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

Literature notes on the Lenny’s Podcast conversation (recorded ~early 2025). Jerry Colonna co-founded the coaching firm Reboot after a VC career (Flatiron Partners with Fred Wilson; partner at JPMorgan Chase); he is the author of Reboot and Reunion. Lenny calls these “Trojan Horse” episodes — product listeners arrive for tactics and get the process of being human. The conversation became a live coaching session, with Lenny as the case study.

Four questions [Adler frame]

Q1 — What is the whole about? That better leadership begins with better self-knowledge, not better technique. Colonna’s claim is that the patterns sabotaging leaders and teams come from “unsorted baggage” — unconscious patterns imported from childhood — and that the antidote is radical self-inquiry: asking destabilising questions about one’s own motives and complicity.

Q2 — How is it argued? By demonstration. Colonna defines a few load-bearing questions, then turns them on Lenny in real time (busyness, imposter syndrome, attachment to the newsletter’s growth), so the listener watches the method work. He grounds claims in his own near-suicidal depression at the height of outward success, in Buddhist doctrine (the four noble truths; attachment and self-delusion as sources of suffering), and in named cases (a CEO whose team can’t decide; a client whose executive team deflects pain with jokes “just like my family”).

Q3 — Is it true? It is a wisdom-tradition argument, not an empirical one, and Colonna is explicit about that — he leans on Springsteen’s 25 years of analysis, Jung, Peter Senge, Parker Palmer rather than data. The internal logic is consistent and the live demonstration is persuasive; the strongest claim — teams fail from unsorted baggage, not lack of talent — is asserted from coaching experience [?] and would be hard to falsify, but coheres with the worked examples.

Q4 — What of it? A practice (not a destination): a small set of questions a leader can ask daily, a structure (the Leadership Equation) for why self-knowledge plus shared honesty beats skills alone, and a reframe of growth, busyness, and AI through attachment. The operative move for anyone with power: examine your own complicity before blaming the team.

Glossary

Radical self-inquiry: the practice of asking questions one is socialised not to ask — about motive, history, money, self-worth, complicity — to cut through self-delusion. “Radical” because the questions take your breath away [§ Radical self-inquiry]. See Radical Self-Inquiry.
Complicit (vs responsible): complicit ≠ responsible; think accomplice — “you are driving the getaway car, you’re not sticking up the bank teller.” The word is chosen to evoke agency, not blame [§ The complicit question].
The Leadership Equation: practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience. The circled term is resilience — the real point is not becoming a better CEO but growing up without destroying yourself [§ The Leadership Equation]. See Leadership Equation.
Shared experiences: sitting in a circle of people who “just have your back,” answering breath-taking questions without being fixed or judged — the antidote to the entrepreneurial norm of bullshitting [§ Shared experiences].
Attachment / self-delusion: in Colonna’s Buddhist framing, the two biggest contributors to suffering — attaching self-worth to outcomes (audience, income, title), and pretending everything is fine [§ Attachment].
Spiritual bypassing: using working-out, work, substances, or ayahuasca/mushroom weekends to avoid tending the parts of yourself that need attention, rather than confronting them [§ Unsorted baggage].
Growing up: the subtitle of Reboot — “leadership and the art of growing up” — framed as a practice of continuous inquiry, not a one-time arrival [§ Growth mindset].

The complicit question [§ The complicit question]

Colonna’s signature question: “How have I been complicit in creating the conditions I say I don’t want?” The two halves matter. Complicit is deliberate — not responsible, but accomplice: “you are driving the getaway car, you’re not sticking up the bank teller.” It is not “how am I to blame for the shit in my life?” but a way to evoke your own agency — to see how you have been deluding yourself. His worked example: “I say I don’t want to feel busy all the time, but the truth is I feel unnerved and disconcerted if my agenda isn’t jam-packed.” The question asks: how does it serve me to feel exhausted — and is there a more conscious way to get that feeling? See Radical Self-Inquiry.

