What makes (or breaks) executive hires | A deep dive with Eeke de Milliano (Head of Global Product at Stripe)

Brett: Thank you so much for joining.

Eeke: Thank you so much for having me.

Brett: So I know that you've been spending a lot of time thinking about, um, what makes great leaders? Why is there such a high failure rate? And I think you've also been spending time over the past month talking to people who, you know, really well about this specific topic.

Um, and maybe we could start by just hearing some of your reflections from those conversations.

Eeke: Most of this actually came out of my, my own frustrations as I was going through, you know, having both now at this point done many hiring processes for executives, but also having been on the receiving end of maybe some like worse fit, Leaders who we hired and, I've sort of been lucky enough to talk to a bunch of founders to give them some advice as they were thinking about hiring execs and, you know, particularly product leaders.

so I spent a bunch of time actually talking to, thinking about the stuff myself, but then also talking to a bunch of my founder friends and, talent execs and then, uh, other execs who've been hiring as well.

Brett: you spent the last four weeks kind of chatting with some people like Around the topic that we're talking about have there been interesting insights from that experience?

Eeke: Nothing super surprising. The only thing that was really surprising was how consistent the insights were, like I broadened the search because as soon as I kind of got into this idea of. Wow. Hiring leaders is actually incredibly painful. We spend so much time on it as you know, execs at companies and as founders at companies.

And somehow we come out of having spent all that time still having failed 50 percent of the time. It just baffles me. Like, why does that happen? Also, when the stakes are so high. So initially I was like, I'm just going to ask a bunch of my founder friends. And I was like, I'm also going to ask a bunch of my exec friends.

And then I also asked a bunch of. Talent firm friends, because I thought, Hey, like they probably have some good insight and, yeah, it's so interesting across the board, everyone has more stories about bad hires than good hires. 

Brett: Is that just sticking people's brains in a cognitively strange way?

Eeke: That's probably true. but I actually think it's like just surprisingly hard to find someone just great. or someone who's just a great fit for you. Like the funny thing about all these things, like when you are interviewing someone. Inevitably, they were good for someone somewhere, otherwise you probably wouldn't be interviewing them.

Brett: But it's the hard part is finding the right fit. and then the second thing that sticks out is like, they all at this point are like pretty aware of their mistakes and they still kind of feel like they make them over and over again, like all the biases. Was the perspective was like why it's broken in the eyes of the founder and CEO the same reason that the exec on the receiving end thinks it's broken?

Eeke: definitely not. Well, maybe I, I think the, the, the person who's like on the receiving end who's, you know, either feels like it didn't work out generally feels like the expectations weren't the right ones. Like they weren't set clearly. and the founder and the CEO generally feels like, you know, this person was hired to come and be a leader and either sink or swim.

and they sank But I don't think they generally have done the sort of like extra thinking or the sort of extra retrospection of like, Hey, why did this person sink? Or why did they, why did I think they were originally good, but they didn't end up being good. And that I think to me has been sort of the most interesting learning, like, A lot of the literature even on this is all about how do you onboard these people successfully?

And very little of it is about the like the actual pre interview stage. And I, I actually think 80 percent of the work in hiring a great leader who's a great fit for you is figuring out That piece of it, like not even doing the interviewing, it's the, like doing the introspection of whether this person is a good fit.

Mike Maples, who's a VC has this great book, called pattern breakers. And it's, it's basically his main thesis is like, yeah, if you're a VC and you're going to try and find the right founder, like, you're not just looking for someone who's like generally smart or generally ambitious.

Like you're looking for someone who is the right authentic fit for whatever future idea they're trying to, to put into the world, which as you, you, as a VC, probably you're like, are very aware of that. But, think the same is actually true for leaders, but we don't really treat it that way. Like, we don't spend that much time thinking about, What is it that I need in this leader over the next year or two years? Like really thinking about it. Generally, the way these processes go, it's like founder or, you know, exec is frustrated because something in their org isn't working, or there's a part of their org that they like, don't want to manage anymore.

They will reach out to their network or to some recruiter. And they'll be like, who is the best product leader you've ever worked with? Then they'll do like 50 interviews. And then at the end, a couple of them will have seemed interesting and like, they'll have to make some sort of agonizing decision and like, still 50 percent of the time they fail in their decision after a year or 18 months.

And instead, I think, you know what founders and leaders who are hiring execs or other leaders should be doing, they should spend a good chunk of time sort of understanding themselves better, like. What are my values? What does the team need right now? What's the complementarity that I need on the team?

What does my company need? Like, what is the sort of leader future fit for my company? And then only then really start interacting with these leaders and figuring out, you know, is this person actually a good fit for me?

Brett: How did you land on that being sort of an important idea?

Eeke: Honestly, so much trial and error. Like, I spent so much time interviewing leaders myself and also being on the receiving end, like having been lucky enough to, be considered for a bunch of roles, and I didn't quite understand why it was so hard to do the assessment.

Initially, I thought it was just like, look, I'm just not calibrated. I like need to see more people who are great. But Eventually, I think I just realized like the thing that was missing was like, I did not have a clear idea of what my future needed to look like with this leader. that was really the, the moment for me. 

 Do you think it's, 

Brett: vastly different than hiring non leaders? And if so, why? 

Eeke: the stakes are just so much higher with leaders a bad fit leader is so tough for the organization for like the obvious reasons, like they come in and they You know, spend a bunch of your orgs time and headspace you spend as a leader, spend a bunch of your time with them, and then they sort of end up not accomplishing much.

So that's like, reason number one, why it's bad. But like, reason number two, why it's bad is because Everyone looks at that bad hire or that bad fit, basically, again, like, I don't think they're generally bad people, but like that person who's in a good fit, and they look at the leader who hired that person, either the founder or the exec, and they now all of a sudden don't trust that exec or that founders judgment.

In the end, judgment is almost like the most important value you have as a founder, as a leader, and that gets really bad. And that's when your you know, star employees start quitting because all of a sudden they kind of feel like, Hey, I actually, I'm not sure I trust this person's judgment anymore.

So, yeah, I think the stakes are really high with the sort of leadership hiring, and then it's also just harder to fire them for, you know. Kind of the same reasons the stakes are very high, like you've just spent a bunch of time getting the whole organization excited about this leader, like, honestly, looks bad if you all of a sudden say, like, Hey, I don't think this leader is a good fit.

but also because, like, the work that these leaders do, like, it tends to just be longer term, it just takes a little longer for it to really pan out. Oftentimes they come in, they like probably really want to assess what's going on.

