I've kept careful records since launching my coaching practice in 2006, and an hour ago I conducted the 8,000th coaching session of my career. This only includes formal coaching sessions: 6,936 with private clients to date, and 1,064 with MBA students at Stanford from 2007 through 2020. It does not include countless informal conversations with clients and students over the years. As a solo practitioner I've learned that it's incumbent on me to be deliberate about learning from experience and to organize my own celebrations, so this post is a bit of both.
For many years coaching was a central focus of my professional life, but it was just one of a number of activities I pursued. In my practice I worked with organizations on change management efforts and conducted workshops and offsites for leadership teams and groups of founders. In my role at Stanford I helped to launch the Leadership Labs and Leadership Fellows program, facilitated 1,500 hours of T-groups in Interpersonal Dynamics (aka Touchy Feely) and later taught the course myself, and started my own course, The Art of Self-Coaching.
But over time I found myself drawn to one-on-one coaching more than any other activity. In my practice I stopped taking on consulting projects or facilitating other events. In 2016 I resigned from my full-time role at Stanford to focus on my private practice, although I continued to teach Interpersonal Dynamics and The Art of Self-Coaching one day a week. In 2017 I resigned from the Interpersonal Dynamics faculty in order to teach The Art of-Self-Coaching year-round, in part because my course allowed me to work more closely with students on a one-on-one basis. In 2021 I taught The Art of Self-Coaching for the final time before taking a year off, and last year I resigned from Stanford entirely.
So for the past seven years one-on-one coaching has been my primary professional activity, and for the past three years it's the only thing I've done. I enjoy working with groups, and I'd probably still be teaching The Art of Self-Coaching at Stanford if it weren't for the pandemic, which triggered a host of changes in my life. And I may work with groups again in the future--for example, I've been thinking about doing some small weekend retreats--but it's clear that one-on-one coaching is and will remain my primary passion. So what have I learned after 8,000 coaching sessions? Half-a-dozen lessons come to mind:
1. Initial Conditions Matter
I first learned this from Carole Robin, one of my most important mentors and later one of my colleagues on Stanford's Interpersonal Dynamics faculty. In our work with groups she encouraged me to expand my awareness of a host of factors, often unstated or implicit, that influence a group's development, which I later defined as follows: "Every group is rooted in a set of initial conditions that form the foundation for all subsequent aspects of the group experience. How and why were we gathered together? What will our first meeting be like? What will we discuss there?"
Initial conditions are equally important in a one-on-one coaching engagement, and it's necessary for me to understand something about a prospective client's interest in coaching in order to determine whether I'm going to add value. But I prefer not to over-determine their responses by means of a complex or detailed discovery process. So when I'm meeting with a prospective client I tell them that I have just three questions: Why coaching? Why now? What are your hopes and expectations for a coaching relationship? I've found that how people choose to answer these questions tells me a great deal about the initial conditions for the potential engagement.
If you're a prospective coaching client: How would you respond to my questions above: Why coaching? Why now? What are your hopes and expectations for a coaching relationship?
If you're a current client: What led you to seek coaching initially? What were your hopes and expectations for the relationship? How have those factors influenced the trajectory of your relationship?
If you're a coach: How do you learn about a prospective client's initial conditions? How do you determine whether you can add value? What factors lead you to decline a prospective engagement?
2. Support and Challenge
As I wrote in 2017, "A client once told me, 'It feels like you're always in my corner, but you never hesitate to challenge me.' It was some of the most gratifying feedback I ever got because it precisely describes my intended approach to the process. My clients need to feel supported by me in a number of ways... My clients also need to know that my support will not prevent me from challenging them."
And as I noted just a few weeks ago, "[Coaching will] involve surfacing your assumptions and preconceptions, questioning your interpretation of events, and challenging you to take responsibility for your contributions to the situation. Coaching begins with empathetic listening, but it doesn't stop there."
When I challenge a client, I want them to know that I’m doing so with their best interests at heart, and when I’m providing support, I want them to know that I’ll always be candid and direct. This by no means a skill I've "perfected," because the right balance between the two is always dynamic, varying not only from one client to another, but also from one coaching session to the next. But I pay close attention to what a client might need in a given moment (and may ask explicitly), while observing whether we're emphasizing one mode at the expense of the other.
If you're a prospective coaching client: How do you prefer to receive support? How do you prefer to be challenged? How do these preferences serve you? How might they get in your way?
If you're a current client: How does your coach express support? How does your coach challenge you? How do you feel about the balance between these modes in your relationship?
If you're a coach: How do you express support for a client? How do you challenge them? How do you sense when you've found the right balance for a given client, in a given session? How do you sense when the balance might be off?
