Jerry Colonna
Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.
Hiring & Teams Skills
High-functioning team culture begins with leaders taking radical responsibility for their role in creating the current environment.
"The question that I often ask is how have I been complicit in creating the conditions I say I don't want. The purpose of this question is actually to evoke your own agency... So if you want to create..."
Psychological safety and high-functioning dynamics are built through shared experiences where team members can be authentic without fear of judgment.
"Imagine sitting in a circle of people who just have your back, who really care about you as a person. And imagine then discussing some of the answers to those questions... Imagine sitting in a group o..."
Teams often unconsciously replicate dysfunctional family dynamics unless the leader identifies and addresses these patterns.
"Until you make the unconscious conscious, it will direct your life and you will call it fate. Let's apply it here. Until you make conscious the unconscious patterns operating in the group, the group w..."
Leadership Skills
Difficult conversations are often avoided because of unspoken truths; identifying these gaps is the first step to resolution.
"My famous questions include things like, what am I not saying that I need to say? ... What am I saying that's not being heard? And then, of course, what's being said that I'm not hearing?"
Effective delegation requires leaders to tolerate mistakes and relinquish the need for total agreement on every outcome.
"How can you hire people whom you expect to make decisions without running them through you if you can't tolerate them making a decision that you disagree with? You want to build a scaled leadership te..."
When managing a difficult relationship with a superior, you must examine why you are drawn to that dynamic and how you might be enabling it.
"One of the things to ask oneself is what draws me to this position in the first place? How have I been complicit, not responsible in creating the conditions I say I don't want. How have I benefited fr..."
Decision-making bottlenecks are often emotional issues for the leader rather than process issues for the team.
"Why is it that nobody on my team can make a decision without me? ... How does it make you feel when they make a decision that you disagree with? She said, 'I'm furious.' ... That's your growth edge. H..."