They might want to redo the strategy. They might want to hire some people, like all of a sudden you're a year later. And it's like, it's just really hard to fire these people as quickly as you would. Maybe someone who's an IC,

Brett: You've hired so many product managers. And like, if you think about the difference between

hiring accuracy and an average product manager and hiring accuracy as a chief product officer, VP of product or whatever leadership role, do you think the accuracy is wildly different or you just truly don't know?

Eeke: anecdotally, I think it is like, I think it is just easier to hire. even like a line manager or an individual contributor, like there's the pattern matching is easier. It's like, at least like anecdotally, like there seems to be less turnover there. You just, I think, seem to hit or miss less often.

but I don't have a sort of actual data to back it up. 

Brett: think that your, your point is correct that when you get to executives, The difference between amazing and okay and bad is so 

consequential,

 What's 

your thought on like globally excellent execs versus sort of like context dependent excellent execs? Is there a small percentage of, of people in around your orbit that you've observed that can be in so many different environments and be an incredible C suite executive?

By globally excellent execs, you mean like just put them anywhere and they'll, they'll crush it.

Of a reasonable shaped company. So like put a pin in culture that are in between Stripe's culture and Amazon's culture or pick other 8000 person companies

that are selling generally to a developer audience or generally to a business, uh, to sort of other businesses. So take 20 of those companies. They're all valued between 10 billion and 30 billion.

They all have, you know, one to 5, 000 employees or whatever. And you take this C level exec and you have them operate across each one of those.

Eeke: it's really hard for execs. The other thing that came out in all of these conversations with folks is like, if your values aren't aligned, there's like literally no way it's going to work. think it's just actually pretty hard for there to be like globally relevant execs.

Like there's just like the right exec at the right time for your company is totally right. 

 There's something about this idea of values, particularly in the context of executive hiring that I put into like the eyes are glazing over sort of category.

Brett: And yet it feels like to your point, if you correctly define values, that has to be one of the top reasons why there's organ rejection in one form or another.

Eeke: I actually think that that part is so incredibly hard. Correctly defining your values. When I was at Stripe, my first round, we, we had to serve like a couple of operating principles and at one point, like Patrick pinged me and he was like, Hey, like, I really want us to write a guide to Stripes culture, and I want us to share it with candidates when they join, when they are considering Stripe, and ideally, half of the candidates who read it are like, I'm out.

I don't want to be a part of this. writing that doc is maybe the hardest thing I've ever done in my life. It's so, like, how do fish describe water? It is so hard to describe the thing that you are in every day in a way that actually A like sort of like is understandable to people outside of it.

And also in a way that doesn't feel like a platitude. . Of course, every product manager should talk to customers, but it's like, okay, well, how are you going to manage that amidst all of the other things that you have going on? How are you going to get the right customer feedback at the right time?

And how are you going to relay that back to the organization and there's like so many nuances to how it actually shows up that I think it's like, it's just so incredibly hard to articulate. Most early stage companies they really struggle to articulate what they want to be yet.

They don't quite know. And then the other piece of it is, like, in some ways you're bringing in a new leader or an exec because you want them to, like, you want them to change the culture a little bit. Maybe not the whole thing, but you want some sort of change, otherwise, you wouldn't be getting this leader. And change is like, by definition, pretty uncomfortable. So how do you differentiate between the change that feels good or that's actually ultimately good, even though it doesn't feel good and the change that's like ultimately bad, I think that's pretty hard to do as well.

So like my only like good litmus test for that, or like red flag is if a leader comes in and they're starting to make a bunch of changes without deeply, deeply, deeply understanding the company or the company's problems. And without bringing like real humility, they're just copy pasting whatever else it is that they brought over.

That to me is always just like a recipe for disaster.

Brett: There's also the inverse of that, though, which is that the person spend months just sort of building context and doing nothing, which is like another, again, all of these things are about trying to be in equilibrium and in anything being in equilibrium is sort of very difficult. But I think the number one failure thing is we did it this way.

I'm doing it this way at this company.

A hundred percent. Yeah, but I also, I agree with you, I think the number two failure is like, I'm going to spend three months on a listening tour. What was the process of writing that doc?

Eeke: a couple of people have asked me that actually, because they've wanted to do it for their own companies. Um, It started with Patrick and like kind of like jotted down some ideas like this is stuff that's like kind of important to us. 

Brett: Just sort of sitting down and collecting your own

Eeke: Yeah. And like writing, um, and it was like, I don't want to say it was kind of mediocre. It was, it was not that good. the document now I love, I like refer to it back all the time. We ended up taking it down or stripe ended up taking it down. Like, you know, at some point, like companies kind of outgrow this stuff. There, there was some controversial controversial, there was some stuff in there that was basically just like, like, you gotta be willing to work really hard to actually, you know, be successful here long term. 

Brett: true I

Eeke: my gosh, it was so controversial when it came out on Hacker News, it was eviscerated.

Yeah.

Brett: feel like we're in a different phase now though 

 I do also think it's true that at some point, I don't know, companies get big enough that you have folks who, who maybe are just not up for that. And like, you just have to kind of be okay with that if you want to have that many employees in your company. Yeah.

Eeke: Anyway, so it was after I kind of wrote that first shitty draft, shared it with a bunch of folks who were, I thought, both culture carriers and really great writers. And they took a bunch of stabs at it. And then myself and Sir Patrick took the last stab and that was really it. 

Brett: I don't know if you can remember this What are the types of things that they contributed that didn't occur to you when you wrote the first draft?

Eeke: honestly, some of the writing, just like the way they described it was way better. Um, like we would do the, the actual search principle and then we would do this, like questions you should ask yourself if you're joining Stripe. and one of the sort of. Revisions that someone made who was, a friend of Stripe's who actually wasn't at Stripe themselves.

they said something like your LinkedIn is never going to be as tricked out if you work at Stripe, like there's just never going to look as good. it was very true because like Stripe doesn't do titles. but just the way it was said was just like, I think that really stuck with a lot of people who read it.

there was another thing where one of The revisions was from a fantastic writer, where he said something like, Stripe is not a competitive place in that, like someone else needs to lose for you to win, but it is the kind of place where like someone else is going to do something amazing and it's going to push you to want to like work way harder.

so it was like that kind of stuff that just like made it much clearer, like how this place was kind of different. thought was, yeah, very good.

