A Running List of Questions I Like to Ask Successful People

I’m an interviewer at heart. These days, when I meet just about anyone, I approach a first conversation with the mindset of a learner and the goal of really digging into the stuff that normal small talk won’t touch on.

This is a list of questions I’ll ask just about anyone I find interesting (and just asking them can make anyone interesting and interested). I’m posting them here in reserve and in reminder for use when I meet with phenomenally successful people. The goal? Asking the questions you won’t normally get answers for in their public interviews and appearances.

Who are “successful people”? I admit that I’m skeptical of how much the term “success” is thrown around, often without definition. For my working, evolving definition, I’ll say that a “successful person” by my standards is the following:

Successful Person, n. – Someone who is in the process of achieving mastery over the conditions of their own existence. They do not suppress reality or ignore it – they work with it. They have come to a place where they enjoy the process of being.

By that definition, a successful person could be a tennis star Serena Williams, BB&T CEO John Allison, or your old farmer grandfather who never lies, always keeps his word, and is just happy as a clam.

My Questions for Successful People: A Work in Progress

  1. What is one piece of conventional advice that you disagree with most strongly?
  2. What is one piece of unconventional advice that you disagree with most strongly?
  3. What was your biggest mistake? What helped you to identify it? What helped you to get over it?
  4. What is your biggest weakness? What helped you to identify it? What helps you to get over it?
  5. What do you do to gain self-awareness when everyone is out to flatter you? 
  6. When are you closest to a state of “flow”? How do you get there?
  7. How did you find your definition of success? What is it?


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James Walpole

James Walpole is a writer, startup marketer, and perpetual apprentice. You're reading his blog right now, and he really appreciates it. Don't let it go to his head, though.

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