"What is the best question I can ask myself right now?" is one of the best questions you can ask yourself each day.
Your questions can lead you in the right direction or the wrong direction. That is why it is so important to know the patterns of the best questions you can ask yourself and others.
"What do I need to know about this?" is a tremendously helpful tool to help you gather the type of information that you need to reach your goal. Then ask yourself, "Where and how can I get this knowledge?"
When you meet someone who is a highly knowledgeable expert in a specific area, you can always ask, "What are some of the best questions that you have been asked on this subject?" and "What do you consider the basic principles for understanding this subject?"
(from Rabbi Zelig Pliskin's book: "Conversations With Yourself", pp.183-4) [Artscroll.com])