CL224: The Power Of A Well Asked Question – Interview with Jerry Colonna

Jerry Colonna

Jerry Colonna is CEO and cofounder of, an executive coaching and leadership development firm, and he is also the author of REBOOT: Leadership and the Art of Growing Up. Prior to his career as a coach, he was a partner with JPMorgan Partners, the private equity arm of JPMorgan Chase. He joined them from Flatiron Partners, which he launched in 1996 with partner Fred Wilson. He has used the knowledge gained as an investor, executive, and board member for more than 100 organizations to help people lead with humanity, resilience, and equanimity.

In this episode, we cover:
  • 2:15 – The coaching/client relationship
    – Your first coaching session
  • 7:17 – Smuggling in mindfulness
  • 8:45 – The role of mindfulness as radical self-enquiry
  • 10:46 – Five times a day
  • 12:20 – Red, Yellow, Green
  • 15:07 – Hal Gregerson – Asking Better Questions
  • 16:20 – Ed Catmull’s great question
  • 17:34 – Dealing with imposter syndrome
  • 18:00 – The power of a well-asked question
  • 19:08 – What does success look like?
  • 19:33 – What kind of company are we building?
  • 19:47 – What kind of leader am I?
  • 20:11 – Writing your first book
  • 23:59 – The Crow

Resources mentioned in this episode:

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