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

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.In our conversation, we cover:1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience3. Why teams most often fail (hint: it’s not lack of talent or strategy)4. How busyness often masks deeper issues of self-worth5. Why a “growth mindset” can be problematic6. The importance of legacy and what it means to live a meaningful life7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity—Brought to you by:Eppo—Run reliable, impactful experimentsContentsquare—Create better digital experiencesOneSchema—Import CSV data 10x faster—Where to find Jerry Colonna:• X: https://x.com/jerrycolonna• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/• Website: https://reunion.reboot.io/—Where to find Lenny:• Newsletter: https://www.lennysnewsletter.com• X: https://twitter.com/lennysan• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/—In this episode, we cover:(00:00) Introduction to Jerry Colonna(04:12) Jerry’s key question(06:55) The equation for great leadership(09:37) The big lie of success and happiness(12:12) The consciousn