Brett: When you look at the document, do you think it's just by and large a, encapsulation of John and Patrick? Or there's a delta between their behaviors and what they value and what ended up kind of being the, the way that the company behaves?

Eeke: Oh man, I would love to hear their answer on that. I think they felt it really reflected, how they felt about yeah, their values in Stripe.

Brett: Tell me the story of an exec or two that has come into Stripe in your tenure. Who is the positive case? That was just extraordinary. 

Eeke: Well, this person isn't less known, but I think they're the perfect example, which is Claire Hughes Johnson. Claire joined Stripe when we were around 150 people and we were very, very close to organizational rejection with her. she interviewed and there were many, many people who were like, I don't know, she's like big Google exec.

I don't think this person's going to be a good fit for Stripe. Patrick, to his credit was like, I think this person will be exactly the right fit and actually even in her book, scaling people, Claire mentions that, you know, Patrick kind of told her, it's like, Hey, I think people, people are kind of worried here that like, you're a good fit for Stripe at, you know, 500 people, but maybe not the right fit for us right now. But, you know, we're going to get to 500 people pretty soon. and of course he was right about that. I think that the most key thing was the complementarity between her and Patrick and John. Like she was just such a great balance to, to them as leaders.

We were just talking about my, you know, my podcast that I do it with some friends. And like, what we do is like, we, we research enduring companies. One of the themes that has come out of that, that has been surprisingly consistent, especially with these sort of like deeply technical companies, is that there's almost always a pairing of like, a deeply technical founder with a, more operations, peoply person who can help scale that vision. We call them Bert's and Ernie's. And like, once you see it, you see it everywhere. It's yeah. Tim cook and Steve jobs, the co founders or the co CEOs of ASML. it's I, the pairing, I think works really, really well.

Billy was also on the, the leadership team and Patrick and, and John and Claire. and then I think the thing that's like actually kind of amazing that happened after that is that they then hired Will Gabrick who, you know, initially came in as the CFO of Stripe

now is Stripes. 

Uh,

well, yeah, he was an investor and, you know, incredibly impressive background, but like no operating experience really. And Claire writes in her book as well at the time, Claire was like, I think we need to make him take a personality test to see how he's going to fit in with the rest of the leadership team.

And she like her intuition to kind of been right that he was like, the perfect sort of compliment to the rest of the team. And that team that leadership team was so strong. And so they were so tight, they really felt like a unit, everyone looked up to them as like, this is the unit of the team.

They were, you know, There for a long time, I think it was like phenomenally successful. probably a lot of how Stripe got through some, very hard times.

Brett: aside from that sort of yin and yang sort of dynamic is there anything else that is useful to understand that other people can positively pattern match against?

Eeke: I really think it comes back to that, like initial introspection of like, what do you think your company really needs? Like in the, the sales leader example is like a very apt one I think, like almost never have I seen like a founder or an exact hire a sales leader and like actually be able to articulate very clearly, like,

I'm going to be a sales led company, or I'm going to be a product led company. if they are going to be a product led company, then to be able to articulate to the sales leader, what that means for that sales leader and having them sort of operate in that kind of environment, I don't actually know if John and Patrick did this with Claire, but I think because Claire came from Google and like that was already a product led company, she fit quite well into the sort of product led sales mindset. And that worked, I think, quite well for that stage of Strive's life cycle, You know, I've also seen it work the other way where folks bring in a sales leader who's just like, well, now we must focus entirely on enterprise and do an enterprise sale.

You must completely change how you build your product. That just doesn't work at all. So to me, it all comes back to like, have you done the upfront work to really understand, what is this future with this leader look like? will they fit into that future? And have you guys talked about that together?

Like what that actually means for that person's job.

Brett: What about sort of the opposite? Are there threads that tie the people that haven't worked out together?

Eeke: Other than like the values misalignment, which I think everyone would say, and it's kind of obvious, I think they really are all dysfunctional on their own dysfunctional way. I was talking to Andrew Abramson, who, who works at Fusion is like a talented exec.

And he's like, you know, I think one, one mistake that founders make is they hire this extremely, potentially like expensive exec and they just expect them to come in, like, be able to be successful without helping them. There's work you need to do to set up the, these execs for a success, a hundred percent.

It's like baseline, like, you know, give them your social capital, make sure they are introduced to all the right folks to get all the right work done. But like, ultimately, I feel like the good ones will make it work and the bad fit ones don't. 

Brett: So going back to what you were talking about a little while ago, maybe you can share more about when you think about doing this introspection ahead of the search, which I think is kind of one of your ideas of the things that will increase the hiring accuracy, sort of an exec,

maybe talk about that in more detail, like what that actually looks like in its like most concrete way.

Eeke: I think you need to do three things. you need to understand yourself. You need to understand your team and you need to understand your company. So on yourself as a leader, I think you really need to spend the time understanding like, what is it that I like doing? What I don't like doing? Where do I really want to be involved?

Where do I not want to be involved? What am I good at? What am I not good at? And like, really do that work. I actually, again, think very few people really. understand themselves in that way. piece. Number two is okay, now you're, you're hiring this leader. What do you actually want them to do for the team?

Do you want someone who's going to set vision and strategy, or do you want, do you want like a leader or do you want a manager? Do you want someone who's going to go like manage the product managers? Cause you don't want to do that anymore. think you have to sort of be pretty concrete with yourself on exactly like what success looks like in year one and what success looks like in year two.

Nothing past that because you have no idea what your company is going to look like past that. but until then, yeah, you're, you're really kind of need to that. And then the third piece is do you you need to like have this future view of what your company is going to look like in the next year or the next two years?

And what do you think it's going to need? Do you think you have to upscale to enterprises? And if that's the case, that's going to be a very different type of leader that you might need versus you really want to focus on that product led growth motion. So those are the sort of like introspective things you have to do.

And then I do think you also have to go and get data on the person once you go and like interview them and talk to them, et cetera. But you have to start with that first piece and have a pretty succinct list and understanding of those three pieces.

