A confidential coaching conversation between two business leaders at a table overlooking a lake.

Insights · Executive Coaching

When Does Executive Coaching Make Sense?

– and when it does not

By Mads Cronquist · Cronquist Consult ApSReading time: approx. 10 minutes

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Most leaders have plenty of people around them. Yet many lack what may be the most important thing of all: A confidential sparring partner with no agenda of their own, who can listen, challenge and understand the business.

At the same time, the coaching market is a jungle of titles, certifications and beautifully wrapped promises. How do you find out whether coaching is the answer at all – and if so, whom to choose?

This article is about when executive coaching creates real value, when it does not, and how it can be organised for both the executive team and for managers and middle managers.

Lonely at the top – and in the middle

The higher you rise in an organisation, the fewer people speak completely freely with you. Employees have a relationship with their boss. Fellow executives have their own areas to defend. The board expects results. And your family has heard more than enough about work.

But loneliness is not only found at the top. Many managers and middle managers are caught in a cross-pressure where they have to translate the strategy downwards and bring reality upwards – often without anyone to discuss the difficult dilemmas with before the decision has to be made.

In my article on blind spots I wrote about the value of a co-pilot: Someone who sees what you cannot see yourself, and who has the mandate to say it. An executive coach is exactly that – an external co-pilot. Not someone who takes over the controls, but someone who keeps an eye on the instruments and speaks up when something seems wrong.

The question, then, is what characterises the co-pilot who actually makes a difference.

Choose a sparring partner who has held the post

When I look at the leaders who have chosen a coaching programme with us today, there is one clear common denominator: They have chosen a sparring partner who has held one or more of the positions represented in their own company.

That creates resonance and an understanding of everyday challenges – where operations are tricky, where customers are demanding, and where growth is needed on both the top and the bottom line. But it also creates something more: An outside perspective that can challenge habitual thinking.

Over more than 35 years I have held positions as an officer, incident commander, project manager in Denmark and abroad, sales manager, HR director and head of business development – and today as managing director of my own company. That does not mean I have the answers to other people’s challenges. But it does mean the conversation does not stop when it turns to business. And that it does not drown in long-winded explanations and classic consultant gobbledygook.

Experience alone is not enough, though. What matters is how that experience is used in the conversation.

Coaching, sparring – and constructive challenge

Classic coaching is about asking the right questions so that leaders find the best solutions themselves – and act on them. That is still the core. But sometimes the right help is not just a good question. It may also be an analysis, an experience, a concrete tool, a different perspective or qualified challenge.

That is why I deliberately switch between coaching, advice and business sparring depending on the situation. In a single conversation we may work on the leader’s personal patterns under pressure, a difficult relationship in the executive team and a concrete decision about customers, finances or organisation.

The toolbox combines recognised models such as Immunity to Change, Lencioni’s five dysfunctions, the Johari window, the Change Wheel, Success Analysis and my own method Ildstorm (Firestorm). We often use a JTI profile as a shared language at the start. But the methods are never an end in themselves.

A typical pattern: A managing director comes to the conversation to talk about a difficult employee issue. Along the way it becomes clear that the real issue is an unresolved priority in the executive team, causing two departments to pull in different directions. The conversation then shifts from people management to strategy and back again. It is precisely in that shift that the value is created – because the leader and the business cannot be separated.

Coaching is not therapy, nor is it life guidance. It is a confidential space where leaders get help to see their own situation more clearly, make the choices they have been putting off and turn them into action. And that is exactly why it is important to know when coaching is not the right answer.

When does coaching not make sense?

One of the most important things a serious coach can do is say no. In my experience there are three situations in particular where coaching is not the answer – or at least not the first thing needed:

Three warning lights:

  • When therapy is needed: If the challenge is fundamentally psychological or personal and not linked to the leadership role, the leader needs help from a different profession.
  • When it is always someone else’s fault: A leader who consistently places responsibility on the outside world – employees, the market, the boss – has not yet taken ownership. Without ownership, there is nothing to coach.
  • When there is a hidden agenda: If the top manager in reality wants an imposed behavioural correction of a manager or middle manager, coaching has become a way of shifting responsibility. Then the problem lies elsewhere – often with the person commissioning the programme.

