Why Most Executive Coaching Fails, And What to Do Instead

By Ton de Graaf | Chartered Business Coach™ | Quest Coaching International

Ton de Graaf, Executive Coach and Chartered Business Coach™

Executive coaching has become one of the most widely used leadership development interventions in the world. Billions are spent on it annually. And yet, in twenty years of working in this field, I have met very few senior leaders who describe a previous coaching experience as genuinely transformative.

Useful, sometimes. Interesting, often. Occasionally even enjoyable. But transformative, the kind of experience that fundamentally changes how a leader thinks, decides, and operates, rarely.

This is not because coaching does not work. It does, when done well. The problem is that most coaching is not done well. And because the industry has a low bar for entry and a weak culture of accountability, mediocre coaching has become normalised to the point where many senior leaders have quietly concluded that coaching's value is modest at best.

They are wrong about coaching. But they are right about most of what they have experienced.

Here is what I have observed, over two decades, about why executive coaching so often underdelivers, and what the conditions look like when it genuinely does not.

1. The coach is selected for comfort, not for fit

The most common way coaching engagements are initiated in large organisations is through an HR-managed process in which the leader is presented with a shortlist of approved coaches and asked to choose one. The selection criteria are rarely explicit. What drives the choice, in most cases, is rapport, specifically, how comfortable the leader feels with the coach after a brief introductory conversation.

Comfort is not irrelevant. A coaching relationship requires sufficient trust to have honest conversations. But comfort and trust are not the same thing, and selecting for one does not guarantee the other. In practice, leaders who select coaches primarily on the basis of comfort often end up in relationships where the coach is skilled at making them feel understood but not particularly skilled at making them think differently.

The best coaching relationships I have seen, and the most productive ones I have been part of, are characterised not by comfort but by a specific kind of productive tension. The leader respects the coach's judgment. The coach is willing to challenge the leader's assumptions. Both parties are committed to honesty over harmony.

If you are selecting a coach and the most notable thing about the conversation is how nice it felt, keep looking.

“The best coaching relationships are characterised not by comfort but by productive tension. The coach is willing to challenge assumptions. Both parties are committed to honesty over harmony.”

2. The goals are too vague to measure

A coaching engagement without clear, specific goals is a conversation without a destination. It can be stimulating. It will not be transformative.

This failure mode is surprisingly common, and it is shared between coaches and clients. Many coaches, particularly those trained in non-directive approaches, are reluctant to impose structure on what the coaching addresses, preferring to follow the client's lead. Many clients, particularly senior leaders who are used to setting agendas, arrive without having thought carefully about what they actually want the engagement to produce.

The result is a series of individually interesting conversations that cover a broad range of topics, produce some useful reflections, and leave the leader broadly satisfied but unable to articulate, three months later, what specifically changed as a result.

Effective coaching begins with a rigorous goal-setting conversation, not ‘what would you like to explore?’ but ‘what would need to be measurably different in six months for you to consider this engagement successful?’ The answer to that question, when both parties are honest, is often more specific and more challenging than either anticipated. That specificity is what makes the work possible.

3. The coaching stays in the room

One of the most persistent limitations of individual executive coaching is that its effects are contained within the coaching relationship. The leader has insights, makes commitments, and develops new perspectives in the coaching sessions. Then they return to an organisation that has not changed, a team that has not been involved, and a set of structural and cultural conditions that actively reinforce the old patterns.

Real behavioural change at senior level is not primarily a function of individual insight. It is a function of what the environment around the leader makes possible, rewards, and expects. A leader who leaves a coaching session determined to be more decisive will struggle to sustain that change if their organisation’s culture punishes bold decisions and rewards cautious consensus.

The most effective coaching engagements I have conducted have involved, at appropriate points, the leader’s direct reports, peers, or stakeholders, not to expose or manage the leader, but to create a broader context in which change is visible, supported, and reinforced. When the people around a leader know that development is happening and have a role in supporting it, the rate of sustainable change increases dramatically.

“Real behavioural change at senior level is not primarily a function of individual insight. It is a function of what the environment around the leader makes possible, rewards, and expects.”

4. The coach lacks genuine business credibility

Executive coaching has its roots in psychology and counselling, and the best coaches bring real psychological sophistication to their work. But senior leaders in complex global organisations are not primarily dealing with psychological challenges. They are dealing with strategic decisions, organisational politics, board dynamics, performance pressures, and the specific experience of operating at the top of a large institution.

A coach who has never operated at that level, navigated those dynamics, or been accountable for outcomes of that consequence is working with a significant disadvantage. They can ask good questions. They cannot always recognise which answers matter most, or understand the real complexity of the environment their client is navigating.

This does not mean every effective executive coach needs to have been a CEO. It means they need to have accumulated enough genuine exposure to senior leadership, through their own career, through years of working at that level, or through a background that gives them a credible frame of reference for what the work actually involves.

Leaders know the difference, even when they cannot articulate it. The coach who has earned the right to challenge a senior executive is the one who demonstrably understands the territory. The one who has not earned that right is the one who gets politely managed.

5. There is no accountability between sessions

Insight without action is interesting but not developmental. The leadership behaviours that most need to change in senior executives are not changed by conversations, however good those conversations are. They are changed by practice, by trying something different, observing the result, reflecting on it honestly, and adjusting.

Many coaching engagements produce good conversations and weak accountability. The leader leaves each session with a broad sense of direction but without specific commitments that will be reviewed at the next session. The space between sessions, which is where the real work of change happens, is unstructured and unsupported.

Effective coaching treats the time between sessions as seriously as the sessions themselves. It involves specific, observable commitments. It involves honest review of what happened when those commitments were tested. And it involves a coach who is willing to hold the leader accountable for the gap between their stated intentions and their actual behaviour, not punitively, but with the directness that genuine development requires.

What good coaching actually looks like

The conditions that produce genuinely transformative coaching are not mysterious. They require a coach with real credibility and the willingness to use it. They require specific, measurable goals that both parties are committed to. They require a structure that extends beyond the coaching room into the leader’s actual working environment. And they require an accountability relationship that is honest enough to be uncomfortable when it needs to be.

These conditions are not the norm in the executive coaching market. But they are achievable, and when they are present, the outcomes are qualitatively different from what most leaders have experienced.

If you have been through a coaching engagement that felt fine but did not fundamentally change anything, you have not experienced what coaching can do at its best. The bar is considerably higher, and considerably more demanding, than the industry’s average offering suggests.

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Ton de Graaf is the founder of Quest Coaching International and a Chartered Business Coach™ with over 20 years of experience coaching senior leaders in Fortune 500 and FTSE 100 organisations across 30+ countries. His background in the Royal Dutch Military Police and Royal Dutch Airforce informs a coaching practice built on precision, directness, and accountability.

To explore working together: coachton@qci-coaching.com  |  www.qci-coaching.com