What is Reboot about?

Reboot is Jerry Colonna's examination of the connection between a leader's inner life and their organizational behavior — the argument that how you lead others is shaped by who you are, and that who you are is shaped by experiences, traumas, and stories that most people carry unexamined into leadership. Colonna, a former VC turned executive coach, writes from decades of working with CEOs and founders who were technically accomplished but internally struggling in ways that affected their organizations.

The book's organizing question is: "How are you complicit in creating the conditions you say you don't want?" It's a deliberately uncomfortable question, and Colonna applies it to the leaders he works with who find themselves in painful situations — toxic team dynamics, disconnected co-founders, organizations that feel more like prisons than places of purpose. In almost every case, his answer is that the leader's own unexamined patterns are contributing to the problem they're blaming on others.

Colonna draws on his own difficult history — a challenging childhood, professional failure, depression, and recovery — to model the kind of self-examination he asks of his clients. This is unusual for a leadership book: the author's vulnerability is structural, not incidental. The book is as much memoir as management, and the combination creates a different tone from most leadership books — more honest about the emotional cost of leadership and more direct about what genuine development requires.

The leadership model Colonna advocates is built on "radical self-inquiry" — the practice of asking hard questions about your own motivations, patterns, and histories rather than optimizing your techniques. His premise is that leaders who do this work are more effective not because they've acquired new skills but because they're less driven by unacknowledged fears and childhood patterns that distort their decisions under pressure.