Questions to Ask an Executive Coach

Choosing an executive coach is a major decision. The right coach can help you strengthen your leadership, improve decision-making, and navigate complex challenges with confidence. But not every coach is the right fit—and asking the right questions upfront can save you time, money, and frustration.

Below are the most important questions to ask when interviewing an executive coach, along with insights to help you find someone who aligns with your goals and leadership style.

Questions That Reveal Real-World Experience

A great executive coach brings more than theory. They bring lived experience. Before committing, ask questions that show how their experience shapes their coaching.

“What leadership roles have you held?” Leadership experience matters. Coaches who have managed teams or navigated growth bring practical insights.
“Can you share examples of challenges you’ve helped clients work through?” This shows whether they’ve handled situations similar to yours.
“Do you have experience coaching leaders in my industry?” Not essential, but helpful when your field has unique pressures or expectations.

Real-world experience builds credibility—something Matt Logan emphasizes in every mentorship relationship.

Questions About Their Coaching Approach and Methodology

Every coach works differently. Understanding their process helps you decide whether their approach matches your goals.

“What coaching frameworks or models do you use?” Look for structure, not guesswork.
“How do you define and measure success?” Good coaches track progress through clear goals and accountability.
“How do you tailor your approach to different personalities?” This shows whether they adapt or rely on a one-size-fits-all method.

The right approach makes coaching more effective and consistent.

Questions About Session Format, Logistics, and Professional Standards

Practical information impacts the coaching relationship. Get clarity early.

“What does a typical session look like?”
“What do you expect from me between sessions?”
“How do you maintain confidentiality?”
“How do you stay updated with new leadership tools?”

A professional coach should give clear, confident answers.

Questions That Test Chemistry and Communication Style

Chemistry matters just as much as credentials. Coaching only works when communication feels open, honest, and productive.

Ask questions like:

“How do you balance support and challenge?”
“How do you handle disagreement or pushback?”
“What do clients appreciate most about your style?”

You should feel comfortable—and also challenged. The right coach doesn’t avoid tough conversations.

Questions About Your Growth, Discomfort, and Change Leadership

Meaningful growth requires discomfort. A strong coach knows how to guide leaders through it.

Helpful questions include:

“How do you help clients step outside their comfort zones?”
“What’s your strategy for guiding leaders through change?”
“What obstacles do your clients commonly face, and how do you help them overcome them?”

These questions reveal whether a coach can support real transformation, not just surface-level improvement.

Questions About Accountability and Measurable Progress

Talk is helpful—but only when it leads to real progress.

Ask the coach:

“How do you hold clients accountable between sessions?”
“How do you measure progress over time?”
“What happens if goals shift or progress slows?”

Strong accountability drives lasting change, something Matt Logan often highlights in his coaching and mentorship approach.

Questions About Boundaries, Scope, and Ethics

Coaches should understand what coaching is—and what it isn’t.

Questions to clarify this include:

“What issues fall outside your scope?”
“How do you handle situations that require HR or legal support?”
“How do you maintain ethical boundaries?”

This protects both you and the coach.

Red Flags to Watch For

Knowing what not to hire is just as important.
Watch for coaches who:

Promise quick, guaranteed results
Lack a clear process
Can’t explain how transformation happens
Avoid accountability
Overstep boundaries or create dependency

If something feels off, trust your instincts.

Questions to Ask Yourself After the Interview

Once the conversation ends, reflect on your experience.

Did the coach listen well?
Did they challenge you?
Did their experience match your needs?
Did you feel comfortable being honest with them?

Self-reflection helps ensure you choose a coach who aligns with your expectations and leadership goals.

Final Thoughts

Finding the right executive coach starts with asking thoughtful, honest questions. The right partner will offer structure, accountability, and support while challenging you to grow in ways that matter.

For leaders looking to strengthen their leadership and make meaningful progress, Matt Logan’s Mentorship & Coaching programs offer guidance grounded in real-world experience. His approach focuses on measurable growth, clarity, and long-term success for entrepreneurs, executives, and rising leaders.