Winston Cox

Facilitator · Washington, DC · he/him

Winston is a passionate and visionary educator, leader, and activist with 30 years in professional practice.

Now based in the DC area, Winston began his career as a Humanities teacher in the Cambridge and Boston, MA public schools. Winston went on to become a principal at the elementary, middle, and high school levels, in Boston and in Washington, DC.

Winston served as the national Director of Turnaround Schools for Expeditionary Learning (now EL Education) and as National Implementation Director for Turnaround Arts at the John F. Kennedy Center for the Performing Arts.

As a facilitator and coach for Inspiring Educators, Winston’s client list includes Boston Public Schools, Teach for America, LEE, NYC District 75, the New Blue Project, and Mastery Charter Schools.

Winston’s activism includes the roles of Chairman of the Board for the Center for Black Educator Development and Board Member at the Fender Play Foundation.

Winston and his wife, Laina, also a career public educator, recently launched their own consultancy, Cox LEADS, LLC. As proud parents and community members, they share a passion for and commitment to empowering school administrators, teachers, students, and parents to be bold leaders of their own learning and growth. And they extend their expertise in public education to support leaders in other fields in the areas of leadership presence, emotional intelligence, culture and climate, authentic assessment, arts integration, and equity and belonging.

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    “Wow, INCREDIBLY effective! Winston is an all-star facilitator and can respond in the moment and with strong and wellpracticed plans. I was so touched by his genuine nature and his skill.”

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    “Winston is a model of what it means to be an authentic leader. He got us where we needed to be, he used time well, and he conveyed his values through his facilitation. I thoroughly enjoyed our sessions with him – He was an inspiring person to work with before starting the school year.”

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    "Winston is knowledgable, flexible, and engaging! I appreciate the content and especially Winston's flexibility to adjust to our specific needs in real time."

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    "I especially appreciated Winston's facilitation because he has an understanding of all the technical and adaptive work needed in this role. I think it would be helpful to have Winston come observe and support our individual schools and lead us through the same exercises."

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    "Throughout the session, Winston often validated our experience as school leaders and was able to share ideas and strategies in an authentic way that we, as school leaders, could replicate in our schools."