Jerry Colonna on Radical Self-Inquiry, the Leadership Equation, and Why Teams Fail

Jerry Colonna co-founded Reboot, an executive coaching firm, after a career as a VC partner at Flatiron Partners with Fred Wilson. His first book, Reboot, uses the lens of radical self-inquiry — the practice of asking destabilising questions about one’s own motivations — to argue that better leadership begins with better self-knowledge, not better technique.

Key ideas

• ‘How have I been complicit in creating the conditions I say I don’t want?’ This is Colonna’s signature question. Complicit is deliberate: not responsible, not guilty, but an accomplice — driving the getaway car. The question evokes agency rather than blame, and opens space to ask what one actually wants and whether current behaviour serves it.
• The leadership equation. Practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience. The goal is not becoming a better CEO but becoming a better adult — one who does not destroy themselves or others in the process of building something.
• Teams fail from unsorted baggage, not lack of talent. The most common source of team dysfunction is unconscious patterns imported from founders’ and executives’ histories. Until patterns become conscious, teams repeat them and call the result bad luck or bad people. The leader with the most power is the highest-leverage point for change.
• Growth mindset can become a fixed mindset. When people attach their identity to ‘having a growth mindset’, they create exactly the rigidity the concept was designed to dissolve. The ego categorises behaviours as growth or non-growth and attaches to the category. Loosening attachment to the label — not abandoning the orientation — is the point.
• Attachment as the source of suffering. Colonna draws on Buddhist framing: when external validation (audience size, revenue, title) becomes load-bearing for self-worth, the threat of its removal creates chronic anxiety. The antidote is not indifference to outcomes but separating outcomes from self-worth.

Topics covered

• ‘How have I been complicit?’ — the most important question for leaders
• Leadership equation: practical skills + radical self-inquiry + shared experiences
• Radical self-inquiry in practice: journaling questions and what makes a question powerful
• Busyness as addiction and what it substitutes for
• Shared experiences and the value of honest circles
• Why teams fail: unconscious family patterns in organisational life
• Growth mindset as a fixed mindset risk
• Buddhist framing: attachment, suffering, and the noble truths applied to career
• Lenny Rachitsky as live case study: imposter syndrome, growth anxiety, identity
• Legacy, purpose, and what it means to live into one’s elderhood
• AI and coaching: can self-inquiry be outsourced to Claude?

See also

• Deep notes — Adler frame, glossary, claims by section
• Radical Self-Inquiry — the practice and the “complicit” question
• Leadership Equation — the dry-erase-board model
• Reboot — Colonna’s first book; source of the frameworks
• Jerry Colonna — speaker
• Emotional Fluidity, Nervous System Mastery — adjacent inner-work concepts