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What it argues
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.
What it gets right
- 1.
How you lead others is shaped by who you are — your histories, fears, and unexamined patterns — more than by your skills and techniques.
- 2.
The key question for any leader in a difficult situation: 'How are you complicit in creating the conditions you say you don't want?'
- 3.
Radical self-inquiry is not therapy — it's the deliberate practice of asking hard questions about your own motivations so they don't drive you unconsciously.
What it covers
Who wrote it
Jerry Colonna is the co-founder and CEO of Reboot.io, an executive coaching and leadership development firm. He spent nearly a decade as a venture capital partner at JPMorgan Partners and Flatiron Partners before transitioning to coaching, driven partly by his own experience of burnout and depression during the dot-com era. He is known in Silicon Valley and the startup world as "the CEO Whisperer," and has coached hundreds of founders and executives. Reboot is his first book and draws heavily on his own story alongside the experiences of the leaders he has coached.
