The question behind the question
Whenever someone asks me a question, I see two things: the surface question and the thing that is driving the question. Someone, for instance, may ask me how to break the grips their opponent keeps getting on their legs, when they are defending with their Guard. That is the surface question. But what is driving that question, is the fact that something 'bad' happens after an opponent gets a grip on their legs - and they feel that by breaking those grips, the 'bad thing' will go away. The sub-surface question, then becomes " What can I do when someone gets grips on my legs?" as distinct from 'how do I break those grips?'. There is a big distinction here - because perhaps the best result can come from answering the sub-surface question first. 'What can I do when someone gets grips on my legs?" - Answer: Armdrag. This provides a far more meaningful solution than teaching the student how to break the grips.
The bottom line is this. Sometimes the people who do not know the answers are usually the least qualified to come up with the correct question in the first place. Here's my advice - if you are with someone who is an expert in their field (and you trust their opinion) - instead of asking very focussed and specific questions - outline your situation/problem/set of circumstances - and then say 'HELP ME'. Tis will allow them to help you rather than 'constraining' them to provide you with an answer to an ill-informed question.
Often, in my past, my questions themselves have directed the answers that were given to me - when the SOLUTION to the problem was not even addressed. So now, when I coach/instruct, I listen to students questions and try to give thoughtful, insightful and helpful answers - but I also look for the 'question beneath the question' - and if time and circumstances allow - I ry to address that, as well.