Ask HN: Interview tomorrow – How to learn whether an org is “healthy”?

1. Why are they looking externally for a candidate instead of an internal candidate that is more familiar and has a track record with the company than a brand new leader?

2. What were the specific expectations of the incumbent leader and how long have they been in the position? Someone needs to explain what happened and realize that this very same dynamic could happen to you. If nobody communicates with a person that they think their communication is bad, it's a passive-aggressive culture that won't lead to good outcomes more often than not, especially long term.

3. What's the turnover rate for the team? Don't believe whatever they tell you, but make a note. Then try to assess its veracity based upon Linkedin stalking of both currently employed and past employees.

4. What's the highest level of management that is in agreement of replacing this person? If something came from really high up, I'd ask if there was a specific incident. I've seen people let go because they made exactly one hot-headed executive very angry for flippant reasons and while everyone in management that actually knew these people were fine, their hands were tied. That kind of leadership style is micromanagement oftentimes and the toxicity and blame games will eventually make their way down the longer the leader stays.

If the manager was "let go" and offered to stick around until a replacement could be found, that's a much better situation.

The OP writes "they want to replace the existing manager". Chances are this would have been phrased "the existing manager is moving on" if no deceit was involved.

> Would you say the same of someone who gives significant notice of their departure

When to make the information known to the rest of the team should be a management team decision. I don't think there is a one-size-fits-all answer.

> What if that person were a fairly high ranking one in the organizational structure

Finding a replacement before announcing the departure to the team makes sense. It sounds like in the OP's situation the outgoing manager is not aware of his/her status.

> Confidential replacement is pretty typical when the outgoing leader has no apparent (temporary) replacement and transitioning duties twice would be difficult/disruptive. It's not broken culture to ensure the wheels keep turning despite a pending high-profile departure.

Not sure if you are referring to keeping it confidential from the employee being replaced or from the rest of the team.

> ...the presumption that the nature of the search is somehow underhanded or deceitful is pretty one-sided

I think you are suggesting that it is appropriate (not deceitful) to attempt to hire the replacement before informing the current manager. Ideally in situations where something isn't working out, both parties can collaborate to phase things out in a mutually respectful way, especially in a startup.

Yes, in big companies there is an HR department and all sorts of reasons why "typical" HR practices make sense. But a person joining a startup should feel that the team he/she is joining is not typical and has the sort of integrity to act cooperative (in a game theoretic sense) in these sorts of scenarios.

FWIW these sorts of scenarios are inevitable. Sometimes employment arrangements don't work out. How they are handled offers an indication of the character of the management team.