The website Fast Company has a great article on how to ask better questions and there are a lot of great takeaways (make sure you read the article to fully get the impact).
I have seen the first problem with questions all too often. People tend to ask multiple questions at once and you can only answer one at a time. In the skeptical community it is similar to “the Gish Gallop”, where there are too many things to answer. In my own experience I had a manager, John Slater, who was great at training you how to ask only one question at a time by simply stating “I will answer you last question first, and if we have time we will go back through the others”.
The other item I was trained in early on was getting comfortable with the silence. A great salesperson I worked with, Gail Mercer-McKay, would prep me before sales calls that she was going to ask a question and that it would become very uncomfortable as you wait for the answer. I was directed, rightly, not to say anything, but to let the person think through the question fully so they could answer. It was a difficult lesson to learn, however it paid dividends. One sales meeting we went to Gail had pre-warned me to let the silence linger when she asked the question. It felt like minutes ticking by. Dead silence. Finally the VP we were meeting with spoke up and we won the deal.
Finally, don’t fish. The quote from the article by Clive Thompson is spot on “The really ‘bad’ questions are leading ones — the questions where you’re fishing for a particular answer.”