Tears, truths, and transformation: How Jerry Colonna challenges us to lead differently

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🔊 Jerry Colonna puts belonging at the center of everything

Back when I was covering technology’s rising stars, there were certain coaches on whom founders relied. You wouldn’t hear their names when you learned about the startups. But their advice and their steady presence was crucial in helping founders blossom into leaders capable of managing big companies. And if you asked founders, they’d usually tell you who they worked with. 

Often, it would be folks like today’s guest: Jerry Colonna.

Earlier in his own career, Jerry founded a company, and he’d spent years as an investor. He has credibility because he’s done the work, but he also has a novel approach. In a hustle culture that has prized “grinding it,” Jerry asks people to look inward, to chart their feelings, to be vulnerable. 

He regularly makes CEOs cry, and they love it and come back for more.

I invited Jerry into the studio to talk about leadership. He has just released a new book called Reunion: Leadership and the Longing to Belong. Jerry’s vision of leadership requires us to redefine the term itself. It's less about how successful a person or a company can be financially.

Successful leadership, in Jerry’s experience, expands agency, reduces suffering and invites everyone to feel they belong.

Jerry asks leaders—and to be clear, we are all leaders—to ask hard questions of ourselves. He helps us examine our roles in the systems around us. Our offices, our communities. I hope you find his advice in this episode immediately useful. You can find it here, or listen below:

☕ Office Hours: Leadership and belonging

Join us on Wednesday at 3pm EST for Office Hours. Bring your lunch or your coffee. I'm sticking to tea this week. We'll talk about the episode, check in with each other, and settle into our weekly gratitude practice. You can find us by clicking on the image below, or clicking this link to RSVP.

💻 ➡ Transcripts available upon request.