Jerry Colonna is an executive coach, author, and the co-founder and CEO of Reboot.io, a leadership development firm. Known for his focus on “radical self-inquiry,” Colonna helps entrepreneurs and executives navigate the psychological and emotional challenges of leadership. Before transitioning to coaching, he was a prominent venture capitalist and partner at Flatiron Partners.

Colonna’s work connects effective leadership directly to personal growth, asserting that inner development is essential to guiding others. His core teachings invite an ongoing examination of the self-awareness, responsibility, and humanity that authentic leadership requires in practice.

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Key Learnings & Philosophy

These points encapsulate some of the core tenets of Jerry Colonna's teachings on leadership and personal growth.

  1. Better Humans Make Better Leaders: The foundational belief of Colonna's work is that leadership development is fundamentally about personal development. To lead others effectively, one must first commit to their own growth and humanity. [1][2]
  2. Radical Self-Inquiry is Essential: Leaders must courageously and compassionately examine their own inner worlds, including their fears, self-deceptions, and unresolved issues. This process is crucial for authentic leadership. [3][4]
  3. Embrace the art of growing up: True leadership involves a continuous process of maturation, which means facing difficult truths and taking responsibility for one's life and choices. — Reference: Reboot: Leadership and the Art of Growing Up
  4. Confront Complicity: A cornerstone of Colonna's coaching is asking the question: "How have I been complicit in creating the conditions I say I don't want?" This prompts leaders to recognize their role in their own struggles. [2][7]
  5. Leadership is Not About Having All the Answers: Many leaders feel pressured to know everything. Colonna teaches that true leadership lies in asking the right questions and creating a space for others to find their own answers. [8]
  6. Work Can Be a Place of Self-Realization: Colonna challenges the idea that work must be a depleting force in our lives. Instead, it can be a primary vehicle for achieving our fullest potential. [3][9]
  7. Embrace Failure as a Learning Opportunity: Fear of failure is a significant obstacle for entrepreneurs. Colonna advises viewing failure as an inevitable and valuable part of the journey toward success. [10]
  8. Cultivate Resilience and Adaptability: The entrepreneurial path is volatile. The ability to recover from setbacks and adapt to changing circumstances is more critical than any single strategy. [10]
  9. Lead with Purpose and Passion: A deep sense of "why" is what sustains leaders through difficult times. This purpose provides the motivation to persevere when challenges arise. [10]
  10. Focus on Your Unique Value: Leaders and organizations should have a clear understanding of what makes them unique and stay true to that, rather than trying to be everything to everyone. [10]
  11. Authenticity is the Core of Effective Leadership: To lead authentically, one must have a deep understanding of oneself, including both strengths and weaknesses. [11]
  12. Difficult Relationships are Opportunities for Growth: People who frustrate or challenge us often mirror our own unresolved issues. They present a chance for profound self-development. [11]
  13. Unresolved Personal Issues Manifest in Leadership: Leaders often project their own unrecognized traits onto others, leading to conflict. Self-awareness can mitigate this. [11]
  14. Find Fulfillment in Purpose, Not Just Achievement: True satisfaction comes from aligning one's work with a personal sense of purpose and living with honesty day-to-day. [11]
  15. The Journey of Radical Self-Inquiry: This process involves skillfully and compassionately exposing self-deception to reveal one's true self. [5]
  16. On culture as repeated creation: A company's culture is not defined by abstract values on a wall, but rather by what is repeatedly and intentionally created through ordinary interactions and decisions about accountability and forgiveness. — Reboot Blog
  17. On what performance reviews reveal: Performance reviews are more than just evaluations; they reflect an organization's core beliefs about human nature and the possibility of growth and redemption for its people. — Reboot Blog
  18. On truth without fixing: Fostering environments where colleagues can speak their truth without fear of judgment or the pressure to be fixed helps eliminate isolation. — Lenny's Newsletter: Jerry Colonna

