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The most successful method is to have a list of prepared questions that you plan to ask. Asking profound questions does not happen naturally right away. If questions are prepared in advance, the questions will be more thoughtful and having a list of questions will help prompt you to ask them. If it doesn’t work very well the first time, don’t give up. Keep trying. Write down better questions. Like anything the more your practice and apply, the better you will become at that particular skill. Asking profound questions is an art as well as a science. Having prepared questions to ask in advance will help you kick start learning that skill.

Tracy O'Rourke

Tracy is a Managing Partner & Executive Advisor at She is also a Lean Six Sigma Green Belt Instructor at University of California San Diego and teaches in San Diego State University’s Lean Enterprise Program. For almost 20 years, she has helped leading organizations like Washington State, Charles Schwab and GE build problem-solving muscles.