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Reboot

Leadership and the Art of Growing Up

By Jerry Colonna
15-minute read
Audio available
Reboot: Leadership and the Art of Growing Up by Jerry Colonna

Reboot (2019) shows us that to become better leaders, we must first become better human beings. Through the process of radical self-inquiry, Jerry Colonna asks us to reflect deeply on all of the things that have shaped us and continue to influence our professional behavior. Drawing from raw personal experience, he guides us toward a more rooted, humane form of leadership.

  • CEOs struggling with existential crises
  • Businesspeople who’d like to learn how to slow down
  • Anyone who wishes to be a humane leader

Jerry Colonna is the CEO and cofounder of Reboot.io, an executive coaching firm, whose main focus is developing leaders with humanity, resilience and flair. He also cofounded Flatiron Partners, one of the most successful early-stage investment programs in New York, and is a former partner at JPMorgan Partners. He lives in Boulder, Colorado.

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Reboot

Leadership and the Art of Growing Up

By Jerry Colonna
  • Read in 15 minutes
  • Audio & text available
  • Contains 9 key ideas
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Reboot: Leadership and the Art of Growing Up by Jerry Colonna
Synopsis

Reboot (2019) shows us that to become better leaders, we must first become better human beings. Through the process of radical self-inquiry, Jerry Colonna asks us to reflect deeply on all of the things that have shaped us and continue to influence our professional behavior. Drawing from raw personal experience, he guides us toward a more rooted, humane form of leadership.

Key idea 1 of 9

To face up to our problems as business leaders, we first need to learn radical self-inquiry.

At the leadership workshops that author Jerry Colonna runs across the United States, a CEO will sometimes interrupt him and demand a quick fix to her problems.

As a high-powered executive, she just can’t understand why her world seems to be falling apart. She wants to know the “One Quick Trick” to remedy this feeling of professional anxiety or helplessness. But Jerry tells her, kindly but firmly, that there is no immediate fix, no “One Quick Trick” that will solve it.

What he recommends instead is called radical self-inquiry.

This process is often difficult for CEOs and business leaders. To rise to the very top of an organization, or to make it as an entrepreneur, requires a certain degree of mental toughness. This means hiding deeper feelings, locking up vulnerability – focusing only on the practical how of running an organization and forgetting the more fundamental why. 

What can happen, then, is that underlying psychological problems begin to accumulate and make themselves felt in the workplace. This might manifest in overbearing professional oversight, a lack of connection with the team, or irrational, emotive decisions.

To understand these problems, leaders need to go right back to the roots of who they are. They need to move beyond the illusory stories they tell about themselves and look at the difficult truths that have shaped them.

As the author has found at his workshops, the reason why a high-powered executive may feel anxious often isn’t because of something specific in running an organization, but because of unresolved trauma from childhood. A hectoring father. A whole year at school being bullied. Poverty. Loneliness.

When the author conducted his own radical self-inquiry after a personal crisis in 2002, he found that his feelings of professional anxiety were linked to his poverty as a child growing up in Queens. Even though he’d become successful, he was still troubled by the latent memory of having little to eat or the ferocious arguments he witnessed his parents having over money. What was driving him, but also fuelling terrible anxiety, was this old fear of being left with nothing.

So rather than digging desperately through management books to solve seemingly inscrutable problems, we need to pause, take a deep breath – then peer beneath the surface into who we really are.

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