It is indeed lonely at the top. The opportunities are huge but so are the responsibilities. Which is where CEO coaching comes in, because even the most seasoned leaders benefit from a trusted thought partner. This guide will walk you through everything you need to know about executive coaching, tailored specifically for CEOs.

More about me: I spent the first half of my twenty plus year career at Deloitte Consulting and at HM Treasury. I became an executive coach in 2013. Based in London and working globally, I coach founders, CEOs & executives in high-growth technology businesses & the investment industry.

What is CEO coaching?

John Whitmore is one of the founders of the modern coaching movement. In his book Coaching for Performance: The Principles and Practice of Coaching and Leadership, he explains that coaching involves “unlocking people’s potential to maximise their own performance”. Coaching helps someone to learn rather than being directly taught. The coachee “does acquire the facts, not from the coach but from within himself, stimulated by the coach”. 

The International Coaching Federation offers another definition: “the process of partnering with clients in a thought-provoking and creative process that inspires them to maximize their personal and professional potential. The process of coaching often unlocks previously untapped sources of imagination, productivity and leadership”.

A CEO coach draws upon these principles to serve as thought partners for their client, to help them examine their own thinking, provoke new ideas and insights, reach considered decisions and commit to action steps that help them to become the best they can be.

How can a CEO coach help you?

By virtue of your position, you are already surrounded by high-performing individuals, but it’s often difficult to open up vulnerably to them about certain things on your mind. Objective, and without a financial stake in your business to bias them, you can talk much more openly about these things with your coach. They are your trusted partner, who provides a private space for you to share and discuss your innermost thoughts and feelings and reflect upon them.

Typically these conversations focus around business and leadership but, given that our work and personal lives are so intertwined, there’s often much crossover into life outside work.

Here are the main areas across which I help my CEO clients:

• Leadership development – defining leadership values and principles, executive presence and communication, time management and prioritization, delegation and empowerment, feedback and difficult conversations, 90 day plans, startup founder to CEO transitions, 360 degree feedback.
• Business growth – strategic thinking, culture and organisational design, high performing teams, operations, recruitment and talent management, stakeholder management, crisis management, governance and Board effectiveness, risk management, fundraising and exit strategy.
• Personal mastery – ambition and motivation, work/life balance, family and relationships at home, self-awareness, Imposter Syndrome, resilience, habits and accountability, health and wellbeing, mental models, judgement, cognitive biases and decision making, and complexity fitness.

Using a range of tools and techniques, including intelligent questioning and deep listening, a coach helps you further develop self-awareness and facilitates self-directed learning. They build upon your own knowledge and intrinsic motivation to get you to your own decisions and outcomes.

Coaches are highly supportive but they won’t do all the hard work for you. Objective and unattached to the outcome, a coach will help you determine your own way forward. They won’t just tell you what to do, though they’ll lend their own experience where appropriate to do so.

CEO coaching Vs mentoring

Mentoring originates from Greek mythology, when Odysseus sets out for Troy and entrusts his house and the education of his son Telemachus to his friend Mentor. He leaves Mentor with the instruction to “tell him all you know”. Those words are significant; the essence of mentoring lies in more directive learning, based upon the mentor’s knowledge and previous experience.

In spite of the wide variety of names it is given… all the experts and communicators appear to agree that it has its origins in the concept of apprenticeship, when an older more experienced individual passed down his knowledge of how the task was done and how to operate in the commercial world.

Everyone Needs a Mentor, by David Clutterbuck

Mentors may or may not be older, but they are always more experienced. For any leader, having the ear of someone who has been on a similar journey to them is very reassuring. It is because a mentor’s approach is more experienced-based that it is referred to as being Directive, as opposed to the more Non-Directive approach used in coaching.

A good mentor will be an inspiring individual who you look up to and respect for their knowledge, wisdom and sense of shared values. They will pass on advice, share opinions and help you navigate tricky situations with greater ease. They’ll likely open up connections for you among their network. Because they are more Directive, they may help you make decisions and reach conclusions quicker than your coach might. That’s not to say they are always right, and you might want to use your time with your coach to process their advice and arrive at your own conclusion.

Should I look for a mentor instead?

