When I interviewed with an early-stage startup, I met with the CEO and interviewed him just as much as he interviewed me, and I asked questions like: - are you

When I interviewed with an early-stage startup, I met with the CEO and interviewed him just as much as he interviewed me, and I asked questions like: - are you profitable? - if you had zero revenue starting today how long would you last? - have you ever missed payroll? His candor in answering these questions was a big plus for my decision to join. Note, these were asked near the END of the interview process, actually after they made me an offer. In general, after you get the written offer is a good time to ask any final hard questions to confirm whether you want to hitch yourself to their wagon for the next couple years. You should be prepared for many of the questions you listed to be legitimately answered with "I don't know exactly what the future will hold". E.g. A business planning for a buyout might later realize they are better off on their own, so it's better for all if they hadn't told you one thing before and then changed course.