Brett: somebody's listening to this, they go do this, like what's the most likely things are going to screw up when they go try to do the introspection?

Eeke: I don't know if it's that hard. I just think people don't really do it. It's like, why are meetings bad? it's the same thing. It's like, there's actually just a set of things that you have to do to just make them good, but how many people actually send out the agenda in advance? And how many people send out the notes afterwards?

And how many people actually write down the action items? Very few people. So it's just you just got to do the work. I actually really don't think it's that hard. You just got to know to do it.

Brett: And so then once you do it, how does it actually map to the interview process or the sourcing process or any of that type of stuff?

Eeke: on the interview process itself, the thing you really need to figure out is like, You're going to have a bunch of biases going into it, regardless of whether you've done this process or not, that are really going to, I think, influence how you view these leaders, one of the biases that I've seen a lot is, This leader is just awesome publicly.

Like I've seen them, post cool stuff on X or like great blog posts. that's just one piece of bias. another bias is sort of like the one hit wonder bias. Man, I got, I have a list of companies that I really admire. This person's worked at one of these companies, but have they done anything else?

Another bias is the tailwind bias. they just happened to like ridden a bunch of great waves in the market. 

Piece one is like being very aware of the biases. Piece number two is okay, now try and figure out, what is it that this person did that no one else could have done? what is the counterfactual of them having been in the role that actually made it such that they were successful in some way that, no one else could have done. I think really what you have to do is you have to try and figure out with this person, if they hadn't been there, what would have happened? oftentimes I, I asked sort of like the before and after, Hey, like, what happened?

what is the team that you inherited or what it looked like? And what did it look like after? And oftentimes I try to get examples of things that other people had filled out before them that they somehow succeeded at. And if they were able to do that a lot over time, that's always like a really, really good signal.

Brett: And you do that in, in sort of the actual interview or it's mainly in referencing?

Eeke: No, I did that in the interview. my main view on references that I actually don't think they're that useful, unless you can find someone who has more incentive to tell you the truth than to like have the back of the person they're giving the reference on and someone who really understands you and your company.

So like, you kind of need those two pieces to work together because on that second piece, it comes back to is this person actually a fit for your company or like what you need at this time? So you kind of need someone who's pretty close to your company to be able to give you like pretty good advice on that.

And then the first piece, just most people don't want to say bad things about people 

Brett: But why does it not work to ask the reference what was the state of the org before the person joined, what was the state of the org after, and then did that match what the person said 

in the interview? 

Eeke: You can definitely do that. Like you can just fact check that this person say real things for sure. but I, I think the most useful references are the ones who like really, are going to go a little deeper on Hey, how much of this was like this person's role and like, what did they specifically do and how did they get that?

Oftentimes the person you're doing the reference with was not that close to the work to be able to give you all those details in a way that you probably need to. so you just kind of need to trust their judgment and trust that they're telling you the thing that's true about this person.

Brett: Do you think most of the time when you, when, you know, a cross section of the employee base thinks that person X is a star, they actually are?

Eeke: Hmm. 

Brett: there's a lot of noise in that?

Eeke: Oh my goodness. I have a lot of thoughts on this. I think there's a lot of noise, unfortunately. Yeah, which is why you have to go back to like, is this a person who whose judgment I really trust? Yeah, I think it's just like pretty hard to, to really know how good someone is from even like a medium distance.

Brett: Is the inverse also true? If a bunch of people think the person sucks, they might not suck.

Eeke: No, I think it's easier to see when someone isn't good at their job.

Brett: That's interesting.

Eeke: Yeah, I think that is a really interesting insight. 

I think it goes back to like, well, I mean, maybe this is an unfair way to put it. you know, I think generally like no excuses. if things aren't going well in your org, I think it's generally like,

person X has to figure out how to fix that. If things are going well in your org, to me, the question is always is it going well because of tailwinds, exogenous reasons or is it going well because you did something really different here? and like, if you had not been here again, what's the counterfactual, if you had not been here, which is what I ask, in every performance review cycle of the people who work for me, if they had not been here, what would have happened?

Brett: going back to sort of the interview process with execs. Talk more about like how, the end-to-end process you think is the best.

And who's involved and who shouldn't be involved and how are you spending the time and sort of that type of stuff

Eeke: I think the first chunk of the process needs to be basically just the founder and or like hiring manager and the exec just spending a whole bunch of time together. Then there's like the in between chunk of

like a relatively unscruptured fashion?

totally relatively unstructured fashion, choose a problem together that you want to work on that, maybe you're like dealing with as a founder or as an exec spend like a couple of hours in a room together, how would you actually work through problems together?

that to me is like step number one. Step number two is bring in the sort of core people who's judgment, you really value and then also who are going to work very closely with this person. and then step 3 is you know, let's say they kind of get past that is okay, now get him buy in from the rest of the team that shouldn't be a like a decision making for him.

That's more of a hey, I want you guys to like, meet this person and get a sense of who they are. But that's not a like, you get to veto this person. 

and then the final step is sort of doing your like actual references. 

Brett: how should the decision be made? In terms of the hiring decision, is it just single trigger, the founder should just unilaterally make it?

Eeke: Absolutely. Yeah, I don't, I don't think any. Important decisions like this can be made by committee, like they should, I mean, they should use input from all the folks who, you know, were part of the interview process, but ultimately the founder has to decide that or the hiring

manager. 

Brett: hmm. Mm hmm.

Something you haven't talked to a lot about yet is what about how the exec relates to other execs and works with other execs and what's like the role of that or reflections on that specific kind of working dynamic on the team that is the exec team?

Eeke: I do think the complementarity really matters. So that was like, you know, some of the stuff that we were chatting about a little earlier. Are they going to fit in with the team well, and are they going to work well there? Sometimes you bring in an exec because you want them to shake it up a little bit, or maybe you'd like, don't know how you feel about the rest of your leadership team.

But generally, if you're feeling good about your leadership team, it's like, I think it's pretty important to, bring in that complementarity for sure.

Brett: How do you think about, the kind of classic question of growing people internally versus hiring externally?

