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11 Min Read

Q+A With Jerry Colonna: Become A Better Leader Through Radical Self-Inquiry

David Mizne
David Mizne

We all know someone in power who chooses to hide behind the comfort of their authority. The real task is thinking up senior executives who embody what it means to lead with transparency, honesty, and sincerity.

For a company to naturally thrive, those tasked with leadership must take the time to truly understand their inner self. While it’s vital for a person to know where their strengths lie, it’s also important to understand the vulnerable parts of ourselves we often try to ignore. Accomplishing this takes fierce emotional courage and radical self-inquiry.

Jerry Colonna is no stranger to fighting these personal demons. Known as the “CEO Whisperer,” this former venture capitalist found his calling as an executive coach, helping many in C-suite positions overcome their destructive behavioral patterns and psychological traumas to become happier leaders.

In Colonna’s new book, Reboot, launching today, he shares his approach to coaching, the magic of radical self-inquiry, and the powerful journey that led him here.

The stress, anxiety, and demands of our every-day work don’t have to be the things that destroy us. Colonna believes that we are actually capable of becoming our best selves within the walls of our workspaces, but we must create opportunities to recalibrate ourselves and reignite connections with each other first.

Below, Jerry joins in a Q+A through which he shares some of the fascinating learnings he’s gained as an executive coach, and details of his new book, Reboot.

Jerry Colonna Radical self-inquiry

Jerry Colonna is the CEO, and co-founder, of, an executive coaching and leadership development firm whose coaches and facilitators are committed to the notion that better humans make better leaders. For nearly 20 years, he has used the knowledge gained as an investor, an executive, and a board member for more than 100 organizations to help entrepreneurs and others to lead with humanity, resilience, and equanimity. Previous to his career as a coach he was a partner with JPMorgan Partners (JPMP), the private equity arm of JP Morgan Chase. He joined JPMP from Flatiron Partners, which he launched 1996 with partner, Fred Wilson. Flatiron became one of the most successful, early-stage investment programs in the New York City area. He lives in Boulder, Colorado.

Leadership and radical self-inquiry

Q: Why are high-achievers often the least prepared to become leaders?

A: The challenge for high-achievers is that they’ve often linked their self-esteem, their self-worth, to achievement of a goal. As a model for development, that link can be a powerful motivator and is often used to propel someone forward. But when someone is asked to lead, they are often confronted with more unknowns and more uncertainty than they’ve ever had to face. Then, when these unknowns undermine perceptions of success, the high-achieving leader often faces a profound loss of self-confidence and, worse, lose an internal sense of self-worth.

Q: What is radical self-inquiry?

A: I chose this term to describe the way we can slow down, stop the spinning and constant pitching (to ourselves and the world) that we’re some magical unicorn or that we’re some unique expression of utter failure. It’s the process of stopping, unmasking ourselves—with laughter, love, and compassion—and allowing ourselves to feel what we are truly feeling so that we may ask ourselves the most important questions. Questions such as: How do I define success in my endeavors, and where does that definition spring from? What do I believe about the world and how does that shape who I am, and what I strive for?

Q: Why are questions instead of answers more essential to the process of becoming a leader?

A: Because no one but you knows the answers. No one but you is leading your company, your organization, in this moment, under these conditions. No one but you has lived your life. Indeed, it’s often another form of story-making, a leftover childhood survival strategy that believes one is safe if one stays small, that leads one to believe someone else must have the answer.

When we outsource to someone else the answers to our life’s questions, we often end up with answers that don’t fit. And because they don’t fit, they unintentionally make us feel inadequate. They won’t work, and therefore, there must be something wrong with us.

Unpacking personal baggage to reboot and transform

Q: What are some of the most common situations a leader encounters in which their personal baggage might hold them back from leading effectively?

A: One of the most challenging, and common, situations is dealing with conflict. I’ve found that leaders will often respond with either more aggression, shutting down disagreement with too much energy, or—more commonly—be conflict avoidant, driving the naturally occurring tensions underground only to pop-up throughout the organization as passive aggressive “politicking” or active-aggression and fighting.

Another common challenge is that the leader, out of a childhood fear of being wrong (with all of its shameful and fearful consequences) will fail to be clear—clear about objectives, clear about roles and responsibilities, clear about definitions of success and failure. The result is the organization drifts and bumps along, with the best people leaving because, without clear direction, they miss the pleasure of doing good work.

Q: What was your reboot awakening like and how did it guide you toward your current phase of your life as leader of reboot workshops and author of Reboot?

A: Well, it didn’t feel so much like an awakening—a moment of transformation like Saul on the road to Damascus becoming Paul–as it did a gradual realization that everything that had worked in the past was no longer working. It was a multi-step process that began with me, in effect, hitting an emotional bottom. I was standing near the smoking remains of the World Trade Center. At that moment, I could have chosen to fall even deeper into the pit. Instead, I began to climb out.

So I hit that broken-open-heart moment. And then I did something, which in hindsight, was probably really wise: I sat still. I sat down and didn’t simply meditate but, in effect, turned my whole life into one extended meditation session. Reading, journaling, getting healthy, taking workshops—sitting under a virtual Bodhi tree—like the Buddha—and, saying “F*ck it. I’m not moving until I figure it out.”  I give myself a lot of credit for having the guts to sit still and face what I’d been running from. From that moment, I began to build the man I am today.

Q: How can we reboot, grow up, and lead?

A: Start by standing (or sitting) still. Then, bravely, turn around and look at the demons you’ve been running from. Then, take your seat as the leader, sit royally as if you have every right to your role. Drop the self-delusions and ask yourself what matters most to you. Then, despite your uncertainties, make decisions and offer a vision. In other words, from that place, lead.

For so many, the majority of our lives are spent chasing the light of success by any means. The success we do find defines our happiness, but often falls short of fulfilling our deepest human needs. What if we spent a fraction of that time working to become our true selves? Instead of turning away or filling our time with things that distract us, what if we unpack our personal baggage and face it head-on?

This is when we begin our journey of rebooting. By focusing on our interpersonal relationships, holding ourselves accountable through radical self-inquiry, and becoming more emotionally courageous, Colonna believes we will become more “compassionate and bold” leaders.

Purchase your copy of Reboot by Jerry Colonna today!

Reboot radical self inquiry Jerry Colonna

David Mizne 15Five

David Mizne is Communications Manager at 15Five, continuous performance management software that includes weekly check-ins, objectives (OKR) tracking, peer recognition, 1-on-1s, and 360 reviews. David’s articles have also appeared on The Next Web & The Economist. Follow him @davidmizne.

Photo by Laurenz Kleinheider on Unsplash