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When Leadership Coaching Works (and when it doesn’t)

“We’ve invested in other leadership coaching and training. But you’ve reached a deeper level of work and progress than we’ve ever had someone get to before.”

A client shared this with me in a conversation recently.

We were discussing the results of an Organizational Performance Audit we completed, and having a “midway meeting” to touch base on leadership development progress thus far (and where we are headed next).

The thing is, I have never had someone tell me they regretted working with a leadership development coach. Not when they were ready and willing to stop tolerating their status quo. Not when they were ready and willing to create real progress for their organization.

And this client (along with the rest of their leadership team) was very ready to stop repeating the same people-problems, stop being ‘kinda-sorta’ successful, and start moving the organization toward reaching it’s full potential. They know that this level of success starts with enhancing leadership. So they called me.

When Coaching Works

If I hear someone tell me about a negative experience it’s either because they weren’t really quite ready for the coaching, or the coach they worked with wasn’t a good fit for them.

When a coach is not a good fit for you or your organization, it can be like eating a piece of fruit cake. You might pretend to like it, because you feel like you’re supposed to, but if you’re honest with yourself you’d rather volunteer to shovel out the barn.

And when they are a good fit real magic happens. It can feel like that first sip of champagne; When those bubbles hit your tongue, and that sweet tang creates a sense of excitement and celebration, and you just want more (secretly wishing you were a sommelier who could describe the tasting notes of ‘opportunity’).

The clients I work with get to take advantage of my education in psychology, human behavior, and effective communication allowing us to get down to what’s really important for their development, accelerating growth and progress. (This is what the client was talking about in the quote above).

In my opinion, leadership development means a commitment to expanding your perspective, enhancing your self-awareness, improving your ability to navigate people-problems, asking questions and being open-minded, trying new things, and a willingness to pretend that you find my puns funny.

[That last one is super-duper important]

Some of that development feels like effortless “aha” moments, and some of it requires digging deeper.

  • So, it really is important to be ready for it.
  • It really is important to find the right coach for you.
  • It really is important that your coach meets you where you are, and that you move at the right pace.

The results of working with a good-fit leadership coach should boost your confidence, expand your skills, enhance your decision-making, balance your energy and time, help you find more purpose, and decrease the loneliness that often comes with being a senior-level leader. Sometimes I find that my primary role is to help a leader clear out the “bull,” and find the release in “setting things down” sometimes.

You can’t create trust and dig deep like that if you’re not ready for it, or if you’re not working with the coach that’s a fit for you.

Something to Consider When it Doesn’t Work

When leadership development becomes prioritized within your department or organization, make sure you take the time to really decide what your goals are and the purpose of the development. I say this because glazing over this step opens opportunities for the leadership coaching to seem like it fails.

Here’s what I mean…


I believe that leadership development should not feel like another job or more work. That it should make the job you already have as a leader easier. However, my reach is limited despite my influence. And there is a level of energy and effort that is required by you (as the leader) to apply and implement the coaching. So be sure you see the purpose and a clear goal. Ensure that you’ll feel like the energy and effort is worth it.

You can absolutely collaborate with your coach and leverage their expertise to really hone in these goals. But avoid being willy-nilly about it or you might just set yourself up for unfulfilled expectations. It might appear that the end results were disappointing, when there was actually a front-end problem.


If you are not sure what it is you are really after in the end, then it’s much harder to know if you’ve achieved it. This sounds more obvious when we are talking about the organization itself (increase revenue, expand our customer reach, improve our services…). It is easier to determine whether or not you’ve achieved those goals.

And sometimes it can feel a bit less clear to set goals related to leadership development, which makes the results also feel less tangible. But that does not have to be the case.

I’m actually asked about this often because there is a misconception about the results people see with leadership development. Seeing them as “less tangible” are the words of people I’ve spoken with, not mine. I believe that the results you get from leadership development should 100% be tangible. If you don’t see clear results from your leadership development coaching, then you might want to consider whether or not you were clear about your goals in the first place.

All this to say…

Sometimes I am asked “What do you tell people when they are hesitant to prioritize paying for leadership development?”

I say “Why wouldn’t you prioritize it? It’s not a cost, it’s a strategic advantage.”

Often times this question comes from a place of hesitation because someone has misconceptions about the tangibility of results, or they have experienced coaching “fail” in the past. But we’ve debunked all of that today.

Leadership development is a prerequisite for solving your people-problems and achieving organizational health that leads to rises in revenue. It’s necessary in order to stop tolerating the status quo and start moving the organization toward reaching it’s full potential.

Working with a leadership development coach offers the strategic advantage of having a high-level of expertise that can accelerate progress. And remember that leadership development is collaborative. You need to be ready and willing. You need to determine the right-fit coach for you and your team.

But, do it.

Because real progress starts with leadership (it’s the Leadership First Approach™).


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