Eeke: I have a, a good, good friend and, um, technical sort of leader, founder, who, I asked him sort of about just generally, like, hiring and his thing was like, oh, you should really try and look for future potential. Often the mistake that people make is like, candidate A is good now, candidate B will be better in 6 months or like, they'll invert. But generally, people tend to think just about like whether a candidate is good in This moment. The nice thing about hiring internally is that you have a really good view of like a person's trajectory. So like you could probably project out Hey, I actually think in six months time, this person will actually be really, really good.

So that's great. I think oftentimes when you're looking for a new leader, you're looking for a skill set that, doesn't exist in the organization. And the question I think you should always ask yourself, like, what are the skills you want to build versus the skills you want to buy? If you're hiring internally, you're like, You're buying, you're just getting for free, someone who has the domain knowledge, someone who understands the culture, like you're not taking any risks on, you know, whether or not they are a good fit for your company from a values perspective, but you're probably going to have to build a lot of the like, the knowledge of whatever function you want them to take over and like the sort of that kind of experience.

Whereas if you're hiring someone externally, you're like. You're buying their external experience and they're probably like going to be bringing in a lot of things that like no one at your company knows about yet, but you're going to have to teach them probably taking a little bit of a risk on like, are they a good fit for your company from a sort of culture perspective?

But I do think generally it's really, really good for a company culture to promote internally.

Brett: you think there's some general rule of thumb? Like, it's good if you can have a third of your execs be homegrown versus external or those type of things.

Eeke: I haven't really seen that sort of rule of thumb.But I'm just like thinking about my own, like what I've seen at companies so far, it's probably about right. It's like a third of the execs are homegrown. And that's 

Brett: Hmm. 

seems really good. Like they, yeah,Do you think you're more likely to be successful if you're hiring an exec that is stretching up into the role? Or coming down into the role?

Eeke: I think you're way more likely to be successful when someone is stretching up into the role because they're going to have a chip on their shoulder.

And like, you really want them to prove themselves, or they want to prove themselves, whereas like, I think someone who is kind of stretching down into a role or I guess like, detracting down into the role, they're going to get bored.

They like, just might feel like the role isn't big enough for them. They're going to want to hire a team that's bigger than it needs to be. They're going to just, they're just going to want to do things that are like, just generally, I think unnatural for what you need them to do for that period of time.

With that said, I've seen plenty of counterfactuals, obviously, obviously the Clare Hughes Johnson counterfactual is a totally good one, but then you really have to test for humility. Is this person willing to kind of take on a smaller role for some period of time.

And even then I think, in a lot of those cases, those leaders are stretching, but in different ways, because they've been leaders at these large companies with a big support system that already had built a lot of these systems and processes and like their stretches actually, like I'm actually building all this stuff from scratch for the first time.

it's just a different stretch.

Brett: Going back to sort of a thread from a couple minutes ago, how do you think about managing the existing org? A thing that happens all of the time at scaling companies, is there's lots of people that want the exec role that have been there for four years and seven years and eight years and I can't believe you're hiring a VPN when I'm the director and I should obviously be promoted. And the reality is a lot of times those people actually end up leaving, there's nothing you can do. But is there anything around doing anything in the way that you communicate or go about it that increases the chance they'll stay and do great work as opposed to be sort of disenfranchised?

Eeke: Truly the best thing you can do is hire an incredibly inspiring leader. Really great people want to work for really great people and learn from really great people. So like, number one thing you can do. The second best thing you can do, I think it's just be super transparent and open throughout the process, like really good high performers want to hear how they can get better.

Generally telling them like, look, you're not ready for this role. And here are the reasons why you're not ready for this role. but here are all the ways in which like, you're going to have opportunities to grow, especially under this new leader. Generally, I think works honestly, really well, or even saying like, look, like if you, if we'd had you here for another two years, you would have been ready for this role, but we don't have two years.

We need this person today. Just being honest, I think really, I've seen least work really well in my career so far the place where this all falls down is like you hire this leader and they suck. And then, you know, you go that that's, you know, that's obviously just like bad for everyone involved. 

Brett: How long do you think it takes to figure out if somebody is going to be successful as an exec?

Eeke: I think like way faster than people realize, um, if they're like a bad culture fit three months max. If it's like a, the harder, the harder cases are the like, I think they're like a pretty good culture fit, just like not totally clear to me whether they're going to be able to like, whether they're really executing as well as they could.

And this is where something comes in that I like, I call this sort of the new leader dilemma where like new leaders have in almost every single scenario, a huge incentive to say that they need to change the strategy and like the reason for that is I just think about sort of like the outcomes a leader who comes in is like, actually, the strategy is fine, like, really hard to prove that you, you know, you're kind of proving your value, like the worst thing you can be called as a leader is non strategic.

So that's kind of like, you know, reason number one, why they kind of want to say, like, I don't know, guys, I think we should go and change the strategy. Reason number two is you come in and you kind of buy yourself six to eight months. If you say you need to change the strategy, which means that if execution is poor, or you're not hitting your numbers or whatever it is, that's been expected from you, you just be like, well, the strategy was wrong. We were working on the strategy. So, I think there's like a lot of reasons for new leaders to like want to change the strategy. But I think it's like really incumbent on the founder or on the like you know, who the leader is manager to push very hard on what is the key insight is from that leader as to why they think they really need to change the strategy and if it's true that they really think they need to then to push them to change it over one to two months versus like the six month period. And then to push them to actually like test sort of the impact of that change very, very quickly. so like, sure. to really live out the strategy you have to like, let's say your strategy is Hey, we have to move from self serve users to enterprise users to like really see that play out.

You have to look at it over many, many years, but you can start testing it pretty quickly

by, you know, building a prototype of a product and, you know, getting it out to enterprise users and seeing how they feel about it. So I think it's like really important that as the founder, you don't create the, like sort of this weird incentive structure where the leader has to feel like they have to change the strategy.

Same with reorgs, like that's just another, I think, like really funky incentive structure where like, it, feels like you're doing a lot as a new leader because you're doing this big reorg and everyone's talking about it. But like rarely, is that really the answer to solving your problems? and then I think also same with like changing tool stacks or platformizing.

That's like another sort of like thing that comes up a lot. That's just like a, like multi year project. It's really hard to assess whether it's going to be successful very quickly. And so like, it's really, really important when your new leader suggests this, that as the their manager or founder, you're, you're pushing to understand, like, how do we figure out that this is going to work as quickly as possible?

Brett: Maybe sort of on a, on a similar thread, what are your perspectives on the entering exec and how they should behave or what they should do to increase the chance that they're effective?