The Leadership Equation [§ The Leadership Equation]

Improvised on a dry-erase board at Naropa University (the Buddhist university where he was a trustee), the equation:

practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resilience

Practical skills — the “how” people come to a coach for (how to do the job, how to live).
Radical self-inquiry — where Colonna “drives them crazy” by asking instead: tell me about your father, your relationship to money, to self-worth.
Shared experiences — the act of talking about “the craziness in your head” with others.

On the board he circles “resilience”, because that is the real purpose. In his late 30s, despite outward success, his lifelong depression had become so bad he was suicidal. “I get you want to be a great CEO — what I really care about is you not killing yourself in the process.” The whole equation reduces to: how do we become the adults we were born to be without feeling like crap? The big lie, socialised from childhood, is that reaching success — the money, the house — will make you happy. Its rebuttal is the 19-year-old at a Philadelphia talk who summed up everything Colonna is about: “you don’t have to be an asshole to be successful” — and the corollary, “you don’t have to feel miserable just because you’re trying to create a career.” See Leadership Equation.

Radical self-inquiry: the questions [§ Radical self-inquiry]

The “hack” is consciousness — raising your level of awareness so you are in the driver’s seat rather than running a learned childhood behaviour. Journaling has grown popular, but people don’t know what to journal. Colonna’s questions:

How have I been complicit in creating the conditions I say I don’t want?
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?
And, more radically: What is it you believe being successful will do for you? How do you define success? Where does that come from?

“You know you’re in the radical self-inquiry zone when the questions take your breath away.” You need share the answers only with yourself (though a group, coach, or therapist can help) — because self-delusion, with attachment, is the biggest contributor to suffering. The questions that startle and slightly frighten you are “where the gold is.” Origin story: Reboot’s “pursuit of lemon drops” — Colonna grew up amid chaos and insecurity; his grandfather Guido (an immigrant iceman) kept an endless supply of lemon drops, which became his image of safety and wealth. By his 30s he “had lemon drops but didn’t feel safe,” which opened the core inquiry into how his relationship to money shaped his choices and self-worth.

Unsorted baggage and why teams fail [§ Unsorted baggage]

People are socialised to develop bypassing skills rather than consciousness skills, and to plaster over discomfort with band-aids — sometimes healthy (exercise), sometimes not (overwork, substances), sometimes “spiritual bypassing.” But avoidance doesn’t make the source go away. Colonna cites Springsteen’s autobiography — “Bruce fucking Springsteen, 25 years in psychoanalysis” — on the “unsorted baggage of our childhood,” and the warning that the price of not sorting it eventually comes due, “more often than not, in tears.” Better fewer tears now than ten times more later.

Applied to teams [§ Why teams fail]: the most common source of dysfunction is not lack of talent, strategy, or execution — it is “unresolved demons from childhood,” the unsorted baggage. Teams are groups with group dynamics (the scapegoat, the truth-teller); without individuals’ self-inquiry skills, groups repeat the patterns of their family of origin. His case: a CEO’s executive team that deflected every painful moment with a joke — “Jesus Christ, that’s just like my family.” Citing Carl Jung (“until you make the unconscious conscious, it will direct your life and you will call it fate”) and Peter Senge (“it is virtually impossible to challenge the assumptions that made you rich in the first place”): until the unconscious patterns are made conscious, the group repeats them and blames someone. Therefore, “if you want to create a high-functioning team, do your work — and it starts with the person who has the most power.” If the most powerful person refuses, the whole group becomes a manifestation of that person’s early dysfunction. Parker Palmer, building on Socrates: “if you choose to live an unexamined life, please don’t take a job that involves other people.”

The complicit question applies to both sides of a power dynamic. For the person with less power: what draws me to this position? How have I benefited from the dysfunction? (“Boy, this feels familiar — I always find myself on teams dysfunctional in this way.”) For the person with more power: the more power you have, the more moral responsibility you have to examine your complicity. His example — a 15-person CEO frustrated that no one decides without her: “Who hired them? … How does it feel when they make a decision you disagree with?” (“I’m furious.”) You cannot build a scaled leadership team you can’t tolerate making boneheaded decisions; that intolerance — sharpened “in founder mode” — is the growth edge.

