Executive coaching is a strategic investment in leadership effectiveness. Whether you’re a senior leader navigating change, stepping into a bigger role, or simply seeking more clarity and confidence, coaching can be transformative.

With so many executive coaches offering services today, how do you choose the right one? What should you be looking for? And once you start, what should you expect from the coaching relationship?

Here’s a practical guide to making a strong coaching match, including five questions to ask your potential coach.

Why Coaching Matters at the Executive Level

Executive coaching offers a confidential, structured space for reflection, decision-making, and growth. It’s where leaders can sharpen their strategic thinking, enhance emotional intelligence, and work through challenges that often don’t have clear answers.

According to the International Coaching Federation (ICF), 86% of companies that used coaching reported a positive return on investment, and 96% of individuals said they would repeat the coaching experience.

Coaching is about amplifying what’s already working, challenging unhelpful patterns, and expanding capacity. To unlock that value, the relationship has to be a good fit.

5 Questions to Ask When Choosing an Executive Coach

Whether you’re vetting a coach for yourself or a member of your leadership team, these five questions can help you uncover quality, alignment, and chemistry.

1. What is your coaching background and methodology?

Look for a coach who can clearly explain their training and approach. Do they work from a specific framework (e.g., strengths-based, cognitive-behavioral, systems thinking)? Coaches should be able to articulate how they help leaders grow—and tailor that approach to your needs.

2. What kinds of leaders do you typically work with?

Experience matters, yet so does context. If you’re a VP in a global organization navigating cross-functional complexity, it helps to work with a coach who understands that world. Ask for examples of clients or industries they’ve worked with, and look for relevance to your challenges and goals.

3. How do you structure a typical coaching engagement?

Coaching should have a clear scope and rhythm. Ask about session frequency, duration, and length of engagement. Strong coaches often work in 3-, 6-, or 12-month cycles. At ImprovEdge, for example, we use defined coaching cycles that align sessions to measurable goals with built-in reflection points.

4. How do you measure success or progress with your clients?

Coaching isn’t just about great conversations, it’s about movement. Ask how the coach helps clients set and track progress toward development goals. This could include stakeholder feedback, check-in tools, or qualitative reflection. Look for a coach who holds both structure and flexibility.

5. What do you expect from me as a client?

This may seem like a flip. A strong coach will have clear expectations for your participation, honesty, and follow-through. Coaching is a partnership—and both sides contribute to the outcome. You want a coach who will challenge you, not just affirm you.

What to Expect from a High-Quality Executive Coach

As a client (or someone sponsoring coaching), you should hold your coach to a high standard. Here are key expectations you can and should have:

1. Confidentiality and trust

Your coach should create a safe, judgment-free space for exploration. Everything you discuss should be held in confidence unless otherwise agreed upon (e.g., high-level progress shared with HR or a manager). This trust is foundational to making bold, honest progress.

2. A focus on your goals—not just generic leadership advice

Your coaching should be tailored to your context: your role, your organization, and your aspirations. A good coach helps you identify the right goals, and keeps you accountable to them throughout the engagement.

3. Challenge as well as support

Great coaches don’t just validate—they provoke new thinking. Expect your coach to ask tough questions, reflect patterns you may not see, and occasionally make you uncomfortable. That’s where the growth is.

4. Real-time relevance

Coaching should connect to your day-to-day leadership. Whether it’s preparing for a high-stakes conversation, navigating team conflict, or expanding influence, the work should feel practical and immediately applicable.

5. Professionalism and boundaries

A coaching relationship is not therapy, mentoring, or friendship. It’s a professional engagement with clear roles, boundaries, and mutual respect. Your coach should be reliable and prepared for your work together.

Right Person, Right Time

Choosing the right executive coach is both a personal and strategic decision. The best coach for you will be someone who brings experience and insight and also listens, challenges, and tailors their support to your growth.

Remember: coaching isn’t just about solving problems, rather it is about expanding what’s possible for you as a leader.