The Exchanges

Q Do you think it's, it's vastly different than hiring non-leaders? And if so, why?

A 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 org's 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 isn't 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 founder's judgment. In the end, judgment is almost like the most important value you have as a founder or 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, 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 lik…

AI assessment note: “The stakes are just so much higher with leaders.”

Q 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?

A On the interview process itself, the thing you really need to figure out is, like, you're gonna 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 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 Tillman bias. They just happen to have, 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 did it look like, and what did it look like after? And often…

AI assessment note: “On the interview process itself, the thing you really need to figure out is”

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

A 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 gonna be able to, like, whether they're really executing as, 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 leade…

AI assessment note: “if they're, like, a bad culture fit, three months max.”

Q 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 sector, how important is any of that?

A 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 I mean, 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, I get, you know, again, my sort of friend Id Raverson 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's space.

AI assessment note: “I think it's quite useful just because pattern matching is quite useful.”

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

A Even some of his 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, 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, MAUs, 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, 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. So you want, you want to be able to track your false positives. You also want to be able to track your false negatives. If you fire, or like if you…

AI assessment note: “how big were this person's teams? How did this team change over time?”

Q 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.

A 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 worst fit leaders who, who we hired and haven't sort of been lucky enough to talk to a bunch of founders and 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.

AI assessment note: “Most of this actually came out of my, my own frustrations”