How To

A Framework for Choosing a Leadership Coach

January 26, 2022

Choosing a leadership coach for the next phase of your growth requires some art and science.

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A framework for choosing a coach
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If you're leading your own company, team, or program, I can help you gain clarity and alignment in your work.

If you’re interested in working with a coach, how would you go about choosing the best person for your goals?

Like all honest answers to most big questions: It’s a bit science, a bit art. 

I had a call with a potential client this week. We had a connected, alive conversation. As we wrapped up, he point-blank said, “I’m not sure how to evaluate a coach.” 

My immediate feedback was, “Well, I’m not too sure about a framework, but the quality of connection and chemistry you have with someone matters.” I wasn’t totally satisfied with my response to him in the moment (and I suspect it wasn’t helpful to him either!).

Chemistry matters, but it’s usually not enough.

I came by my coaches through serendipity and a bit of trust in my gut feel. Something along the lines of: “I believe this person will help me move forward in a big way.” I’ve written about that experience here.

Understandably, “gut feel” isn’t enough for everyone. 

So, I spent the last couple of days considering what’s behind that gut feel. 

The result is a light framework for people looking for a leadership coach. (I plan to retain a coach this year and these are the questions I’ll be using!)

I recommend talking with at least a couple of coaches before you make a decision, so that you can find the best fit.

Ask Big Questions (The Science)

Being coached, first and foremost, is a relationship. And relationships are built on conversations. So, in a first conversation with a potential coach, ask any of the following questions:

  • What is your work experience and background? (You may want someone who is familiar with your industry, or you may want a coach with a very different background so you can benefit from differing perspectives.)
  • What experience do you have coaching leaders like me? (Again, this could relate to your industry, your position of leadership, or your specific development goals)
  • What type of coach training and education do you have?
  • What is your approach to coaching? Do you like to use specific methods or frameworks?
  • How do you think about measuring success in coaching?
  • In what circumstance might you say no to working with a client?
  • What is your experience with being coached?
  • How do you handle confidentiality?
  • Could you provide me references?


And perhaps the chief question of all questions:

Why do you coach?

Evaluate How You Feel (The Art)

A coach’s answers to the above questions should give you a great sense of who they are and how they’ll approach supporting you. 

Some additional reflection questions:

  • Do I have chemistry with this coach?
  • Can this coach help me achieve my goals in a way that I’ll enjoy?
  • Will the coach ask provocative questions, push me to work on growth edges, and challenge me—in a supportive way? 
  • Do I feel comfortable talking to this coach? Can I be candid? Vulnerable? Do I feel championed by them?


Working with a leadership coach has the potential to shape, change, grow, inspire, and develop you in all of the most important ways. Here’s to using a bit of art and a bit of science to choose your best coach.

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I'm Cali, your co-conspirator in charting a new course

I help you uncover your core values—your North Star—and develop clarity and conviction in your career. If you're ready to chart a new course in your leadership, you're in the right place. Welcome.

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