If You’re Doing It Right, Your Clients May Be Frustrated

“I was really not happy to participate in that leadership program. It was uncomfortable and I thought it was going to be a waste of my time.”

This is one of my favorite quotes from a participant in our leadership cohort. She came up to me after an in-person keynote and started with, “Jen, I have to tell you something…”

I listened and nodded. Even smiled slightly.


We have heard it before—actually, we hear it often. A current model in our field is that funders purchase leadership development for their grantees. Then, leaders are required or strongly encouraged to participate. This makes our work to support them about 1000 times more challenging. But, it has also helped us develop a secret sauce that keeps our participants engaged, learning and growing.

In response to the request from Maine’s 21st CCLC State Education Agency (SEA) who we’ve worked closely with for many years, DWL developed  the Kairos Leadership Academy , a customized 12-week leadership coaching group. Over the course of this experience, Directors invested at least two hours per week in their own leadership development. They worked to strengthen core leadership competencies, and foster emotional intelligence (EQ) to become more fluent in understanding emotions and creating an equity-focused organizational culture where administrators, staff, young people and families feel valued, respected, and empowered to collaborate. 

At face value, this experience could seem like just another professional development offering. Right? Another requirement upon an already high pile of requirements.

But, for us, it’s not only about what that is offered—it’s about how we we do it. That’s the secret sauce.

We take a heart-centered approach. We create shared processes where we actively:

  • Create and support a community of belonging and trust which means that we are establishing and reinforcing ways of being and working together.

  • Facilitate—not dictate—the learning that happens which means that we are elevating the knowledge and experience from the group…not telling them “the way it should be”.

  • Continue and contextualize the learning by being accessible and fostering adaptation and application of learning to each participant’s unique situations.

This approach is messy. It causes discomfort immediately because we are not telling participants what to do…we’re asking them what they need.

Systems change and capacity building is messy, tangled and challenging just like this knot!

And when it comes to supporting systems change, it’s even more important to rely on guiding principles rather than specific outcomes. Why? Because systems are messy. Very very messy.

  • Because systems are made of people, we remain human-centered in our work. Not centered on producing a deliverable or output.

  • Because systems are multidirectional, we remain discovery-based and curious in our work. Not telling others what will work for them, but rather, helping them find out what may work in their contexts.

  • Because systems are dynamic, we adapt in our engagement. Not relying on one set of slides or handouts, one research paper or one presentation. We draw from a wide variety of tools, resources and research and offer them when and where it’s helpful.

  • Because systems are purpose-driven, we keep our eye on the big picture and help participants do the same. Not letting egos, funders or organizational priorities cloud where we are really going, what we are really doing and why we are doing it.

Now, I’m very aware that facilitating talent and leadership development is something similar to teaching where many people think they know how to do it…and that they can do it better than those who are doing it. But, if you’ve tried it then you know it’s actually much easier said than done.

One of my colleagues shares a story of how she facilitated a weeklong seminar for educators. She gave each person an empty folder and invited them to take whatever resources and articles they wanted from the back table during the course of their time together. This made participants uncomfortable. They were not being given all the information, they had to choose what resources would best support them. One participant fully revolted—leaving the seminar with feedback: “This is the most unprofessional…'“

Personally, I’ve talked down many a client, witnessed the stricken look on a funder’s face after the first session where a participant says she’s more confused now than before, and continued to coach and be coached on how we live the values we promote.

💥 If we say we want young people to be curious, manage their own learning, find their own meaning—we need to do that ourselves.

💥 If we say we want young people to understand their own needs and be able to advocate for themselves—we need to do that ourselves.

💥 If we say we want young people to be powerful, in relationship, in community, and in themselves—we need to be that ourselves.

It’s not comfortable. We’re creating the plane as we fly it. We’re iterating. We’re shifting gears. We’re adapting.

We have created a whole framework to help us stay on course. And we have learned that our best way to navigate this is to do it together.

So, in the Kairos Leadership Academy while participants find themselves delving deep into their leadership style and values, fleshing out their philosophies on workplace relationships, and discovering areas for personal growth, the coaching group acts as a safe space for many to explore and be vulnerable, allowing them to embrace discomfort and emerge stronger.

“This program made me feel incredibly uncomfortable in the beginning! After the first couple of sessions I knew that unpleasant feeling was a sign that I was ready for learning and growth. I had to take an honest look at myself and allow myself to be vulnerable, which is something that does not come easy for me. The academy has been a safe place to explore myself as a leader and get to know other leaders on a meaningful level.” - Program Director, Maine 21st CCLC

What I love is that this is just another example of our work—where we provide a supportive environment that fosters growth, reflection, and self-discovery.

Now, back to the person who said she was sure this would be a “waste of time”: A few months after the cohort ended, she came into a tough conversation with a staff member. And she remembered a strategy that came up during the cohort with her peers. Incredulous, she said,

“Wow. I somehow connected back to a thing we talked about and tried it. And, geez, it really worked. Thanks.” ❤️

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Break Out of The Rut: An Activity for Your Next Team Retreat

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The Executive Director in a Flat Organization: The Many-Faced Leader