A serious coaching engagement has four phases: a conversation about fit, two or three sessions of assessment, a long middle of working sessions organized around experiments the leader runs between them, and a deliberate close. A working session examines what happened since the last one, names the pattern underneath it, and ends with something specific the leader will do differently. The change happens between sessions. The session is where the results are examined.
Leaders who have never been coached often imagine something between a performance review and a therapy appointment, and are unsure which would be worse. Those who have been coached badly imagine an hour of being asked how they feel. I want to describe what the work actually contains in a well-run engagement, because the mystery serves nobody and the structure is most of what makes it effective.
Before the Engagement: The Fit Conversation
Everything begins with a conversation about whether coaching is the right instrument. In my practice this is thirty minutes, free, and confidential. The leader describes what is going on; I ask questions; we decide together whether this is a coaching problem, something else, or nothing that needs intervening in at all.
Roughly a third of the time I say no, or not yet. The problem is structural and needs a consultant. The leader needs a mentor in their industry. Or what is being described sounds clinical, and the right first step is an evaluation rather than a coaching plan. I have written about how to tell those apart. Saying no at this stage is the most important quality control in the whole process.
Phase One: Assessment
The first two or three sessions are about understanding the person and the problem well enough to work on it. This is where my practice differs most from the conventional model.
We cover the obvious: how the leader came to this, what they want different at the end, the history of the pattern they are describing, what previous attempts to change it have looked like. We also cover what a conventional intake omits: sleep, appetite, concentration, alcohol, the timeline of any change in how they function, family history, and the physical toll of the role. Most of the time the answers are reassuring and we proceed as ordinary coaching. Occasionally they are not, and the engagement changes shape at week three rather than month nine. I have written about why that clinical first look matters.
Where it is useful and the leader agrees, assessment includes structured feedback from the people around them. A short set of conversations with the chair, two or three direct reports, a peer, sometimes a spouse. I have written about what that feedback shows and what it misses. The purpose is not a report card. It is to see the gap between how the leader experiences themselves and how they land, because the gap is usually where the work is.
Assessment ends with a written statement of what we are working on, in terms that other people could observe. Not "be a better leader," but "the executive team can disagree with me in a meeting without consequences, and does."
Phase Two: The Working Sessions
This is the long middle, usually every two weeks for sixty to ninety minutes, over several months. Every session has the same skeleton.
What happened. We start with specific events since the last session: the board meeting, the conversation that was supposed to happen, the hire, the moment the leader noticed themselves doing the thing we have been discussing. Not how the fortnight felt in general. What happened, concretely.
What was underneath it. From the event we move to the pattern. Why did the delegation get taken back? What was the leader afraid would happen if they let the silence sit? What did the chair's question activate? This is where the clinical lens does its quiet work, because the answer is often a learned response to something older than the current role, and seeing it clearly is most of the way to changing it.
What will be different. Every session ends with a specific commitment for the interval before the next. Open the next executive meeting by stating the decision to be made and then saying nothing for two minutes. Have the conversation with the underperforming CFO by Thursday. Leave the office at six on three of the next ten days and record what happened. These are experiments, not homework. Some fail, and the failures are often the most useful data of the engagement.
Between sessions, the leader runs the experiment in real meetings with real consequences. This is where the change actually happens. The session is where the result is examined and the next experiment designed. Over months the pattern that brought them in becomes visible, then optional, then absent, and the sessions move on to whatever sits behind it.
What the Conversation Is Like
It is direct. I ask questions nobody else in the leader's life is positioned to ask, and I say what I see, including things that are unwelcome. It is not an interrogation, and it is not an hour of being asked how things feel, though how things feel is sometimes exactly the point. The tone is closer to a very good consultation with a physician who has time: curious, precise, unhurried, and honest.
It is also entirely confidential, which is the condition under which any of it works. I have set out what stays private and what the limits are, and how that works when the company pays.
Phase Three: The Close
Engagements should end, and the ending should be planned. Around the three-quarter point we begin asking whether the stated outcome has been reached, whether the people around the leader see it, and what the leader can now do for themselves that the sessions used to do. The last session or two consolidate: what changed, what the early warning signs of relapse into the old pattern would be, and what the leader will do when they notice them.
Some leaders return later for a new question, which is appropriate. What I try to avoid is the engagement that never ends, because an open-ended coaching relationship drifts toward dependence, and dependence is the opposite of what the work is for. I have written about how long the whole arc should take.
If this structure sounds like what you are looking for, or if you would like to find out in a single conversation whether coaching is the right instrument for what you are facing, the first step is a free, confidential consultation.