Radical self-inquiry: why leaders fail and how to grow up

Executive overview

Leaders fail not from lack of skill, but from unexamined psychological patterns — childhood conditioning that drives behaviour below the level of awareness. Jerry Colonna's framework combines practical skills, radical self-inquiry, and shared experience to build both leadership capacity and resilience.

The goal is not to become a better executive. It is to not destroy yourself in the process of becoming one.

Better humans make better leaders — and that starts with asking questions that take your breath away.

The complicity question

• "How have I been complicit in creating the conditions I say I don't want?"
• Complicit does not mean responsible — you are driving the getaway car, not robbing the bank
• The question targets agency, not blame
• Example: claiming you hate busyness while feeling unnerved when your calendar is empty
• Self-delusion and attachment are the two primary sources of suffering (Buddhist framing)
• Asking the question daily keeps it a practice, not a one-time event

The leadership equation

• Practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience
• People come for the "how"; the deeper work is the "why"
• Resilience is the point — not just performance
• Colonna nearly died from depression despite outward success; the equation is built around preventing that

Radical self-inquiry: key questions

• What am I not saying that I need to say?
• What am I saying that's not being heard?
• What's being said that I'm not hearing?
• How have I been complicit in creating the conditions I say I don't want?
• You know you're in the right zone when the question takes your breath away
• You don't have to share answers with anyone but yourself — though a coach, therapist, or trusted group can help
• Journaling works best when anchored to specific, uncomfortable questions

The childhood roots of adult patterns

• Success-seeking is often driven by childhood beliefs about love and safety, not by the goal itself
• Colonna's "lemon drops" story: his grandfather's pantry symbolised security; he became a hotshot VC chasing that feeling — and still didn't feel safe
• Carl Jung: "Until you make the unconscious conscious, it will direct your life and you will call it fate"
• Unsorted childhood baggage does not disappear; it surfaces later — often as sabotage of the success you built
• Bruce Springsteen spent 25 years in psychoanalysis and writes about the cost of not sorting your baggage
• Avoidance strategies (overwork, substance abuse, spiritual bypassing) push suffering away temporarily and increase it long-term

Attachment and the growth trap

• When a project succeeds, stakes rise, identity attaches to outcome, anxiety follows
• The deeper attachment is not to money or comfort — it's to the belief "see, I'm not nobody"
• Buddhist second noble truth: that which we do to push away suffering increases suffering
• The couch, the house, the subscriber count — when acquired to prove self-worth, they become sources of fear, not safety
• Approaching work as an art project — holding the outcome loosely — is a more durable motivator than fear
• Self-compassion, not anxiety, can drive ambition without the crash

Growth mindset: where it goes wrong

• Growth mindset is useful; the problem is when the ego fixes it as doctrine
• Peter Senge: "It is virtually impossible to challenge the assumptions that made you rich in the first place"
• Beginner's mind opens possibilities; success tempts the ego to close them down
• Holding mindset loosely — staying present to changing dynamics — is the actual growth
• "Stay attached to the growth. Hold mindset a little loosely."

Shared experiences

• Solo self-inquiry is powerful; doing it in a trusted group multiplies it
• Reboot's original CEO boot camps: strangers sitting in a circle, holding space without fixing or judging
• Entrepreneurial culture socialises people to perform success and hide struggle
• A circle of people who just have your back creates conditions for truth-telling
• Good podcasts and intimate public conversations can open the same space

Teams and the leader's shadow

• Teams rarely fail from lack of talent or strategy — they fail from unresolved individual patterns playing out in the group
• Groups, like families, develop roles: scapegoat, truth-teller, jokester who defuses tension
• Example: an executive team that made jokes every time a painful topic arose — the CEO recognised it immediately as his family dynamic
• Without individual self-inquiry, groups repeat the dysfunctional patterns of their founders' families of origin
• The person with the most power sets the emotional template for the whole organisation
• If the leader won't do the inner work, the team becomes a manifestation of the leader's unresolved issues

For team members when the leader won't change

• Ask: how have I benefited from the dysfunction here?
• Benefit doesn't mean money — it means familiarity, comfort, a known role
• If you keep finding yourself on dysfunctional teams, the pattern is worth examining

On AI and what remains human

• The current AI shift is different in kind from previous technology transitions
• Likely outcome: tasks that don't require presence and connection get automated away
• What may be elevated: strategic thinking, conceptualisation, genuine human-to-human contact
• AI can be used as a radical self-inquiry partner — upload journals, ask it the hard questions, use it to surface blind spots
• Presence and connection are the things worth protecting

Legacy and meaning

• The question animating Colonna now: what kind of ancestor to my descendants do I want to be?
• Not about ego — about having a frame of meaning that settles the anxiety of daily uncertainty
• Eulogy thinking: at the end of my days, what would I like people to say about me?
• His answer: he gave a shit about the world, he cared, he tried, he was kind
• Meaning — not achievement — is what eases suffering and makes presence possible
• The toppled oak tree: lived its purpose of providing shelter and shade, now slowly dissolving into the earth