Five questions before you sign
The interview is over and the leverage is at its peak. This is the last moment anyone will answer you candidly.
Between the offer and the signature there is a short window in which an employer wants something from you and will therefore answer questions they would deflect at any other stage. Most candidates spend it entirely on salary. These five are worth more.
1. What does success look like at month six, in writing?
You will have asked a version of this in the interview. Ask again now, and ask for it in an email. A manager who can answer specifically has a plan for you; one who answers in generalities has a vacancy to fill. The difference shows up in your first review.
2. Why did the last person in this role leave?
If it is a backfill, this is the highest-information question available to you, and at offer stage you are far more likely to get a real answer. Promoted internally is a good sign. Left after eight months, twice in a row, is a question about the manager rather than the candidates.
3. What is the structure — basic, allowances, variable — and what has the variable actually paid?
Ask what the bonus has paid out at for the last two years, not what the target is. Targets are aspirations; history is evidence. The same question applies to any commission or profit-share scheme, and a straight answer is easy to give when one exists.
4. What is the team's shape going to be in a year?
Is it growing, flat, or quietly being restructured? Are there roles open above you, and is anyone being hired who would change your reporting line? You are joining a trajectory, not a snapshot, and people rarely volunteer a restructure that is already planned.
5. What does the team find hard about working here?
Every workplace has friction — legacy systems, a punishing season, a reorganisation under way, a founder who changes direction. A confident employer will name it honestly. Silence, or an answer that is too polished, is a signal in itself; there is no organisation for which the true answer is "nothing".
And then the paperwork
Once you are satisfied, get everything material in writing before you resign from your current job — the full package, the title, the start date, and any commitment made verbally. Verbal offers are withdrawn more often than people expect, and a resignation submitted against a phone call is the worst position in this entire process.
You are not being difficult by asking these. You are doing the same due diligence they did on you.