How to Choose an Executive Coach (Without Wasting Time or Money)

The coaching industry is largely unregulated. Anyone can call themselves an executive coach. That means the burden of due diligence when it comes to how to choose an executive coach sits squarely with you, and most leaders don’t know what they’re actually looking for.

After two decades of coaching executives and building a team of coaches at SkyeTeam, here’s what I’d tell you to look for, and what I’d tell you to watch out for.

Chemistry matters, but it’s not everything

The first thing most people think about when considering how to choose an executive coach is whether they like the person. Chemistry matters. You need to feel safe enough to be honest, and challenged enough to grow. But a coach who only makes you feel good isn’t doing their job.

The coaches who create the most lasting change are the ones who will sit in discomfort with you, call out the patterns you’d rather avoid, and tell you what you need to hear — not what you want to hear. Warm and challenging are not opposites. The best coaches are both.

Credentials are a starting point, not a destination

Look for coaches with accreditation from a recognized body, the International Coaching Federation (ICF) is the most widely respected. But credentials tell you someone has been trained. They don’t tell you whether that person can work effectively with someone like you, in a context like yours.

Ask about their background. Have they worked with leaders at your level? In your industry? With challenges similar to yours? A coach who has spent their career in the tech sector may not be the right fit for a healthcare executive navigating a merger. Experience is contextual.

Ask the questions most people don’t ask

What’s your coaching philosophy? You want to understand how they think about change — whether they’re more directive or facilitative, whether they lean into the behavioral or the systemic. Neither is wrong, but you need to know what you’re signing up for.

How do you measure progress? Coaching without accountability is an expensive conversation. A good coach will have a clear view of how you’ll both know it’s working.

What happens if it’s not working? This is the question most people are too polite to ask, and it’s one of the most important. You want a coach who will surface concerns early and adjust — not one who waits until the engagement ends to tell you it wasn’t the right fit.

Consider having more than one coach

This might be the most underused idea in executive development: you don’t have to have a single coach for everything. I work with leaders who have a coach for leadership presence, another for board relationships, and another focused on peak performance or executive wellbeing. Different coaches bring different lenses. A portfolio approach — matching the coach to the specific challenge — often produces better results than expecting one person to do everything.

Think about where you want to grow, and match the coach to that goal.

Trust your instincts — but verify them

After the first conversation, ask yourself: did I say something I haven’t said out loud before? Did they hear it? Did they push me in a direction I didn’t expect? If the answer to all three is yes, pay attention to that.

The right coach doesn’t just make you feel understood. They make you think differently about something you thought you already understood.

Where to start

Since I just told you to ask these questions of any prospective coach, it’s only fair that I answer them myself.

My coaching philosophy. Connection before content. I believe the coaching relationship itself is the primary vehicle for change, not the frameworks, not the tools, not the models, though I use many of them. My work is grounded in the Relationship Ecosystem™ from my book Cultivate, and the Ally Mindset™ practices from You, Me, We. I lead with candor, not comfort. I will tell you what I observe, including the things that are harder to hear. And I will stay in your corner while I do it.

How I measure progress. Not by how you feel in sessions, but by what changes outside them. We track behavioral shifts that other people notice, not just self-report. I use the Relationship Pulse Check and a stakeholder-centered approach. Three questions: what’s working, what’s not, and what’s one thing we can do to ensure mutual success, to keep us both honest about whether the work is landing. Progress in coaching should be visible to your team before it’s measurable in a survey.

What happens if it’s not working? I name it early. If the chemistry isn’t there, if the timing is wrong, or if a different coach would serve you better, I will tell you that directly, not at the end of a six-month engagement. Referring you to the right person is not a failure. It’s the job.

If you’re still figuring out whether you’re ready for coaching at all, start with the first post in this series: Is It Time to Get an Executive Coach? And once you’ve chosen your coach, the third post — How to Be Coachable — will help you get the most from the engagement.

I work with senior leaders and executives who are ready to do the real work, on their leadership, their relationships, and the impact they want to have. If you’d like to explore whether we’re a good fit, I’d welcome a conversation with no obligation on either side.

And if I’m not the right coach for you, I’ll tell you that too. I have a global network of coaches, including my SkyeTeam colleagues Eric Spencer and Ruby Vesely, both exceptional coaches in their own right, and I’m glad to connect you with the right person for where you are right now.

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Morag Barrett is a keynote speaker, executive coach, and USA Today bestselling author who helps leaders tackle one of today’s biggest workplace challenges: disconnection. Her work focuses on human connection at work, workplace relationships, employee engagement, and team culture — giving leaders practical tools to build trust and perform better together. Her signature keynote, Fine Is a Four-Letter Word, has been delivered to Fortune 500 companies and industry conferences worldwide. Member of Marshall Goldsmith’s 100 Coaches. She’s a regular contributor to Fast Company.

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Frequently Asked Questions about Choosing an Executive Coach

What qualifications should an executive coach have?

Look for accreditation from the International Coaching Federation (ICF) as a baseline — it tells you someone has been trained to a recognized standard. Beyond credentials, relevant experience matters more: have they worked with leaders at your level, in contexts similar to yours? Credentials open the door; experience and fit close it.

What questions should I ask a coach before hiring them?

Three questions matter most: What’s your coaching philosophy? How do you measure progress? And what happens if it’s not working? A coach who can answer all three clearly and specifically — without deflecting — is worth a second conversation. Vague answers to these questions are a signal.

How long does executive coaching typically last?

Most executive coaching engagements run six to twelve months, with sessions every two to four weeks. The right length depends on the depth of the work, not a standard package. Meaningful behavioral change — the kind other people notice — takes time to embed. Be wary of any coach who promises transformation in a few sessions.