How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna
Executive Summary
Lenny's Podcast episode, sponsored by Eppo and Contentsquare, in which Lenny Rachitsky talks with Jerry Colonna, co-founder and CEO of Reboot, former co-founder of Flatiron Partners with Fred Wilson, and author of Reboot and Reunion, about the inner work of leadership. Colonna unpacks his signature question - how have I been complicit in creating the conditions I say I don't want - explaining that complicit means accomplice, not responsible: you are driving the getaway car, not robbing the bank, and the point is to recover your own agency. He illustrates with busyness: the leader who hates being busy but feels unnerved by an empty calendar. He shares the equation he sketched on a dry-erase board at Naropa - practical skills plus radical self-inquiry plus better humans make better leaders - why startup culture trains everyone to claim they are crushing it, and why team change starts with the person holding the most power. PARTIAL COVERAGE: this summary highlights the core question and equation; later discussion is not covered. These are Colonna's own views and methods, not independently verified, and this is not therapy or mental-health advice.
Key Takeaways
The complicit question
His signature prompt locates your own hand in the situations you complain about.
Accomplice, not culprit
Complicit is chosen deliberately - you drove the getaway car; the question restores agency, not blame.
The busy trap
His example: saying you hate busyness while feeling disconcerted by an empty calendar.
The leadership equation
Practical skills plus radical self-inquiry, in service of better humans making better leaders.
Crushing it is a lie
Startup culture socializes founders to claim everything works; he calls it shared self-deception.
Power goes first
If you want a high-functioning team, the person with the most power does the work first.
Ask about the father
Clients come asking how; he responds with questions about money, self-worth and family.
The Conversation Breakdown
The complicit question
⏱ Untimed topicHis signature prompt locates your own hand in the situations you complain about.
Accomplice, not culprit
⏱ Untimed topicComplicit is chosen deliberately - you drove the getaway car; the question restores agency, not blame.
The busy trap
⏱ Untimed topicHis example: saying you hate busyness while feeling disconcerted by an empty calendar.
The leadership equation
⏱ Untimed topicPractical skills plus radical self-inquiry, in service of better humans making better leaders.
Crushing it is a lie
⏱ Untimed topicStartup culture socializes founders to claim everything works; he calls it shared self-deception.
Power goes first
⏱ Untimed topicIf you want a high-functioning team, the person with the most power does the work first.
Ask about the father
⏱ Untimed topicClients come asking how; he responds with questions about money, self-worth and family.
Core Frameworks & Ideas
Radical self-inquiry - Colonna's method
Cut through your own delusions by interrogating what a feeling is doing for you.
Complicity audit - his agency move
For any persistent condition, ask what you get from keeping it alive.
Power-first change - his team rule
Cultural change starts with whoever holds the most power in the room.
Actionable Next Steps
- ✓Answer the complicit question for one recurring frustration this week.
- ✓Check whether your calendar reflects what you say you want.
- ✓Name one place your team performs crushing it instead of telling the truth.
- ✓Do your own work before asking your team to change anything.
Notable Quotes
“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”
The One Thing to Remember
Jerry Colonna's leadership mirror: ask how you have been complicit in the conditions you say you don't want - then use the agency it gives back.