How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna
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.
Executive Summary (TL;DR)
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.