Should I Hire an Executive Coach?

by Matt, on 26 May 2020

I roll my eyes each time I read a blog post that uses a sports analogy to make its point. That is, until I sat down to capture my thoughts on the merits and methods of hiring an executive coach. Because … well, you see my dilemma.

If one aspires to (or hopes one’s child might) become a professional athlete, all roads lead through a professional coach. You wouldn’t expect to find anyone performing at a serious amateur level, let alone professionally, without benefitting from some type of paid instruction.

The same is true of musicians, artists, chefs, and all the trades you can name.

So why, then, do so many people end up running companies without ever receiving formal instruction or professional coaching?

In this edition of SPT, I’ll share my thoughts on why this phenomenon exists, why it’s daft, and how and when to bring in the right coach.

people sitting in front of table holding pens


Two things strike me about the entrepreneurs and early-stage business leaders I encounter:

  • Most of them are – or, at least, appear to be – very confident in themselves
  • Many – if not most – of them are flying by the seat of their pants

The subculture in which these individuals operate values both characteristics unusually highly. I can’t think of another line of work in which excessive self-confidence and making things up as you go along are sought-after traits (except, perhaps, improv comedy, but I’ll save that analogy for another blog post...)

Starting and running a company is a high-risk, fast-paced, overwhelming experience. From the start, you’re statistically doomed to fail but nevertheless thousands of people take the risk each year.

Self-belief and a willingness to ‘go with the flow’ are understandably valuable ingredients when striking out on such a precarious adventure.

A few months – sometimes, years – later, after the other ninety-odd percent have fallen by the wayside, the fortunate few among those hairbrained entrepreneurs are running viable businesses.

They are now in charge of a proto-company, having launched their minimum (loveable) viable product, convinced some early adopters to pay for it, and sold their vision to a band of early employees and probably some seed investors.

They are, nevertheless, still hairbrained. Their self-confidence is running high because they’ve done the near-impossible. And they are definitely still flying by the seat of their pants (or what’s left of it).

Here’s when things get interesting.

The risk of early failure (often referred to rather darkly as ‘infant mortality’) has been vanquished, only to be replaced by the perpetual risk of insolvency (we call that ‘commercial risk’).

The entrepreneur needs business and finance skills to navigate this stage. Judiciously managing cash flow while cranking up marketing, building out a sales team, scaling up operations, formalizing the employee experience, and delighting customers is going to wear a serious hole in the seat of those pants.

From a coaching point of view, one of three things can happen:

  • Nothing
  • The board of directors recommends bringing in a coach
  • The entrepreneur or leader seeks out coaching

Nothing – no coaching – comes in two flavors. The entrepreneur survives, figuring things out by themself, learning by trial-and-error and from informal advisors. Or, the entrepreneur crashes and burns.

The first flavor can lead to a wide range of outcomes. An elite few, for whom leadership comes naturally or whose business succeeds without running into any serious challenges, will do just fine.

The rest will keep their businesses afloat but not without some cuts and bruises along the way, failing to reach their or the business’ full potential.

When coaching is recommended by the board, it’s a slap in the face for most entrepreneurs. Their ego gets bruised. It’s the report card that reads ‘could do better, would benefit from some extracurricular tutoring’.

Although some shareholder representatives probably do recommend a coach as a last resort (“if this doesn’t fix her, we’ll need to make a move”), I think most are well-intentioned. It’s the recipient – the self-confident entrepreneur – that isn’t open to hearing the suggestion.

This is a great opportunity for one of the directors – often the chairman, especially if they are an independent – to sit down with the entrepreneur and have a friendly chat about long-term development and maturation.

The third possibility – that the entrepreneur recognizes by themselves that coaching would be valuable – is by far the most productive.

It takes self-awareness and courage, since the defense shields of confidence must be lowered and vulnerability expressed, risking ridicule and rejection by the ego-worshipping early-stage community.

The entrepreneur’s request must also be welcomed by the shareholders or board of directors. Executive coaching is never cheap. Plus, if they believe their company quarterback is invincible, it’s going to come as a nasty surprise to hear them ask for help.

Successful first-time entrepreneurs and executives must realize and accept that they need professional coaching if they want to succeed in the big leagues.

Shareholders and directors must realize and accept that the leaders of their businesses need and deserve coaching if they want those businesses to flourish.

Mountain lake in camera lens


Well-run businesses define a long-range vision, from which strategies and plans are cascaded, resulting in a clear statement of short-term business objectives.

The same process can be followed when thinking about a business leader’s development.

  • Where do they want to be in 5-10 years’ time?
  • Where do they need to be in 2-3 years’ time to be on track toward that vision?
  • What should they accomplish this year?
  • What are their short-term developmental objectives?
  • Where is effort most urgently needed to close gaps or deliver results?

These development objectives should form the basis of an individual coaching engagement. A budding musician doesn’t leap straight into a Mozart concerto any more than an emerging sports enthusiast walks onto a professional team. Skills must be honed and proven along the way.

Each leader’s unique set of objectives will determine which of the many executive coaches and coaching methods is most suitable for them.


Where the coach lives, their personality and background, and how they work will all be key to finding a successful combination with the person getting coached.

