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 12 insights Episode Page ↗
Jerry Colonna, co-founder & CEO of Reboot, discusses radical self-inquiry, the dangers of a fixed "growth mindset," and how leaders' unresolved personal issues often cause team failures. He shares an equation for cultivating great leaders and resilience.
Actionable Insights

1. Embrace Radical Self-Inquiry

Regularly ask, “How have I been complicit in creating the conditions I say I don’t want?” to evoke your own agency and cut through self-delusion, rather than blaming external factors.

2. Cultivate Leadership & Resilience

Develop enhanced leadership and greater resilience by combining practical skills, radical self-inquiry, and shared experiences, which helps you grow without feeling overwhelmed or miserable.

3. Ask Powerful Self-Inquiry Questions

Regularly ask yourself: “What am I not saying that I need to say?”, “What am I saying that’s not being heard?”, and “What’s being said that I’m not hearing?” to uncover hidden truths and foster personal growth.

4. Confront Your Unsorted Baggage

Address discomfort and unresolved personal issues now, as ignoring your “unsorted baggage” will inevitably lead to a higher price in future suffering, depression, or self-sabotage.

5. Detatch Self-Worth from Outcomes

Recognize that your value as a human being is unshakable, independent of success or failure, to reduce suffering caused by attachment to external achievements and the need to quiet self-doubt.

6. Hold Mindsets Loosely

Approach concepts like a “growth mindset” with flexibility, avoiding the trap of rigid adherence, as fixing on one “proper” way can lead to attachment and therefore suffering.

7. Leaders: Do Your Internal Work

If you hold power in a team, commit to radical self-inquiry and resolve personal issues, as your unresolved “demons” will otherwise manifest as dysfunction within the group.

8. Focus on Intrinsic Purpose

Engage in work and projects for the enjoyment of the challenge and the intrinsic satisfaction of creation, rather than solely to quiet self-doubt or achieve external validation.

9. Create Shared Experience Spaces

Seek or create environments (like circles or trusted groups) where you can authentically share truths and vulnerabilities without judgment or the need for “fixing,” fostering connection and reducing self-delusion.

10. Leverage AI for Self-Reflection

Utilize AI tools (like ChatGPT or Claude with memory) as a “writing and thinking partner” by uploading journal entries or meeting transcripts to gain new perspectives and generate further self-inquiry questions.

11. Examine Your Life

Embrace the responsibility to examine your own life and “shit” through self-inquiry, particularly if your role involves leading or impacting other people, to avoid unconsciously repeating dysfunctional patterns.

12. Identify Benefits of Dysfunction

If you’re on a dysfunctional team with less power, ask yourself how you might be complicit or benefiting from the dysfunction to understand your role and learn from the experience.