier, once, once you have that conviction. And I think it ties to this ice cream
CLAIRE: Yeah, it does. a different version of
that but you're
[01:26:00] so right.
LOGAN: Can you expound on that concept and
you
CLAIRE: great, connection you're making. I think what I've gained more conviction, in, I knew Patrick and John read the book, the earlier, the earliest manuscript version I had they could read and few, Patrick's 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 sort of like leadership. So
LOGAN: an interlude of so you wrote a section of a book for Elagh Gill, who's been
CLAIRE: Wertheim
LOGAN: before, High Growth Handbook. a sec
in that
and it was well received.
Yes And then
CLAIRE: yeah, so I did this chapter in Eli Gill's book, High Growth Handbook, which was our best selling straight press book, because I think it's a great book, by the way, and highly recommend it.
And my chapter... even though I was definitely one of the lesser known contributors to that book in terms of tech luminary types, became, got a lot of traction because I think it was very tactical and concrete in a way that's maybe, it's hard. Management leadership advice is often abstract.
You're like, how do I actually do the thing? And so [01:27:00] I did some of that discussion in Elad's chapter. It got some traction. I also, there's like a YouTube video of me, how to run an effective meeting that's got. Some many millions of views, which I find scary and
LOGAN: For
CLAIRE: Yes, I did it at COSLA conference.
Yes. 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. But point is Patrick observed those things, but also John and Patrick observed that a lot of you Stripe, a lot of Stripe customers are.
really interesting companies that are growing quickly around the world, wanted to spend time with me on their scaling stuff and less on payments and stretch products, which would drive us a little crazy. But I was like, Hey, I'm happy to have dinner with them. I'm happy to talk about it. And Patrick's you just have to write stuff down.
And I said, I don't know that I'm the right person to write this book, but yes, wrote it. And it came out in March. I knew that he was cringing. There's a section on managing people out and firing people. [01:28:00] And I talk about how long it can take. And 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.
And I think that makes sense to everyone. It's they've got a whole team, they've got an org, you spend all this time hiring them. They've had a successful career. Can they course correct? There's costs, there's a high cost. And so I talk about, 30 days, 60 days. And Patrick and I joked, because I said, I got in front of it.
I said, I know you're cringing. At the section on how long it can take to get someone out and he's yeah, I am because he's of the mind, like the faster, the better. And I think 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 30, 000, 10, 10 to 20. 5, 000 feet away from a company and you're talking to the CEO, the founder, you're sitting with the executive team and there's clearly a leadership issue. In one department and it's [01:29:00] so it feels like someone is painting neon paint on this person for me now
I'm like,
Oh my gosh, this is holding the whole company back.
Holy crap, we have got to move, it's really interesting you get much more clarity on how critical it is to address. when you've got some separation from it. So that's why I really have more conviction. It's because since writing the book, and since I changed my role at Stripe, I've gotten involved with a lot more organized, not just companies, nonprofits, schools, you name it.
And I'm like, having an issue in, and I don't care if it's your team of individual contributors, or it is your executive team, but I'm talking about in the executive level, having a performance issue is a killer.
LOGAN: I've never seen it come back around. I'm sure
CLAIRE: no one ever says, I wish I'd move more slowly.
LOGAN: It's never happened which means our bias. We need to overcome our bias to keep someone and give them a
CLAIRE: And by the way, the key is I still think, and I talk in the book, you can do this with empathy. You can do this with [01:30:00] good, honest, direct, open conversations. In most circumstances, some of these go sideways and it will cost you money usually, but.
I, I just think if you're not talking directly to the person about we have a, there's a, I'm worried we have a problem. You are doing them a disservice and as I see now, you are killing yourself on your strategy.
LOGAN: And
CLAIRE: and probably the team people
LOGAN: I was just about to say great people hate mediocrity. And if they're saying, hey, this is acceptable here, it kills their perspective on it. And the people think people will delude themselves into thinking is that you're being fair to the person that you've made the on.
I'll give them more time so that they can get settled. And that's actually,
CLAIRE: or that you're keeping things stable for their team.
LOGAN: supremely unfair, right? actually that person should be given an opportunity to go to a business that doesn't all the
CLAIRE: doesn't believe
that
LOGAN: ready to get
CLAIRE: and 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 [01:31:00] team where you're like person managing you isn't trusted you may not know it, but you feel it unconsciously.
