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

AI Summary

5 min read

Jerry Colonna, CEO of Reboot and former VC, discusses how leaders often perpetuate the problems they complain about through unexamined patterns from childhood, using radical self-inquiry to build agency, resilience, and better teams without added suffering.

Core Question for Agency

Colonna's key prompt—"How have I been complicit in creating the conditions I say I don’t want?"—highlights subtle ways people contribute to unwanted situations without implying full blame. "Complicit" evokes being an accomplice, like driving the getaway car, not robbing the bank. It uncovers delusions, such as claiming to hate busyness while feeling unnerved by an empty calendar, because busyness quiets deeper insecurities. This fosters agency by revealing how behaviors serve hidden needs, like proving worth or avoiding discomfort.

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What you'll learn

1 `* (04:19) **Core Question: How Have I Been Complicit?**`
2 `* (07:14) **Leadership Equation: Practical Skills + Radical Self-Inquiry + Shared Experiences = Enhanced Leadership & Resilience**`
3 `* (12:34) **Pivot from Success Myth to Consciousness**`
4 `* (23:40) **Radical Self-Inquiry Questions for Journaling**`
5 `* (27:11) **Shared Experiences: Bootcamps & Truth Circles**`
6 `* (30:24) **Busyness Trap & Attachment to Growth**`
7 `* (40:46) **Buddhist Insights: Four Noble Truths on Suffering & Attachment**`

+ Full timestamped outline available in the app

Show Notes

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 resilience

3. Why teams most often fail (hint: it’s not lack of talent or strategy)

4. How busyness often masks deeper issues of self-worth

5. Why a “growth mindset” can be problematic

6. The importance of legacy and what it means to live a meaningful life

7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots

8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity

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