Reflect & Refract Virtual Roundtable Series
From Leader to Strategist: Building the Capacity That Organizations Need Most Today
Twenty years across higher education — faculty, staff, administrator, and at community colleges, liberal arts colleges, public and private universities — and none of it prepared her for the moment she sat across from a Chancellor and Provost, hands shaking, and realized that three highly credentialed people couldn't even agree on how to describe the problem in front of them, let alone solve it.
That moment of total unpreparedness — after a career that should have prepared her for everything — is where her thinking about strategy began.
Not strategy as a modifier (“strategic planning”) or as a deliverable (“the strategic plan”). Strategy as something harder and more specific to name.
A distinct identity. A cultivated capability. Something leaders have to consciously work to build in themselves, and something most organizations are missing without knowing it.
That last part is what makes it costly. The gap isn’t in the credentials. Every room has credentialed people. The gap is in whether any of them have become strategists.
Since that shaking-hands moment, Maya has spent nearly four years doing the harder work: rebuilding a struggling initiative from the inside out at the University of Wisconsin-Madison, testing a thesis she’s been developing her entire career. Her microfirm, The Education Strategist, carries that thesis into the field. Her podcast, Beyond the Ivory Tower, puts it into public conversation.
The thesis: there is a discipline of strategy, it is distinct from leadership writ large, and the leaders who build it internally are the ones who move their institutions forward.
On September 23, she brings that thesis to a room that reaches well beyond higher education.
“The question isn’t whether your organization has smart, experienced leaders. The question is whether any of them have become strategists.”
— Maya Evans
A conversation that goes well beyond higher ed.
This roundtable explores a core question of organizational effectiveness: How does a leader become a strategist, and why does it matter now?
We'll examine what strategy actually is — a distinct identity, discipline, and set of capabilities. We'll challenge the language we use, interrogate what we actually mean when we call something "strategic," and co-create a clearer picture of what strategy looks like when it's genuinely embodied by the people doing the work from the inside out.
Drawing from lived experience at the intersection of leadership, institutional complexity, and a hard-won organizational turnaround, this conversation invites participants to test their own strategist identity and to build it together.
A few of the questions we’ll wrestle with:
- Is strategy a missing ingredient in your organization, or do you simply lack the language to describe what’s already there?
- What does it look like when strategy is done well, from the inside?
- What does it actually take to develop the capacity to lead strategically, rather than just think strategically?
The identity underneath the plan.
When I launched this Roundtable series in 2023, I wasn’t entirely sure what it would become. What I knew was that the leaders I work alongside were navigating a level of complexity that our usual frameworks weren’t quite built for. I wanted to create a space where we could think together, not just consume content, but actually reflect and refract what we’re learning back into our practice.
Six sessions into the 2026 iteration, I’m convinced this year’s series has found its footing.
Christophe Kempkes (April) helped us think about what it looks like to hold coherence when systems are fragmenting. Mary Ann Allison (May) helped us name the deep currents and patterns beneath the turbulence. Louis Diez (June) thinks like someone who has watched real teams grapple, sometimes brilliantly, sometimes awkwardly, with what it actually means to bring AI into mission-driven work; his conviction, earned from the field, is that the relational work of leading people isn’t going anywhere. Tanja Horan (July) brought the question that had been building all year: before you accept scarcity as your only frame, what do you already hold that you haven’t fully seen yet? And Ken Hubbell (August) opened something quieter and perhaps more fundamental: what does it mean to live and lead as the artist of your own life?
And now Maya.
She arrives with the question underneath all of those questions: whether anyone inside your organization has actually become a strategist, and what that even means.
As you know, this same inquiry has been part of my own consulting work for a long time. The organizations I’ve seen flourish under real pressure aren’t always the ones with the most resources or the best plans. They’re the ones where someone, somewhere inside the organization, has developed the identity and discipline to hold the whole picture and work from it.
Maya has a name for what that takes. She’s spent twenty years testing it. I can’t wait to think alongside her.
This series exists because I believe each of us has something to teach and each of us has something to learn. Reflect & Refract is the practice of bringing those two truths into the same room, every month, with people who are doing this work in the field. What you carry in matters. What you leave with has changed shape. That’s the whole point.
— In gratitude, Gary
You'll recognize yourself here.
- You carry leadership responsibility in any kind of organization, nonprofit, higher education, philanthropy, or otherwise. Maya’s lens is higher education, but the question she’s asking belongs to any sector navigating rapid change. The gap between leader and strategist shows up everywhere.
- You’ve sat in a room where smart, experienced people couldn’t agree on how to describe the problem in front of them, let alone solve it, and you’ve wondered what was missing.
- You’ve used the word “strategic” and quietly suspected you couldn’t define what you meant.
- You want to understand what building genuine internal strategy capacity actually looks like, not as a plan or a process, but as a way of working from the inside out.
Session Format
A 75-minute facilitated conversation, not a presentation. Gary and Maya will offer a brief framing through their interaction, and then the room takes over. Gary facilitates. Questions guide. Participants think together.
Live only. Not recorded for distribution. Limited to approximately 20 participants so everyone has a chance to actually speak.
