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therufs comments on "Stupid" questions thread - Less Wrong Discussion
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When I'm in the presence of people who know more than me and I want to learn more, I never know how to ask questions that will inspire useful, specific answers. They just don't occur to me. How do you ask the right questions?
Start by asking the wrong ones. For me, it took a while to notice when I had even a stupid question to ask (possibly some combination of mild social anxiety and generally wanting to come across as smart & well-informed had stifled this impulse), so this might take a little bit of practice.
Sometimes your interlocutor will answer your suboptimal questions, and that will give you time to think of what you really want to know, and possibly a few extra hints for figuring it out. But at least as often your interlocutor will take your interest as a cue that they can just go ahead and tell you nonrelated things about the subject at hand.