Jerry Colonna is the founder of Reboot and one of the most sought after CEO coaches in the world. Before he began coaching executives, Jerry was a burnt out VC, convinced that there must be a better way to impact the world—and also convinced that if he could influence the upper reaches of corporate structures, if he could help leaders heal, he could vastly improve the lives of all the employees. After all, he had observed the ripple effect of unhealed emotional wounds being taken out on other people—specifically people with less power. This is the focus of Jerry’s two great books about leadership: His first one is Reboot: Leadership and the Art of Growing Up and his second is Reunion: Leadership and the Longing to Belong, which takes a probing look at power and privilege and how it can alienate those who already don’t feel like they belong. In today’s conversation, we talk about all of this and specifically one of Jerry’s main queries. This passage is from Reunion: “While necessary, it’s not enough for us to do the inner work of unpacking our childhood wounds and, with fierce radical self-inquiry, free ourselves from the need to reenact the old stories of our pasts. Radical self-inquiry that stops at the question of how we have been complicit in creating the conditions we say we don’t want—a core tenet of my coaching and my book Reboot—is insufficient if it fails to look out to the world as it exists and ask how it could be better.”

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