What does a CEO coach do?

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Listening to other people’s problems all day?

It hit me recently that this month marks five years since I began working as a CEO coach. In that time, I have coached over a hundred CEOs, investors, and other coaches. Looking back over these years, I am honored to have been a part of so many profound, intimate conversations.

My very first coaching call does not feel very long ago. I remember how honored I felt in that first conversation as the person in front of me opened up about the deepest challenges of her work and life. I wanted to be helpful, to assist her in seeing that the doubts she experienced were common to all leaders. To help her move toward a more profound knowledge that she had what it took to lead. I wanted to help equip her with practical tools to feel more effective in her role. After the call ended, I remember sitting back in my chair and feeling my whole body buzz. This was it; this was what I wanted to do with my time from now on.

Before that call, there was no point in my life where I thought a ‘coach’ was something I wanted to be.

I remember the first time my own coach suggested I explore coaching. My response was abrupt, “There’s no way I want to spend all day on Zoom listening to people complain about their problems!” Hilarious in hindsight.

He responded with assurance that was far from his experience of the work. Only later, when I began coaching training and took on my first few clients, did I begin to understand what he meant. This was not dreary, dull work; it was fun and energizing.

In desperate need of help

My first exposure to coaching was not great. When my last company, Twenty20, raised our first sizable outside capital, I asked our new investors to introduce me to a couple prospective CEO coaches. After interviewing two or three, I hired one.

Then, promptly fired him after our first couple of sessions.

While he came highly recommended from a top venture firm, he had no experience as a founder or CEO. I couldn’t help but feel that in our conversations, he was applying frameworks without understanding what I was going through or how to be practically helpful.

A year or so later, I met Jerry Colonna at a CEO bootcamp in Colorado. Sitting with Jerry at dinner, I shared my story about hiring and firing my first coach. Jerry laughed and asked me what had gone wrong. As I explained my experience, it became clear Jerry got it. Coaching had to be about something more. Jerry and I decided at dinner that night to begin a coaching partnership that would span several years as we built and sold Twenty20.

When I met Jerry, my life and work were fraught with challenges. On the work front, we had just raised a sizable Series A but were struggling to find traction after a significant pivot of the business. My co-founder and my relationship had fallen apart. I felt like a total imposter in my CEO role. Every other founder I read about seemed to have things figured out; I did not. At the same time, I was going through a divorce and the loss of my second child. I was learning to be a single parent while navigating grief and trauma. I was in a difficult place.

While I had a great therapist at the time, my work with Jerry began to add something more to my life. It created a space to knit together the changes I was going through as a human with my role as an entrepreneur and leader. It also gave me a relationship where I could share all I was struggling with in my work with someone who had the context of what it was like to run a high-growth, venture-backed company. I felt like Jerry got it.

As we went through the sale of the business and I found myself navigating tremendous life change including the beginning of a new marriage, I went on to work with another incredible coach and guide, Jim Marsden. Jim was the one who would eventually suggest I explore work as a coach and who met my rebuff with a smile.

Eventually, the idea of going through coaching training captured my curiosity. As I wound up my time working with the acquirer of our business, I made a list of things I wanted to spend my time on over the coming two years. Coaching training made the list.

I did not imagine at the time I would go on to work full-time as a coach. I thought training as a coach would make me a more effective CEO the next time around. Also, I experienced working with Jerry and Jim as a bit of magic. Being a client of coaching had changed my life: my experience of being me, my understanding of leadership, my closest relationships, and my acceptance of myself. But if you had asked me at the time how coaching did that, I could not have explained it. I just knew it worked. I was curious to learn how it worked. So, I signed up for my first coaching training.

After that first session with my very first client, I was hooked. I wanted to spend as much time as I could in the years ahead in sessions doing deep change work with other humans. Five years into that work, here is a peek behind the curtain on the magic of coaching. By no means do I have it mastered or figured out; I view coaching as a craft that is equal parts science and mystery. And I still learn every day. But here is my take so far on some of the core elements of the magic of coaching.

What is it we are actually doing here?

The what

I often get asked about the difference between coaching and therapy. The line is not concrete. Even my own sessions with my own coach often look like therapy, and my sessions with my own therapist often look like coaching. Loosely speaking, therapy looks at past trauma and helps us find healing. Coaching looks at our present state, contrasts it with where we would like to be, and helps us accelerate our arrival at that place. In my years as a CEO, I found it deeply helpful to have both a coach and a therapist; I often suggest such to my clients.

As a client of coaching, I also found coaching to be a powerful resource for learning to manage my own psychology. So much of leadership, entrepreneurship, and any creative act is about getting out of our own heads. On my strongest day as a leader, I was grounded, curious, and creative. On my weakest days, I was stuck in mental doom loops: questioning my own worth or ability or fearing the future. My time with my coach helped me get out of my head, into the present, and into informed action.

As a result, my performance improved. In the way, executive coaching has commonalities with athletic coaching. I became a better CEO and a better operator.

Coaching also helped me to lift my head up and see the whole chess board. Building a company or leading any organization is like playing a multi-year game of four-dimensional chess. And in the midst of the daily fires, I found it easy to lose long-term perspective. I also found it easy in the midst of challenges to get stuck in obvious options instead of seeing more creative solutions available to me. Coaching helped me pick my head up, get out of the day to day, think bigger, and see paths available to me and our team I could not have seen alone.

