Coaching Senior Leaders: What Most Programmes Get Wrong

Coaching senior leaders is not the same as coaching anyone else. The stakes are higher, the egos are more complex, and the gap between what someone presents in a session and what is actually driving their decisions can be enormous. Done well, it shifts how an organisation thinks. Done poorly, it is expensive theatre that makes everyone feel like something useful happened.

The most effective coaching at senior level is commercially grounded, specific to context, and honest enough to say the uncomfortable thing. It does not start with frameworks. It starts with understanding what the person in front of you is actually trying to solve.

Why Senior Leaders Are a Different Coaching Challenge

I have sat in enough boardrooms to know that seniority and self-awareness do not always travel together. Some of the most commercially capable people I have worked with had almost no visibility into how they were being experienced by the people around them. Not because they were indifferent. Because nobody had ever told them directly, and they had been rewarded for so long that the feedback loop had effectively broken down.

That is the first thing that makes coaching at this level different. By the time someone reaches a senior leadership position, the honest feedback they receive has often been filtered, softened, or withheld entirely. People do not challenge them in the same way. They get agreement in rooms where disagreement would have been more useful. The coaching relationship becomes one of the few places where the unfiltered version of reality can be explored.

The second challenge is that senior leaders are usually time-poor and results-oriented. They are not looking for a reflective space in the abstract. They want to think more clearly, make better decisions, and move faster. Coaching that does not connect to those outcomes will be deprioritised the moment something urgent lands on the desk, which is always.

If you are thinking about how coaching fits into a broader growth and leadership strategy, the Go-To-Market and Growth Strategy hub covers the commercial and organisational dimensions that senior leaders are most often handling.

What Does the Presenting Problem Actually Tell You?

In my experience, the thing a senior leader says they want to work on in the first session is rarely the thing that is actually limiting them. It is not that they are being dishonest. It is that the real issue is often harder to name, sometimes because it involves admitting something uncomfortable, and sometimes because they genuinely have not connected the dots yet.

I spent the early part of my agency career watching talented people get promoted into roles they were not ready for, myself included, and then being given no real support to figure out what had changed. The technical skills that got them there stopped being sufficient. The interpersonal and strategic demands of the new role were entirely different. But because nobody named that gap clearly, people would work harder at the thing they were already good at rather than developing the thing they actually needed.

Good coaching creates the conditions for the real issue to surface. That takes patience. It also takes a coach who is not so attached to their own process that they cannot follow where the conversation actually needs to go. The presenting problem is a starting point, not a destination.

The Psychological Safety Problem at Senior Level

There is a version of senior leadership coaching that is essentially performance. The leader shows up, says the right things, demonstrates that they are reflective and coachable, and then goes back to operating exactly as before. It is not always cynical. Sometimes they genuinely believe they are engaging. But if the coaching relationship does not have enough psychological safety for the person to say something that could make them look uncertain or wrong, you are not getting anywhere near the real work.

I have been on the receiving end of this. Early in my career, I was in a development programme where the facilitator was clearly more interested in being liked than in being useful. Every session ended with everyone feeling validated. Nothing changed. It took working with someone who was willing to say something genuinely uncomfortable, with care but without softening it into meaninglessness, to understand what productive coaching actually felt like.

Psychological safety in this context does not mean the absence of challenge. It means the leader trusts that the coach is on their side, even when what they are hearing is not easy. That trust is built through consistency, through the coach being honest about what they are observing, and through making it clear that the goal is the leader’s growth rather than the coach’s approval.

Tools like feedback loops can help organisations understand how leaders are being experienced more broadly, but they only add value if the leader has a relationship in which they can actually process what the feedback means and what to do with it.

The Commercial Dimension That Most Coaching Programmes Miss

A lot of senior leadership coaching is almost entirely behavioural. It focuses on communication style, emotional intelligence, stakeholder management, presence. These things matter. But if the coaching is disconnected from the commercial and strategic context the leader is operating in, it can feel abstract and fail to produce lasting change.

When I was turning around a loss-making agency, the challenges I was handling were not primarily about my leadership style. They were about making hard commercial decisions under pressure, restructuring teams, cutting costs in ways that affected people I respected, and simultaneously trying to win new business to replace what we had lost. The most useful conversations I had during that period were with people who understood what it felt like to be responsible for a P&L, who could hold both the human and the commercial dimensions of those decisions at the same time.

Coaching that operates only in the behavioural lane can leave senior leaders feeling like the programme does not quite understand their world. The best coaching at this level is grounded in the actual pressures of leadership, which means the coach needs to have enough commercial literacy to engage meaningfully with the context, not just the feelings.

This is particularly relevant for marketing leaders, who are often handling the tension between brand investment and short-term commercial pressure. Understanding how to structure that argument internally, and how to hold your ground without losing the room, is a coaching challenge as much as a strategic one. Organisations like Forrester have written about how scaling leadership capability sits alongside scaling operating models, and the two are rarely separate conversations.

