Speaker

Jerry Colonna

Jerry Colonna

Jerry Colonna co-founded Reboot, an executive coaching and leadership development firm, grounded in the belief that better humans make better leaders. Before coaching, he co-founded Flatiron Partners with Fred Wilson, one of the most successful early-stage investment funds of the 1990s, and was a partner at JPMorgan Chase. He is the author of Reboot: Leadership and the Art of Growing Up and Reunion. His approach combines practical leadership skill-building with radical self-inquiry — the practice of asking destabilising questions about one’s own motivations, history, and complicity.

Key ideas

  • The complicit question — “How have I been complicit in creating the conditions I say I don’t want?”; complicit means accomplice, not perpetrator — it evokes agency, not blame. See Radical Self-Inquiry.
  • The Leadership Equation — practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience; the circled term is resilience.
  • Teams fail from unsorted baggage, not lack of talent — until unconscious patterns become conscious, groups repeat their family-of-origin dynamics; the highest-power person is the leverage point.
  • Attachment is the source of suffering — separate self-worth from outcomes (audience, income, title); treat the work as an art project.
  • Growth mindset can become a fixed mindset — hold any frame loosely or the ego nails it to the floor.

Episodes