When I interview, I don't ask many questions. Instead, I simply open with, "What can I tell you about the company?" It forces candidates to think of questions to ask me, rather than inviting them to recite canned, rehearsed responses about their background and goals.
When the interviewee finishes answering my first question, I continue, "What else can I tell you?" I do this over and over again for most of the interview.
Probably for this reason, a current employee told me he felt intimidated during his interview with me. But I was surprised. I'm not trying to be tricky. It's a legitimate question. I learn a lot more about someone--and his thought processes--from the questions he asks.
I have found that the smartest, most agile and innovative people are those who ask a lot of questions. I pay careful attention to the quality of the questions job candidates ask, the way they ask them and listen to the answers, and then construct follow-up questions. This process tells me if candidates are good learners, and gives me an idea of how they navigate the unknown.
It also tells me a lot about what's important to my interviewees. For example, if someone asks me about technology, she's likely a person who thinks most about the product and innovation. If the first questions she asks are about vacation policies, that's also very telling.
I usually wrap up my interviews with two simple questions. The first is: "What are you not good at?" This often throws people off. They're used to giving a "pitch" about their strengths. But I explain that I need to know what they're not good at because, as a manager, I need to help them develop. And I need to make sure I can either help them develop in that area of need or surround them with other people who can.
My final question is: "Do you want this job and would you be successful doing it?" I explain that I hate firing people, so I need them to be honest with themselves and with me about whether or not they truly feel they could be superb in the role.
To summarize, here are my questions:
Remember, you learn a lot more from the questions people ask than the answers they give.