The higher you climb, the more nuanced the questions get — and the less the old answers fit.
This was a particularly good month for the career questions that Lenny’s newsletter get from senior leaders. The pattern with these is that the obvious answer is usually the wrong one — and the real issue is rarely the one being asked. If you’re not at the leader level yet, they’re still worth a read — a window into what your manager is wrestling with, and a couple of them might be you in a few years.
According to Lenny’s newsletter, here are some common questions bubbling up from senior product leaders right now :
1) When the person you sponsored becomes unmanageable.
Years ago you took a bet on someone, gave them scope past their level, watched them crush it. Now they’re a pain to manage, and you’re the obstacle in their way. How did things get so out of hand — and how do you get control back ?
2) When the safe move is also the lucrative one.
A senior product exec is being heavily recruited — double or triple the pay of just a few years ago, especially at big tech. With AI washing out the little guys, taking the money and the safety looks like the obvious play. So when does it not make sense ?
3) The PM on the merry-go-round.
A director-level PM has had three short stints in five years — a layoff, a fit issue, a performance miss — and is asking whether AI-native roles or founding is the right reset. Conventional wisdom says find the best job at the best company. But once you’re on the merry-go-round — a pattern of abrupt endings, not just layoffs — the honest answer flips : you need a new northstar, one that has you play defense and even settle, perhaps for the first time in your career.
4) The “find a great manager” trap.
A PM executive interviewing for her next role is optimizing hardest for finding a great manager. But most managers at the top of a company didn’t get there because of their management skills — so a great one is rarer than you’d hope. The real question isn’t how good your next manager is — it’s how much the role actually requires one.
5) Managing someone far more senior than you.
An IC PM at a hot startup is suddenly asked to manage someone who was a director at their last job. The intimidation is real. The mistake is assuming they don’t need to be managed.
To conclude, What changes across all five is that the playbook that worked earlier in your career doesn’t fit the same way once you have reports, real comp on the line, and the credibility that comes with seniority. The fuller diagnoses live on the podcast itself.
