Reboot Yourself: Our Expert Interview With Jerry Colonna

I've had several great bosses in my career: people who knew how to show appreciation, look for the best in others, and forge strong bonds based on trust and respect. In short, they treated others as human beings. And I've had one boss from hell.

The Big Bad Boss

It was my first job out of journalism school, as a reporter in a busy radio newsroom. Yvette, the news editor, was a larger-than-life character who stomped around shouting at people, when she wasn't out on a smoke break.

I remember her chiding me through my headphones during an interview I was conducting. When the interviewee said something she didn't like, the rant spilled into the open newsroom where the interviewee could hear everything she said. I didn't stay there long.

Eventually, she had a nervous breakdown.

The CEO Whisperer

Looking back, I wish Yvette could have read "Reboot: Leadership and the Art of Growing Up" by executive coach Jerry Colonna. It might have transformed the culture of our workplace, and given her story there a completely different ending.

Known as the "CEO Whisperer," Colonna has a knack for cutting right to the human heart of the hardest of professionals. In his "reboot" boot camps, grown men and women are sometimes reduced to tears. It's not because he's mean; it's because he's not.

A Different Kind of Guy

Colonna found his calling as a coach via careers in journalism and venture capital. He's an appealing blend of new-age healer and Brooklyn-born straight talker.

Authentic and reflective, he doesn't take himself too seriously. He told me that, the week before we spoke, a client had called him, "Kind of woo-woo." 

"Because there I was, wearing these Indian mala beads on my wrist and I had a quote from His Holiness the Dalai Lama on the wall," Colonna recalls, with a laugh. "And then I pointed out I also had photographs from Yankee Stadium when the Yankees beat the Mets in the World Series. So I was like, 'Well, I'm a little bit of a different kind of guy.'" 

Losing Your Mask

Colonna is open about his personal struggles. He'll often use stories from his own journey to help impart insights to clients.

"I knew that I had hit a point in my life, in my late 30s, where the inner part of me was not matching the outer part of me," he reflects. "I had outward success and inwardly I was miserable, so much so that I was suicidally depressed. This was no joke, because in my late teens I had attempted suicide."

"So what had been a life-long relationship to depression came back, with a kind of meanness and power that really stopped me and made me just walk away from the life that I had created."

Now, through his coaching company Reboot.io, he advocates "radical self-inquiry," defined as "the process by which, with compassion and skill, we strip away the masks that protect us."

Radical Self-Inquiry

He encourages everyone – not just his high-level clients – to "cut through their own delusion," so they can figure out who they really are and what they want.

"Imagine spending a few minutes every day saying, 'Why did I have that conversation that I just had?' or, 'What is it about this failing that is going on in my organization that's so scary?' That's the kind of day-to-day practice that one doesn't need a coach for, doesn't need a therapist for," Colonna says. "You just sort of look at your life, instead of looking away."

Part of this is paying attention to – and taking responsibility for – the effect that we're having on other people.

Paying Attention

Say you had a fight with your partner one weekend. You arrive at work on Monday tired, cranky and upset. Should you announce to the office, "I'm freaking out here"?

No, says Colonna, because that will come over as a cry for help. Your colleagues might feel they have to prop you up, and that's not their job. Should you say nothing, then?

That's not such a good idea either, as it might worry your team. "They're going to walk in and feel the tension that exists in your body and they're going to say, 'Uh-oh, the company's going out of business. Better polish up my resume. I'm on my way out,'" Colonna points out.

So what does he think we should do?

Making Your Choice

"You don't necessarily have to share the content of the argument, but you can say something like, 'Hey, just want to give people a heads-up. I'm not feeling my best today, had a rough weekend, so if I come across as a little short that's what's going on.' And that's it. Just nice and light."

From this perspective, I can see that my former boss Yvette was likely going through serious personal issues and was taking that out on her team. If only she'd stopped and asked herself one of Colonna's favorite questions: "What kind of adult do you want to be?"

We all have a choice about that.

Listen to Our Interview With Jerry Colonna. 

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How often do you stop for a moment of reflection? Let us know in the comments section below!