Sean DeLaney

An Essay on the Craft

The Art of
Executive Coaching

The art of helping another person change. Built from thousands of hours of private work with CEOs, founders, investors, and professional athletes.

S
Sean DeLaney
Executive Performance Coach
12 min read
The greatest privilege of human life is to become a midwife to the awakening of the soul in another person.
Plato

The longer you spend in any craft, the things you thought were important in the beginning tend to fade into the background, and what was in the background becomes the foreground.

That's what happened in my coaching work. I used to think it was all about the tactics, the frameworks, the morning routines, the habits, the business systems and KPIs. All of those are important and worth exploring, but they're not what actually makes another human being change.

Maybe you are searching among branches for what only appears in the roots.
Rumi

Everything I focus on after a decade of sitting behind closed doors with CEOs, investors, founders and professional athletes, lives beneath the surface. In the roots. And almost everything that matters in an executive coaching relationship is invisible. That's why it's an art.

What follows is how I think about my craft at the deeper levels that make the whole thing work.

TheWomb

We do not create music, we only create the conditions so that she can appear.
Sergiu Celibidache

It took me almost ten years of coaching to understand my main job is to create an environment that acts as a womb. That's the most precise image I've found for it. A womb provides what the growing thing needs without doing the growing for it.

A womb is warm, protected, and designed to hold what is not yet ready to exist fully in the open world. When a coach creates these types of conditions, then growth can take place for the client.

If someone told me ten years ago that the first thing I needed to do was create a womb for the other person, I would have rolled my eyes at them and showed them a great morning routine or how to be more productive. But without this, anything I give them doesn't seem to take root. This is the critical foundation that allows everything else to grow.

This is why creating the womb is more important than the frameworks. You could have one person work with five different coaches, all using the same frameworks, asking the same questions, having the same amount of time with a client, and the client will experience vastly different things with each person.

I don't pull on the flowers in my garden demanding they grow. I create an environment that has the ideal conditions so they can flourish. I'm doing the same thing with a client that I do in my garden. I'm trying to create the conditions where the person feels seen, protected, supported, totally accepted, and has a genuine connection with me. If those are created, then human flourishing can take place.

Programs don't change people. Relationships change people. Coaching is a relationship, and it's different from consulting, therapy, or mentorship, though there's elements of all of them woven in. Coaching at its core is a relationship specifically designed to help someone access a fuller version of themselves than they can access alone.

The most empowering relationships are those in which each partner lifts the other to a higher possession of their own being.
Pierre Teilhard de Chardin

The coaching relationship is the most unique relationship you'll experience, because it's the only one where there is nothing expected of you to reciprocate. A coach is solely focused on you and your growth. Every other relationship in your life will come with expectations. This one doesn't.

One of the things I see in almost everyone I coach is the isolation of the role. They have people around them, but nobody who actually understands what they're going through. Everyone in their life is either adding pressure, expecting something, or biased by the advice they give them. Every client I've ever worked with has said some version of the same thing: there is no one else in the world I can say this to.

How can you possibly share the lack of confidence you have within yourself to your board or to your investors? How do you tell your partner how exhausted you are by them without creating massive backlash? So who do you share the deepest realities you're facing and get unbiased feedback from someone who has spent thousands of hours helping people navigate these very things? If you don't have a coach, you navigate it alone.

The people I've ever worked with are ooking for the same thing at the deepest level. To be seen.

And in our modern world, people are starving for this and rarely ever getting it. Great coaches see people and let people feel seen. They acknowledge what others don't notice. They challenge where there's a clouded view of reality. And they do all of it from a place that communicates, in every moment, this coach truly has my back.

The seeing itself can be an intervention. Before any question is asked, just the experience of being genuinely seen by someone is itself transformative. It gives people permission to be more fully themselves than they have allowed themselves to be in most contexts. When you get someone in your life like this, it's like a release valve that dissipates much of the built up pressure almost instantaneously.

And this extends beyond the formal sessions. Part of what I work to build with clients is the sense that they carry the environment with them. That the quality of acceptance and awareness and presence and self-honesty and non-judgment that is present in our sessions begins to be something they can access on their own, when I'm not present. The womb extends, because what has been developed in that space begins to belong to them.

