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Jerry Colonna, “The CEO Whisperer,” Says Vulnerability Is The Key To Strong Leadership. Here’s How

Christopher Lochhead

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When in a position of power, there is strength in vulnerability. 

I recently had a jam session with Jerry Colonna on my podcast to discuss positional power in the workplace—more specifically, how to lead properly in a place of professional power. For those that don’t know, Jerry is the founder and CEO of Reboot.IO, a coaching company aiming to “foster a revolution around work because better humans make better leaders.” As noted by WIRED magazine, this guy can make founders cry—for their own good.  

His new book, Reboot: Leadership and the Art of Growing Up, is really something—powerful and intimate. It’s not the same, worn-out business leadership narrative that’s been penned time and time again. As a certified professional coach, he believes in the corporate world leaders should take what’s called “a warrior stance.” Displaying a position of stability and strength, but also openness and non-aggression—and never with a “strike-first” attitude. 

If anything, he urges every business leader to always remain humble and vulnerable—characteristics you don’t hear to describe people in positions of power very often. 

Here’s some of the wisdom he shared:

To put it simply, better human beings make better business leaders.

Before becoming a great CEO, you have to first make sure you’re a great human


This requires what Jerry calls “radical self-inquiry.” Or, “stripping away the bullshit mask.” Dropping our manufactured personas, and self-defining with complete honesty. 

He went on to explain that only once you’re completely comfortable and confident with your true, human self, can you be a great leader. Because true faith in yourself is so much deeper and stronger than false machismo

This is what it takes to become a Warrior Leader.

And it all comes down to mindset.

In our darkest hours—when our co-founder quits, investors pull funding, we lose our best client, our board fires us—these are the moments when business leadership is defined. In these situations, a true warrior leader does one important, definitive action: acknowledge they created the conditions that led to their misfortune. 

Carl Jung, the father of analytical psychology, once said, “Until you make the unconscious conscious, it will direct your life and you will call it fate.” Jerry loves this quote.

We must always recognize that we are complicit in our failures. We influence everything that happens to us, good and bad. People should not be afraid to ask, “In what ways have I been complicit in creating these conditions I say I don’t want?” 

Of course, some of what happens is out of our control. Warrior leaders accept this. Because a warrior leader is confident, secure, has an open heart, and says to the world: “Do what you will with me. Screw you. This is who I am. This is where I stand. I don’t have to be aggressive. I don’t have to attack—but I get to be me. Now, let’s do some great work.” 

Positional power isn’t always true power in business leadership—and can be toxic.  


Organizations experience power struggles all the time. I’ve seen this happen firsthand and it is nauseating. People need to grow up. 

One of Jerry’s biggest points was how your job title doesn’t matter as much as you think it does. 

In my own professional life, I’ve been in plenty of “powerful positions” where I could hire and fire whoever, and spend a lot of company money on whatever I wanted. But at some point, I realized that unless I had the power to effectively communicate and influence people, I was powerless. 

Because true power is in collaboration. 

Business leaders who say, “Do this or you’ll be fired” are powerless, really. The greatest power isn’t granted through a position or title. Because a title can be revoked. Bonds with people can’t.  

When we lead from a place of love, however, we bring out the best in others. But when leaders just leverage their power and neglect to be truly compassionate, they create toxicity and fear. 

Jerry firmly believes those who hold positional power need to be confident and unwavering, but also humble. They need to be willing to share their story—including both successes and failures—to connect with people. Great business leadership creates a safe environment conducive to growth through its own actions.

The first step is committing to a warrior stance: stable and confident, but also respectful, personal, and accessible. 

To listen to the full podcast with Jerry, click here to Follow Your Different.

Here are a few other articles you might find helpful:

Is There A Formula For Happiness? Science Says There Is

According To NBA Star Andre Iguodala, Success On And Off The Court Is All About Designing Your Life. Here’s How

How To Build A Legendary Company: Say ‘No’ To Business Models, Forecasting & Projections (And Do This Instead)


Co-Author of “Niche Down” and “Play Bigger” | Podcast “Christopher Lochhead | Follow Your Different” Advisor & Investor to over 50 Silicon Valley startups, entrepreneur, former three-time public company CMO. Mediocre surfer & skier.

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