Executive Leadership

Why You Are Not Getting What You Want Out Of Executive Coaching

Executive coaching is only valuable if it is not being masked as mentoring or consulting. Great coaching will always lead you through assessment, clarity, conversation and action.

Joe Woodruff


November 11, 2021

Photo credit:
Doruk Bayram

In the movie Open Range, Kevin Costner plays Annete Benning’s love interest. Benning’s character is a strong, independent woman, and Costner’s is a rough, old-fashioned cattle-driver reflecting the values of the movie’s 1882 setting.

At the end of the story, as Kevin and Annete set out on a life together, he says to her, “How is this ever going to work if you don’t do what I say?”

It’s a great line. It’s a lousy expectation for a relationship. Yet, do what I tell you is what is often mistaken for coaching today.

I’ve been coaching since 1991. I was coaching before it was a thing, and certainly before it was ever an accredited discipline. I have grown up with the movement, and as with all movements, I have seen it grow, adapt, be subject to misunderstanding, and fall prey to poor practices.

Hopefully, you have had a good coaching experience in the course of your career. But, more so than not, I have seen executive coaching miss the mark. There are three reasons you are not getting out of coaching what you want, and four dynamics you must contend for in coaching.

Reasons Coaching Is Missing The Mark

Coaching is masked as mentoring.

I love mentoring. I have mentors. I am a mentor. But I draw a critical distinction between mentoring and coaching (and I’m grateful to my own coach for bringing clarity to this).

Mentors pour in; coaches draw out. Mentoring is the impartation of wisdom learned over time and applied to specific problems and needs. When I turn to my mentor, I say, “Teach me.” No matter how she approaches it, whether she teaches directly or indirectly, she is filling a deficit I bring to her. I come with a need, I leave with an insight she imparted.

An effective coach will not give you the answer. They will, however, draw the answer out of you (more of that below). The goal of coaching is to help you discern your situation, clarify your thinking about it, and dial you in on the best response. The critical difference between mentoring and coaching is ownership: from discernment and clarity comes action that you decided upon.

If I tell you what to do, you may or may not do it, may or may not believe it, may or may not invest in it. But if you tell me what you believe you must do, then the investment is more likely to follow.

Coaching is masked as consulting.

Whereas mentors tend to pour in to a particular issue or problem presented to them, consultants tend to camp out in a larger terrain. The task of a consultant is to identify problems and recommend solutions. I am a consultant. I don’t mean to negate our value; I’m just being clear on distinctions.

Consultation has value; but it is not coaching. Coaching develops a whole person; consultation designs a program. Consultants ask questions in order to better tell you what to do; coaches ask questions in order to better help you think and understand.

Coaching is without advocacy.

Mentors pour in; coaches draw out; advocates stay with.

The most effective coaches adopt a relational posture with you and chart a long course with you. Great coaches become aware of what you are dealing with at the personal, relational and missional level. They are holistic.

As a mentor, I often want to know if my insight worked. As a consultant, I want to know if my plans and ideas worked. As a coach and advocate, I want to know that you work.

The Coaching Turnaround

Effective coaching that hits the target employs four consistent practices:


Coaching isn’t done in a vacuum. Even though you determine the agenda with your coach, a great coach will have helped you identify your needs and prioritize what you want to work on. Coaching is progressive, building from one session to the next, but sensitive to needs in a moment that you feel are essential to be addressed.


The problem executives voice to me is that their coaching doesn’t seem like it is dialed in. Ineffective coaches do not help their clients define what success will look like. That is why great coaches begin with assessment, and then move into priorities that are defined by clear outcomes.


Coaching is a relationship in which questions are the bond. Questions have the power to elicit insight, resolve conflict, bring awareness and clarify perspective. In every coaching session, you need to have said, “That’s a good question.” If not, your coach has failed you.


The coaching relationship is about results. As much as I like my clients, they don’t pay me to just be their friend. I am alongside them to help them succeed at something. Every coaching session needs to end with an actionable step. Coaching is not a check-in time, it’s a move-on time.

I wouldn’t be where I am without coaching, and I have the privilege of people saying the same of me as their coach. Every leader needs a coach. No exception. But they need a good coach, distinct from mentors and consultants, and alongside them as well.

When you are coached, it is not a matter of doing what I say; it is a matter of you doing what you say, and that should only be spoken from a mind that has become clear and a path that has been laid by you.

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