How to Choose an Executive Coach Who Will Make You Better

Seven practical steps to finding an executive coach who challenges your thinking, strengthens your leadership, and helps you achieve meaningful personal and professional growth.

Why Even Successful Leaders Need an Executive Coach

I’ve spent more than two decades coaching CEOs, business owners, and senior executives, and one of the things I’ve learned is that successful people aren’t always particularly good at recognizing when they need help.

In fact, some of the very qualities that helped them become successful can eventually get in their way. Confidence becomes stubbornness. Independence becomes an unwillingness to ask for help. Decisiveness becomes impatience. And the ability to solve problems becomes a reluctance to let other people solve them.

I’ve seen business owners build successful organizations through determination, hard work, and a willingness to make difficult decisions, only to discover that the leadership approach that got them there is now holding them back.

That’s one of the reasons I believe executive coaching can be so valuable. We all have blind spots, and sometimes we need someone who can help us recognize what we’re not seeing.

However, simply hiring an executive coach doesn’t guarantee anything. I’ve seen leaders spend more time selecting a new technology platform than choosing someone who may have a significant influence on their professional and personal development. They rely on a referral, an impressive biography, or a pleasant introductory conversation without giving much thought to what they actually need.

I believe choosing an executive coach deserves more consideration than that. If you’re thinking about making this investment, I’d encourage you to consider the following seven steps.

1. Executive Coaching vs. Consulting: Understand What You Really Need

Before hiring an executive coach, make sure you understand what you’re looking for.

There is an important difference between coaching, consulting, and mentoring. A consultant typically provides expertise to help solve a specific problem. A mentor shares wisdom based on personal experience. An executive coach should help you examine how you think, make decisions, and behave so you can become a more effective leader.

That doesn’t mean a good coach never offers advice. I believe experienced coaches should know when to ask questions, challenge assumptions, share relevant experiences, and offer a different perspective.

I remember a business owner who was dealing with the consequences of an employee leaving because of burnout. As we explored the situation, he made an observation about himself that changed the direction of our conversation.

He said, “I know how to function in scarcity. I don’t know how to function in security.”

His business was doing well financially, but he was still operating as though the next crisis was right around the corner. What initially appeared to be an employee problem was actually something much deeper. His leadership approach needed to change.

That’s where coaching can be especially valuable. Sometimes the problem isn’t simply what’s happening around us. It’s how we’re responding to it.

2. What to Look for in an Executive Coach: Experience Matters More Than Impressive Claims

Executive coaching has become a significant industry, and there are many talented professionals doing excellent work. Unfortunately, there are also people who call themselves executive coaches without having much relevant experience or preparation.

Unlike many other professions, executive coaching isn’t subject to a universal licensing requirement. Professional organizations such as the International Coaching Federation provide credentials based on training and demonstrated coaching capabilities, which are worth considering. However, I wouldn’t make credentials the sole basis for your decision.

I’d also pay attention to practical experience.

I don’t believe every effective executive coach needs to have been a CEO. However, there’s something valuable about working with someone who understands the realities of running a business. Managing cash flow, making payroll, dealing with difficult employees, navigating ownership issues, and balancing business demands with family responsibilities aren’t abstract leadership exercises.

At the same time, experience in your particular industry isn’t necessarily essential. Sometimes an outside perspective is precisely what you need.

Research generally supports the value of executive coaching, particularly in personal development, learning, and leadership effectiveness. However, the results vary, and I’d be skeptical of anyone promising extraordinary financial returns or guaranteed outcomes.

The same applies to fees. Charging more doesn’t automatically make someone a better coach.

Look for relevant experience, sound judgment, professional integrity, and a genuine commitment to your development.

3. Define Your Leadership Development Goals Before Hiring a Coach

One of the biggest mistakes I see leaders make is beginning a coaching relationship without being clear about what they hope to accomplish.

They tell me they want to become better leaders, improve communication, think more strategically, or delegate more effectively. These are worthwhile aspirations, but what would success actually look like?

For example, becoming more strategic might mean spending less time managing daily operations and more time thinking about the organization’s future. Improving delegation might mean allowing your leadership team to make important decisions without constantly second-guessing them.

I remember an owner who had gone through four general managers in a relatively short period. Each time someone left, he was convinced the next person would be better.

Eventually, the group challenged his thinking. If four people had struggled in essentially the same position, perhaps the problem wasn’t simply the people being hired.