Top Quotes

  1. "Until we make the unconscious conscious, we will be dictated by it and call it fate." [7][12]
  2. "How have I been complicit in creating the conditions I say I don't want?" [7][8]
  3. "What am I not saying that needs to be said?" [7][8]
  4. "What am I saying that's not being heard?" [7][8]
  5. "What's being said that I'm not hearing?" [7][8]
  6. "The first act of becoming a leader is to recognize this being so. From that place, we get to recognize what skills we need to develop and who we really are (and are not) as leaders." [7][13]
  7. "Listening opens that which pain has closed." [8][14]
  8. "When we stand still, we run the risk of remembering who we are." [14]
  9. "Remember, the higher up the pole the monkey climbs, the more his ass shows." [8]
  10. "Stop spinning, stop pitching me, stop telling me you're crushing it. Sit still and ask yourself why things are the way they are and why they aren't the way you'd like them to be." [8]
  11. "Learning to lead yourself is the hardest part of becoming a leader." [8]
  12. "The alchemy of becoming yourself is the ultimate magic act and the fullest expression of leadership." [8]
  13. "When leaders fail to look at themselves, they turn their inner turmoil and very human contradictions outward." [8]
  14. "How would we feel if our children were to work for the company we've created or the team we lead?" [8]
  15. "We need dreams. But willfully ignoring what is true is not the same as dreaming. It's delusion; and delusion leads to terrible decisions and, even worse, the destruction of trust." [7][13]
  16. "I am not what has happened to me; I am what I choose to become." [14]
  17. "To live well is to see wisely and to see wisely is to tell stories." [14]
  18. "Taking your seat means defining your life." [7]
  19. "One of the hallmarks of mental health is the ability to hold conflicting feelings." [7]
  20. "The way to guide is to ask and not to tell." [7]
  21. "I came to understand that, while people might not see you, might not get you, you could use that fact to survive." [14]
  22. "If you could give up the need for measurable progress... and then focused on doing what is right and true each day... you'd live in congruency with your truest self." [8][12]
  23. "Time and again I've watched hearts break open, so that true and authentic leaders can emerge." [13]
  24. "The quality of a leader is reflected in the standards they set for themselves." [1]
  25. "Better humans make better leaders." [1]
  26. "What is not encouraged in our children is being yourself." [1]
  27. "Your mission is not just to be a better person or to make a better company, but to work towards creating a better world." [3]
  28. "The necessary first step is for leaders and others who hold power to see themselves clearly." [3]
  29. "We are effectively cutting off access to 50% of The Human Experience because we don't know what to do with it." [5]
  30. "There is something powerful and purpose-driven in acknowledging and living in that gap between who we are and who we'd like to be—without getting sucked into guilt, without getting sucked into shame..." [2]
  31. "We tend not to teach our children how to speak in a way that is life-giving and life-affirming." [2]
  32. "My co-founder, Ali Schultz, taught me the wisdom of horses. Horses... do not base their choice of the leader of their herd on strength or intellectual wisdom." [7]
  33. "I'm no longer striving. Seat taken, he no longer needs to define himself by what he's doing." [7]
  34. "Are you using work as a prop for self-meaning?" [8]
  35. "Failure is inevitable in entrepreneurship. But it's not the end of the world. In fact, failure can be a valuable learning opportunity." [10]
  36. On redemptive leadership: "Redemption is the work of restoring something to its intended purpose. A redemptive leader does not lower standards. A redemptive leader refuses to reduce another human being to their worst moment." — Reboot Blog
  37. On work as self-development: "The best work of our lives isn’t simply what we produce. It is the work we do on ourselves while we are producing it." — Reboot Blog
  38. On coaching that challenges illusions: "Good therapy and good coaching exist not to protect our illusions and projections but to challenge them." — Reboot Blog
  39. On growth through friction: "Healing requires rupture. Presence requires friction. Growth requires moments where we feel our defenses tremble." — Reboot Blog
  40. On the ethics of inner work: "If unexamined suffering becomes harm, then how we relate to our inner life is not just a personal matter. It is an ethical demand." — Reboot Blog
  41. On confronting what we avoid: Discarding someone else is often easier than confronting what we have not yet been willing to face in ourselves. — Reboot Blog
  42. On the price of bypassing baggage: "If you continue to bypass sorting out your baggage, there’s going to come a day where you’re gonna have to pay that price." — Lenny's Newsletter: Jerry Colonna
  43. On what belonging costs: "What do I need to give up that I love in order to have the systems of belonging that I want?" — Reunion: Leadership and the Longing to Belong

Learn more:

  1. Jerry Colonna On Rebooting Your Life And Leadership - Robert Glazer
  2. Jerry Colonna: The CEO Whisperer The Knowledge Project Ep. #178
  3. Reunion: Leadership and the Longing to Belong by Jerry Colonna - Reboot.io
  4. Reboot: Leadership and the Art of Growing Up: Jerry Colonna
  5. Leading with Empathy and Cultivating Connection in Leadership with Jerry Colonna
  6. Reboot: Leadership and the Art of Growing Up by Jerry Colonna | Goodreads
  7. Quotes by Jerry Colonna (Author of Reboot) - Goodreads
  8. Reboot by Jerry Colonna: Worth the Read - Denise Corey Coaching
  9. Jerry Colonna - On Coaching & Speaking - Reboot.io
  10. Overcoming Adversity in Business Lessons From Jerry Colonna | by Srinivas Rao | Medium
  11. Reboot by Jerry Colonna: Book Overview & Takeaways - Shortform
  12. Top 2 Jerry Colonna Quotes (2025 Update) - QuoteFancy
  13. Quote by Jerry Colonna: “Time and again I've watched hearts break open, ...” - Goodreads
  14. Best Quotes Of Reboot By Jerry Colonna With Page Numbers By Jerry Colonna - Bookey