r/Fitness does a weekly "Moronic Monday", a judgment-free thread where people can ask questions that they would ordinarily feel embarrassed for not knowing the answer to. I thought this seemed like a useful thing to have here - after all, the concepts discussed on LessWrong are probably at least a little harder to grasp than those of weightlifting. Plus, I have a few stupid questions of my own, so it doesn't seem unreasonable that other people might as well.
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?
For the narrow subset of technical questions, How to Ask Questions the Smart Way is useful.
But if you don't have a problem to begin with -- if your aim is "learn more in field X," it gets more complicated. Given that you don't know what questions are worth asking, the best question might be "where would I go to learn more about X" or "what learning material would you recommend on the subject of X?" Then in the process of following and learning from their pointer, generate questions to ask at a later date.
There may be an inherent contradiction between wanting nonspecific knowledge and getting useful, specific answers.