Eric Siu spent years avoiding firing people because he feared conflict, modeling himself after Gary Vaynerchuk's compassion. He's since learned that direct, honest feedback about specific problems, paired with actionable guidance, works better than vague excuses or hoping employees will quit on their own.
Chapters
I've done well with promoting. I've done worse with firing because Gary Vaynerchuk, the executive, is too much of a bleeding heart, and I've been overly nice. But that used to be my excuse. But the reality was, I don't like the candor and the conflict of telling someone that I subjectively think they stink at their job. And I thought it would instill fear. Hey Dustin, I don't think you're a good manager. You're too snarky to this. I would think like Dustin's gonna walk out of that meeting being like, fuck, I'm gonna get fired. And that was never, like, I didn't know how to get to that place. I've gotten a lot better at sitting down with people and being able to tell them, Hey, hey, hey, this is not working, but real talk, fix it, 'cause this is working great and this is working great and we just tweak this and we're like fucking cruising.