Maybe the expectations were unclear. Maybe the organizational structure was flawed. Or maybe the owner was having difficulty giving someone else the authority necessary to succeed.

Business leaders are often very good at explaining why something happened. They’re also capable of developing convincing narratives that protect them from confronting uncomfortable truths.

One of the most valuable things a coach can do is ask:

What if the story you’re telling yourself about this situation isn’t entirely true?

Before engaging a coach, identify two or three meaningful outcomes you’d like to achieve over the next six months. Then ask yourself another question I use frequently in my coaching practice:

What is my contribution to the problem I’m trying to solve?

It’s remarkable how often our thinking changes when we’re willing to examine our own role in a difficult situation.

4. How to Interview an Executive Coach: Find Someone Who Will Challenge You

I’d recommend interviewing at least three potential coaches before making a decision. Ask other business owners and executives about their experiences, but don’t simply ask whether they know a good coach. Ask what the coach helped them accomplish and how the relationship made them better.

During the interviews, explore their experience, approach, and philosophy. Ask how they handle disagreements, measure progress, and hold clients accountable. I’d also ask them to describe a coaching relationship that didn’t work and what they learned from it.

Beyond qualifications, however, pay particular attention to the relationship.

I’ve always believed that effective coaching requires two things that might initially seem contradictory. You need to feel safe enough to be vulnerable and uncomfortable enough to grow.

If all your coach does is make you feel good about yourself, you’re probably not getting your money’s worth. On the other hand, if every conversation feels like an interrogation, you’re unlikely to develop the trust necessary to be completely honest.

The real value exists somewhere between those extremes.

I would also distinguish between chemistry and compatibility. It’s easy to like someone who agrees with us and makes us feel understood. However, the coach you enjoy talking to most may not be the one who helps you grow the most.

Two Essential Questions to Ask When Choosing an Executive Coach

• Would I feel comfortable telling this person something I haven’t been willing to tell anyone else?
• Would this person be willing to tell me something I don’t want to hear?

If the answer to either question is no, I’d keep looking.

And before making your decision, ask the coach to spend fifteen or twenty minutes helping you think through a real issue. Watching someone coach is often more revealing than listening to them describe how they coach.

5. Set Clear Expectations for a Successful Executive Coaching Relationship

Once you’ve selected a coach, make sure you agree on how the relationship will work.

A good coaching agreement should clarify the purpose of the engagement, expected outcomes, frequency of meetings, fees, confidentiality, and how progress will be evaluated. It should also explain how either party can end the relationship.

In my own practice, I’ve always believed clients should have a reasonable opportunity to discontinue an engagement if they no longer believe they’re receiving value. My agreements include a ninety-day exit provision.

I’d be cautious about committing to a lengthy prepaid arrangement before you’ve had an opportunity to experience the relationship.

Confidentiality is particularly important. One of the greatest benefits of having an executive coach is being able to discuss things you may not feel comfortable discussing with employees, colleagues, board members, or even close friends.

When an organization is paying for someone’s coaching, I believe it’s helpful to bring the sponsor, the individual being coached, and the coach together at the beginning to clarify expectations and boundaries.

The objective isn’t to create unnecessary bureaucracy. It’s to make sure everyone understands what success looks like and how the relationship will operate.

6. Executive Coaching Success Depends on Your Willingness to Do the Work

You can hire the most talented executive coach in the world, but if you’re unwilling to do the work, the relationship isn’t going to accomplish very much.

Coaching isn’t something that happens to you. It’s something you actively participate in.

Over the years, I’ve watched leaders make extraordinary progress because they were willing to examine themselves honestly, experiment with different approaches, and follow through on their commitments.

I’ve also seen talented people make relatively little progress because they enjoyed the conversations but never translated those conversations into meaningful action.

There’s an important difference between activity and progress.

A leader can attend every coaching session, complete every assessment, and read every recommended book without fundamentally changing how they lead. The real question is whether their behavior is changing and whether that change is making a difference to the people around them.

Come to your coaching sessions prepared. Think about the decisions you’re struggling with, the conversations you’re avoiding, and the patterns you’re beginning to recognize in your own behavior.

Then be willing to make specific commitments.

One of the questions I regularly ask is, “What are you committing to do, and by when?”

It’s a simple question, but it moves the conversation from good intentions to personal responsibility.

I don’t believe accountability should feel punitive. Done well, it should be a source of encouragement, support, and learning. However, it also requires a willingness to acknowledge when we haven’t done what we said we would do.

