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I’m very interested in what makes a good interview, and I like to remember the questions that I hear again and again from interviewers like Charlie Rose, Tim Ferriss, and others.  Below are some of the questions I like.

Tim Ferriss asks:
  • Do you have any quotes or quotations that you live your life by?
  • What are three sources that you have learned a lot from in the last year?
  • What is the best investment of money time or energy that you’ve ever made?
  • What $1 or less purchase has made the best impact on your life recently.
  • What is your favorite documentary or movie?
  • If you could put something on a billboard, what would it say?
  • What historical figure do you most identify with?
  • What is an entrepreneur?
  • What are you most courageous about?
  • When have you lost your way?
  • What would you do if you knew you couldn’t fail? (Tony Robbins)
  • What have you changed your mind on in the last year?
  • What is the book that you have gifted most often?
  • When you hear the word successful, who is the first person to come to mind.
  • Who would you most like to emulate?
  • Are there any start up founders or CEOs that you would like to emulate?
  • What would the “old you” think about or say to the “new you”?
  • What advice would you give yourself 10 years ago?
  • What problem do you confront every day that no one has yet solved?
  • How do you grade yourself?
Martin Sorrell asks: 
  • What’s the one thing that keeps you up at night?

Charlie Rose asks asks the shortest questions of any interviewer, as he explains here. Things like: 

  • “What do you mean? Why? Were you surprised? How did you get there?