I looked at dozens of coaches’ websites and testimonials, interviewed four, and held second conversations with two before informing my board of directors who I thought would make the right executive coach for me.

Each of the candidates looked different, sounded different, brought a different set of experiences and beliefs to the table, and followed their own coaching philosophy. It’s not until you try to find the right match that you realize just how wide and varied the field of candidates can be.

I was fortunate to work with Angie Morgan, Founding Partner at Lead Star, Marine, mother, and NY Times best-selling author of SPARK. We clicked, I learned far more from her than I would ever have imagined, and we’ve remained friends ever since.

But she wouldn’t have been right for everyone. In fact, she wouldn’t have been right for most people. Select your coach carefully.

Frankfurt architecture


Some coaching is highly structured. It follows a curriculum and there is a clear pathway from start to finish that’s visible to everyone.

Other coaching is informal and fluid. It’s more like therapy, with each session picking up threads from the former, digging into what’s going on in the moment, adapting to an ever-changing scenario.

I see significant merit in both. Having some structure ensures that ends can be met and assures sponsors of a deliverable in return for their investment. Retaining some fluidity allows the coach to provide whatever support the leader needs at that moment, even if it isn’t what was proposed for that day of the curriculum.

Spontaneity allows for teachable moments, using real-life situations to illustrate and practice skills.

Most coaches will, I suspect, profess to deliver both. In reality, some are more strongly biased toward structure than others. Ask them for examples and listen carefully to how they describe their methods.


In addition to individual coaches, there are several organizations that manage confidential groups where entrepreneurs and CEOs coach each other.

There’s a lot to be said for a ‘Mastermind Group’ – the term coined by Napoleon Hill in his 1937 classic, Think and Grow Rich, for what we today call a peer-to-peer mentoring group. Hill cited luminaries such as Henry Ford, Thomas Edison, and John D. Rockefeller as having relied on ‘two or more people coming together in harmony to solve problems.’

However, this is not the same thing as individual skill development. Focused, one-on-one coaching may be more appropriate, depending on the leader’s needs and objectives.

One of the requirements of the mastermind groups that I have encountered is that the leader shares real-world business issues with the group, hears their advice, and agrees to implement some of it and report back. My boards of directors (at VC and private equity backed companies) weren’t thrilled with the idea of me taking business direction from third parties, so the concept garnered less favor than having an individual executive coach.

Membership in many of these groups is also quite expensive, especially on an entrepreneur’s or small company budget.


Another key decision is whether the coach will work exclusively with the entrepreneur or individual leader, with the leadership team as a whole, or a combination of both.

When I first worked with Angie, she and I spent some time on my individual needs, but she also ran a series of sessions with the wider leadership team. Later, we widened the audience to front-line leaders across the company (which had about 200 employees at the time).

black and white photo of men rowing

Again, this will depend heavily on the individual leader’s needs, seen in the context of the company’s leadership team and business situation.

An advantage of having the same coach work with both the individual and the team is that a common language can be established, which can help to free people from some of their pre-existing fears and barriers to communication.

Since the coach isn’t a full-time team member, they can speak the unspoken, remove emotion from particularly contentious issues, and take the blame (play the bad guy) when sacred cows need to be addressed.

The determining factors here will probably be how experienced and effective (or not) the team as whole is, and how much budget the company (read: shareholders) is willing to invest in coaching and developing the group.


Some coaches are individual consultants, operating by themselves, and others are part of a company or larger organization.

My preference is to work with consultants who collaborate with associates because it gives them a broader knowledge base to tap into and their approach gets tested across a wider range of clients.

They can also bring in colleagues with different skillsets or backgrounds to help facilitate working sessions – especially useful when coaching the leadership team rather than an individual – or to help unpack and troubleshoot a particularly thorny issue if the primary coach gets bogged down.

This is not to say that individual coaches aren’t worth their salt. Just something to weigh when choosing between potential candidates.


The bottom line – both for the company and for this post – is that providing an entrepreneur or leadership team with executive coaching can be highly valuable, but it’s also quite expensive (typically several $10,000s).

To ensure the best chance of seeing a return on that investment, the company and the entrepreneur should think carefully about the eight points we’ve covered:

  • The realization and acceptance that coaching is needed and valuable
  • The leader and/or leadership team’s development objectives
  • Finding the right coach for the person/team and situation
  • Balancing a structured approach with less-structured coaching
  • Working with an individual coach versus joining a mastermind group
  • Focusing on an individual leader versus coaching the leadership team
  • Choosing an individual consultant or a coach with associates
  • How much the company is willing to invest

I believe there’s a point in every emerging leader’s career where receiving focused coaching from the right person will make the difference between succeeding and taking flight. Angie opened my eyes to new ways of thinking about many dimensions of leadership (not least, the merits of servant leadership) and her books are both very worthwhile reads.

Hopefully, this post will help some of you move from indecision into action and set you on the path to a great coaching relationship and the rewards it can bring.

Photo Credits

Photo by Paul Skorupskas on Unsplash
Photo by Dylan Gillis on Unsplash
Photo by Maarten Deckers on Unsplash