Last Thursday, March 13th, I conducted the 9,000th coaching session of my career, and the milestone has prompted a look back at how my practice has evolved over the past two decades. I'm not suggesting that there's one right way to run a practice, or that anything I do should be emulated. But I've always tried to be thoughtful about what will work best for me and my clients, and perhaps these reflections will prove useful to colleagues as they experiment with their approach, or to clients who are curious about what this work looks like from a coach's point of view.
When I conducted my 8,000th coaching session in May 2024, 1:1 coaching was my only professional activity and had been since I last taught MBAs at Stanford in 2021. This was a stark contrast to my orientation when I launched my practice in 2006 under the mantle of "Executive Coaching and Change Management." At the time I envisioned that my work would be split equally between coaching individuals and various types of group engagements.
But as the years passed several factors led me to reset those expectations. My participation in Stanford's Group Facilitation Training Program that same year opened up more opportunities to work with groups at the university, including an invitation to join the first team of Leadership Coaches at the Graduate School of Business, where I'd earned my MBA in 2000. In parallel, it became more difficult to fit group engagements into the space available in my private practice.
These developments weren't accidental, but resulted from deliberate choices made in response to my evolving capabilities and skills, the fulfillment I derived from different types of work, and my growing understanding of the respective markets for these services. I was increasingly drawn toward 1:1 coaching, not only because I felt most capable and fulfilled in that work, but also because it was much more straightforward operationally. Today I regularly talk with aspiring coaches, and I encourage them to be very intentional about their business model.
Over time I concluded that I would be best served by focusing on 1:1 coaching rather than group engagements. Coaching experience compounds rapidly, given the consistency with which issues emerge in leaders' lives. The specific circumstances vary considerably, and all my clients must feel acknowledged as individuals, but I also add value simply by reassuring leaders that many of the challenges they face are quite common.
I accelerated my learning process by writing frequently, ultimately sharing more than 900 essays on coaching and related topics on this site since launching my practice. That's the equivalent of one post per week for nearly 19 years, although I usually write in productive bursts (and my pace has slowed recently, in part because I'm so busy coaching.)
My writing primarily serves two purposes: to integrate and solidify lessons distilled from multiple clients and my reading in a wide range of fields, and to create a library of content to share with current clients that augment our discussions in coaching sessions. I've never written with the expectation that anyone encountering my work would become a client, and that's proven accurate--my referrals have almost all come through word-of-mouth. Nor did I seek to monetize my writing--everything on my site has always been freely available to others under a Creative Commons license.
But this meant that I had to monetize my time, which was another reason why I focused on 1:1 coaching instead of group work in my practice. Coaching is time-efficient, particularly given my use of a flat hourly rate rather than a retainer, and less effort is required for discovery and scoping than in group work. I decided to dedicate some of that time saved to handling all of my practice's logistics, from scheduling to billing. Years ago I considered hiring an assistant as my practice grew but concluded that I preferred owning every aspect of my clients' experience. And so after a decade my practice consisted solely of 1:1 coaching engagements, and I was working with groups almost exclusively at Stanford, with occasional workshops for company founders or leadership teams.
During those initial ten years some of the most rewarding group work I did was facilitating T-groups in Interpersonal Dynamics (aka "Touchy Feely"), and I ultimately spent more than 1,500 hours in that role. One of the reasons I pursued that work so intensively was because I found it highly synergistic with 1:1 coaching. Engaging someone on a challenging topic in a T-group with 12 other people observing and joining in the interaction made the challenges in 1:1 coaching seem easier, and the coaching orientation I brought to T-groups made me a better facilitator.
My practice continued to grow during these years in part because I was honing my skills, but also because I simply said yes as often as possible. This was easier because I'm not a parent, nor did I have many obligations beyond work. My role at Stanford was sufficiently flexible that I could see clients in San Francisco in the morning or evening before or after class. I also began working virtually, holding my initial long-distance coaching sessions via phone or Skype. I assumed that this would always be a minimal part of my practice, but I found that virtual coaching was as effective as in-person, although it was a different experience.
Looking back on this period I joke that as a coach I was a "five-year overnight success," meaning that it took that amount of time to develop the critical mass of former clients who turned out to be the most fruitful source of future referrals. This became evident in 2012 when I began earning more from my private clients than from my full-time role at Stanford, seven years after I started coaching and six years after formally launching my practice.
Despite this development, I opted to stay at Stanford for a number of reasons, including my commitment to the Leadership Labs course and the Leadership Fellows program, which my colleagues and I had helped to establish in 2007. While those initiatives had proven successful, after four years the school wanted us to revamp them, and we spent 2011-12 rolling out a radically different LeadLabs course and integrating Fellows with the pre-existing Leadership Coaching & Mentoring curriculum. These efforts were daunting, but they were also highly energizing and a tremendous source of learning.