It depends. Here’s a few things to consider:

• Mentoring is more Directive; it helps you get to an answer more quickly, rather than taking you through a more Non-Directive process to find your own answer.
• Mentoring tends to focus on offering more immediate actionable and tactical advice. Working with a coach is typically part of a longer, developmental journey.
• Whilst a good coach, with the necessary experience, can be a good mentor, a good mentor won’t necessarily be an effective coach. Experienced coaches have years of training, and a multitude of tools and techniques at their disposal, mentors typically less so. Because mentoring and coaching are used so interchangeably, it’s not uncommon for people to say they’re coaching when really they’re mentoring.
• That said, coaching and mentoring are not mutually exclusive. Back to John Whitmore, who tells the story of of Mike Sprecklen, the coach and mentor to the famous rowing pair Andy Holmes and Sir Steve Redgrave:

“I was stuck, I had taught them all I knew technically.” Sprecklen said on completion [of one of Whitmore’s coaching courses]. “But this opens up the possibility of going further, for they can feel things that I can’t even see.” He had discovered a new way forward with them, working from their experiences and perceptions rather than from his own. Good coaching, and good mentoring for that matter, can and should take a performer beyond the limitations of the coach or mentor’s own knowledge.

Coaching for Performance: The Principles and Practice of Coaching and Leadership

What about a therapist?

Therapists are trained to help people who are facing mental illnesses. Coaches are not.

If a client appears to have mental health and well-being challenges that are impacting their day to day functioning then they should seek the support of therapist, not a coach. Whilst there are a number very well-regarded coaching qualifications, it is not a regulated profession like therapy. Therapists are therefore more qualified and experienced to deal with these sorts of issues. Professional coaches are clear about this distinction and if they think the support of therapist is more appropriate they’ll let you know and help direct you to the right support.

As a general rule of thumb, coaching is forward looking whilst therapy delves backwards into our past to help us make sense of our present. However, because coaching is about opening up clients to possibilities in themselves that they did not even know about, an experienced coach may be backward looking, exploring deeper issues that might be driving certain ways of thinking and behaviours. But whilst any good coach should be comfortable working in that space, exploring the true depths of our actions, cognitions and emotions is the job of a therapist.

In terms of support, again, you have options. Here’s a few things to consider:

• Because therapy is a regulated profession that draws on many similar tools and and techniques as coaching, a therapist can also serve you in a coaching capacity. But this doesn’t work the other way around: a coach who is not also a trained and regulated therapist cannot offer you therapy. Fortunately, there are many therapists who operate as coaches too. In my experience, their style often leans, as you’d imagine, to a more therapeutic approach so it’s really a case of talking to them and working out what works best for you.
• People often seek the help of a therapist when they have hit the wall, burnt out, or otherwise reached a point at which they can no longer continue in their current state. This situation is not uncommon for CEOs, so if you recognise this in yourself, it may be more appropriate to talk to a therapist. If you’ve not reached that tipping point, an experienced coach may be able to help you earlier. There’s no exact line in the sand.

Psychoanalysis, coaching and leadership are all concerned with searching for what is true and facing it. Psychoanalysts help clients face the contents of their psyche. Coaches help clients face their current reality, however uncomfortable, and find steps forward. Leaders help their organisations confront the most brutal facts of their situation. All are searching for what’s true and facing it.

On coaching and therapy

Does a coach need CEO experience?

Marshall Goldsmith has coached over 200 Fortune 500 CEOs. Randall Stutman is Jamie Dimon’s coach at JP Morgan. Despite being the best in the world at what they do, neither have ever been CEOs themselves. That’s because previous CEO experience doesn’t replace coaching expertise, which the best coaches build over many years and with many clients.

In I want a coach who has done my exact job before – but bigger! executive coach Brian Underhill draws on research which shows what really matters:

• The ability to build rapport and trust is the most critical factor in any coaching relationship
• Experience and skills as a coach are highly valued
• Experience with specific leadership challenges is also important

Ultimately it depends what you want from your coach. If it’s more experienced-based mentoring support (a Directive style) then previous experience of your role is likely beneficial. But don’t underestimate the perspective-shifting ability of a great coach who is able to blend a good level of previous business experience with a honed intuitive coaching approach developed over time.

How to find a CEO coach

You’ve decided that you would like to work with a coach but where do you start? Tap up your trusted network. Ask around to see who people have worked with and who they would recommend. Ask your Chief People Officer or Head of Talent as they’ll often have a roster of coaches they turn to. Ask your investor network and Board members, and reach out to other CEOs in your network.

Narrow your list down to about three coaches (it doesn’t need to be more than that) and get in touch with them. 

Book a Chemistry Call

Most coaches will offer an initial conversation to understand what you would like to get out of coaching and explain how they work (and if they don’t then be nervous about why not).

They’ll make this investment of time because they know it’s the best way to establish rapport, build early mutual trust and for both parties to test if the relationship feels right. Coaching is a two-way process and the best coaches will only work with you if it feels right for them too.

