The Wrong Question to Ask When Choosing a Leadership Coach

"Has this person done what I am trying to do?"

If you’re using this question to decide whether a coach is right for you, you’re setting yourself up for mediocrity. And in leadership—just like in adventure—the goal isn’t to play it safe.

The Flawed Thinking Behind This Question

I recently listened to a podcast where two experienced executive coaches and senior businessmen in Japan discussed the idea that there are basically two types of coaches:

1. The coach who only asks questions.

2. The coach who has "been there, done that" and can mentor you through their lived experience.

Their conclusion? If someone hasn’t done what you’re trying to do, don’t hire them as a coach.

I think they’re getting this mostly wrong.

The conversation also took a swipe at the idea of a 32-year-old life coach, implying that someone that age couldn’t offer value—especially not to someone older or more experienced.

These perspectives are not only outdated; they are fundamentally flawed.

The Hidden Assumptions That Limit Your Growth

There are two dangerous assumptions baked into this thinking:

1. The way things work is working. If this were true, leadership wouldn't be facing the crises it does today. Young leaders, more than anyone, see the cracks in the system. They know we don’t need more of the same. We need a radical shift.

2. Wisdom only comes with experience. Yes, experience matters. But wisdom doesn’t follow a linear path. Some of the most transformative insights come from those who haven't been conditioned by "the way things are done." If you dismiss someone simply because they haven't walked your path, you might be shutting the door on the very insights you need.

   

How to Actually Choose the Right Leadership Coach

If you’re serious about leadership development, here’s a better framework for selecting a coach:

1. Are you willing to fully commit to partnership with this person?

If leadership transformation is what you are seeking, your relationship to your coach will be one of the most vulnerable and challenging in your life.

• Do you feel chemistry with them?

• Can you trust them?

• Do they create a space where you feel both brave and safe?

2. Are they doing their own developmental work?

This is the key area where you want your coach to have experience, the experience of trusting and paying someone else (another coach) to partner with them in their own breakthroughs.

• Do they invest in their own leadership coaching?

• Can they articulate how that work has impacted them?

3. Does their coaching approach inspire you?

There are a plethora of ways to create leadership transformation, and none of them is 'right', there is only what is right for you.

• Is it clear and easy to understand?

• Does it open up possibilities you hadn’t seen before?

4. Are they deeply dedicated to their craft?

There are many coaches out there who also wear the hats of mentor, consultant, adviser, expert. This can be a benefit, and it can also be a dilution of their dedication to becoming deeply skilled in the art of leadership coaching, which is distinct from those other modalities.

• What kind of training and certifications do they hold?

• Are they continuously investing in their professional development?

(Note: You may notice two key things missing here—how much experience a coach has with other clients and how much they charge. These two factors are closely linked. A highly experienced coach will charge more, while a less experienced one will charge less. The reality is that no one has experience in their work until they gain it. If a coach meets the four key criteria above for you, their experience level may only be as relevant as your budget allows.)

Mentors vs. Leadership Coaches: Know the Difference

If you want a mentor—someone to tell you what worked for them—then by all means, find someone who has done what you want to do.

But if you want a leaderhip coach—someone who will expand your capacity to lead in your own way—then the real question isn’t whether they’ve walked your exact path. It’s whether they are the right partner for your growth.

The difference between the two can be particularly relevant and and blurring the two can be particularly insidious in Asia. Often executive leaders who are native to Asia and who work with coaches are (consciously or unconsciously) looking to coaches to take on the role of sensei, or teacher. This limits those leaders to only developing as far as the coach has expertise and experience. Standing firmly for those leaders in the role of leadership coach invites them to go far beyond that.

Transformation isn’t a straight line. It’s an adventure. And the best guides aren’t the ones who’ve already arrived at the destination. They’re the ones dedicated to helping you navigate your own way there.

Choose wisely.

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I'd love to help you work through those four questions above to see if I'm a fit for you, or if there is someone else I could refer you to. Book some time with me and we can discuss.