Lenny's Podcast: Product | Growth | Career

How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

1433 snips
May 8, 2025
Jerry Colonna, a renowned executive coach and CEO of Reboot, emphasizes radical self-inquiry as a tool for transformative leadership. He poses a thought-provoking question about complicit behaviors in creating undesirable conditions. The conversation explores why teams fail beyond mere talent and the personal implications of busyness. Colonna also critiques the concept of a 'growth mindset' and discusses the evolving role of AI in self-discovery. Ultimately, he urges listeners to redefine success by prioritizing authenticity and meaningful legacy.
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Agency Through Radical Questioning

  • Ask yourself how you've been complicit in creating the conditions you claim to dislike.
  • This question evokes your agency and reveals unconscious patterns holding you back.
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Leadership Equation Explained

  • Leadership success combines practical skills, radical self-inquiry, and shared experiences.
  • This blend fosters enhanced leadership and greater resilience.
00:00 / 00:00

Success without Assholery

  • A 19-year-old once asked Jerry if he had to be an asshole to be successful.
  • Jerry affirmed you can be successful without being miserable or unkind.
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