I will say we're talking about, I don't know, maybe obviously if you've a hundred percent know someone needs to leave, then you're moving them out. But we're talking to the upper where, yeah, we're talking about a gradient here. I do think it's hard when there's someone who's clearly not the best.
And those are the ones that actually dragged out more. And maybe my conviction is more, in your heart of hearts, if it's going to work or
not
and you've got to start trusting your gut and moving.
LOGAN: And the hardest part about that is if they were the right person for six months ago in the company, but the company's outpaced
where
they are.
That's when it's
CLAIRE: And you've started to have that. A lot of this is stuff. I'm sounding like a weird Californian and I'm now back on the East coast. So I want to say I'm not a weird Californian, in your body. It's a weird thing. like
Six months ago. Yeah. You're feeling 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. Like our executive team meeting was fine. [01:32:00] And that's probably true by the way. And then all of a sudden you're not feeling it and you got to listen to the feelings.
LOGAN: And your feelings. Now you referenced me on a bunch of boards.
You're on Hallmark's board.
CLAIRE: I was on
LOGAN: Oh, it was on homework,
CLAIRE: was
LOGAN: But
that was a purposeful decision. That's unusual,
CLAIRE: was a personal development decision.
Being on the board of a company built to last
LOGAN: And can you talk a little bit about being on a board of a company that has been built to last?
CLAIRE: A hundred year old company? Yeah.
LOGAN: so
What did you learn from being on something that has been that endurable?
CLAIRE: Yeah. Hallmark was interesting to me because one, if you're at Google as an executive, Google is supportive of you joining boards. Not every big company is actually, which I appreciate. However, you can't join a board that as a competitor, competitive in any way to any of Google products, which eliminates a lot of
LOGAN: a high percentage
CLAIRE: So I want to own that first of all, but Hallmark was interesting because I don't think there's enough respect played, especially in Silicon Valley, but in tech generally. Some people are the exception to this, but to look at [01:33:00] companies that have existed for 80, 100, 120 years, there actually aren't that many in the world.
There's like a soy sauce company. There's Caswell and Massey. It's like a soap company. Like we should study them because that is a sustainable, not just business. Like you built a business that has sustained and had revenue and had growth for a hundred years, but often also the culture through multiple generations of leaders and past founders, by the way that's astonishing.
Like how do we harness what's happening in those companies? So Hallmark became really interesting to me. It was also is interesting because it runs like a public company, but it was private, which meant less time commitment, but actually as meaningful amount of revenue, which is private, but. in the billions of dollars of revenue, owned a media company, Crown Media, that are, I think we all love our Hallmark movies and the Hallmark channel, owned Crayola, which is actually a very interesting company they bought in the 1980s.
And then obviously the core Hallmark cards business, which you would say, Oh isn't that a dying thing? [01:34:00] That's an interesting thing to think about. It's like a very There's only a few players. It's an oligopoly. So it's actually competitively really interesting greeting cards. Weirdly I learned, but.
But I, I was most interested in how had they 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? And one of the big things we did is that crown media, the media properties, which is the content.
And I think, but content is very at a pre it's fragmented, but it's at a premium, good content. Crown media was public. And so we took it private. So we didn't own, we owned like 96 percent of it. But that was one of the biggest decisions as a board was like, we have to own our own destiny.
And our content is going to matter to us more than whereas the greeting card business sort of mattered more, right? Like it was like the media business actually matters quite a lot, but only if you can control it. So it's just, it was really good to take me out of Silicon Valley, put me [01:35:00] in a situation, by the way, also, oh my gosh, the legacy systems.
have a stranglehold on these companies that have been around a long time. And you realize like how, these are smart. That's another thing. Silicon Valley is like, these, what's wrong with these leaders, these executives of these companies? Why don't they get themselves like, just rip up your stack, put in, move it to the cloud, you idiots, right?
Like 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. And they are like fighting a war with two hands and one leg tied behind their back.
Because ripping out those systems is so disruptive. And it's just really existential threat to the business, especially if you've got physical goods. Oh, how are, it's a total Jenga game that is way more complicated than you realize. And it was really hurts your head when you think about it, but very instructive when you're trying [01:36:00] to sell B2B and sell SaaS.
And you're like, Oh, I see. It's not
that
don't, why they don't get that. Yeah, it's exactly, they get that they need a different solution. It's how they get to there that is brutal. So that was really helpful. But yeah, I sit on a bunch of boards of actually different stage companies and some not companies.
