Meet Courtney Caldwell
Director of Innovation and Program Delivery, Facilitator, and Possibility Enthusiast
What guides your work?
I’m oriented toward possibility—what’s wanting to emerge—and how we can co-create environments where real growth and transformation happen. Whether designing curriculum, managing complex projects, or facilitating a team session, I’m paying close attention to outcomes, feedback, and what’s most alive in the room. At the heart of it all is a belief that people are capable of extraordinary things, especially when they’re met where they are and given space to tap into their potential.
What’s your background?
For over 25 years, I’ve worked in education as a teacher, administrator, facilitator, and consultant. I’ve trained and coached educators across career stages and developed inclusive curriculum through a social justice lens. Along the way, I became a leadership development facilitator and Enneagram teacher (I’ve been studying it for 30 years!). I bring communication skills, agility, and a deep commitment to helping people believe they can do new and challenging things.
What qualifies you to do this work?
M.Ed. in History Education, University of Notre Dame
Graduate work in Interdisciplinary Studies, University of Washington
B.A. in Political Science & Interdisciplinary Studies, University of Portland
Certified iEQ9 Enneagram Practitioner
National Board Certified Teacher
I’m a generalist by design—I connect the dots across disciplines, people, and ideas. That lens helps me design experiences and facilitate conversations that go deep and create real change.
What are you learning these days?
Everything. Always. I usually read six books at once and half-listen to 20 podcasts a week. Recent standouts include Emergent Strategy by adrienne maree brown and Disability Visibility, edited by Alice Wong. I’m drawn to work that explores what motivates people, how systems function, and how we can better listen—not just to respond, but to learn. I’m inspired by podcasts like Wiser Than Me, Normal Gossip (my not-guilty pleasure), The Antiracist Enneagram, Peak Travel, Good Hang, What Now, and A Bit of Optimism.
What brings you joy outside of work?
Travel. I've visited and gone for a swim on all seven continents (yes, even Antarctica). I’ve explored over 100 countries—often solo—but also with friends, students, and fellow educators. I’m also a passionate auntie, a New Year’s Adam karaoke devotee (December 30th, because Adam came before Eve), and a fiercely loyal friend who believes in celebrating womanhood, big birthdays, and life’s small moments. Oh, and I cook like I live: creatively, without following recipes.
What are you most proud of?
Surviving cancer changed how I make choices about work, relationships, and what matters most. I’m proud of making bold shifts, learning from failure, and growing in community. I’m proud of our work at HLG. I’m proud of the possibility I see in people, and that I keep showing up with curiosity, humor, and heart.
What’s a standout moment for you as a facilitator or coach?
When someone sees themselves or their team differently—and something clicks—their eyes light up, and suddenly, what felt stuck begins to move. I live for those moments. We can all be transformed if we’re willing.