Attachment, busyness, and the Lenny case study [§ Attachment]

The live demonstration. Lenny names his own busyness and the fear that the newsletter’s growth stalling means “it’s all over.” Colonna surfaces the whispery voice (“you’re not as good as you think — they might find out”: imposter syndrome) and shows that being busy and on a growth trajectory quiets that voice. The reframe: treat the work as a Seth Godin-style art project — enjoy the puzzle of making something from nothing while your self-esteem is not attached to the outcome. (Lenny: that’s how he started, “no expectations” — then it worked, income came, “the stakes went up,” and attachment set in.) The deeper attachment isn’t financial — it’s “see, I’m not a nobody, I’m a somebody,” and that is the source of suffering. The rewiring: the people who actually love you (his wife Michelle would love him if the podcast failed — “what, is she an idiot?”) don’t love you for your success; a child shouldn’t learn they’re loved only for the A on the spelling test stuck to the fridge.

Grounded in the four noble truths: (1) life is filled with suffering; (2) that which we do to push away suffering increases suffering; (3) there is an end to suffering; (4) the eightfold path. The second is the operative one — buying the couch to enjoy it is fine; buying it to push away “am I good enough to be loved, safe, and belong?” only deepens the suffering (now “what if they take my house away?”). Colonna lives this: on Dan Harris’s advice, he read two Amazon reviews of Reboot in the first hour and never again — he can’t experience them without becoming attached. He writes mainly to answer his own questions (“what will the world need two or three years from now?”); whether it sells is secondary.

Growth mindset as fixed mindset [§ Growth mindset]

Colonna’s objection is not to growth mindset (helpful) but to how the ego turns it into a fixed mindset: categorising “this is growth / this is not,” then nailing the label to the floor — “I ought to always have a growth mindset.” Buddhism: everything is falling apart all the time, even your growth mindset. Hold the mindset loosely (with non-attachment) and you can stay present and responsive; fix it and you set up attachment and suffering. Succinctly: stay attached to the growth; hold “mindset” loosely. The common fear — that non-attachment kills ambition (the “fear of complacency”) — misreads it: we’re socialised to ward off complacency with anxiety (achieve or lose your parents’ love). The alternative motivator is self-compassion — “I enjoy the hard work; two finished books on my desk make me happy.” Holding that contradiction (satisfaction from hard work without anxious attachment to the outcome) is, for Colonna, a hallmark of adulthood. The meditation-retreat formulation Lenny offers and Colonna endorses: don’t attach to the goal, but “point your cart in that direction and head there.”

Legacy, elderhood, and AI [§ Legacy and AI]

Asked about legacy (and Mike Tyson’s “I don’t give a shit about my legacy”), Colonna disagrees: in a disturbing time (“Captain Chaos running the country,” a normalised drumbeat of violence), he can’t shake the question, “And what did you do, grandpa?” — and wants the answer to be “I tried.” He feels a moral responsibility to use his gift (putting sentences together in a way people listen to) to help make “a world of kindness and empathy… where people feel safe however the fuck they identify.” The Reboot oak-tree image: torturing himself with “have I been a good man?”, his wife Allie says “enough — you’re a good man, stop”; on a walk he finds a toppled oak, roots torn up, and thinks “here lies a good man” — a life of gnarled limbs (good and bad choices) that nonetheless provided shade and shelter, now dissolving back into the earth. Easing his own suffering this way makes him more present for others. At 62, he’s working out what he wants his elderhood to be — finding meaning as “a voice of comfort, maybe even sanity.”

On AI: unlike the IP-address/dial-up transitions he lived through, “this is different.” It’s like putting on very sharp glasses — disturbing because it challenges what our role as human beings is. His hope: that AI burns away “that which does not matter in being human” and elevates what does — presence, connection, strategic thinking. He and colleagues use ChatGPT/Claude as a thinking-and-writing partner (one colleague uploaded 10 years of journals and asked Claude “what am I not saying that I need to say?”) — alongside, not replacing, live human writing buddies. Best case: more time on what matters; worst case: “we’re all out of work making sure the robots are well-oiled.” Crucially, AI’s value may be in giving you more questions to ask yourself — and the art of growing up is exactly that, “continuous inquiry,” exhausting to contemplate but enlivening to live.