Coaching the 'water' versus the 'glass'

If the mind was a cup and all our problems, decisions, challenges were the water in the cup, what is a coach's real work? Do we coach the content or the shape of a client's thinking?

I am now in the middle of facilitating another session of our Foundation Diploma in Developmental Coaching. The program lasts 4 months and the middle bit is always the hardest. I call it the ‘dark deep pit of despair’. It’s when new coaches hit the edges of their skill, but also the edges of their own inner growth. It’s when they start seeing that our mantra, “you always get the clients you need”, is actually, weirdly (and sometimes freakishly) true.

I always share this ‘mantra’ the beginning, though nobody truly believes it until they reach the ‘dark deep pit’ and see their own existential anxieties reflected back at them in every session. If they themselves are struggling with job insecurity, a client comes worrying about their job. If they’re embroiled in deep conflict with someone in their life, a client pops in complaining about the relationship to their boss. If they’re afraid of conflict, a combative client comes in who really needs some challenge and forces them to step into deeply uncomfortable territory.

In the ‘dark deep pit’ it becomes obvious great coaching is not so much about the topic of the conversation, but the shape of our - coach and client - thinking. It’s not so much about the ‘water’ as it is about the ‘cup’.

The metaphor, born out of Robert Kegan’s work, is simple but powerful. The mind is like a cup. Inside it sit all our thoughts, beliefs, stories, and emotions. As we grow vertically, the cup itself expands, giving us more space to hold complexity. The content, the water, doesn’t vanish, but it’s experienced differently. It moves. It rushes. It flows. It takes on the shape of whatever vessel contains it. And sometimes that shape isn’t working.

When people come to coaching, they usually bring their “water.” The content of their lives. The dilemmas, tensions, decisions, and messy problems that fill their mental cup. The coach’s instinct, especially in the early years of practice, is to swirl that water around, to help the client see it more clearly, analyze it, or decide what to do about it. But developmental coaching invites a more radical question:

What if the problem isn’t in the water, but in the shape of the glass itself?

In coaching, this means that the practical challenges clients bring - the team conflict, the career decision, the struggle between ambition and impact - are all held inside a particular mental structure, the “glass” shaped by the client’s meaning making system. When a client feels stuck, it’s rarely because the water is the wrong temperature. It’s because the glass is too rigid, too small, or not quite the right shape for the choices they’re trying to make or the life they are now wanting to live.

Developmental coaching doesn’t dismiss content, it uses it as the entry point. The outer world dilemma a client brings into a session is the anchor that helps us, coaches, understand where the client is heading, what they are trying to get to, what is the destination we can accompany them towards. But the work of the coach isn’t about helping the client figure out how to solve their problem. If it were that easy, they would have done it already. Our job is shedding light on how the client is thinking about the situation, on illuminating aspects of their thinking structure that don’t allow them to see other possibilities or make it seem like the problem is intractable.

“What makes this decision significant for you?” “What assumptions are you holding about ‘success’ or ‘failure’?” “What does ‘impact’ mean to you?” “Who would you be if you didn’t have this [whatever they’re afraid of losing]?” These are all ‘cup’ questions. They turn the client’s attention from the water to the invisible structure that holds it, from ‘content’ to ‘process’.

As one coaching student put it, “focusing on the cup keeps us out of the solution trap”. The moment we zoom into content, we risk slipping into problem solving. We get tangled in the client’s concerns, in facts, details, narratives. When we zoom out to the cup, we often step into intriguing territory, shifting the client’s attention to notice the shape of their thinking, that which holds all their stories. In those moments we’re not trying to empty or clean the water, we’re exploring the nature of the vessel itself. But that is easier said than done.

We, coaches, have our own mental cups to contend with and the shape of our own thinking can make it hard to notice what is happening to the client in front of us. In one of our recent practice sessions, the coach held space for a client who was contending with some very unpleasant challenges at work. A difficult relationship. Unfairness. Being given ill-intended feedback. Anger.

The client talked and talked, downloading their emotional baggage, and the coach patiently listened and listened, almost not daring to interrupt. Then came a moment when the client spoke of what annoyed him in the other person they were in conflict with: “He talks and talks and never stops to listen or reflect,” the client said. By this point the client had talked almost without taking breath for some 15 minutes. Here was a golden opporunity. To pause. To invite reflection. To notice ‘the cup’.

Could it be possible this client was blind to their own moment of talking without slowing? How might the coach have gently and courageously invited them to pause and reflect in that very moment, to notice their talking? To make it ‘object’, watching how their own process of dealing with difficult things seemed to mirror that of the person who angered them? What might have emerged from such a moment of capturing the dynamic of the ‘cup’ as it revealed itself in dialogue with the coach and inviting the client to notice the form of it, the impact of it, the way their cup shaped their content?

What about the coach’s ‘cup’ prevented them from interrupting? Was it a desire to not upset the client? Was it a fear of breaking their flow? Was it over-identifying with their coaching strength of being a wise, calm, gentle presence? Was it an uncertainty about what to do/ask/say in that moment and worries about their own competence? Was it a discomfort with the client’s discomfort?

As we debriefed that session, which had been observed by several other coaches, we held these questions about the cups. As I offered my feedback, I held my own questions about how do I give honest feedback to the coaches I support, nudging them to see what they’re not seeing, while also holding them with kindness and full expresion of my complete faith in their potential to grow into exceptional coaches. My own discomfort-avoidant cup mirrored my student’s, but staying aware of it allowed me to do my very best speaking my own truth with kindness, balancing challenge and support, and then to encourage open feedback from my students, just as they stay open to mine. I have my own blind spots as a mentor, and their honest feedback is the biggest gift I could ask for.

This process is never-ending. It’s fascinating. Every person’s glass is different. Some are square, some oval, some a little (or more) warped from past heat and pressure. The coach’s work is not to judge the shape, but to help the client see it. Because when the client can see their glass, they can also begin to reshape it. A coach’s work is also to notice how their own glass skews what they can see of the client’s.

A square glass will always produce square water. If the shape of the mind limits what we can see or imagine, no amount of stirring will change the result. Our work is to make the shape visible, to gently tilt the glass, to notice how our assumptions contour the flow of experience. Does the shape of our glass fit how we want to show up in that moment? Does it, more broadly, fit the shape we want for our lives in this season?

There’s a beautiful paradox here. We work on the glass in service of the water. The goal is not abstract insight, it’s movement in the world. As another participant from our session the other week noted: “We explore the cup in service of making a different choice in the outer world.” Developmental coaching isn’t a detour from action, it’s an enabler of wiser action.

Ultimately, success in developmental coaching isn’t measured by the elegance of our questions or the brilliance of the client’s insights. It’s measured by subtle shifts in the shape of the mind, the small expansions that allow new choices to become possible. The glass grows. The water finds new ways to flow. And with each round of reflection and experimentation, a little more of life can be lived.

If you are a coach, how do you keep track of your own ‘cup’ in your coaching? How do you train your attention so you can stay curious about your own assumptions, particularly when you catch yourself not able to respond to the world in a way that feels balanced or fulfilling? How do you keep an eye on the in-the-moment process when your cup might clash with the client’s?

Think of one context of your life where you feel stuck, caught in the ‘content’, drowning in water. What might happen if you rise above it to see what is holding the water? If you’re keen to experiment, you might want to write down what your ‘cup’ is made of: what do you assume, believe, have taken as ‘truth’ in a situation that feels challenging? What might happen if you gently question some of that? Do any interesting (small) experiments arise, where you might try something different, just to see if the ‘cup will hold’?

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