3. Many Teachers, No Guru
I've had so many different teachers over the course of my development as a coach. When I was considering coaching as a path I spent the better part of a year under the mentorship of Joe Murphy, who was training a friend to join his practice and invited me to work with them while I documented his methodology. I read voraciously in the process, and the single most impactful book was Susan Scott's Fierce Conversations, although I'd later add Coaching with the Brain in Mind, by David Rock and Linda Page. (Here are lists of the other books and articles I've found useful.)
Before launching my practice I talked extensively with a number of coaches about the discipline and the field, most notably Andrea Corney, Rebecca Zucker and Ricki Frankel. (Two decades later I continue to talk with fellow coaches frequently, a series of conversations I've been documenting over the last three years in this thread.) And the decision to quit my last role in management and launch my practice was catalyzed by a T-group facilitated by Barbara Brewer and Dietmar Brinkmann.
Six years after earning my MBA I returned to Stanford to serve as a teaching assistant to David Bradford. I was later accepted into the school's Group Facilitation Training Program, where I worked closely with Mary Ann Huckabay, who was previously my teacher and coach (and is still my coach today!) I was then invited to join Evelyn Williams' team that established the Leadership Fellows program and offered coaching to our second-year students. I also served on Carole Robin's staff in the Leadership Coaching and Mentoring course, which drew heavily on the Co-Active Coaching model, and I later helped to integrate that class's coaching curriculum into the revamped version of the Fellows program. I would also work repeatedly with Carole, Scott Bristol, Gary Dexter and Richard Francisco on their staff in Interpersonal Dynamics (aka Touchy Feely).
I could mention even more but am mindful of taxing a reader's patience. Every one of these teachers contributed something unique to my growth as a coach--and yet no one has been my guru. I deeply value the relationships I developed with my teachers, particularly Mary Ann and Carole, and yet I believe I've grown the most by integrating the lessons I've learned from all of them into an approach that reflects not only their influence, but also my independence. I serve neither myself nor my clients by remaining on any one teacher's path for too long.
If you're a prospective coaching client: What would you like to know about a potential coach's teachers and influences? How might this inform your selection of a coach?
If you're a current client: What do you know about your coach's teachers and influences? How do these factors show up in your coaching relationship? How might they get in the way?
If you're a coach: Who are your teachers? How have they influenced you? How have you integrated their lessons into your approach? What have you discarded?
4. Master the Playbook. Throw It Away.
Coaching involves a continuous and cyclical process of learning, unlearning and relearning. Those of us who are drawn to coaching as a profession have often played a "coach" role in prior stages of our personal lives, and that was certainly the case for me. I learned how to connect with people, how to be a good conversational partner, how to offer advice that would be perceived as helpful. This behavior was entirely genuine on my part, but it was also intentional and motivated. In a rudimentary sense, I "mastered a playbook" that enabled me to navigate interactions with a degree of effectiveness.
And yet when I began studying interpersonal dynamics in earnest with the goal of becoming a coach, I realized that I had to "throw out the playbook" and unlearn any number of conditioned responses. A little small talk could help initiate a connection, but too much would keep the discussion at a superficial level. Filling an awkward silence might ease the other person's anxiety, but it might also block a breakthrough. Volunteering advice would allow me to feel useful, but it might also prevent the other person from accessing their own wisdom. I had to relearn how to interact with people--and do so in a way that felt (and was perceived as) fluid and natural.
But coaches don't go through this process once--we repeat it countless times over the course of our careers. All of the teachers noted above had playbooks of their own, sometimes made explicit in formal texts and programs, but also embedded in the implicit norms of their practice and method. My goal was always to learn as much as I could from each new playbook, unlearn practices from prior playbooks that were now getting in the way, and relearn how to apply this accumulating body of knowledge. In order to remain constantly open to learning, I must also feel free to throw away what I've learned at any time.
If you're a prospective coaching client: What would you like to know about a potential coach's training and experience? How might this inform your selection of a coach?
If you're a current client: What do you know about your coach's training and experience? How do these factors show up in your coaching relationship? How might they get in the way?
If you're a coach: How has your training and experience influenced your approach to coaching? What playbooks have your mastered? How is your mastery of an old playbook getting in the way of new learning?
5. Power Dynamics
The longer I coach, the more I appreciate and value the work of Jeff Pfeffer, who I view as our leading scholar on power. I didn't take his course when I was an MBA student, but I included his work on my syllabus when I taught Interpersonal Dynamics years later (and as far as I know I was the only Touchy Feely faculty member to do so.) Jeff's approach is often mischaracterized by the naive as Machiavellian or unethical. In truth, Jeff is a deeply ethical person with strong opinions on right and wrong. But he's also equally pragmatic about the importance of understanding how power works and learning how to wield it, no matter what your goals are.
