How to Choose an Executive Coach, for You or Your Organization
Nov 03, 2020
Choosing an Executive Coach for yourself can be a little confusing, to say the least. Your Executive Coach will be your confidant, and you will need to open up to get the most from the relationship. So whether you are spending your own money or your organization is providing you with a coach, it’s helpful to have more than just a ‘gut feel’ to go on.
Coaching Chemistry Call
Most coaches will give you a no-obligation 30- to 60-minute ‘chemistry’ meeting to assess whether there is a fit for both parties. That’s right: an experienced coach may spot that you are not committed to the process, or the organization has misaligned expectations, and so excuse themselves from the assignment.
I recommend that you meet with at least two coaches but no more than four. Meetings can be face-to-face, by video conference, or by phone. Try to ask each coach the same questions, and take note of the questions they ask you. A good coach will get you to step back and think. You will find yourself saying, “That’s a good question.”
Here are some simple opening questions:

- How long have you been coaching?
- What were you doing before coaching?
- What prompted you to get into coaching?
- Have you worked with people in my industry/organization before?
You want to know the coach's background and experience to build your level of trust. Your Executive Coach does not need to have worked for your organization before or be from the same background – in fact, sometimes, for perspective, it’s better if they haven’t, but it is important that he or she has an understanding of the type of work you do and the challenges and opportunities you are facing.
Being Clear about Coaching Objectives
You may not have all your objectives clarified at the time of the chemistry meeting, but it is important that you and your prospective coach talk about what a successful outcome would look like. This gives you a chance to discuss whether these objectives can be achieved within the agreed time frame (typically 6 months).
Coaching objectives are usually feeling- and behavior-based rather than measured in financial numbers. Some examples are:
- To feel more confident to influence my boss / the board/peers/clients
- To have clarity about how to lead through current ambiguity and have a laser focus on execution
- To think and behave as a natural successor
- To have Executive Presence in global meetings and calls
- To have strategies to step back from tactical work and think more strategically
When executive coaching is paid for by the company, there is usually a sponsor, such as a line manager or HR. Whilst coaching conversations are confidential, it's usual for the sponsor to ask the coach to report progress towards the stated objectives. You should clarify with your prospective Executive Coach how they will handle confidentiality in these situations.
Choosing a Coaching Partner for Your Organization
Everything above applies whether you're choosing a coach for yourself or being assigned one by your company. But if you're the one making the choices on behalf of others, an HR leader building a coaching program, or a manager sourcing support for a growing team, the evaluation takes shape differently.
You're no longer just assessing chemistry with one person. You're assessing whether an approach can work consistently across multiple leaders, possibly delivered by more than one coach.
A few questions I'd ask any coaching partner before committing an organization to them:
- Can you name your methodology, and where did it come from? "I use a personalized, holistic approach" is not an answer. A credible coaching partner can point to a specific framework and explain the thinking behind it.
- Is there evidence behind it, or just testimonials? Testimonials tell you that people enjoyed the experience. Research tells you the method changes behavior. Ask for both, but don't accept one as a substitute for the other.
- Is the approach documented well enough to be delivered consistently? If the entire engagement depends on one coach's personal style and can't be explained, trained, or handed to another practitioner, it won't scale past that one person. That matters if you're rolling coaching out to more than a handful of leaders.
- How will progress be reported without breaking confidentiality? I touched on this above. It matters even more at an organizational level, where a sponsor or HR partner will reasonably want visibility into progress without compromising the trust that makes coaching work in the first place.
The individual chemistry still matters for each leader who goes through the program. But at an organizational level, you're choosing a system first and a person second.
Choosing an Executive Coaching Style
Gender should not really be an issue in selecting a coach. You might think you would prefer a same-gender coach, but an experienced coach will make their gender irrelevant to the process. That said, it’s your right to choose what you feel comfortable with, up to a point. And that point is, that too much comfort may not get you the results you are looking for.

This diagram shows that you should assess your coach on two criteria: supportive and challenging.
- If there is no support and no challenge, there is no interaction.
- If there is high support but a low challenge, there will be confirmation of existing mindsets and behaviors and therefore little or no change.
- If there is a high challenge with low support, the coaching can be overwhelming, and the coachee will likely retreat from the engagement.
The conclusion is that there must be the right combination of support and challenge for coaching to facilitate growth. Most coaches are supportive; therefore, you should consider one who provides the right level of challenge for you.
Coach, Consultant, or Mentor?
If you think of a tennis coach, you can imagine them teaching you how to stand, hold the racket, swing, and move. As you develop your tennis, a great coach transitions from telling you how to do the physical things and helps you play a better ‘inner or mental game ’, such as how to read your opponent, how to come back from a lost set, and why winning is important to you.
An effective executive coach is like an experienced tennis coach: they won’t tell you how to do the fundamentals of your job; they'll ask you questions about your ‘inner game’. Your ideal coach will help you explore your identity as a leader, help you think strategically, consider your next career move, and avoid getting hijacked by out-of-date thinking patterns.
If you need help on the ‘how to’ of your work, then you are better off hiring a consultant. Consultants are paid to tell you what to do; coaches are hired to help you work it out yourself.
Mentors are individuals more experienced than you in the same field. A good mentor is somewhere between a coach and a consultant. A mentor can share their experience to help you navigate your environment. A coach doesn't have to be from the same domain of expertise as you, but it’s helpful if a mentor does.
So the moral of this story is: choose an executive coach who will help you think differently, rather than one who just teaches you stuff.