Do your Due Diligence

You’re investing a significant sum in a relationship that will hopefully dramatically develop you personally and which could last a long time. Ask your coaches for references or reach out to individuals who you know they have worked with before. What was their experience?

How to choose a CEO coach

When talking to potential coaches, here’s a few things to bear in mind, some questions to ask them, and some questions to ask yourself. Ultimately, choosing a coaching will come down to your gut feeling about whether this person is right for you, so don’t be afraid to trust it.

Coaching approach & style

Every coach is different and will bring a different way of working to a coaching relationship. It really comes down to getting a better understanding of the type of support that you want and working out whether the coach’s approach is the right one for you.

Also bear in mind that coaches all have different styles. Are they warm and supportive, or more direct and constructively critical? Do they focus on the practical and tactical, or lean more inwards? Do you want someone warm and empathetic, or someone who will hold you strongly to account and drive your forwards?

Ask the coach: to explain, in their own words, their coaching approach and interpersonal style.

Ask yourself: does their explanation align with your experience during the conversation? Does this person communicate with you in a way that makes me feel comfortable? Will your interpersonal styles work well together? What do I want from my coach and do I think this person can give it to me?

Sensemaking & application of theories

Coaches come in all shapes and sizes, and there is no one way to coach. In her book Changing on the Job: Developing Leaders for a Complex World executive coach and leadership expert Jennifer Garvey Berger explains that:

Coaches – like other reflective adults – tend to have particular theories or beliefs that guide our work on a day-to-day basis. We have common patterns and ways of engaging. We use particular tools or ideas to understand a situation and offer insight to clients.

Like any other human, a coach can only have a partial perspective on the world. Their way of making sense of the world may differ a little, or a lot, from you own. The best coaches “rub theories together… taking new theories and putting them together – especially theories, practices, or ideas that are contradictory,” giving them practice in “holding the paradoxes of what it means to be human.”

A good coach will intuitively meld different approaches, theories, models and frameworks together to suit the needs of their client and the conversation. Be wary of any coach that is overly wedded to any one in particular and tells you that they will not deviate.

Ask the coach: what coaching and other personal and professional development approaches, theories, models and frameworks do they use? How rigidly do they stick to them? How do they make sense of the world?

Ask yourself: can this person see the world from my perspective, or at least empathise with it? Does this person bring a one-size-fits-all approach? If so, am I comfortable with that?

Coaching qualifications

The issue of coaching qualifications is contentious. Some of the best coaches I know don’t have coaching qualifications. Other have a long list of qualifications but lack certain people skills.

Treat qualifications as a helpful guide but don’t discount a coach who lacks them if they have other strong credentials and you feel you could work well with them. But be aware that, unlike therapy or accounting, law or architecture, coaching is not a regulated profession. Anyone can set themselves up as a coach and many do.

Ask the coach: do they have coaching qualifications? What is their attitude towards them? Can they tell you about their coaching experience? Ask them to explain the difference between a coach, mentor, consultant and therapist and be very wary if they can’t do so comfortably.

Ask yourself: am I comfortable that this person has the right level of experience and knowledge of coaching to help me? Does this person know their professional boundaries?

Commitment to continuing professional development

The study of human psychology, development and performance is advancing rapidly. Coaching is a constantly evolving discipline. The best coaches are committed to their continuing professional development. They are fiercely curios and never stop learning. They bring their insights directly to their clients and through the way they work.

Ask the coach: how do they continuously professionally develop as a coach?

Ask yourself: does this person show a genuine commitment to continuous professional development?

Do they have their own coach and/or mentor?

If you have ever tried to coach yourself, you will realise that it’s not impossible but it is incredibly difficult. Coaches are no different. Just like the rest of us, they have not worked it all out, they don’t have all the answers and they have a host of their own developmental needs. For these reasons, the best coaches I know have their own coach and/or mentor.

Ask a coach: do they have a coach or mentor? What function does that relationship play?

Ask yourself: how well did they answer this question? Am I comfortable that they are ‘doing their own work’?

Do I trust this person?

Trust is the most important component of a coaching relationship. You should trust your coach and they should have your back. You are going to be discussing issues with them that you may not talk to many other people about, if at all. Your relationship is likely to last months, if not years.

The strength of the coaching relationship or working alliance between client and coach is the most powerful predictor of coaching outcomes. Spending time building a strong relationship with a client is critical for successful and effective coaching, and it is perceived this way by both coach and client alike.

Does executive coaching work?

Ask the coach: how do they go about building and maintaining trust with their clients?

Ask yourself: do I trust this person and do they have my back?