Eeke: I think humility is like a really underrated value that the thing that really used to grate me when like new leaders would come in is they'd come in and they'd be like, they'd look at stuff that was happening or stuff that hadn't been done yet. And they'd be like, they'd make these very bold statements like, I can't believe we're not doing it this way or like, have you guys even thought about doing X, Y, Z without really sort of understanding, basically asking the question or even just saying Hey, I'm sure you guys have thought about this, but like, why haven't you?

so I think just like, Understanding the problems deeply is kind of step number one.

That doesn't mean like a three month, you know, uh, listening tour, but it does really mean like using the product, understanding the problems, that I think is like number one thing that like a great leader can do in like their first few months.

Brett: what else?

Eeke: Assess the talent pool. pretty quickly, like just fire the people that aren't good. especially if they're not a good culture fit, but also if they're just, not doing well. One thing I've, I've experienced myself, but also I've like seen with other leaders, like you come in and you do your, like, I don't know, your transition talk with whoever's been managing all of the people that you're now going to be managing.

And, During your transition talk, person's like, yeah, so and so's okay, I don't know, they probably need to be performance managed, but I don't, like, there's some good, there's some bad, those people, you just, you just need to fire them immediately, like, if that's sort of the open question already, like, chances are that person's not going to recover.

Even if actually maybe they are recoverable because the organization has kind of already decided they're not that great. So yeah, I think start in, like understand the problems deeply, figure out of the teams, sort of the right team, fire quickly and then come up with the plan. what are you going to do that's actually going to be different for this company.

Brett: What about how should an exec decide if they're going to join the company?

Eeke: I think it's the exact same process as you know what these founders are going through. have you done your introspection? Have you done your like your process of what is my future leader? My leader future fit? does this company fit into that basically. 

 The way I've described leadership hires at companies, it's like, it's kind of like an arranged marriage. You both really have to choose to want to like make it work. It's not like a love marriage where like, you know, which is like, what I think happens with early employees when they joined a startup or just man, I like, I love it here.

Like I never want to leave. I. You know, I'm obsessed with this place, by the time you have a founder and a leader coming together, they have pretty established things, the ways they like to work and opinions. And so like, you both have to decide, is this, is this something I want?

Brett: it's like a second marriage.

Eeke: Yeah, maybe. Yeah. I don't know.

I can't speak to actually either sort of like an arranged marriage or a second marriage. Yeah, exactly. It's

like you. 

Brett: in your ways, you know more about yourself.

Eeke: Totally. Yeah, 100%. you have to be okay with some of the like the stuff grating a little bit. And like, the only way you're going to be okay with that is if you've decided I really see me here as a leader, In the future of this company.

Brett: What about in the first, I don't know, three or six or 12 months disagreeing with the founder? Are there right or wrong ways to sort of go about that? 

I think founders and myself and I've hired leaders, I want them to come in and disagree with me. Like if I didn't, then why was I even, why did I even hire them? So the, the real question, yeah, per your point, I guess the real question is like, how are you disagreeing with this person?

Like, have you really deeply understood the problems? because if you have, and you still disagree with whatever the direction is, then how about it? And like, have the real conversation, like lock yourselves up in a room for, I don't know, a couple of days and like, figure out, you know, where the disagreement is and why, but if you have both have done your due diligence right and like, you're both good thinkers and rigorous thinkers you're going to figure out at some point, like there's some sort of like difference here and like how we understand the world. So you need to understand that together.Do you think there's a pattern in previous tenure for execs that you're hiring that they were a company X for 11 years versus four years versus one year versus their resume is a bunch of two year stints versus two nine year stints. Do you think there's any rhyme or reason to any of that in terms of increasing or decreasing the chance that that they're successful?

Eeke: I personally really worry about the, like the two year stints sort of like multiple, like two year stints. Like it's just actually isn't enough time to show that you've done anything significant, I think as a leader. So like this like gross generalization, but it feels a little bit like those are sort of like the leaders for hire or the like the sort of mercenary type leaders, where it's just they're just jumping from company to company based off of, you know, the next interesting thing.

And so like those, those always I'm wary of, the leaders have like been at companies for a long time, I think generally. Very highly of, because inevitably those companies have gone through hard times. Like there's no way a company did in over a nine year stint. and that to me, really says something about a leader's resilience.

but a leader who's only been at one other company, I think I'd always have a few questions about, because they're going to be very tempted to copy, 

Brett: The 

same thing. Yeah. 

Eeke: Yeah. 

Brett: You hit on this a little bit, but what about, how important is it that the shape of the company is similar? So, the company sold to developers. This company had both the bottoms up motion and an enterprise motion. The company was, hardcore enterprise and were hardcore enterprise.

The company was consumer. Like, if you remove the values and the way that the company behaves, like the shape, the deal size, 

the, you know, Sector how 

important is any of that? 

Eeke: I think it's quite useful just because pattern matching is quite useful. So like, even if you're not going to like copy paste, it's at least useful to have perspective. And you're like, I've actually seen this before, or like, this is something we should worry about, or this is something we shouldn't worry about.

This is, there are some real like playbooks or way to do things with enterprises, you don't always have to reinvent the wheel. I don't think it's necessary. And actually like, you know, again, my sort of friend in was saying that like nine out of 10 times, the first interview between a founder and a leader goes better when that leader has domain expertise because they just have things to say about the founder space.

But his point of view is that is like not at all correlated to ultimate success. I think again, again like useful, absolutely not necessary and certainly not a sort of a positive, indicator all on its own. 

Brett: But all things considered, you lean towards hiring people that have operated in a similar?

Eeke: If I could have that for sure. 100%. It's just like nice not to have to spin up folks on these, on these areas.

Brett: Do you think There's sort of any correlation in terms of people who have worked at a variety of companies, some of which were not successful or are not hot companies versus somebody that, you know, was a Google and then Palantir and then came to Stripe, does that matter in one way or the other?

Eeke: Yeah, I think it really does actually like I, the folks who only been at companies that have themselves done well, it's just really hard to be able to distinguish whether the company did well because of the founder or because of the leader, sorry, or the leader did well because of the company.

Brett: or in spite of company did well in spite of the leader.

