Is Executive Coaching for Me?

Four questions to help the small or medium business leader know


Shane Kinkennon

3 years ago | 4 min read

If you don’t know exactly what executive coaching is, you may be in a majority. Outside of large corporations, misconceptions about executive coaching abound. It’s an observation that in my line of work, I find particularly true among leaders of small- to medium-sized businesses.

It’s unfortunate because, in many ways, the leaders of more nimble enterprises stand to benefit the most from executive coaching. Compared to their big-corporate counterparts, they face fewer and less rigid constraints on creativity and ingenuity. There are more opportunities to put more on the line.

A few months ago, I tackled some the most common misconceptions about executive coaching (“You’ve Got Executive Coaching All Wrong”). I won’t rehash them here. Suffice it to say that that many small-business and nonprofit leaders believe — sadly — that working with an executive coach is a sign of weakness.

During a recent phone conversation, my friend Dave illustrated the point. He has worked in the C-suite for a number of small-business CEOs. He said, “As a rule, the CEOs I’ve worked for who could really benefit from executive coaching have shown little interest in it. The ones who desperately need it would simply never.”

The fact is, resistance in certain corners aside, executive coaching can be an ace up the sleeve for the confident and self-secure executive. For the chief or other senior leader of a small- or mid-sized business, it can be a competitive advantage-maker.

Could executive coaching be for you? If your answers to the four questions below are yes, then there is a pretty good chance:

1. Does your business have a result it needs you to achieve?

Executive coaching delivers its greatest return on investment when there’s a shared specific business outcome to be achieved, and the leader is in a position to be the catalyst for making it happen.

Let’s say the leader is a head of marketing, and the goal is to achieve a target increase in average number of transactions per customer, a milestone that might unlock deeper interest from a sought-after private-equity firm.

Or the leader has a very specific default behavior or mindset that, in certain situations, proves less useful as a C-level leader than it did earlier in her career. (Inability to delegate is a common example.) Or the leader has a mental block on how to get her team past their quirky personality dynamics and firing on all cylinders.

If your business needs something specific of you — either a target metric under your watch or a measurable evolution of your style to bring out the best in your team — executive coaching can be worth its weight in gold.

2. Do you know and accept what executive coaching actually is?

Executive coaching is not getting advice nor some stranger telling you what to do. Instead, it is a process of availing yourself to active open-ended questions about your best ideas, drawn from your own experience, observations and instincts. Those questions are often provocative and challenging.

They are thoughtfully timed, cleverly worded and respectfully posed, all designed to draw out your most creative thinking and relevant learnings from your professional journeys about how to address whatever business challenge you face.

This method of inquiry is based in behavior-change science and has become pretty broadly accepted in management psychology. The long and short is, you’re far more likely to make meaningful change if it’s your idea and you who visualizes the good things that will result.

So, executive coaching does not treat you as someone who needs outside ideas or advice. To the contrary, it treats you as someone who absolutely, positively has the inner wherewithal to meet whatever challenge is before you.

The coach serves as a trained, skilled helper, a confidant to shine a light on the ideas, approaches and solutions that are uniquely yours.

3. Is the result so important that the business views it as investment-worthy?

Individuals sometimes invest in executive coaching out of their own pocket. But if a hard business result is on the line, and it should be, then executive coaching is a logical investment by your business in pursuit of that result.

I once had a young CFO tell me he wanted to build the confidence he needed to run mergers and aquisitions for his company, an employer he loved and hoped to be with for years.

The potential upside for the business should the imagined M&A strategy be successful would be tens or even hundreds of millions of dollars. Yet he couldn’t bring himself to ask the company “to spend money on him.”

Executive coaching gets pigeonholed as something of a light professional-development perk administered by human resources, something that’s more for the individual than the employer.

That shouldn’t be the case. For key senior leaders, executive coaching is a strategic investment in increasing the likelihood that critical business goals are hit and value is created.

4. Are you secure enough to ditch the infallibility facade?

Are you tired of trying to project perfection and invulnerability at work? Or perhaps you’re lucky enough to never have been saddled with the inclination.

Do this thought experiment: imagine saying to your colleagues or direct reports, “I’m working with an executive coach. I’d like to tell you what I hope to achieve. And then along the way, I could use your feedback on how I’m doing.”

Does the thought energize you? Can you imagine workdays as a senior leader in which you simply be your lovely-but-admittedly-imperfect self, no shields required? If so, then you’re a good candidate for executive coaching.

But if the thought of dropping your guard makes you cringe, or you’d at least want to be cagey about the coaching arrangement, then you may not be ready for it.

Executive coaching requires being comfortable enough in your own skin to admit that there is at least one thing you could improve upon to be great for your business. If you’re there, and your business is willing to strategically invest, it can make all the difference.

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Shane Kinkennon

Certified Executive Coach. I work with CEOs of company up to $500M to help them get the most of their human capital and to lead change.







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