The following years also presented me with with some unique opportunities at Stanford. In 2015 I was given a chance to teach my own course, which I called The Art of Self-Coaching. In 2016 I was invited to join the Interpersonal Dynamics faculty and teach the course that I'd facilitated for a decade. And at this point I realized that the balance I'd established in my professional life was no longer tenable--I needed more time for 1:1 coaching in my practice, and that could only come by spending less time with groups at Stanford. So in 2016 I resigned from the full-time role at Stanford that kept me involved with Fellows and LeadLabs, and in 2017 I facilitated a T-group for the last time.
I enjoyed all of that work immensely, particularly the opportunity to guide Leadership Fellows as both a group facilitator and a 1:1 coach. And while each T-group is a unique entity composed of a set of unique individuals, there are a number of patterns that reliably emerge in every group. I'll always be fascinated by group dynamics, and my grounding in this topic makes me far more useful to my coaching clients, who are often seeking to help their leadership teams operate more effectively. But I felt that I had more to learn in other settings, and it was time to move on.
I settled into a new professional routine where I taught one day a week and spent the rest of my time with clients in my private practice. The Art of Self-Coaching proved sufficiently popular that I was invited to teach it in all three academic Quarters, and so in 2017 I stopped teaching Interpersonal Dynamics in order to focus on my course, but the overall balance of teaching and coaching remained the same. These years, 2016 through early 2020, were some of the most gratifying of my career, and I will always view it as a special era. The balance between coaching and teaching was very fulfilling, and although teaching consumed 20 percent of my time and provided 3 percent of my income, it still felt like a fair exchange.
What I enjoyed so much about teaching The Art of Self-Coaching was the opportunity to create the optimal environment for experiential learning, which entailed constant evolution and refinement. I'm not a brilliant lecturer, nor am I particularly gifted at the Socratic method. I am, however, a world-class experiential educator, a role whose closest analogue is perhaps circus ringmaster. The ringmaster merely entertains, of course, and while I was a lively presence in the classroom, my intent was to help my students feel at ease while inviting them to challenge themselves, to go deeper, and to learn more in the process.
I loved being in the classroom one day a week, and I loved the fact that I was able to spend the rest of my time with clients in my private practice. I gave some thought to teaching less often, just once or twice a year instead of three times, because Amy had correctly observed that I ended each Quarter feeling depleted, and my commitment to teaching required me to maintain a waitlist for my practice. So life wasn't perfect, but I was content, and I expected to spend the rest of my career in some form of that arrangement. And then the pandemic hit, and many things changed.
Because I was already conducting roughly one-third of my coaching sessions long-distance, it was relatively easy to go 100 percent virtual. I taught The Art of Self-Coaching virtually in Spring 2020, including a version that I made freely available to the public, and it was a great experience, largely because everyone was coming together to face this unprecedented threat. But I decided to drop down from teaching all three Quarters to just one, primarily because I was exhausted and overwhelmed. My clients were facing the greatest challenges of their careers, and I didn't think I could sustain my support for them while also teaching all year.
I taught virtually again in Spring 2021, and it was not a great experience, largely because I failed to adapt to the needs of students who were also exhausted and overwhelmed. So I took a year off from teaching entirely in order to assess the role I wanted it to play in my life, and in January 2023 I concluded that it was time to retire from Stanford and focus solely on my practice and 1:1 coaching. Sixteen months later I conducted my 8,000th coaching session, and at the time that orientation still seemed right. And then things changed yet again.
In addition to triggering an even sharper focus on 1:1 coaching in my practice, the pandemic led to monumental changes in my personal life. Amy and I left San Francisco, our home for 30 years, and moved to a working sheep and cattle ranch in the far northwest corner of Marin County. It was a deeply affecting experience that taught me much about the natural world, the cycle of life and death, and my evolving identity in middle age. The seclusion we enjoyed was at first simply a respite from the chaos of life under lockdown. But it also allowed me to hone my craft like never before.
I coached all day, every day. I coached more people than ever, from all over the world. I coached more sessions in a day, and more days in a year, than ever before. In 2019, teaching all year and coaching 4 days a week, I held 672 sessions with private clients. In 2020, teaching just once, I held 851 coaching sessions. In 2021, without teaching at all, I held 988 sessions. In 2022 I expanded my hours in order to work with clients in a wider range of time zones and held 1,042 sessions. In 2023 that process continued, and I held 1,132 sessions. Last year I held 1,164 sessions, and I expect to equal that figure in 2025.