I don't know Jeff well, but I consider him a colleague, and last year I shared this line with him, from the anthropologist and philosopher Ernest Becker: "If you are wrong about power, you don't get a chance to be right about anything else." He found it striking, and I think it's an apt headline for his body of work. It's certainly one of the most common themes I've observed in my practice over the years. People who are seeking coaching have typically found, in one of countless possible ways, that they have been wrong about power.
This isn't to say that obtaining power is necessarily an explicit goal of theirs, although that's not uncommon. But whatever their goals, if the client is to succeed, typically they must recognize how they have misunderstood power and how it works in their particular context. They must improve their ability to engage in and win power struggles, and as I've written before, "We often think of a power struggle as a rancorous, zero-sum battle between bitter enemies, but that's just one version, and it's relatively rare. Far more common are the everyday efforts noted above: influencing others, wielding authority, maintaining status."
It's also important to consider the power dynamics within the coaching relationship. I take great care to emphasize to clients that our relationship must be a partnership of equals, and I say explicitly, "'I'm not an authority figure, nor am I a subordinate. We’ll work together as equal partners in this process and share responsibility for its success. If we ever feel that we’re not acting as partners, we’ll say so."
If you're a prospective coaching client: How might you have been "wrong about power"? How might this be preventing you from achieving your goals?
If you're a current client: What are you learning about power through coaching? How are you applying these lessons? How would you characterize the power dynamic between you and your coach?
If you're a coach: What role does power play in your coaching? How do you incorporate an understanding of power dynamics in your approach? How do you manage the power dynamic between you and your clients?
6. It's a Journey
A coaching relationship is a type of journey, each one unique, but collectively possessing some similar features. As I learned many years ago, it's the client's boat: "Coaching inevitably involves helping a client reach a destination, and as a coach it can be easy to fall prey to the illusion that it's my boat, I've invited the client on board, and after we've reached our destination they'll step ashore. But that gets things exactly backwards: it's the client's boat, they've invited me on board, and after our work is done I'll go ashore while they continue on to the next leg of the voyage."
While a journey should be a meaningful experience, the coaching process must also be normal: "Coaching...must challenge established norms, from clients' internal mental models to the surrounding organizational culture. But even as we're challenging these norms, coaches and our clients must also find ways to work within them. In a word, for coaching and other interventions to achieve their goals they must be perceived as normal--stimulating and thought-provoking, certainly, but also applicable under everyday conditions. But too often coaching and related services are perceived as special--applicable only under unusual circumstances or too far beyond everyday norms to be practical or sustainable."
On this journey client and coach rely on each other as traveling companions, which entails a degree of intimate distance: "Meaningful coaching is always an emotionally intimate experience, no matter what’s being discussed. In part this is a function of the context: two people talking directly to each other with no distractions... Intimacy in a coaching relationship also results from a willingness to 'make the private public'--to share with another person the thoughts and feelings that we usually keep to ourselves... And yet an essential factor that makes such intimacy possible is a clear set of boundaries defining the relationship, which create an inevitable and necessary sense of distance... The relationships I have with my clients are warm and friendly ones, and yet it would be inaccurate to say that we're friends--they need me to be their coach, not their friend, and we do the relationship a disservice if we confuse the two."
If you're a prospective coaching client: Where are you going? How might coaching help you get there? What are you looking for in a traveling companion?
If you're a current client: How would you characterize the journey to date? How are you assessing progress? In what ways does coaching feel "normal," i.e. applicable under everyday conditions? In what ways does it feel "special," i.e. impractical or unsustainable? How would you characterize your coach as a traveling companion?
If you're a coach: Whose boat is it? How do you know? How do you make coaching applicable under your clients' everyday conditions? How do you make coaching a practical and sustainable experience for your clients? How are you showing up as a traveling companion for your clients? How are your clients showing up for you?
Thank you to my clients and students over the years. It was and continues to be a privilege to accompany you on a stage of your journey.
For Further Reading
Connect, Reflect, Direct...Then Ask (On Coaching) (2023)
Self-Care for Coaches (2023)
Work with Whatever Shows Up (2022)
Coaching and Emotion Management (2018)
Deference Kills Coaching (2018)
Three Paradoxes (Another Coaching Manifesto) (2017)
The Six Layers of Knowledge and Better Conversations (2016)
Tips for Coaching Someone Remotely (2015)
How Great Coaches Ask, Listen and Empathize (2015)
How to Find (and Choose) a Coach (2013)
Coaching and the Cult of Done (2012)
In Defense of Normal (A Coaching Manifesto) (2012)
Coaching Is a Journey (2011)
Hammering Screws (Bad Coaching) (2011)
Gestalt Coaching (2009)
Image via Wikimedia.