Insight without action rarely produces meaningful change.

7. How to Measure Executive Coaching Results and Leadership Growth

One of the things I’ve learned over the years is that we have a natural tendency to continue doing things simply because we’ve always done them.

This can happen with executive coaching as well.

A leader develops a comfortable relationship with a coach. They enjoy their conversations, appreciate the perspective, and look forward to their regular meetings. However, at some point, they may stop asking whether the relationship is actually helping them grow.

I’m not suggesting that long-term coaching relationships are inherently problematic. Some of the most rewarding relationships in my own practice have lasted many years.

The important question is whether the relationship continues to create value.

If your objective was to become a better delegator, are more decisions being made without your involvement? If you wanted to develop your leadership team, are your people demonstrating greater confidence and accountability? If you wanted to become more effective at handling conflict, are you having conversations you previously avoided?

These are observable changes, and they matter more than whether you simply enjoy your coaching sessions.

I’d also encourage you to seek feedback from people who work with you. Sometimes a few thoughtful questions to trusted colleagues can tell you more about your progress than an elaborate assessment.

I’d recommend reviewing the coaching relationship after approximately three months, again at six months, and periodically thereafter. Discuss what’s working, what isn’t, and whether your goals need to change.

Sometimes the right decision is to continue. Sometimes it’s to adjust the frequency or focus of the sessions. And sometimes it’s to recognize that you’ve accomplished what you set out to do and it’s time to move on.

A good coach should be comfortable with all three possibilities.

Frequently Asked Questions About Executive Coaching

What does an executive coach actually do?

An executive coach helps leaders examine their thinking, recognize blind spots, improve decision-making, and develop more effective leadership behaviors. A good coach combines thoughtful questions, constructive feedback, relevant experience, and accountability to support meaningful personal and professional growth.

How do I know if executive coaching is right for me?

Executive coaching may be particularly valuable if you’re navigating a significant leadership challenge, struggling with recurring problems, preparing for greater responsibility, or recognizing that some of your existing habits are limiting your effectiveness. The most important consideration is whether you’re genuinely willing to examine your own behavior and make changes.

How long should I work with an executive coach?

There’s no universal answer. Some engagements focus on specific challenges over several months, while others become valuable long-term relationships. I’d recommend establishing clear goals at the beginning, reviewing progress after three and six months, and making a deliberate decision about whether continuing the relationship makes sense.

Final Thoughts: The Right Executive Coach Will Challenge You to Become Better

After more than two decades of doing this work, I’ve become convinced that most successful leaders don’t suffer from a lack of intelligence, ambition, or work ethic. More often, their greatest obstacles involve the things they’ve stopped questioning about themselves.

We all develop habits, assumptions, and ways of thinking that serve us well until they don’t. We become comfortable with our own explanations. We surround ourselves with people who may hesitate to challenge us. And occasionally, we confuse being successful with having everything figured out.

A good executive coach can help you recognize those patterns, but they can’t do the work for you. They can ask better questions, offer a different perspective, and hold you accountable for your commitments. Ultimately, however, you’re the one who has to decide whether you’re willing to change.

I believe the best coaches don’t try to make themselves indispensable. They help you develop the self-awareness, judgment, confidence, and discipline necessary to become increasingly effective on your own.

So, as you consider hiring an executive coach, I’d encourage you to ask yourself one final question:

Am I looking for someone who will help me feel better about how I’m leading, or someone who will help me become a better leader?

There’s a significant difference between the two, and I believe the answer will tell you a great deal about the kind of coaching relationship you’re ready for.

Sources and Further Reading

• de Haan, Erik. What Works in Executive Coaching: Understanding Outcomes Through Quantitative Research and Practice-Based Evidence. Routledge, 2021.
• International Coaching Federation. Compare Credentials.
• Jones, Rebecca J., Stephen A. Woods, and Yves R. F. Guillaume. “The Effectiveness of Workplace Coaching: A Meta-Analysis of Learning and Performance Outcomes from Coaching.” Journal of Occupational and Organizational Psychology, 2016.
• Sherman, Stratford, and Alyssa Freas. “The Wild West of Executive Coaching.” Harvard Business Review, 2004.
• Theeboom, Tim, Bianca Beersma, and Annelies E. M. van Vianen. “Does Coaching Work? A Meta-Analysis on the Effects of Coaching on Individual Level Outcomes in an Organizational Context.” The Journal of Positive Psychology, 2014.