Why Executive Coaching Fails Without Business Context

A while back I heard about a leader who had stopped getting anything out of his coaching. He put it in one sentence. His coach, he said, does not understand the business, does not speak the language of the business, and therefore asks the wrong questions.

I have thought about that sentence a lot since.

What interests me is the order he put it in. Three clauses, each one causing the next. Not understanding leads to not speaking the language, and not speaking the language leads to questions that land in the wrong place. He had not lost confidence in coaching. He had lost confidence in being understood, which is the thing the whole arrangement rests on.

The coach had probably done nothing wrong. Present, curious, disciplined about not giving advice, asking open questions that would look correct written down. He was doing the job as the profession defines it. That is what makes this worth writing about.

Not knowing is not the same as not understanding

Coaching has a principle that outsiders find strange and practitioners defend hard: the coach does not need to know the client's business. The leader is the expert on his own situation. The coach opens the thinking and stays out of the content.

I hold that standard and I am assessed against it. When I develop coaches, the failure I watch for most closely is the experienced person who cannot stop solving.

But two different things sit inside that principle, and I do not think we have pulled them apart.

Not knowing is a discipline. The coach follows the business perfectly well, understands what is at stake, could offer three suggestions, and does not. The restraint is the skill. It is difficult precisely because he could do otherwise.

Not understanding is a limitation. The coach who cannot follow what the leader is describing is not exercising restraint. He is lost, and asking open questions because open questions are what is left when you cannot follow the substance.

From the outside they look the same. Both produce questions instead of answers. On a recording, both look like a coach staying properly out of content. That resemblance is why the confusion has lasted, and why a leader can sit opposite someone genuinely skilled and still come away feeling he has not been met.

What the understanding is actually for

It is not there to supply the answer. It does four other things.

**It tells you which detail matters.** A leader describing a bad quarter gives you thirty pieces of information, and two of them are load-bearing. Knowing which two is not intuition. It is familiarity with how businesses actually come apart. When a country manager tells me the quarter went badly, the significant detail is often not the number. It is who set the number, or what was committed regionally before anybody checked what the market could carry. Without that ear you weight everything equally and end up asking about whichever detail he said with the most feeling, which is often not the one that counts.

**It lets you calibrate.** The team missed the number: catastrophe, or an ordinary Tuesday? Senior people are not always reliable narrators of their own situation. Some describe something genuinely serious in a flat voice, and others describe a difficult month as though the business is ending. If you have no feel for what normal looks like in that kind of business, you cannot tell those apart, and you will spend the hour in the wrong place.

**It lets you hear what is being avoided.** Leaders steer around things, usually without noticing they are doing it, and often around a decision they have already made privately and would rather not have examined. In multinational structures it is frequently a decision about a person, and frequently one that will have to be explained to somebody in another country. You cannot spot that circling in a business you cannot follow. You cannot hear what is missing from an account when you do not know what should have been in it.

**It lets you refuse the brief.** Organisations misdiagnose more often than they realise. A leader is sent for coaching on his influence when the actual situation is that he has been handed accountability without the authority to go with it. No amount of work on personal impact will resolve a structural problem, and a coach who cannot read the structure will spend a year on the wrong thing while everybody involved wonders why nothing is shifting.

Nothing goes wrong. That is the problem

The first sessions are a test, whether anyone calls it that or not. The leader brings something real: a market that has moved, a plan that will not survive contact with the region, a leadership team that is not delivering. He is watching what comes back.

What comes back is well formed and one level too high. So he translates. He simplifies. He explains the background that should have been assumed, and the explaining eats the hour he came to use. He does it without irritation, because he is a reasonable man and the coach is clearly trying.

By the third or fourth session he knows what this room can hold. The material changes. Now it is the difficult direct report, the diary, the balance between work and the rest of life. All legitimate. None of it the thing keeping him awake.

