The failure mode of a senior appointment is rarely that the executive could not do the job. It is that the job was not what it appeared to be, and that was knowable beforehand.
Ask directly, and ask again of someone who is not selling you the role. A seat that has turned over twice tells you something the job description will not.
Find out where authority genuinely sits, which is not always the org chart. Many senior roles fail on this alone.
If they want you to fix something, someone has attempted it. Knowing what happened tells you whether the obstacle is the problem or the organisation.
If three people give three different answers, you would be walking into an unresolved argument with your name on it.
The people best placed to tell you the truth about a company are the ones who no longer work there.
Understand who owns it and what they want. A founder-run business, a listed company and one owned by an investor with a five-year horizon are three different jobs with the same title. Ask what has to happen for the owners to be satisfied, and when — the answer defines your actual mandate more than any conversation about the role does.
Frame every question as being about doing the job well, because it is. “What would I need to fix first?” and “what has already been tried?” read as seriousness, not suspicion. Any company that treats rigorous questions as a bad sign has answered a different question for you.
You will not learn everything, and some things only become visible from inside. The aim is to eliminate the failures that were knowable — which, in senior appointments that end badly, is most of them.
The early period is not for proving yourself. It is for buying the right to make the decisions you were actually hired to make.
Read → Pay and the offerThe headline number is the least informative part of an equity grant. These are the questions that decide what it is actually worth to you.
Read → Stepping up a levelChief roles are not senior versions of the jobs below them. They are a different contract — with the board, with peers, and with uncertainty.
Read →A short call, your target list, and an honest answer about whether this fits how you are running your search.