A great coach gives you the experience of Neo in The Matrix where time slows down and suddenly he can dodge bullets.

Lastly, coaching helped me to identify beliefs and patterns that were limiting my success and damaging our company culture. We all have beliefs and patterns we picked up in childhood to help us fit in in our families of origin, stay connected, and survive. Part of becoming a fully-formed adult is understanding the patterns at play for us, sorting which our authentic us vs. which no longer serve us, and moving past the unhelpful ones. This is the core of self-work and of what we do in coaching.

As examples, I learned in my work with Jerry that I had patterns of:

• Seeking to please others
• Avoiding failure instead of aiming for success
• Avoiding conflict
• Numbing my emotions

And that is just the start. Each of these patterns got in the way of my ability to be an effective leader, partner, and parent. Jerry helped me to hold compassion for myself, understand where these patterns began, and move through them to a place of leading and relating that was more me. That change marked the beginning of my ability to lead from the fullness of my true self. And to live from the fullness of my true self. It was a reclamation of the gift I had been given at birth but had abandoned in the ensuing years.

Coaching restarted my life.

The how

The question of how coaching brings about such powerful change is still mysterious to me. I understand far more than I did five years ago, but I sense I could coach for the next 50 years and still be discovering. That said, let me share a bit of what I have come to see so far.

First, coaching creates a different kind of space than most of us have anywhere else in life. When I begin a coaching engagement with a client, we enter into a shared bond aimed at helping her or him find relief and make the changes she or he is desiring to make. We are in it together.

I find even with my closest friends, even in our deepest moments of connection, it feels like we are dropping in and out of each other’s stories. We might catch up over dinner, share some stories or advice, and head on our way. Coaching offers something different. We are on a journey together.

That togetherness, over time, creates a shared context that is similarly hard to find elsewhere. The time is scheduled regularly and held sacred. The time is also:

• Highly focused
• Protected from distraction
• Held in confidence
• Focused entirely on the client

As a result of these agreements, some powerful things happen. Most clients describe an ability to be far more raw and open in a session than they can be even with their closest friends or romantic partners. Because the time is focused entirely on the client, and because coaches are trained in asking powerful questions, more listening happens in an hour of coaching than most of us experience in a given week.

When I coach coaches, I often remind them, “If you do nothing besides listen, you are giving your client a powerful gift.” We tap into our own wisdom best when being listened to. We see ourselves most clearly when being witnessed by others.

This effect is perhaps most significant in the hardest moments.

When I would meet with Jerry or Jim, I would bring the single greatest challenge I was facing at the time. And we would work it together. Some of those challenges were the darkest moments of my life - others simply the fire of the week running a startup. In either case, I knew I had a trusted partner showing up on the call. As a result, whatever the challenge at hand, I did not have to navigate it alone.

Going from feeling alone - to feeling a sense of partnership - in a huge challenge is a monumental shift.

I become a superhero when I feel connected to and supported by the people around me. But even the smallest challenge can feel overwhelming to me when I feel alone. The teachings of modern Attachment Theory suggest I am not alone in that dynamic.

The last reflection on the how that I will offer is that effective coaches bring in proven tools for the task or challenge at hand. While many coaches view tools and frameworks as the crux of coaching, I offer this last because I view it to be the least important or helpful element of coaching. But they do play a role.

In our work my firm, Sanity Labs, we offer two types of tools:

1. Traditional coaching tools
2. Company building tools

Coaching tools include things like active listening, breath or body work, self assessment tests, parts work, power frameworks, and the like. Many of these tools are deeply helpful to have in our quiver as humans or leaders. In my time as a CEO, I learned practical tools from my work with my coaches that helped me to be my own best coach in the moment, to more effectively manage my own psychology, etc.

The second bucket of tools are methods we as at Sanity, in our time as founders, operators, and coaches, have seen be effective in hundreds of companies over the years. Reliable ways of doing the work of bringing together groups of humans around a shared mission, resourcing the work, and bringing clarity and care to the people involved. Sometimes, it is nice not to have to re-invent the wheel. The benefit of exploring these tools with a coach, rather than an advisor, for example, is that coaches are trained to operate in the grey. In short, we understand and honor that no tool is right for every company or person every time. We help our clients learn about tools and trust them to assess what to use when - building a powerful quiver and the needed skills - rather than prescribing any given solution or action. This removes that feeling you may have had of asking five different advisors for advice on a challenge and receiving five different recommendations - only to find yourself more confused than when you started. Coaching offers a different and I believe far more powerful approach to building powerful leaders.

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Closing

I have mixed feelings about this post as it comes to an end. I am reminded of the parable of the blind men and the elephant - where three men are each touching an elephant. One has the trunk and describes the elephant as a rope. Another has a toenail and describes the elephant as a rock. Etc. Similarly, this post offers 1% of what I know about coaching. And I probably only know 1% of what there is to know. But this is the toenail as I see it. I hope you found it helpful in your own exploration.

Both sides of the coaching desk, as a client and coach, have offered profound connection, clarity, and joy in my life. However you find yourself exploring coaching, I hope it can offer the same to you.

If I can be of assistance in any way to your exploration, please reach out.

In the meantime, sending you a big hug from my dining table in Los Angeles.

-Matt

Looking for some support? If now is the time to consider coaching (or a CEO peer circle) reach out here.