I would like to know more about asking questions to find out information from people you don't know about a how-to skill that I need to know about. How do I interview these nice strangers I call up who have a little time to tell me what I need to know?
I've worked at developing the idea of using the phone book to call up person after person who was doing the thing I wanted to learn more about. I asked each person who seemed to have time to talk with me a couple of questions at at a time, then called the next person and asked them the next few questions. By the time I'd talked to six people, I knew how to do the thing that I wanted to learn. I also had someone to call up for advice when I ran into a snag.
First, try to establish some sort of framework for yourself by being able to ask your question using the proper terminology. All questions are stupid, unless the question is one the asker already knows the answer to. All questions will be rhetorical to the person who already knows the answers. Questions are combative when they have a certain emotional result in mind, for instance, something asked in order to irritate the person and get them to "dance." (This could be an innocent combative irritation, like a five year old who keeps saying "Why?" in case something else interesting will occur.) In some people's eyes, some "combative" questions challenge the authority of the answerer. An example of this is in a debate forum where the questions are deliberately designed to logically trap the answerer to contradict themselves, therefore supposedly proving themselves wrong.
I think one of the more effective strategies to asking effective questions is to admit one of your own assumptions and how it did not match what you expected to happen. This may come from observing and questioning the topic until it tells you about one of its assumptions beforehand. Changing or challenging one of those assumptions often happens for beginners by mistake; making mistakes will reveal even more specifics to ask questions about.
Most people are trained by their education to spot "what is wrong," or "conflicting results" and to ignore what is "normal" or to try to preserve normalcy at all costs. Your job if you can watch someone doing something you want to learn is to observe what is special about how they make the job or activity effortless and problem-free. Sometimes you can ask just that question and get some very useful replies from a good teacher - but sometimes it's up to you to put this together for yourself.
It's very difficult to influence crucial differences when you can't perceive that they exist. It's a tricky job to uncover what we are in the act of taking for granted - but that's a gold mine for learning!