Dave Kashen discusses how to handle employee departures in startups. Founders often wait too long to let people go, then find the team culture improves once a poor fit leaves. The conversation covers timing, conflict, and why leaders should act sooner rather than later.
when someone's let go, I usually let them go a little late and I'm usually already telling them that they aren't doing a good job in ways that are not the nicest way to do that. And for what it's worth, I think like my way tends to result in like chaos fast. But luckily that also means that I let go of people fast. There's also like the alternate personality type that has no chaos but lingers for, you know, months and years. And what you don't realize in that situation is, yeah, there was no conflict, but also subconsciously there was a lot of damage being done.
Yes.
To, you know, if there was a lack of confidence in the relationship and you were sort of not giving that person their full opportunity to do what they wanted. So either way, you know, I think that when a departure occurs, yeah, sadness, embarrassment, frustration, you know, guilt.
Yeah. And so who wants to feel all those things, right? So, you know, that's, I think, the trap that a lot of founders fall into is like, I don't want to feel that. So then they avoid it. And then, you know, like you said, I've— it's probably the most cliché and also true line that I've heard from founders, which is like, I always wish I had done it sooner. I've literally never met a founder who's like, oh God, I wish I'd waited a little longer to let go of that person. Literally never. And so every time, at least I've seen it, once they let the person go, first of all, the stories they made up about the bad things that might happen, especially with senior people. Oh my God, if I let go of my head of sales or head of engineering, you know, like that could be catastrophic and the company will burn down and We won't be able to raise money, all these things. And then in many cases, I see the literal opposite happen. Be curious if you have examples like that, where like team members step up in surprising ways. The, like, you know, the culture sort of uplifts because there was a way that that person, because they weren't a fit, were kind of, you know, anchoring down the culture or the team.
So.
I think your earlier point, like, churn is normal and it's a part of the experience, um, is important both if you're a team member, that you don't make it mean too much about you, right? Like, startups are an evolving creature, and you might have been a perfect fit for year 1 or year 0 to 2, and it's no longer a fit. It doesn't mean you're a bad human, that you're not valuable and valid. It just may no longer be a fit. And then, you know, for founders and leaders, Um, I, you know, there's this, there's this kind of meme, um, that I learned in, in Joe Hudson's masterclass around, um, called Enjoy Over Manage. And he makes this point that like, if you think about your best team members, best employees, they don't actually require that much management.