Eeke: Exactly. Uh, yeah, a hundred percent. So like, I, I like seeing leaders who've like gone off and like worked at some honestly, like less known company for a little bit, A, like it shows that they have, it's probably a strong opinion about some wanting to have gotten somewhere that like, maybe it was like less popular or like less well known, like they just went there because

of X other reason. And then B, if they can show that they were successful at that company, then I feel like, okay, that's like a real data point. Hey, you actually were able to. Yeah, you were really able to move the needle here, in a way that wouldn't have happened without you. again, like these are all like heuristics that aren't perfect all the time.

Like there are plenty of people who have a beautifully pedigreed resume and are fantastic leaders. But I think, I think it's good to have some, to have some experience where you're like, just weren't always at the sort of place that was the winner, so to speak.

Brett: Something you didn't talk a lot about is the role of the leader in creating an incredibly talent dense org underneath them. And do you have any thoughts on that? And is it something you spend a lot of time thinking about? Or if the exact delivered results, it doesn't really matter one way or the other?

Eeke: I don't think they could have delivered results without having a incredibly talent dense org, but results that they actually were themselves responsible for, yeah, I think about that a lot, actually, some of the better indicators are like, did people, but in interview processes, actually, per your, per your point of like, what are questions you should ask?

How many people moved to the next company that you worked at that you worked with before? I think it's always a really, really good sign.

Brett: What about how much firing they did? Do you like somebody that's fired a lot of people or you don't care?

Eeke: No, I do. Per your point, if the, if you just have to assume that the distribution of failures is like pretty much the same across the org, I think it's always a pretty good sign of people have fired, a lot. It's only because like, they're going to have to in whatever job they're taking on, if they don't have that experience, they're going to take way too long.

Brett: What is a high functioning executive team look like and what is a low functioning executive team look like?

Eeke: It's like parents. as a child, you kind of know that you can't go to one parent and get a different answer from, you know, them versus the other. A high functioning executive team is like that. They're like, they're consistent. You feel like you're going to get the same answer from every single executive, but you also know that the, like the, how they do it or like how they're going to get it done is like, they have different strengths, they'll be able to show up differently.

A low functioning executive team, honestly, you can just tell, like, you just tell how they show up at the all hands. It's they're not coordinated. You can tell that they don't agree with each other and like, they kind of air their dirty laundry out and towards the rest of the company. They don't run the company well, like they don't, They don't hold their teams accountable in the same ways.

They're like, they're not consistent across the board. you know, they're not following up on commitments that were made. think you feel it pretty quickly.

Brett: If you think about these two sort of hats that you're wearing that are sort of overlapping, one is the function that you're owning and delivering results in the function and the other hat is your role as an executive on that team. when you're wearing the executive hat?

What is that look like to do well?

Eeke: Well, actually, it's interesting you mentioned that, like, in that order, like your team has to, though your main team has to be the executive team over your functional team, even though I think it's very tempting to want to, like, spend more time with your, your functional team. In terms of like within the executive team, I think it's like, a very high, divergence, It's able to have like different opinions, able to sort of speak up and share those opinions kind of teams tend to, I think personally, I think are the sort of the ones that are the most high functioning, but with a lot of trust.

So you need both the trust to know that like when this person says Hey, I kind of really disagree with that or really need to push on like why you're saying that it's coming from the right place, but you also need to be pushing on those things. 

Brett: Something you talked about a little while ago is just there's nothing worse to be called not strategic as an exec. How do you define being strategic? 

I think it's like the difference between managers and leaders. So like leaders are able to set the direction and the vision and the prioritization and the focus of the organization and have a clear reason for why that is and be able to explain and articulate why that's going to help the company or the organization when, whereas, yeah, I think managers they're just like, they're, they're good, like they're good like keepers of the team, like they can like hold the team and they can like help run it on day to day basis, but they're not directing it. you think charisma matters in as a leader. I do, but I don't think it's like charisma in the turf in the traditional sense. I, I know very, quote unquote, charismatic leaders who are not incredible speakers, but are great writers or, are wonderful one on one. so like in, you have to, you have to be able to get people behind the thing that you believe and people have to want to follow you, doesn't have to be in the, like, uh, Tony Robinson way.

If you're an up and coming star and you aspire to be an exec and you're trying to sort of. Exercise and get really good at that strategy piece. How do you go about doing that? Or do you think it's like either you have that thing in your brain or you're just don't have it?

Eeke: I think there's absolutely people who are natural strategic thinkers. 

Brett: Since they were a teenager, basically, like their brain just works in that way?

Eeke: I don't know since they were a teenager, but like kind of, yeah, their brain just works that way. Like they, they just think about these things in that way. Like they, they read an article and they like, they immediately see the link on like why this business is going to win or why it's good. Or they also just like interested in it, but I also think you can learn it.

And I think part of it is just like practicing, like writing, like writing the little strategies for like your products or for your areas and just like doing that over and over again and getting feedback from, you know, your leaders and seeing if it like resonates. so that's one piece of it.

Part of it is also just like. Looking at how, what other companies are doing, just articulating their strategies in itself. I think a really good way to like practice, uh, if you can get a good sense, Hey, what, why is this company able to win? He'll like help you. I, I know there's people who like swear by Porter's five forces and, there there's good literature, pretty good literature out there, but I think it's like practice, practice, practice, and then you have to kind of,

you have to see it play out in person. You have to, um, you have to be wrong a few times, basically. Like you're going to put forward a strategy and like, test it out. Maybe it wasn't quite right. but like when you're younger and up and coming, that's actually like a great. That's a, that's fine.

It was like, the stakes aren't that high.

Brett: What did being at Stripe for a long time, leaving and joining Retool and then coming back to Stripe teach you that you didn't know

Eeke: Yeah. 

Brett: until you left and came back?

Eeke: I thought there was one great way to build a great company. Like leaving, seeing that there was a complete different way to build an awesome company. And in fact, like seeing that I grew so much as a leader in that way, was like a huge Huge learning for me, and actually, now that I'm back, it just made me a better leader because it just also made me question sort of how we do things at Stripe sometimes, in a way that I probably would have not really done before, because I'd really only seen it in one way.

And I was, I think I felt very breathless about how we did it and like very loyal to how we did it. 

Brett: What's like an example of that?

