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Context is a big thing. For example, giving us more context would be helpful. You've mentioned elsewhere that you work in tech. Why is Cheney speaking at your work? Will he know who you are? What can you get away with asking him? How do your co-workers feel about Cheney?

In regard to asking questions, what kind of outcome are you after? If you're after an answer that could be useful to you personally, you might ask a question that he's been asked before, but framed in the context of your own circumstances. If you're interested in asking questions for the benefit of others, then why not coordinate with those others so that the Q&A moves in the direction of most interest to the group?