Counterpoint: I've performed hundreds of interviews at early-stage startups, and this is spot-on, fantastic advice. If you can ask questions about things that I

Counterpoint: I've performed hundreds of interviews at early-stage startups, and this is spot-on, fantastic advice. If you can ask questions about things that I have spent time thinking about, that's a really good sign to me that you were able to look at the company from the outside and apply your knowledge to understand what's important. If you can ask questions about things I haven't been thinking about but that subsequently get me thinking, even better. Questions really distinguish you from other candidates more than answers because the fact that they're unprompted means they tell me more about where you focus your attention than do the answers to my questions. > My advice would be to not overthink it. Just ask the questions that are genuinely important to you, and don't try to focus on impressing your interviewer. With all of that said, I still 100% agree with this. The ideal result is that you ask me questions about things that are important to you and that I find those questions compelling - then we've probably got a good match. But do make sure you have some thoughtful, researched questions. Those are always better than "what's the best thing about working here?" regardless of topic.