It was 2005 and I was sharing office space with Fred Wilson when I met a young man who changed my life.
Fred and I had been friends since 1996 when we'd started Flatiron Partners. In 2001, we parted ways as partners but remained friends. I joined JP Morgan in 2002 and, within months, was miserable. The existential questions that had been haunting me for years were so loud, so relentless that I had no choice but to pay attention.
When I told my colleagues I was leaving, I said I wanted a business card with no company name, no title. I wanted to understand who I was stripped of any persona.
And so for the next few years, I sat on boards of directors, consulted here and there but mostly, I read, and sat, and learned to be still. I learned to listen.
Derek Walcott's poem Love After Love comes to mind; I learned to love again the stranger who was my self who had loved me all my life, whom I ignored for another, who knows me by heart.
Then one day a young man came to see me. He wanted to leave his law practice and join a startup. Someone suggested that seeing the former VC would be a good first step. After asking him why he'd become a lawyer in the first place, especially considering he obviously hated his job, he began sobbing. I realized then that, through the act of listening, I had found my own way. Those years of sitting still began to pay off; I had to coach. And I've been coaching ever since.
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A number of years ago, one of my teachers told me to “meet your clients where they are.” To do that, my practice blends pragmatic, practical advice with a psycho-spiritual awareness. Most often, I’m working with clients at critical junctures in their life--those sweetly juicy existential moments that are usually, but not always, career/work related. At those moments, they have an opportunity to consciously design their own life.
In his book, Soulcraft, Bill Plotkin writes:
Harley Swift Deer, a Native American teacher, says that each of us has a survival dance and a sacred dance, but the survival dance must come first. Our survival dance, a foundational component of self-reliance, is what we do for a living—our way of supporting ourselves physically and economically…Finding and creating one is our first task upon leaving our parents’ or guardians’ home.
Once you have your survival dance established, you can wander, inwardly and outwardly, searching for clues to your sacred dance, the work you were born to do. This work may have no relation to your job. Your sacred dance sparks your greatest fulfillment and extends your truest service to others. You know you’ve found it when there’s little else you’d rather be doing. Getting paid for it is superfluous. You would gladly pay others, if necessary, for the opportunity…Cultivating right livelihood, as the Buddhists call it, is essential training and foundation for your soul work; it’s not a step that can be skipped.
So, in a sense, often times the point of coaching is find out what our deepest longing is and work towards fulfilling it.
My clients vary. Many are CEOs and senior leaders of start-up businesses but others are simply trying to sort through key decisions regardless of career. I typically work with a client a few times a month for an hour, in person or by phone.
I began coaching with a focus on individuals and their moments of stress, their times of existential challenge, their crucible times when who they are mixes with what they do to be heated by the fires of what they believe. Today coaching individuals remains the foundation of my practice. But to really be of service to individuals, especially leaders first facing the rigors of leading, I’ve had to expand my efforts to support entire teams.
Sometimes that means navigating between co-founders and helping them find their way back to the core beliefs that caused to go into business together in the first place. Sometimes that means extended, consistent work with whole leadership teams, helping them co-create safe, meaningful containers for their work; helping the entire group thrive.
Coaching partners and teams requires an expanded set of skills. Sometimes it requires conflict resolution and mediation. Often it means helping people to re-learn basic listening skills.
The style of work varies depending on the team’s needs. For some, it’s meant a steady one-on-one presence with a series of individuals at the same organization, enabling the process to benefit from the multiple perspectives that can be shared. For others, it’s meant working with entire groups simultaneously and with me holding the container for the work, facilitating deeper understandings and communications.
For at its root, the challenge of managing teams is really a challenge of communications: we all benefit from learning to speak in a way that we can be heard and listen so that we can understand.
I’ve written about the essential lack of scalability in the coaching business. Indeed, I’ve referred to myself as a “lousy businessman” because of it. As deeply satisfying as is the personal transformational work implicit in one-on-one connections, I’ve found coming together in larger gatherings to share and break open to what is to be equally—if differently—satisfying.
To have a larger impact, to spread the message even further, I’ve expanded the notion of working with teams to include working with larger and larger groups. Some folks will write, in a section such as this, about their availability for public speaking. For me, though, it’s not about my availability for speaking as much as its about my willingness and capacity to hold the container of work for larger and more disparate groups of people.
Recently, for example, I spoke at a gathering of CEOs—each of whose companies had received an investment from the same venture firm. I exhorted them to face their demons, to put their heads up to the mouths of the worse demons and say, Eat Me If You Wish, to really fully and courageously face the awful challenges confronting themselves and their companies.
One brave CEO stood up and told how, on the day when the government had seemed to rule against the very essence of their business model, when investors seemed to be balking, their spouse asked for a divorce. Then magic happened; this group of strangers ended up supporting each other in ways unimagined.
In the end, I suppose, that’s what I strive to create with my public speaking: a container for people to do real work in the deep process of learning to be the leader they were born to be.