For the past 12 years, Jerry Colonna has been one of Silicon Valley’s most renowned CEO coaches. He draws from his long career as an influential startup investor, but he’s quick to point out that he’s not a performance coach you bring in for implementing new workflows. He’s the guy you bring in when a founder needs a full-blown life realignment if the business is going to have any chance of moving forward.
From 1996 to 2001, Colonna ran Flatiron Partners in New York, helping to establish a startup culture in the city that would survive the dot-com bubble. He then had a stint as an investor at JPMorgan’s private equity branch before founding his coaching firm, Reboot, which is also the name of his new book.
Colonna has an emotional transparency that can at times be shocking — he has spoken at length about his own battle with depression and a period in the 2000s where he struggled with thoughts of suicide — and he takes his clients to personal places they may not have even discussed with loved ones. His coaching style is based on a mix of analytic psychology and Buddhist philosophy, coupled with years of experience in the relentless, and at times brutal world, of building million- and billion-dollar businesses.
This unusual approach has resonated with entrepreneurs in and outside of Silicon Valley, and while he cannot reveal his roster of clients, founders of companies like Etsy, SoundCloud, Twilio, and Gimlet have publicly praised Colonna’s ability to free themselves from self-imposed barriers.
Colonna recently spoke with Business Insider about his book, and he told us that his popular characterization as the coach “who makes founder cry” can distract from his real aim. “What I end up asking people to do is feel the fullness of who they are,” he said. “Lead from that place. Oh, by the way, sometimes tears show up.”
Colonna said that because his coaching sessions are so personal that he cannot offer a general audience something like “five steps to becoming a leader.” There are, however, two deceptively simple questions, and some follow-ups, that can take anyone into a mindset required for positive change.
‘How do you define leadership?’
The first step is dismissing the idea that there’s a one-size-fits-all approach to leadership, or that it’s worth mimicking celebrity CEOs like Amazon’s Jeff Bezos. “My fundamental belief is everybody has to do the harder work of discovering what kind of leader they are meant to be — and that’s really hard,” Colonna said.
He told us he defines leadership as an act of bravery overcoming fear and uncertainty, in a way that can inspire others to do the same. He said that this does not require being a CEO or even a manager of any type.
Colonna gave us his definition of leadership, which he said is a “moment-to-moment experience” and doesn’t require followers.
He explained at length:
There’s a moment in your life where you will have to assume a leadership position, and no one will know it, and you’ll have to make an ethical decision. You’ll have to make a moral decision. You’ll have to make a choice in which you’ll have to reach deep down inside and lead yourself, if not other people. And it may be a moment in which you’re confronting fear, or failure, or disappointment, or opportunity. But you have to find that space within you, and I think that that is leadership.
These moments of leadership are a universal experience, according to Colonna, and it’s the frequency of them that increases as one rises through an organizational hierarchy.
True leadership, then, requires both an understanding of one’s self and a willingness to share that self with others. It’s much easier than it sounds, of course, but in his book Colonna recommends other questions to assist in this journey:
- “What am I not saying that needs to be said?”
- “What am I saying (in words or deeds) that’s not being heard?”
- “What’s being said that I’m not hearing?”
These questions, Colonna writes, are meant to bring someone to a headspace where there is no fear, of failure or of disappointment, and that allows the entire team to focus on their work, rather than distractions.
‘How do you define success?’
This one is more straightforward, but is just as important.
Because it is so easy to get wrapped up in goals that we’ve accepted for their own sake, Colonna encourages his clients to get to the core of what they are trying to accomplish and why.
He gave an example from his own life. It was a few weeks after his book came out, and he got the first batch of numbers on how it sold. He said that while, as a first-time author, he didn’t know exactly what to make of this data, he was happy that his book was connecting with its audience. His goal, he explained, was to have an impact on people’s lives, and receiving a note from a reader who attended one of his workshops that said, “You are transforming the way I see myself,” was more satisfying than any “No.1 bestseller” title.
When he works with his clients, he looks for an alignment of business and personal ideals in a founder’s concept of success, which will, in theory, make all stakeholders happy.
He has a go-to metaphor for illustrating the dynamic: “A container without content is meaningless, and content without container is useless,” he said, like a cup without liquid, or, conversely, a liquid without a vessel to hold it. “You actually need a good, fiscally-disciplined, structure of a business,” he added, that in turn has “a good, healthy culture.” Bring both together and your company have a “nice glass of water” in terms of your company.
For leaders, it’s about owning your personal beliefs — and understanding how they fit into the structure of your organization.
Colonna told us that it is never his place to determine what is right and wrong for a client’s belief system and how it fits into a business. What he’s going for instead is a self-awareness of inner drive that is tempered by an empathy for one’s team members. That’s how you get that refreshing, life-giving glass of water.