I’m really honored and excited to announce that I’ve joined forces with my friends at Reboot and am now a CEO coach and facilitator under their umbrella. Reboot is helping shape the next generation of leaders who are reimagining the way business is done and I deeply identify with the vision. Jerry Colonna is a co-founder of Reboot and has been my coach since the summer of 2011, when I stepped into the CEO role at Etsy. When Jerry started coaching me back then, he was more or less a solo operation. Jerry reached a point where he wanted to scale his vision for coaching but realized he needed to build an organization to do that. I was honored to witness Jerry conceiving of Reboot and scaling it with his equally amazing co-founders. Jerry and Reboot have life-changing impact on the lives of entrepreneurs as evidenced by some of the testimonials and this beautiful portrait of Jerry and his work in Wired. Working with Jerry and Reboot has definitely been a life-changing experience for me and very much shaped my high-level philosophy on leadership as stated in my Reboot bio:
I believe “strong back, open heart” leadership is the key to building great companies. The strong back is represented by fiscal discipline, strong process, and accountability. The soft, open-hearted front are values, purpose, connectedness, and compassion. Organizations and people are at their best when they manifest both in equal balance.
I’m profoundly honored to be coaching under the Reboot umbrella and to have the opportunity to help and support CEOs in their leadership journeys. (Yes, I used the word “honored” a lot above because I truly am!)
With that bit of news out of the way — what is “coaching” anyway? Doug Silsbee’s book The Mindful Coach: Seven Roles for Facilitating Leader Development offers a simple definition that I really like: “any relationship where you are interacting with another person in service to his or her learning, growth, and change.” Being a CEO can be absolutely insane all by itself and Jerry helped me deal with the pressures of the roles during a period of extraordinary growth and change at Etsy, from chaotic startup to public company. But it wasn’t just “business.” During my time as CEO of Etsy, my wife and I adopted a child and I became a father. The coaching experience was highly integrated, meaning that it took my whole life into account. The same heart and soul that you put into being a CEO are the heart and soul you put into the rest of your life and relationships. As much as our culture demands the separation of “personal” and “business,” they are fundamentally integrated. Thinking of them separately means “dis-integration” and ultimately harms organizations and teams.
I see the work ahead as paying forward at least a small part of the generosity, care, and presence that I have received in being coached by Jerry. One Saturday morning last May, I got the call that meant my time at Etsy was over. My last day was Tuesday, just three days later. I hung up, stepped away from the phone, told my wife the news, and then immediately called Jerry. In the blur of the next three days, I was in regular contact with Jerry as all the logistics of my departure left little room for anything else. On my last night as CEO, Jerry came over to the Etsy office and we sat in the dark on the roof and talked. I don’t remember much of what we we talked about but I remember that Jerry was there and present for me during a difficult time. If I do nothing else in my role as coach, I hope to model the presence that Jerry taught me through his presence.
I am focusing on a very small number of high-impact engagements with my coaching practice. If you think I can be helpful to you, feel free to reach out or fill out the contact form over at Reboot and someone will be in touch.
Chad Dickerson's blog 