Presence

The belief that there is some future moment more worth our presence than the one we're in right now is why we miss our lives.
Cory Muscara

If there is a single word that sits at the center of everything I do, it's presence. It sounds obvious, and it is, but you'd be amazed at the lack of presence I've witnessed in almost every organization, leadership meeting and coaching session I've sat in on.

All great coaching begins with the art of Presence. All changes I can help with come downstream from it.

The deepest levels of presence for me sits at the intersection of three things: emotional presence, physical presence, and spiritual presence. All three are required and if any one of them is absent then something is missing that the client will feel, even if they can't articulate it.

Emotional presence means I am genuinely with this person. I'm not coaching from a playbook or rehearsing what I'm going to say next, I'm entering their world. Their reality is my reality for the duration of this conversation. I am moved by what is moving them and I am troubled by what is troubling them. I am not faking anything, I am in genuine contact with another human being's experience.

Physical presence means I am fully here, in this body, in this moment. Not distracted (I've spent years tracking and making a list of every element in my environment that might distract me or take me out of presence and I've removed it). There is something that happens when a person is fully physically present that other people feel before any words are exchanged. I have walked into sessions and immediately known something was different, not because of what the client said, but from how the energy in the room felt. The body communicates before the mouth does and a great coach is fluent in this language.

Spiritual presence is harder to define but you can sense it when it is there. It is the quality of being genuinely with someone at the soul level. With the full weight of what they are carrying, what they are capable of, what they are afraid to admit, what they are longing for. Almost everything that matters in a coaching relationship is invisible. Spiritual presence is what allows you to perceive the invisible.

I could have two clients sit in the same chair on the same day and need entirely different things from me. One might need to be pushed while the other just needs someone by their side. And being deeply present is how I know what that person needs.

People sense when they are in the presence of someone who is completely with them. It is rare enough that when it happens it unlocks something that has often been locked for a very long time.

When presence is established, portals open in people.

This is why I say coaching is an art rather than a science. All of the coaching frameworks are learnable. The questions are just words arranged in a certain order and can be memorized. But deep Presence, the particular quality of being fully, genuinely, completely with another person at the moment they need it most, is something different. It requires that the coach do their own work, continuously, so that they are not carrying so much of their own unresolved material that it interferes with their ability to fully enter someone else's world.

Beneath the Surface

Until you make the unconscious conscious it will guide your life and you will call it fate.
Carl Jung

The pattern is almost always the same, clients come to me wanting to fix the external things in their life and once those are fixed they believe they will feel better internally.

They want help scaling the business or learning how to have better one-on-ones. These are important problems and we'll certainly tackle them in our work. But these are surface problems, and they have nothing to do with the deeper work.

The deeper work lives beneath the surface. And most people don't get results with coaching because the majority of coaches stay on the surface. But until you bring awareness down deep beneath the surface to the roots of the person and the issues, no amount of external fixing will matter.

Osho wrote, awareness is the greatest alchemy there is. What you're aware of you can change.

You're trying to heighten someone's awareness of the blockages, the patterns, the stories, the fears, the places where you're getting in your own way. And awareness of their own potentialities and possibilities by opening up their imagination to see new ways of being and doing that they couldn't see before because the old patterns had blocked them.

I used to think this work was about giving the client more. More tools, more frameworks, more ideas. But now my work is almost fully focused on helping people navigate the inner game by removing, letting go and shedding what's getting in their way.

The work isn't only about becoming a better version of yourself, but shedding the layers to become more of yourself.

What the Question Does

Questions may be the greatest tool in any coach's toolkit. But you have to be so in tune with the person and the situation that you know which question, even if it's a very basic question, can unlock the most profound results.

About a month ago, just a few minutes into a session with a client, I asked a question that brought up his daughter and what her experience being with him is like. It struck a deep emotional chord that had him instantly erupt into tears. There was nothing profound about the question or the phrasing of it. But I could sense that is what he needed to discuss, not what he wanted to discuss, but what he needed. His pre-call notes didn't mention his daughter once, but it was the most important thing I could bring up based on what I was sensing in the moment. If I was only locked into the agenda or what he was saying and not what he was feeling underneath, that would never happen.

So often it's not what the question is, it's what the question does. The best coaches know which question will have the effect that's needed in that moment.