Actually spending time on, I'm on the board of the Atlantic which is used to be the Atlantic monthly. It's publication. It's won the national magazine award the last two years. I had nothing to do with that. I'm on more on the business side of things, but I'm going to visit with them tomorrow. But yeah I think it's really, I will say as a development thing, Patrick and I talk about this, like it's really good to try to be on.
It's hard cause it's time consuming. It's a commitment, but to see for me be 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. I was like, I am not Brian Halligan.
We were talking about Brian at the [01:37:00] beginning of this, who's the founder and the chair of the HubSpot board, previously CEO. We have a new board member who's 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.
LOGAN: There's better places
CLAIRE: There's better places. Yeah. For the board. Like you're also inviting, by the way, you don't want to invite me and operator into the how details. Cause I'll be like, Oh, what about this? Have you tried this? And then you're not talking about the stuff that moves the needle for the business, right?
LOGAN: Now we I think we both have places to be at some point in couple hours. So as succinctly as you can, what makes the Collison's so special?
CLAIRE: Patrick and John... Collison are really multi dimensional humans and they're very different from each other, I think, but have, there's like a Venn diagram where they're very complimentary in certain ways.
And I think obviously have some [01:38:00] shared values, which is a good foundation to have, but high IQ, high EQ, a 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 and a lot of vision.
I think the amount of energy they both bring, but in different ways to, they discover a problem. 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 just, I think the energy level for tackling really horrifically heinous problem spaces is amazing see, and sustained.
They both sustain it, the level of commitment to that. And I don't know, I think there's an element of solving problems they themselves faced as engineers and doing that at a scale.
LOGAN: I,
CLAIRE: think they have not [01:39:00] gotten cynical about that, that feels like an important responsibility that they have.
And I really appreciate that too. And just flat out super intelligent let's not kid ourselves,
LOGAN: they're in a rare
CLAIRE: you could be really intelligent and not. Respect others and others' contributions and intelligence. And they're the opposite.
LOGAN: There's a lot of different types of Yeah. Which is something I've found more and more.
CLAIRE: There,
Absolutely.
LOGAN: the, I thought it was all SATs
And g p
a once upon a time, and that is not just intelligence. I want, I wanna back up and talk about, I guess your parents, but your dad in particular instilling in a value of autonomy to a young age.
So he had you Shang shingle your roof. Taught you how to fix a car
CLAIRE: to a point.
LOGAN: never had you, yeah, maybe build a
CLAIRE: Yes.
LOGAN: never helped you with your luggage
suitcase
CLAIRE: Family rule. You pack it, you carry it.
LOGAN: can you talk about like how those little things impacted who you are today?
CLAIRE: Yeah, I think and my parents are both teachers, and I think another thing is, if [01:40:00] 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 can't leave the dinner table.
You better add some value. And that's
LOGAN: if you went to business and you were the black sheep in the
CLAIRE: I know. I know it was very unpopular when I business school. It's not very intellectually deep,
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 is bringing that out of young people which is what you hope teachers are doing, but how do you yeah, it's a combination of confidence, interested in learning and sharing ideas and being, feeling comfortable being independent.
I do think as a parent, I fail some on this, which is
LOGAN: your
CLAIRE: kids can do a lot for themselves, but a lot of parents. Don't ask them to or don't expect them to. And I think my parents were busy with their lives [01:41:00] and their careers. That's one of the benefits of having two working parents, I think. And I had to get, figure my own stuff out.
I planned my whole, I'm laughing now because I've just been working with my daughter on her college visits, and I planned my whole thing. I scheduled my visits. I scheduled, at the time there used to be interviews for colleges, there's not as much anymore. And I'm looking at am I an enabler?
I am. Oh no, I'm not listening to my own advice you and I were talking about. Sometimes you give good advice and you don't always take it
LOGAN: being,
VC That's being
CLAIRE: that's being a PC. That's your secret tagline. give great advice. We just don't take our own advice, right? But I really value my father's not with us anymore, but he talked about people who had no biases.
Like he believed that every human, you could do something interesting with your life and he expected it of us. And I think that's one of the best things you can do for other people.
LOGAN: And to the point of, he also, back to the victim mindset there, you told the story of [01:42:00] him being robbed at gunpoint in Paris, was it.
