Winston is a career public educator with 30 years of experience as a teacher and principal in the Cambridge, Boston, and DC public schools. He has led school reform efforts at the national level as Director of Implementation at the John F. Kennedy Center for the Performing Arts, Director of Turnaround Schools for EL Education and as Board Chair at the Center for Black Educator Development. Winston and his wife are co-CEO’s for Cox LEADS, LLC, a family-owned leadership development firm.
Winston has successfully led workshops for clients in a variety of industries. His areas of expertise include authentic leadership presence, company culture and climate, arts integration, and equity and belonging. His clients include the Executive Office for United States Attorneys at the US Department of Justice, Smithsonian Enterprises, Teach for America, Boston Public Schools, and Mary’s Center.
Winston attended the McDonough School of Business at Georgetown University where he attained an Executive master’s degree in leadership. His many years of leading schools have honed his skills with budgeting, negotiation, strategic planning, data informed decision making, staff development, media and public relations, and conflict resolution to name a few.
Sample Coaching and Facilitation Assignments
Trained multiple cohorts of Assistant US Attorneys in the science and strategies to mitigate the impacts of bias. He utilized the practice of psychodrama to help participants develop their capacity to train their peers.
Trained several cohorts of first- and second-year Boston Public school leaders in leading through challenging times and development of authentic leadership voice.
Coached school and district leaders at Teach for America in the use of storytelling to motivate and build relationships.