Reboot: Leadership and the Art of Growing Up
I've always been drawn to leadership development and the pursuit of becoming a better human. It makes perfect sense when these two ideas come together in one conversation.
My introduction to Jerry Colonna came through an online event hosted by the Modern Elder Academy (MEA). He joined Chip Conley and Hermina Ibarra—two other authors I admire—in a discussion about career reinvention. Jerry's practical advice and emphasis on self-awareness immediately resonated with me, so I decided to pick up his book Reboot: Leadership and the Art of Growing Up. Jerry, the CEO and co-founder of Reboot.io, a leadership development and executive coaching firm, operates on the belief that better humans make better leaders. Before transitioning to coaching, he worked as a partner at JPMorgan Partners and co-founded Flatiron Partners.
In Reboot, Jerry begins by asking a powerful question: "What do I believe to be true about work, leadership, and how we live our lives?" His answer: "I believe that better humans make better leaders. I further believe that the process of learning to lead well can help us become better humans. By growing to meet the demands of leadership, we're presented with the chance to finally, fully, grow up."
The book feels like a series of coaching sessions, challenging readers to reflect on their personal stories and whether they still serve them. Radical self-inquiry sits at the core of Jerry's approach. He encourages readers to ask themselves tough questions, such as:
How did my relationship with money first form, and how does it shape my work today?
How can I lead with dignity, courage, and grace?
How can the challenges to my self-esteem inherent in leadership help me grow into the person I want to be?
Where have I depleted myself? What am I running from, and what am I running toward?
Jerry also shares personal anecdotes and insights from his work coaching CEOs and entrepreneurs, making the book relatable and deeply insightful. One of his key ideas is this: "Choosing requires knowing: How are you complicit in creating the conditions of your life that you don't want?" This question highlights the need for authenticity, vulnerability, and emotional intelligence—qualities essential to real self-awareness. In my experience with leadership training through the ALF Fellows Program, I've found that challenging our narratives is vital for building empathy within our communities.
Jerry's latest book, Reunion: Leadership and the Longing to Belong, is now on my reading list, and I can't wait to read it and absorb its insights into belonging and leadership.
--
Tanja Powers is ALF Insights' newest faculty member and will launch an Executive Coaching cohort for corporate women through ALF Insights in 2025.
Tanja is an ALF Senior Fellow (Class XLII), Executive Leadership Coach, and former biotech executive with over 30 years of experience.
