My advice is geared towards factual questions, so I'm not sure how helpful it would be for more pure intellectual questions. The most important point I was trying to make was that you should be careful not to pre-bake too much analysis into your question.
Thus, asking "what should I do now to get a high paying job to donate lots of money to charity?" is different from "what should I do now to make the most positive impact on the world?"
Many folks around here will give very similar answers to both of those questions (I probably wouldn't, but that's not important to this conversation). But the first question rules out answers like "go get a CompSci PhD and help invent FAI" or "go to medical school and join Doctors without Borders."
In short, people will answer the question you ask, or the one they think you mean to ask. That's not necessarily the same as giving you the information they have that you would find most helpful.
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.