In addition to opting out of teaching, working virtually, and expanding my hours, what made this increased workload feasible is that on the ranch I had very few distractions, living among a flock of sheep and a herd of cattle on 250 acres. I think coaches are well-served by living a boring life, and I practice what I preach. And for more than three-and-a-half years it was a wonderful existence, occasionally even magical.
To be sure, rural life posed many challenges, from unreliable Internet to lost sheep to downed tree limbs that trapped us on the property until I learned how to use a chainsaw. We weren't responsible for the livestock, but we were the only full-time residents, so we still had plenty of responsibilities. But Amy grew up on a farm, and I followed her lead, and with the occasional mishap we managed just fine. And yet as we approached the fourth anniversary of our time on the farm, it became clear to me that yet another season of change was upon us.
Focusing my practice on 1:1 coaching while also living on a remote ranch for four years ultimately came to feel somewhat narrow. I still loved coaching, I woke up every day eager to talk with my clients, and I knew I was doing the best work of my career. But eventually I realized that missed the stimulation of group experiences in my personal and professional life, from walking down a busy street to leading a workshop or teaching a class.
This was one of the reasons we decided to leave the ranch in mid-2024 and move to Petaluma, the town of 60,000 people in Sonoma County that had been our primary commercial center while living in the country. And it was also why I considered expanding my practice beyond 1:1 coaching for the first time in many years and began seeking out opportunities to work with groups again.
I explored a range of options, including returning to Stanford. I reached out to a faculty member I knew for guidance, and he was decidedly ambivalent. There were reasons I might want to come back, and there were reasons I might not want to come back, and I might not be welcomed back. Amy was definitely not ambivalent--she thought it was a terrible idea.
I had to conclude that I'd been right in January 2023: "Today I'm struck by the extent to which the courses and programs that were products of the 'new curriculum' are now viewed as features of the landscape, as if they'd always been there. This is gratifying, but it also reminds me that it's time to move on before I, too, am viewed as a feature of the landscape."
I reflected on what I was trying to accomplish in working with groups again. I wanted to work with people like my coaching clients--senior leaders who feel responsible for building a culture that enables their employees to do their best work. I wanted to foster connections between individuals and to create a sense of connection among members of a group. I wanted to draw upon the Art of Self-Coaching curriculum that I'd been developing since 2009. And whatever I did had to be complementary with my existing practice.
The first initiative that came to fruition was a 6-week virtual version of my course, The Art of Self-Coaching for CEOs, which I now offer to small groups of 6 leaders. The first cohort in late 2024 was sufficiently successful that I've planned several more for this year, and Cohort #3 begins tomorrow. I'm still pursuing other efforts, including a retreat for leaders in midlife and collaborating with colleagues to coach a company's leadership team, and I'm contemplating even more, such as a program to help coaches improve how they structure engagements and manage their practices.
We're now nine months into our new lives in Petaluma, and although we miss aspects of life on the ranch--the huge sky, the endless pastures, the addle-headed flock--it's good to have neighbors again and to be able to walk downtown. I know that 1:1 coaching is my ikigai: I love it, I'm good at it, the world needs it, and, happily, I'm paid to do it. And I feel re-grounded with new forms of group work in my professional mix, although I'm increasingly mindful of the limits on my capacity and the need to preserve open space in my life.
But even as I strive to manage my boundaries, as all happy workaholics must, I find it fulfilling to be so busy and am grateful to be of service to my clients. Barring any unexpected developments, I'll conduct the 10,000th coaching session of my career in early 2026. Maybe by then I'll know what I'm doing.
Acknowledgments
Always: Thank you to the hundreds of clients who have entrusted me with the opportunity to play a unique role in your lives and careers. It is truly a privilege that I never take for granted. Thank you to the MBA students with whom I conducted 1,064 coaching sessions at Stanford from 2007 through 2020. I'm thankful to the GSB for bringing us together. And thank you, Amy, for your care and counsel on every step of this journey.
