Coaching Senior Leaders

Why coaches can struggle at senior levels

Danny Taylor

Coaching a senior executive is not the same as coaching a team or middle level leader. Senior people live in different worlds to everyone else. It’s the context, and the impact of that context on the emotional and cognitive life of the leader, that drives this.

Everyone has an opinion about their leader or executives above them in their organisation. People in modern organisations often view senior leaders with suspicion and cynicism. Yet few people making these judgements have any real sense of what senior people do. They want things from their leaders, and if they don’t get them, they rate them poorly. Everyone looks up and wonders “what do these people do?”. It’s the same question a coach must ask to add value to their client. What do these people do? Too often we assume we know or know enough. Too often we don’t.

What makes senior leadership different?

The nature of work itself is more challenging at senior levels. There is a complexity inherent in work, that increases with organisational hierarchy. The modern mind wants everything to be democratic and flat, but some level of hierarchy is essential. Hierarchy is not a problem per se. It’s rigid hierarchy that people rightly resist. Yet without an acknowledgement of implicit hierarchy, the capacity to organise at a macro level is lost. And organising via workable structures is one of the responsibilities and accountabilities of a senior leader.

You can’t hold senior people accountable unless they have unique work to be accountable for. What’s theirs and theirs alone? Understanding the reality of a senior leader’s role is important, for both leader and coach. Another unique aspect of their work is to bring together and integrate all the outputs from the people in their domain. This could be 50 people, 500, 5,000 or 50,000.

The more senior the work, the greater the size of the jigsaw puzzle a leader is responsible for (more pieces to be conscious of), the less tangible the pieces they are working with (increasingly working with ideas rather than things), and the more turbulent the environment within which the complex jigsaw is managed (everything is shifting and moving at a faster pace).

While the process of deciding “what gets focus and what gets delegated” is a common challenge for all leaders, the specific contents are very different at senior levels.

The more senior you are, the more challenges shift from problems to context. What occupies a senior leader’s mind is not all about tasks (much of which can be delegated), but sorting and choosing from different moving pieces, disrupting and unifying, and innovating and correcting; all within the context of uncertain market forces and shifting internal demands.

A lot of what happens at team leader level is people management, which is what most current leadership literature focuses on and argues is critical. At higher levels it remains so, but the broader context means you’re also a culture manager, a strategy manager, and a structure manager, all in one. The challenge to remain calm under pressure is also greater, as decisions have larger ramifications, and it’s harder to deal with the consequences of big decisions gone wrong.

Coaching senior leaders

Hence, as an executive coach, we need to move beyond helping senior leaders solve problems, whether task or people, to helping them make sense of their context. This means that coaches also need a feel for the organisation’s context.

Most coaches wouldn’t have a clue about the detail of what executives need to confront. They couldn’t do the job themselves or understand all the threads that make up the leader’s job, which means they usually limit their interventions to areas of an executive’s world that they can comprehend – general topics like having a vision, specific topics like managing people in practical terms, or intrapersonal topics like helping executives develop insight into themselves. This is not so much a criticism as a statement of opportunities for coaches who want to be more successful with very senior people.

The reality is that problem-solving around micro issues of task or people challenges is rarely where coaches can help senior executives – the executive can often sort most of this themselves. By the time they’ve reached this level, they’ve already confronted the domain of problem-solving many times. Probably many more times than the coach. So, the executive won’t value specific problem-solving as much as would a more junior leader and will experience the assistance as helpful but limited.

What the executive values is making sense of the context within which decisions need to occur, to the extent they can then solve emerging problems themselves, because of their increased clarity.

Problems in coaching orientation

To work effectively at a senior level, coaches must lead with “who they are” rather than “what they know”.  Their knowledge is important but more as resource kit. The idea is to draw on knowledge when needed, leaving the sessions open and fluid, rather than having an overly tight coaching process.  If you must consciously follow process all the time, it suggests you’re still not confident in yourself. In time, a good coach will follow process unconsciously, or work to a set of principles that provides scaffolding, but no more.

Many coaches have little belief that the answers lie in the executive rather than the coach. They say they do, but their actions suggest that they don’t. It’s why they focus so much on practical outcomes from each session. While this is sometimes useful, it’s often better with senior leaders to leave things ambiguous, so the executive can make their own sense of things between sessions. This has a more long-lasting impact. We need to move away from the idea that everything important happens in the coaching sessions themselves.

And then there is the problem of extremes. Professionally trained coaches often have a bias to the psychological. They downplay other domains. Retired executives who become coaches based on their business experience, on the other hand, often have a bias to the non-psychological. They don’t understand the way leaders can self-sabotage as a result of their psychological complexity. Both views are extreme. A good coach for a senior level leader will have the capacity to work with all of this.

What senior leaders value in their executive coach
  • Someone to help them make sense of their world.
  • Someone to help them include and integrate all their experience, not just what the coach thinks they should focus on, which is usually a fraction of the executive’s world.
  • Someone to walk alongside them psychologically, providing perspectives as counterpoints.
  • Feedback on the way they turn up in coaching sessions, on the basis that patterns of behaviour could and often will be replicated in their jobs.
  • Someone to accept them and their world as it is. No judgement. No right and wrong. Just challenges to be grappled with.
Capabilities of a senior level coach
  • The confidence and capacity to stay with whatever is happening for the executive. To explore the territory that is most pertinent to THEIR world.
  • The capacity to see and understand the same level of complexity that’s seen and understood by the executive.
  • A non-superficial knowledge of the organisation’s challenges – strategy, structure, culture, financial position etc.
The demand for senior level coaches

There is a real demand for effective senior level coaching. It’s surprising how much senior leaders appreciate good help. Hence great opportunities exist for coaches who want to push and develop themselves. These people will see any training they’ve had in coaching or counselling as just the start of what’s possible. Their journey will require them to face into …

  • The need to develop as a person and have this as a life-long pursuit. As a coach, undergoing personal therapy or counselling yourself is not just about fixing any of your problems. It’s a finishing school for you as a human being. An effective coach will continually work on themselves (and not just through reading and thinking about themselves, but exposing their challenges to another person, like we’re asking clients to do with us). If you decide you don’t want to do this, that’s fine, but don’t complain when executives prefer other coaches to you. They can sense how far you’ve gone in your own journey.
  • An emerging need for non-superficial organisational knowledge. One senior consultant told me years ago that there was no need to understand the world executives were grappling with. Because as a coach we brought psychological knowledge. But that’s not what executives think.
  • A need to be OK with your own vulnerabilities, including revealing this in an appropriate way to your clients. Vulnerability is currently flavour of the month. Yet it’s always been important, but as a way of being rather than a thing to do! It centres around the capacity to acknowledge and say, “I don’t know”. This is a challenge for many coaches, primarily because of the lack of confidence they have in themselves. They think if they reveal this, the client will lose confidence. Yet the opposite occurs, if you say this when it’s true, but from a position of you as coach feeling OK in yourself. Clients often actually need this to drop their own guards. This is because you’re not “doing” something to executives, you’re in relationship with them.
  • Clients can sense your competence, more than you can sense theirs. They do that by virtue of what you acknowledge and address in their experience. So, if you limit the territory to the areas you feel confident with, in terms of your organisational knowledge base and personal self-understanding, the executive will feel and sense your limitation. You can go into the unknown and still come out alive!


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