One general rule: avoid binary/rating questions. So not: "Do you like working at X?" This question has a "right answer" (yes), and you'll always get it. Inste

One general rule: avoid binary/rating questions. So not: "Do you like working at X?" This question has a "right answer" (yes), and you'll always get it. Instead: "What's your least favorite thing about X?" Phrase all of your questions as free-form responses instead of multiple choice. This is very helpful to get interviewers talking. For specific questions, there's a lot of good ones on this thread, so the only specific question I'd add is this one, which I found very helpful for startups and fast-growing companies: "It's 2 years from now, and X has failed. What happened?" Well-run businesses had a well-understood answer about their biggest risks; poorly-run places had platitudes and "it could never happen."