The last one is perhaps the hardest. Coaching cannot replace the feedback and difficult conversations that the leader’s own boss is responsible for. If a director sends a middle manager to coaching instead of having the conversation themselves, the problem is moved rather than solved. Sometimes the right recommendation is therefore not a coaching programme, but work with the leadership team – or with the director.

When the conditions are in place, however, a programme can achieve a great deal in a relatively short time. Let us look at how it typically works.

From conversation to action – how it works

A typical programme consists of 3–10 sessions of 1–2 hours, 2–8 weeks apart. That leaves time to try out new actions between sessions – and for reality to respond.

The programme starts by clarifying what is at stake and what the leader wants from it. Then we create a shared picture of the situation. In the work itself we start from the concrete situations the leader is facing, and every session ends with something the leader will do differently before the next one. Finally, we look at what has really changed – for the leader, for the employees and for operations.

The setting is flexible. Sessions often take place at the leader’s own workplace, but just as often over lunch in town, as a walk-and-talk or on trips into nature – also with entire leadership teams. When you change the setting, the perspective often changes with it.

Uniquely, I also use my own aircraft as part of what I call “Leadership elevation” – in Danish “Ledelse i nye højder”, which will also be the title of my upcoming book. Because when you are in the blue sky with the whole landscape beneath you, something happens to your ability to zoom out. My motto is: Outlook creates insight.

When you change the setting, the perspective often changes with it. Outlook creates insight.

What do the leaders themselves say?

The best evidence for coaching is rarely numbers. It is the leader’s own experience that something has shifted. This is how the head of the media department at a large IT company describes her programme:

“I have gained new insight into and a new approach to leadership, as well as a number of concrete tools for activating resources within myself in my personal development in the leadership role. Mads has been outstanding at listening, supporting and challenging me based on my concrete everyday work, and the learning can therefore be applied directly. All in all, the programme with Mads has far exceeded my expectations.”
— Head of the media department at a large IT company

She also highlighted that she left with a set of action plans, so her development continued after the programme ended. That is precisely the point: Coaching should not create dependency, but decisive action.

At e-conomic, 1:1 coaching was a regular part of the collaboration for several years, especially for new leaders in the transition from specialist to middle manager – one-to-one and as walk-and-talk sessions.

The two examples also show that coaching can be used at very different levels. That is why we work with two tracks.

Two tracks – one approach

Track A – CxO Executive Business Coaching:

  • For managing directors, members of the executive team and C-level.
  • Integrates personal leadership sparring with business advice on, for example, strategy, business development, finances, customers and organisation.
  • Typically longer programmes over one to two years – for example with managing directors of a manufacturing company and a plumbing and heating company, and a COO in a construction company.

Track B – Coaching for managers and middle managers:

  • For managers, middle managers and new leaders moving from professional expertise to leadership.
  • Fully individual, as a punch card for the individual leader – or across several teams and a varying number of people.
  • Can stand alone or be an integrated part of a leadership development programme with buddy sparring and training between modules.

The delivery model is deliberately flexible because needs differ. But the experience is the same across both tracks: Coaching works best when it does not stand alone.

At Poul Sejer Nielsen Service, executive business coaching of the managing director was combined with a leadership programme for eight service managers, so direction and priorities could be translated into operations. And at Entreprenørfirmaet Nordkysten A/S, 1:1 coaching of the COO over several years has gone hand in hand with the development of the leadership team. What is talked about in one place only changes something if it is trained in another.

Conclusion – coaching is an investment in decisive action

Executive coaching makes sense when leaders own their challenge, are willing to act, and when the sparring partner can offer both a mirror and qualified challenge – with an understanding of both the person and the business.

It does not make sense when therapy is needed, when responsibility is consistently placed with others, or when coaching is used to move a problem that belongs somewhere else.

So the question is not whether you can manage without it. Most leaders can. The question is: Who challenges you – with no agenda of their own?

This article builds on my LinkedIn article “Executive business coaching” from 2024.

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