16 Essential Questions Leaders Should Ask Their Coach Or Mentor

Expert Panel® Forbes Coaches Council

Whether a leader is brand new to the role or wants to evolve in their leadership, choosing the right person to facilitate their progress and guide them along their journey is key. While connecting with a trusted mentor or coach can have a major impact on a leader’s career and performance, much of the outcome will come down to how the leader approaches the engagement.

Coaches are experts at asking clients just the right questions, but the questions clients ask of their coaches are also important, as they can help set the stage for the kind of growth and transformation they seek. Below, 16 members of Forbes Coaches Council share the essential questions that leaders should ask their coach or mentor to ensure a productive and beneficial relationship.

Members pictured from left to right.
Members pictured from left to right.

1. ‘What should I expect from this type of engagement?’

One of the most effective ways to grow as a leader is to work with a coach or a mentor. A leader should ask me, “What should I expect from this type of engagement?” Each coach is unique, so it is important to ascertain if your expectations are aligned with what I can provide. If they are, then the leader’s level of engagement and commitment can create impactful and exponential results. – Sheeba Varghese, Coach Sheeba

2. ‘What would make you not want to coach me?’

Ask yourself, “Is this person interested in me, or are they talking about themselves? Is this person attempting to understand my business or my challenges? Do the questions my prospective coach is asking demonstrate insight that makes me think critically?” Great coaches ask great questions. Then—to see what they truly value–ask, “What would make you not want to coach (or mentor) me?” – Jim Vaselopulos, Rafti Advisors, LLC

3. ‘What are your values?’

Leaders need to align with their coaches. For many people, alignment of their “why” will ensure they have similar values. Being coached by someone whose values don’t align may be frustrating and damaging because of the trusted role coaches hold. – Maureen Metcalf, Innovative Leadership Institute

4. ‘How can you support me?’

Your coach is there to push and develop you. This question will help you understand the coach’s philosophy, style and experience. The coach is not there to give answers but to help you gain insight. And if it’s a mentor, ask, “How can I support you?” The best mentor relationships are two-way, with both mentor and mentee invested in the growth and continuous learning of the other. – Kathleen Woodhouse, Nova Leadership

5. ‘What is my biggest weakness?’

The answer to this question does not come without pain. First, the leader’s blind spots need to be identified using a leadership assessment. Second, the leader needs to address their weakness—this necessitates getting outside of their comfort zone. Remember, there is no growth inside your comfort zone. Third, the leader and their mentor or coach need to agree on a development plan. – Antonio Garrido, My Daily Leadership

6. ‘Why did you become a coach?’

Learn the person’s origin story. Work with someone who you connect with. Never settle for working with a coach because they are in your price range. You’ll be sharing personal, confidential things, and it is important to know they will be held in confidence—that your coaching engagement provides a safe space. Stick with your gut here, because the right coach can change your life. – Cara Heilmann, International Association of Career Coaches

7. ‘How will we measure each session’s effectiveness?’

A leader must definitely be result-focused when deciding to work with anyone. The one question that leaders should ask their coach or mentor, as well as themselves, is, “How will we know the effectiveness of our coaching (or mentoring) relationship after every session?” This way, the accountability partnership can be strengthened through timebound expectations from both coach or mentor and the coachee or mentee. – Anilkumar G, ACTIONRICH Business Solutions India Pvt Ltd.

8. ‘Do you have a mentor?’

A leader should always ask their coach or mentor if they have a mentor. A mentor not having a mentor themselves means they’re either egotistical and think they know everything already or are not open to continued learning. You want mentors who are constantly growing and furthering themselves so that they can help you do the same. – Ryan Stewman, Break Free Academy

9. ‘What does progress or success look like to you?’

What does progress or success look like to the coach? This underlines the values of the coach or mentor as well as their “why,” which has to be aligned with that of the coachee or mentee. There has to be common ground between both that will facilitate a better professional relationship between them, with set goals and results. – Sahar Andrade, MB.BCh, Sahar Consulting, LLC

10. ‘Why do you coach?’

Ask this question instead of one around the coach’s qualifications. Here’s why: Their resume will speak for itself, but what it won’t tell you is their purpose behind coaching—their “why.” This gets to the heart of the matter, which is where their heart is in coaching. It’s about being curious about what drives them to do this very specific work and whether or not it aligns with your personal values. – Joshua Miller, Joshua Miller Executive Coaching

11. ‘Do I serve as a positive role model?’

Leaders should ask their mentors if their behavior serves as a positive example for subordinates. While business success is important, the best leaders do not consider any work beneath them, show appreciation for employees, treat others with respect and honor laws as well as their personal code of ethics. – Michael Timmes, Insperity

12. ‘Why are you the right coach for me?’

A leader should ask the question, “Why do you think you are the right coach for me?” This question, answered correctly, should address the value that the coach will bring to the engagement as well as highlight their prior success stories, experience or expertise and, finally, their coaching style. – Dr. Flo Falayi, Korn Ferry

13. ‘Will this be easy?’

Ask your coach or mentor, “Will this be easy?” If the answer is, “yes,” rethink your commitment to the engagement. Real transformation and learning is an uncomfortable act of deep reflection. You will be breaking previous conditioning, meeting your fears head-on and dealing with the inertia of not taking action. None of this will be comfortable. The coach will support you through the discomfort, as the journey will be uncomfortable at times. – Devika Das, CORE Executive Presence

14. ‘How can you help me reach my goal?’

Leaders should ask their coach or mentor, “How can you help me reach my goal?” and, “What will that process look like?” Hearing the answers to these two questions, a leader should understand what an executive coaching engagement is and understand the specifics of how that coach likes to operate. – Michele Cohen, Lead to Growth Coaching

15. ‘What are you most proud of?’

One question I would recommend asking your coach is, “What are you most proud of?” Asking this question allows you to learn more about their values and what’s important to them. It also helps you understand what kinds of things they value in the people around them so that when you’re working with them, you can be sure that those things are being supported as well. – Willena Long, Career Boss Academy

16. ‘What would the ideal duration of our engagement be?’

When considering a coach, a leader should understand the ideal duration of the engagement. Some coaches are more short-term, tactical advisors, and others want long-term, multi-year coaching relationships. And by understanding how a coach disengages from a relationship, the leader will get a clear sense of the coach’s experience and mindset as they approach the next assignment. – Ben Levitan, Cedalion Partners