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?

My favorite question comes from The Golden Compass:

If you were me, what question would you ask of the Consul of the Witches?

I haven't employed it against people yet, though, and so a better way to approach the issue in the same spirit is to describe your situation (as suggested by many others).