CLAIRE: don't think it was a gun. I he was just mugged, but meaning jostled in the metro. And yeah, totally like in retrospect, I'm like, how horrible would that have been to lose like your wallet, your ID, you're in a foreign country. And he was just like, yep. Should have been smarter. He like totally took responsibility and just dealt with it.
And somehow we got home I guess I think he didn't lose his passport But I was young but I remember if you think about how you react to something like that and watching your parent react To what is one might view as a failure at least something really bad happening such resilience like such I'm going to take responsibility.
I'm going to do what I can do, what I can control, control. What I can control is it's amazing. Again, I think leading, especially young companies is a lot like parenting, which is, it's not so much what you say, right? You save, you try to say the right things. Of course, it's your [01:43:00] behaviors, your actions, and even your emotional reactions when under stress, that is what people are really watching.
And they're taking their cues from, and I would say both my parents. It's 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
LOGAN: I the 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 this, but when you zoom out, what actually is important in life, if you're comfortable telling the story of the Google layoffs and and your father's birthday
The
CLAIRE: To think about is, and there's some I think there, I was at a dinner on Sunday night with a bunch of educators who are talking about how they've had a set of employees that they've hired who are of the latest generation.
Every generation is criticizing the [01:44:00] younger but they're like, they're really like. super attuned to boundaries and balance and like more than we were and I have to sit and examine that because the story I'm about to tell is more in the vein of what I think, what I experienced with most of the successful people I know, which is we've worked our asses off.
For a lot of our careers and yeah, we've been successful and some of that was luck, but someone told me luck is when preparation meets opportunity. I really believe that. And I think I was really driven. I was driven even despite, I had young kids. I was at a point in my Google career.
Where I had an opportunity to be in a really I was in the most senior role Cheryl had left I had taken part of her responsibilities. It ended up then being more after this period I come back from maternity leave with my second child and it was 2008 Lehman Brothers Collapse is literally like the week I'm back from maternity leave and I'd come back early because things were shaky [01:45:00] and in the end that 08 Sort of mini recession was not as impactful to tech but at the time it did not look like it was gonna be an easy one and in a very Not well known action because I think the recent layoffs Google did people it's the first time Google's ever done layoffs Actually, no, I laid people off in 2008
LOGAN: off in
2008,
CLAIRE: in my division and I came back from leave and made that call and the day that I had to do That the layoff announcements were happening and I personally spoke to some of the infected employees, meaning laid them off in a conference room with HR.
I talked to my mom said, I really want you to come to New York. We're going to surprise your father for his birthday. And I was like, Oh, I just don't think I I got to do this. Like I'm. under so much pressure as a leader. I've got to deliver this message. It's going to be brutal. And I talked to my manager who at the time, kudos to him could have said, yeah, no way you're going to New York.
Like you got to do this. And I thought about, and [01:46:00] I was like, you know what? I think if I did the mountain view stuff for Google and took a red eye and went We had a team, I had a team in Boston, in Cambridge, actually. I could meet that team, which would actually be a good thing to do back to back geo visits, and then I could fly to New York, and I could be there in time.
And he said to me, he's if you think you can do that, and the red eye isn't going to affect you, and now, I gotta deliver messages in Cambridge then yeah, go for it. So to his credit, and this is for all the managers out there, he was like, if you can make it work in a line, because it's never, you can't always choose one or the other.
You're balancing your professional obligations, your personal life. But yeah I got there, I surprised my father I saw him the next day too, which was really, 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 like sobbing and I was like what if I hadn't gone what if I hadn't gone [01:47:00] and she was like but you did
LOGAN: did
CLAIRE: but really it was me saying to myself oh my god I really high chance that I had not gone because I was just in that mode professionally and my ambition and my sort of priorities honestly and I think that's the lesson that when I share that story I think sticks with people because Now for sure, I'm a certain age like I've had a certain amount of success Of course, I'm gonna go to my parents surprise birthday party But then it was not so obvious. And so I guess I would just ask everybody just
LOGAN: ask just
CLAIRE: can't be there for everything, but having an eye on what's really important earlier in your life, then you're developmentally ready to ends up being maybe the biggest lesson of all.
LOGAN: Yeah. 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 [01:48:00] hiring and managing and all that stuff. But at the end of the day, we're all people with lives and family members and
CLAIRE: Out we're all humans.
LOGAN: important stuff outside of it. Claire,
for
CLAIRE: No, thank you.
No, thanks Logan. great conversation.
appreciate it.