Here's a question I've been pondering a lot: What are good questions to use to actually learn something about a person? (If you suggest "what kind of music do you listen to" ... you're fired.) If they're not the same for everyone, and I expect that they aren't, how do you find them?

I don't think that a prepared interrogation is the way to do it. Instead, I think you need to listen carefully to what is said in casual conversation ("What kind of music?" works fine!) and then ask followup questions to draw them out. Example: "You don't like country? Me neither. What is the thing about it that annoys you most."