Spoiler alert: There’s no playbook. But Jerry Colonna’s new book, “Reboot: Leadership and the Art of Growing Up,” comes close. In it, he…
Spoiler alert: There’s no playbook. But Jerry Colonna’s new book, “Reboot: Leadership and the Art of Growing Up,” comes close. In it, he invites founders to cut through the BS and connect with the person behind the persona. The book proposes that self-inquiry and personal responsibility will create a meaningful foundation and give founders their best shot at realizing the dreams and values they started their companies with.
Rebooted
Three years ago, I was invited to a Reboot Bootcamp with a handful of other startup founders. In the pristine surroundings of the Rocky mountains, we were encouraged to lose the stories we tell the world, and get real about the personal struggles of running our companies.
Honest and vulnerable, we came to understand we weren’t alone and our challenges weren’t unique. Despite being accomplished entrepreneurs, it was eye-opening to understand just how little external success had to do with our well being and happiness. It seemed that the more we got mired in the drama of running our companies, the more we lost sight of why we started them. Bootcamp was a chance to reconnect with the purpose and values that had gotten us started in the first place.
The book, “Reboot” is a mix of autobiography, anecdotes from Jerry’s esteemed coaching career and probing journaling prompts. It’s a powerful guide for any founder interested in connecting to their purpose and capturing some of that Bootcamp magic to inform their leadership decisions.
Impostor syndrome and the elusive playbook
As a founder, member of multiple tech communities and a startup coach, I’ve gotten to know hundreds of other founders well. It’s practically a rite of passage to lament/laugh about how clueless we are about what we’re doing. Recently, in the same day, I had a conversation with a successful founder who felt like a fraud because he didn’t have an MBA… and an MBA who felt like a fraud because he had never started a company. It seems imposter syndrome is par for the course when you’re doing something new.
No MBA can prepare you for the anxiety that strikes when your competitor announces a round of funding, an M&A deal disappears, or a key hire falls through. Founders have to live in a state of continuous change and continuous learning — “building the plane while flying it”. When things are going poorly, we feel like our worst fears are being confirmed. When they’re going well, it feels scary to admit what we don’t know — lest we risk losing the confidence of our stakeholders. Safer instead to go into hiding and simply bluster our way through leadership. We look around at our successful friends and competitors, and the press releases taunt us with the idea that everyone else has it figured out. They must know something we don’t, we think. We go searching for the mysterious playbook everyone else appears to be operating from.
The art of growing up
The big questions, the ones that vex you late at night and wake you up in the morning, require you to “grow up” into the very role of leadership you placed yourself in. Growing up requires you to cultivate your intuition and build your company, not someone else’s.
“Reboot’s” thesis is that self inquiry is the path to growing up and taking responsibility for your company’s success. If you aren’t self aware, you repress your fears and create a dysfunctional feedback loop with your team. In this insidious dynamic, these hidden fears get absorbed into the culture, amplified by your team, and prevent everyone from growing. When your fears tell you to double down, to have all the answers and to keep faking it, they keep everyone trapped in a lie and dependent on your wizardry for answers. Ironically, this just makes you feel more alone and fraudulent. Growing up is understanding that leadership requires the courage to be honest, vulnerable and inclusive.
Growing up is realizing that the skills that got you here aren’t the skills that will get you to your next phase. So, for example, where a CEO embraced a “fake it till you make it” approach to bootstrapping, perhaps now she can find a more honest and inclusive approach. She can realize her job as a leader isn’t to have all the answers, but to create a company where she empowers talented people to find them. In this way, she grows, the team grows and the organization builds durability and institutional wisdom.
You can find out more and order the book here
Why now
We’re living through a time when big tech’s unbridled focus on growth and profit has blinded it to important questions about privacy, harassment, radicalization, monopoly and the integrity of our elections. We could really use some enlightened technology leaders whose values extend beyond “growth at all costs”.
Perhaps books like “Reboot”, with a call to more honesty and personal integrity, can help lead to more meaningful work for founders and their teams. I hope so. I can imagine a time when we have more than just a handful of examples of successful companies committed to this kind of work.
I still remember when consumer technology promised hope, optimism and a sincere belief that giving folks easy access to computing and networks would make the world a more informed, more democratic, more delightful place. Imagine what could happen if founders reconnected with the values that got us here in the first place?