Questions to Ask a Startup Before Joining Startups can be great, but ask about stability politely and directly: - How much runway do you have, and when was the last funding round? - Are you profitable, or what milestone is the next raise tied to? - How has headcount changed in the last year? - How are equity grants structured — vesting, cliff, exercise window? Founders who answer clearly are usually easier to work with, too. Disclosure: I work on Linkjob AI. For real-time help in live interviews, see AI tool for job interviews.