After that the engagement is pleasant and competent. The coach is doing good work on what is in front of him and has no idea the real agenda left weeks ago. It rarely gets cancelled, because nothing has gone wrong. He is not being coached. He is being kept company.

Months later the sponsor asks what the coaching achieved, and the honest answer is that it was useful. Useful is a devastating verdict at this level. That is the moment an organisation starts to believe coaching does not do much for senior people, and the verdict gets recorded against coaching rather than against the thing that actually happened.

In my experience leaders rarely complain about this, and they rarely fire the coach. They just stop telling him things.

What the buying process misses

Coaching is bought on the credential and the chemistry meeting.

A credential proves the craft has been examined. It says nothing about whether the coach can follow a P&L conversation or understands what a matrix does to a country manager's authority. It was never designed to. The chemistry meeting is the weaker of the two, which surprises people. It is conducted in a social register and tests whether two people get on. Two people can get on well and still be unable to work together on the thing that matters.

There is an easy fix, and I rarely see it used. Put a live problem on the table in that first meeting, with the commercial substance left in, and watch what the coach does with it. You are not listening for a solution. You are listening for the altitude of the questions, whether he goes towards the part you were hoping to skirt, and whether you found yourself explaining background you would never explain to a peer.

Some of this traces back to how coaches are trained. Most coaching programmes teach how to coach. Very few teach how to coach inside a business.

Coach training is domain agnostic by design, and for most of the market that is a strength. Executive coaching is a specialisation and the training does not treat it as one, so coaches arrive in this market with excellent craft and no working model of the world their clients live in. That is a problem for the profession and I will come back to it elsewhere. What matters here is the effect on the leader sitting in the room.

The opposite failure is worse

The opposite error does more damage, and it is the one people with my background make.

An experienced executive starts coaching and brings the experience straight into the room. He recognises the situation because he has seen it forty times. He knows what he would do. So he answers. The sessions feel productive and the leader leaves with something actionable most weeks.

That is mentoring wearing a coaching badge, and at senior levels it does lasting damage. It trains a leader to bring problems to be solved instead of thought through, which is the dependency a senior leader can least afford. It also fails on its own terms. Those forty situations were his, not this leader's, and the difference between them is usually where the difficulty lives.

Business understanding earns its place only when it stays behind the discipline. It shapes the question. It does not supply the answer. A coach who cannot hold that line is more dangerous than one who lacks context, because he is confident.

Where the line sits

No coach needs to have run a business like yours. That standard is unprovable, self-serving, and it would rule out some of the best practitioners I know.

The threshold is comprehension. Can this person follow the commercial substance of your world without translation? Does he understand what happens to a country manager's authority when a function starts reporting into the region instead of into him? Does he know why the number matters, who it matters to, and what it costs to miss it twice? That can be built deliberately by someone who has never carried a P&L. Some of them build it, through study, through proximity, through years of paying attention.

One thing I am less sure transfers at second hand is the feel for consequence. Some of it comes only from having sat in the seat, made the decisions, and owned the consequences. Having made the decision that put people out of work, or carried a number you were not sure you would hit, or been the one everybody looked at when it went wrong, leaves a residue. It changes what you notice when a leader says he is under pressure, because you are not imagining the weight. You are remembering it.

Without that, coaching becomes theoretical. Well intentioned, and disconnected from the reality of the job. Executive clients know the difference, and they rarely say so out loud.

What it costs

Two things are true about many of the senior people I work with.

The first is that they carry some version of the same doubt. Why am I here, why was I selected, why me and not someone else. I see it in nearly all of them, and I have it myself.

The second is that leadership is a lonely game. Nobody directs you. You are rarely recognised. Nobody around you is doing the motivating, so it has to come from you.

Most senior leaders have made their peace with both of those. What they have not made their peace with is buying the one conversation that was supposed to be the exception, and finding it is another room where the real thing cannot be said.

That is what is actually being bought. Not insight, not challenge, not a framework. Somewhere to put the thing that has nowhere else to go.

A coach who cannot follow the business cannot take it.