The Wisdom Wall

“The other thing that came out in all of these, like, conversations with folks is, like, if your values aren't aligned, there's, like, literally no way it's going to work. I think it's just actually pretty hard for there to be, like, globally relevant execs. Like, there's, like, the right exec at the right time for your…”

“new leaders have in almost every single scenario a huge incentive To say that they need to change the strategy.”

“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…”

“I, 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.”

“My main view on reference is 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.”

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

“And then step three is, you know, let's say they kind of get past that is, okay, now get in buy-in from the rest of the team. That shouldn't be a, like, a decision-making forum. 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…”

“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, the founder has to decide or the hiring manager.”

“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.”

“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.”

“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 have 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…”

“I personally really worry about the, like, the two-year stints, sort of, like, multiple, like, two-year stints. Like, it just actually isn't enough time to show that you've done anything significant, I think, as a leader. So, like, this is a gross generalization, but it feels a little bit like those are sort of, like,…”

“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 if people have fired a lot. It's only because, like, they're gonna have to in whatever job they're taking on. If they don't have that experience,…”

“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, but it's the hard part is finding the right fit.”

“And I, I actually think 80% 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.”

“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…”

“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 people-y person who can help scale that vision.”

“almost never have I seen like a founder or an exec 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.”

“I 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.”

“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.”

“The second best thing you can do, I think, is 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…”

“Um, if they're, like, a bad culture fit, three months max.”

“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 join a startup. They're just,…”

“The leaders who 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 didn't 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 paste everything that they did.”

“the folks who have 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.”

“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.”

“I know very, quote-unquote, charismatic leaders who are not incredible speakers, but are great writers, or are wonderful one-on-one. So like, 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, but it doesn't have to be in the like, I don't know, Tony…”

“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…”

“I, I think it's, um, ambiguity or 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.”

“You actually, I think, see that surprisingly little. There's always like one or two functions that are like really dominant.”

“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…”

“There's work you need to do to set up the, these execs for success, a hundred percent, this, 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.”

“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.”

“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 like the how they do it or like how they're going to get it done is like they have different strengths and they'll be able to show up…”