I haven't found a single person who, when they slow down enough, when they get silent enough, when they have the right person asking them the right questions, doesn't already know the answers they're looking for in life.

You don't ask the big questions with the strategic mind, you ask them with the meditative mind. You sit with the questions and see what comes up deep inside you. You don't grasp for the immediate answer. You slow down. You relax. You breathe. You see what comes up, and you stay with it through the discomfort. A coach empowers you to be able to do this.

Grabbing theWheel

Am I allowing this person to drive the car, or do I keep grabbing the wheel?

I come back to this question frequently because it captures one of the deepest tensions in the craft. You're sitting across from someone and you know exactly what they need to do and you're dying just to give them the insight they need and hand them the solution that will fix their problem. But you have to resist that urge.

Because if you give them the answer, you've robbed them of the experience of discovering it themselves. And that experience is the pathway to wisdom.

I can tell you to let go of the grip, and you can nod and agree and write it down, and nothing will change. But if I ask you the right question and you sit in the silence long enough and the realization rises up from somewhere inside your own body, now you own it. Now it's yours. Now it has a chance to actually change something, because wisdom can't be handed to you, it has to be a lived experience.

A great coach allows their client to live the experience and extract out their own wisdom.

The Way Up Is the Way Down

This is how he grows: by being defeated, decisively, by constantly greater beings.
Rilke

Often the way up is the way down. But if the client never learns how to go down into themselves, then they will never go up.

Most people have spent their entire lives trying to get past the difficult experiences as fast as possible. We've been taught to try and stay positive or push through, and many people have become very good at that. So good that by the time they're sitting across from me, they need to learn how to go down into themselves again.

Suffering and pain can become the greatest teachers in the world if you learn how to sit with them and learn what they're trying to teach you. And a great coach can help create a container for you to navigate those rough periods.

I used to try to get people out of the pain as fast as possible. I don't do that anymore, because the pain, when looking back, almost always is the greatest teacher they have.

I've sat with clients in moments where everything in me wanted to say something to make it better. And I've learned that my job in those moments is to be still. To just be there. To let the weight of what they're feeling have room to exist without anyone trying to fix it or rush past it.

A coach is trying to expand an individual. To allow them to grow into a person who can handle the devastating complexity, the emotional toll, and all the elements that make a human life rich. We're not trying to limit or diminish anyone. We're trying to open them up and help them evolve into someone who can navigate the full range of the human experience in a more meaningful and authentic way.

Everything I've described so far, the womb, the presence, knowing which question to ask, resisting the urge to give the answer, sitting with someone in their pain, all of it asks something of the coach too.

Trusting Yourself

As soon as you trust yourself, you will know how to live.
Goethe, Faust

One of the things that has taken the longest to learn was to trust myself so fully that I could throw out all the prep work, the frameworks, the plan for the call, and just be there in the unfolding present moment with that person.

I don't believe you can do this the first few years of any craft, because you haven't put in the necessary reps or built time under tension to have earned that trust in yourself. But then one day you cross an invisible threshold and you can sense it's time to let go and trust. And that's when you're in rhythm with yourself.

It's like an athlete in flow. You're not thinking. You're not planning. You're just there, fully in that moment, unfolding with what the moment requires.

I have to be willing to be fully myself, trusting myself, in whatever feels right in that moment. And I have found that it's what the moment needed. There are situations where you would never recommend how you responded or acted the way you did, but you sensed that was what the moment required. You went off script and trusted yourself and that is exactly what the other person needed.

It's why my lived experience of what's transpired in sessions with clients is paramount and my ultimate teacher. What you haven't lived, you don't know. All of this has been lived. Ten years of private reflections on coaching, distilled into what I know to be true because I've seen it with my own eyes.

I would love to live like a river flows, carried by the surprise of its own unfolding.
John O'Donohue

Sean's coaching became the most transformative period of my life. How I view challenges and deal with uncertainty is vastly different today. It is no hyperbole to say that my marriage and relationship with my kids are because of Sean's coaching.
Joe Stolz
Chief Technology Officer

The work is always one-on-one.

If this resonated, the work goes deeper. I work with a small number of CEOs, executives, and founders, and professional athletes on exactly this work. Always privately, over time, at depth.

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