Eeke: Stripes and Retool's leadership teams functioned very differently. Retool's leadership team was, like, a collection of very different personalities. it was, it was a big team of like, you know, I think we had 10 people on sort of the overall operating leadership team Stripe's team was always tight knit five people.

it's different now, but like, you know, back then five people who were just leaders and like, even though they were different personalities, obviously, and like they, you know, in a lot of ways, we're more alike than they were different. And so that to me felt like a verylike, there are actually two ways to run successful leadership teams.

What about you spent some time working on starting a company? What did that teach you about being an executive?

I don't think you learn much starting a company early on being an executive.

Brett: What about what was surprising in the inverse of that experience? Like you had built lots of products.

Eeke: I think the biggest surprise is yeah, I joined Retool when we were 30 people, Stripe when we were 50 people, but there was already so much pull, and the biggest surprise when you start a company, as I'm sure of all the, the founders, if you're listening to this now, it's you're creating the pull, you're creating all the energy yourself.

Like it's literally all, any kind of entropy or heat is coming from you. I think that can be really energizing and can also be really, really, really hard.

Brett: Did the experience teach you that it's just not your jam?

Eeke: No, not at 

Brett: all, no. 

Eeke: I, I think it'd be really fun to do again sometime.

Brett: It's just an entirely different thing.

Eeke: It's just an entirely different thing. It's like you're putting your energy in an entirely different place.

Brett: What else can you kind of say about the difference between building a product in the context of an existing company or a post product market fit company versus starting with a clean sheet of paper?

Eeke: You're, I mean, you're creating the market. You're like when you're joining a company at like, you know, 15, 20, 30, 40, 50 people, like there's already some sort of market already exists. Like you have some sort of like pretty clear direction. but when you're like, you're first starting off, like you are, you're really out there trying to like, figure out how do I get customer number one and customer number two and customer number three. Like you're just, creating it out of thin air a lot of ways. so that's, I think is like one big piece. but you know, I think the sort of like, there's some awesome differences there too. Like you're solely working on this thing that like, the stuff you're working on is stuff that, you think is important all the time. Whereas, like, that might not always be the case that, sort of a, a larger company where, like, there's stuff that is, you know, quote unquote important, but it's more part of, like, the overall big company processes or things you just kind of have to do.

Brett: What data sets don't exist around leadership hiring or execs that if it did exist would make everyone better off?

Eeke: Even some of this core is like, actually, like, how big were this person's teams? how did this team change over time? just the sort of like the timeline of someone's overall career arc and just being able to compare that to like what people say, I think would be just like honestly, super value valuable.

So that's like a small sort of piece of data. If you could get data on, actual hardcore data on like the before and after in like financials or whatever it is that the company uses to measure their, their success, MEUs, DAUs, whatever it is, that would be a, I think a really good piece of data.

I'm personally very curious about what actually is the failure rate and the distribution across all companies, all startups or all, All tech companies, most of the data that I've seen on this is fortune 1000

companies, uh, and it's usually C suite.

So that's also like a little harder to, to get a good sense of. I think the thing that's like. It's weird to me that no interview tool has done this, but like really like you should be able to measure or like track like interview feedback to like how a person actually ends up doing at the company and their talent cycle.

I really don't know why this doesn't exist, but that feedback loop seems important. you want, you want to be able to track your false positives. We also want to be able to track your false negatives. 

If you fire or like, if you decide not to hire someone, what happened to that person?

Brett: Which is hard to know because they could be successful in someone else's company and not in your company. So it has its own set of issues. That's true, that has its own set of issues, 

Eeke: but at least it's data. 

Brett: most of the, the, all the work that goes into interviewing and how much of it is just performative nonsense that 

means 

Eeke: Yes. Yeah. 

Or how 

Brett: much of it is, is removing signal

Brett: is still not well instrumented.

Eeke: I think that's totally right. so yeah, I think all of that would be really useful.

Brett: What about, you hinted to this a little bit, but when you think about kind of different rungs of leadership.

Is there a simple way to sort of think when you go from a VP doing it? Just not to get into titles, but to simplify it, VP, SVP, C suite. Do you think there's very different ways to sort of think about the job or expectations or that there's a clear, the clear difference between an SVP and a C suite executive 

is X sort of those types of things?

Eeke: I think it's an ambiguity of problem. It's just like, it's that scales up exponentially. yeah, they sort of, I can't speak to the specific titles, but like the, the most ambiguous problem should be at the like C suite level. And everything kind of scales down from there.

Brett: Do you ever ask to see someone's performance reviews as a part of interviewing an exec? I

Eeke: I never have, but I love that.

Brett: think that's quite interesting. 

so maybe one place to end. You talked about Claire earlier, but maybe you talk about someone else that sort of an exec that you had the chance to work with that sort of shaped your worldview or kind of imparted something consequential on you.

and like, what's the thing that they shared with you? That's has so much residual value.

Eeke: I worked with this incredible design leader at Retool, who, um, as I think simultaneously, maybe the best design leader and product leader I have ever met. I learned a lot from him, but I, you know, the, I think the thing I really learned from him was that the value of the three legged stool of product design and, engineering,

I had always heard, but per your point was one of those, like eyes glaze over sort of things. and I, he really showed me like what incredible product you can build when those three forces come together in like a very real way.

Brett: Who is the person

Eeke: Ryan Lucas.

Brett: and maybe you can kind of bring that to life in more detail, like, what do you sort of mean by that? Or what, what did you see or what did he explain that brought it into focus for you? 

Eeke: It was just in everything we did, like we, we wrote the product strategy together, with our engineering leader and it's the best product strategy I think I've ever written. And I think it was entirely due to the fact that it wasn't just a, like a product view. It also had sort of a really strong technical view, a really strong design view, Retool's product is like, really benefits from these sort of three, three functions, but, I think that's kind of the case for any company that's trying to build really good product.

And so, it just showed up in at our level, but then at every level below that we had, like, very much the three legged stool as well. Sort of the trifecta, you actually, I think, see that surprisingly little. There's always like 1 or 2 functions that are like, really dominant, and in this way, like, you know, I think all of those sort of functions have to kind of.

fight for it. Like you have to kind of figure out how to work together, if that makes sense. but like it ended up, resulting in fantastic products.

Brett: Awesome. Great place to end. Thanks so much for joining.

Eeke: Great. Thank you so much for having me.