In the Beginning: As a student and early in my career I was blessed with some of the most gifted and caring teachers and mentors a young person could want:
Lloyd Schaefer, Millicent Rinehart, Naomi Duprat, Selby Doughty (Cumberland Valley High School), Tim Dayton (Duke), Richard Lerman (School of the Museum of Fine Arts/Boston), Chris Mauriello, Dagmar Herzog, Tom Simons, Mary Gluck (Brown), the late Don Flaxman, James Van Horne, Joel Peterson, Mary Ann Huckabay, Roberto Fernandez (Stanford), Jerry Fuchs, Kathy Taylor Gaubatz, Vince Stehle, Lynn Labieniec
Getting Started: A number of people played essential roles as I began exploring coaching as a potential path in 2005 and launched my practice in 2006, and I've done my best to pay it forward:
Andrea Corney, Barbara Brewer, Carole Robin, David Bradford, Dietmar Brinkmann, Erica Kisch, Evelyn Williams, Joe Murphy, Justin Sherman, Karin Scholz Grace, Kevin Martin, Lynn Labieniec, Mary Ann Huckabay, Rebecca Zucker, Ricki Frankel, Seth Goldstein, Scott Bristol, Tim Dorman, Vince Stehle
At Stanford: A host of colleagues contributed to my growth and made my work possible at the Graduate School of Business from 2007 to 2021:
Allison Rouse, Amy Kraus, Anamaria Nino-Murcia, Andrea Corney, Agnes Le, Anthony Ramsey, Barbara Brewer, Barbara Firpo, Bob Joss, Bob Sutton, Bonnie Wentworth, Bri' Godfrey, Brian Lowery, Bryan McCann, Carrie Lee, Carole Robin, Chevalisa Bruzzone, Chris McCanna, Chris Sadlak, Christopher Williams, Collins Dobbs, Courtney Payne, David Bradford, Delilah Gallardo, Dietmar Brinkmann, Dikla Carmel-Hurwitz, Domenico Anatrone, Don Hejna, Erica Peng, Evelyn Williams, Garth Saloner, Gary Dexter, Grace Yokoi, Graham Veth, Graham Weaver, Hugh Keelan, Inbal Demri Shaham, Ingrid McGovert, James VanHorne, Jamila Rufaro, Jana Basili, Jed Emerson, Jeff Pfeffer, Jimena Galfaso, Joe Murphy, Joel Peterson, John Cronkite, John Johnson, Johnnie Walton, Joy Hsu, Karin Scholz Grace, Ken Chan, Kevin Martin, Kirstin Moss, Kris Becker, Lara Tiedens, Lela Djakovic, Leslie Chin, Lily Kimbal, Ling Lam, Lisa Kay Solomon, Lisa Radloff, Lisa Schwallie, Lisa Simpson, Lisa Stefanac, Liselotte Zvacek, Lynn Santopietro, Margee Hayes, Marie Mookini, Mark Voorsanger, Mary Ann Huckaby, Melinda Tuan, Michael Terrell, Mike Hochleutner, Mindy Williams, Nancy Dam, Nirit Hazan, Nonna Kocharyan, Nora Richardson, Paul Abad, Paul Mattish, Paul Roberts, Rebecca Taylor, Rebecca Zucker, Rich Kass, Richard Francisco, Richard Haukom, Ricki Frankel, Roberto Fernandez, Sara Stone, Saraswathi Ram Mohan, Scott Bristol, Sharon Richmond, Stephanie Stevens, Sunny Sabbini, Sue Neville, Suzan Jensen, Tony Levitan, Tuquynh Tran, Ursula Kaiser, Vince Stehle, Yifat Sharabi-Levine, Zoe Dunning
My Community Today: I'm privileged to call these people colleagues and friends, and I'm deeply grateful for their encouragement and support:
Agnes Le, Anamaria Nino-Murcia, Andy Sparks, Andrea Corney, Anita Grantham, Annie Riley, Bonnie Wentworth, Brad Stulberg, Brooks Barron, Carole Robin, Cameron Yarbrough, Celine Teoh, Chip Conley, Chris Douglas, Collins Dobbs, Dan Oestreich, Dana Bilsky Asher, Doug Sundheim, Eduardo Andere, Glenn Terrell, Gwen Mellor Romans, Harry Max, Heather Corcoran, Jennifer Ouyang Altman, Jennifer Porter, Joe Dunn, John Baldoni, José Hernandez, Julia Markish, Justin Doyle, Kevin Martin, Khalid Halim, Lauren Weinstein, Lela Djakovic, Lisa Stefanac, Madelyn Sierra, Mario Fraioli, Mary Ann Huckabay, Meredith Whipple Callahan, Michael Chang Wenderoth, Michael Melcher, Michael Terrell, Moshe Ovadia, Natalie Guillen, Nikki Turner, Pam Fox Rollin, Priya Nalkur, Rebecca Zucker, Richard Hughes-Jones, Rick Winters, Rodrigo Lopez, Ronni Hendel-Giller, Scott Eblin, Stephanie Soler, Stephanie Stevens, Steve Magness, Steve Schlafman, Terra Winston, Tim Dorman, Tim Sullivan, Whitney Birdwell, Vineet Rajan
In memory of Roanak Desai and Erik Bengtsson, two people I was honored to know and to coach. RIP
Photo by Michael Whiffen.