What Good Coaching Structure Actually Looks Like

Senior coaching programmes tend to fail in one of two ways. Either they are too loose, a series of conversations without enough direction or accountability, or they are too rigid, a fixed curriculum that does not flex to what the individual actually needs. Neither produces the kind of sustained change that justifies the investment.

The structure that tends to work is built around three things. A clear starting point that establishes what the leader is trying to change and why it matters to them specifically. A set of real situations the leader is currently handling that can be used as the material for the coaching, rather than hypotheticals. And a feedback mechanism that tracks what is shifting over time, not just how the leader feels about the sessions.

When I grew a team from around 20 people to over 100 in a relatively short period, the leaders I promoted into senior roles needed different things at different stages. Some needed help with the transition from doing to directing. Some needed support managing upward, which is its own skill set. Some needed to understand how to build a team culture they had not had to think about when they were individual contributors. A single coaching programme design could not have addressed all of those. The structure had to be responsive to where each person actually was.

There is a useful parallel in how growth frameworks are designed for organisations. The best ones, as covered in resources on growth strategy tools, are built around specific constraints rather than generic best practice. Coaching works the same way. The programme that is designed around the individual’s specific growth edge will always outperform the one designed around a generic leadership model.

When Coaching Should Challenge the Organisation, Not Just the Leader

One of the things that rarely gets said clearly enough is that sometimes the problem a senior leader is experiencing is not a personal development issue. It is an organisational one. The leader is being asked to operate in a structure that is fundamentally broken, or they are being held accountable for outcomes they do not have the authority to influence, or the culture they are working in is actively working against the behaviours the coaching is trying to build.

I have seen coaching programmes used as a way of managing around structural problems rather than addressing them. The leader is sent to coaching because they are struggling, but the reason they are struggling is that they have been set up to fail. No amount of coaching changes that dynamic. It just makes the leader feel responsible for a situation that was never theirs to fix alone.

Good coaching at senior level has to be able to name this when it is happening. That requires a coach who is not so commercially dependent on the relationship continuing that they cannot say the difficult thing. It also requires an organisation that is genuinely open to the coaching surfacing systemic issues, not just individual ones. When that openness exists, coaching can become a mechanism for organisational learning, not just personal development.

This connects directly to how the best go-to-market strategies are built. As explored across the Growth Strategy hub, the organisations that grow well are the ones where leadership capability and commercial strategy are developed together, not in separate silos.

Measuring Whether Coaching Is Actually Working

This is where a lot of senior coaching programmes go quiet. The measurement is often nothing more than a satisfaction score at the end of each session, which tells you almost nothing about whether anything has changed in how the leader operates.

The measure of effective coaching is behavioural change that is visible to the people around the leader. Not just the leader’s self-report, which is subject to all the same blind spots that made coaching necessary in the first place. The question worth asking is whether the people who work with this leader are experiencing something different six months in. Whether the decisions being made are better. Whether the team is more effective. Whether the leader is handling pressure differently.

When I was judging the Effie Awards, the thing that separated the entries that won from the ones that did not was almost always the rigour with which they had defined what success looked like before the work began. Coaching needs the same discipline. If you cannot define what better looks like in observable terms before you start, you will not be able to evaluate whether you got there.

Frameworks like growth loop thinking have become useful in product and marketing contexts precisely because they force teams to define the outcome they are optimising for before they design the intervention. Coaching benefits from the same discipline. Define the outcome. Design toward it. Measure it honestly.

The Coaching Relationship That Actually Changes Things

There was a moment early in my career, a few days into a new role, where I found myself holding a whiteboard marker in front of a room full of people expecting me to lead a creative session I had not prepared for. The founder had been called away. The team was waiting. The internal voice was loud and not particularly encouraging. I did it anyway, and it was fine, but what stayed with me was not the outcome. It was the realisation that the gap between feeling ready and being ready is almost always smaller than it appears, and that the only way to close it is to act before the confidence arrives.

That is what good coaching does at senior level. It does not wait until the leader feels ready to change. It creates the conditions in which they act differently before they feel certain, and then uses what happens to build the evidence that shifts the belief. The belief follows the behaviour. Not the other way around.

The coaching relationships that produce real change are the ones where the coach has enough credibility to be believed, enough honesty to be trusted, and enough patience to stay in the room when the conversation gets difficult. Those relationships are not common. But when they exist, they are among the most commercially valuable investments an organisation can make in its leadership.

Pricing that investment appropriately matters too. BCG’s work on pricing strategy in B2B contexts is a useful reminder that the value of a service and the price at which it is offered are two different conversations, and conflating them is a mistake organisations make in both directions.

About the Author

Keith Lacy is a marketing strategist and former agency CEO with 20+ years of experience across agency leadership, performance marketing, and commercial strategy. He writes The Marketing Juice to cut through the noise and share what works.

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