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Lenny's Podcast: Product | Career | Growth
Lenny's Podcast: Product | Career | Growth

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

May 8, 2025 · 1h 22m
AI Summary
  • Jerry Colonna's radical question 'How have I been complicit in creating the conditions I say I don't want?' unlocks self-awareness and reveals unconscious patterns limiting leadership
  • His foundational equation: practical skills + radical self-inquiry + shared experiences = enhanced leadership; teams fail most often not from lack of talent but from leadership blind spots
  • Busyness masks avoidance of deeper work; combining executive coaching with self-inquiry enables authentic, compassionate leadership and organizational resilience

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