Jason M. Lemkin discusses the stress of “leveling” (promoting or replacing) employees as companies cross revenue milestones. He warns against half-hearted or stealth searches for replacements, recounting anecdotes where leaders at roughly $10M–$30M revenue faced difficult choices — including a case where a promoted person quit immediately after being passed over or moved toward a CMO role — and emphasizes clear, decisive hiring actions.
Chapters
The second point is about leveling or topping someone. Look, it's really stressful and we all go through it. You know, I'm hitting 10 million, 20 million. Third, this. I'm not sure Bob can still do it or Jane can still do it. And I'm worried they'll quit if they do it right. Don't, don't hide the ball. Don't try to do a stealth search unless you magically find someone. Like if you bump into someone here and they're your new VP of sales and they're clearly better, you did a stealth search, Congratulations. Walk her into work on Monday and things will be good. But you can't do a half ass search. You can't do something. And I've recently gone through two of these toppings or levelings with a company at about 30 million in revenue. Went through it with one and the person wanted to be a CMO and immediately quit. Immediately quit. Did a lot of did. And things are worse without him now. They're not bad, but they're clearly worse. And it stinks that they left. And it took a few months to hire the person, but this person was unwilling and able to get to the next level.
