Debbie Millon

About Debbie

Debbie spent nearly two decades serving as Head of School at two independent, holistic and progressive schools, including leading Wingra School through 2022. Her leadership is deeply rooted in the theories, writings, and mentorship of scholars considered to be among the pantheon of holistic education, grounding her work in a belief that schools must nurture the whole human being within an interconnected community.

Today, Debbie’s work extends beyond a single school community. As an educational coach and consultant—and in her role as Director of Operations at Educators Collaborative—she designs systems that support strategic transformation and partners with school leaders across the country. She brings a rare integration of philosophical depth and operational clarity, helping leadership teams align mission, structure, and culture.

Debbie has served in advisory roles within organizations focused on community engagement, educational equity, and justice across multiple levels of the educational landscape. Beyond her work in education, Debbie and her husband opened and led a restaurant and bakery/market in Vermont. Both businesses were committed to local food and farmers and to educating consumers about the importance of supporting sustainable agricultural practices. She also worked in the field of biomechanics, designing prosthetics for children and studying Tai Chi gait in young and elderly adults.

At EC, Debbie strengthens the firm’s search and consulting work by building the internal systems and collaborative rhythms that allow partners and clients to do their best work. She approaches operations not as mechanics, but as culture-making—creating the conditions in which clarity, belonging, and strategic alignment can flourish.