The coaching results will only be as good as the match between the coach and executive. Finding a coach who has the necessary expertise and a connection with the executive is not always easy. It is best to take time until everyone is comfortable with the prospective coach. Whoever is hired, the executive being coached should have some say in the selection. Ideally, the executive is given 2 or 3 coaches to choose from after Human Resources has ensured their qualifications. The following are some questions to ask to determine whether a person is the right coach for an executive.
Questions to ask when choosing a coach:
- What is this coach’s approach or process?
- Does this coach have adequate experience in working with an executive at this level?
- Have you seen an example of a developmental plan created by the coach with a previous client?
- Does this coach appear to have the ability to develop a strong, trusting relationship with the executive?
- Does the person have a style that is compatible with the executive’s?
- Does this coach have the skills and business background required to meet the coaching objectives?
- Does the coach appear to be a team player and can he/she be flexible?
- Does the coach appear to fit with the culture of the organization?
- Is the coach a person of integrity and does he/she appear to be one who can deliver the truth to the organization and the executive?
- Does this person have great insight into people and situations?
- Does the coach have an executive presence that will be respected by the executive?
A practical selection checklist
WJM editorial addition, September 2026.
Start with the leadership situation the coaching needs to address. A newly appointed executive, an established leader preparing for a broader role and a leadership team struggling to make decisions may need different kinds of support. Write down the desired changes before comparing coaches.
Agree on the goals and the sponsor’s role
Ask what the executive, manager and HR partner each expect from the engagement. Choose a small number of observable development goals and discuss what progress would look like at work. Clarify who will provide feedback and when the goals will be reviewed.
Compare relevant experience and personal fit
Ask prospective coaches about work with leaders at a similar level and in comparable situations. Discuss how they would approach the development goals, how they use assessment or stakeholder feedback, and how they adapt when an approach is not working. Give the executive a chance to meet suitable candidates and discuss the working relationship before choosing.
Put confidentiality and scope in writing
Clarify what stays between the coach and executive, what can be shared with the sponsor, and how progress updates will work. Agree on the engagement length, meeting cadence, assessment process, fees and what happens if the match is not right. Ask how any digital tools or AI features handle confidential information before using them.
Decide how progress will be assessed
Ask how the coach will connect the development plan to the executive’s day-to-day work. Plan opportunities to practice, gather feedback and review changes with the relevant stakeholders. At the end of the engagement, agree on how the executive will maintain the new practices.
Choosing the right kind of support
Explore WJM’s executive coaching services to learn about coach matching, stakeholder input and development planning. If the priority is a leader’s transition into a new role, see On-Board Coaching. If the challenge is how a leadership team works together, see team coaching.
