Generate a List of Questions to Ask Before Joining a Small Company as a Senior Hire

The opportunity looks interesting and the founders seem credible. The things that will matter most: the financial runway, how decisions actually get made, why the last person in your role left, and whether the equity is real. This generates the questions you should be asking, organised by area, with a note on what a concerning answer looks like versus a reassuring one.

You are considering joining a small or early-stage company in a senior role and you want to assess the company properly before accepting an offer. Generate a list of due diligence questions across the following areas:

1. Financial health and runway (four to five questions, including the things companies prefer not to answer)
2. Founding team and equity structure (three to four questions)
3. Culture and ways of working (three to four questions that go beyond the standard answers)
4. Your specific role (three to four questions about scope, success metrics, and where the previous person is now if the role existed before)
5. Decision-making and leadership (three questions about how decisions actually get made)

For each question, add a one-sentence note on what a concerning versus reassuring answer looks like.