Leading with Heart: Relationships, Resilience & Rising into Leadership

In this powerful episode of Longwood GradCast: Beyond the Degree, host Dr. Sarah Tanner Anderson sits down with Ebony Cherry (B.S.’04, M.S.’22), a double Longwood alumna, former student-athlete, and innovative school leader, to explore a journey defined by resilience, relationships, and purpose-driven leadership.Ebony shares her full-circle path from navigating childhood trauma and arriving at Longwood as a first-generation student-athlete to becoming a people-first assistant principal committed to creating safe, supportive environments for both students and educators. Choosing Longwood not once, but twice, Ebony reflects on how her undergraduate and graduate experiences shaped her evolution from survival mode to a confident, boundary-pushing leader in educational leadership.While completing her master’s in Educational Leadership, Ebony leaned into the same principles that guide her work today: authentic connection, accountability with empathy, and the belief that leadership is earned through trust. Drawing on her background in athletics and coaching, she brings a “player development” mindset into administration by using data, communication, and relationship-building to help both students and teachers grow.Throughout the episode, Ebony reflects on the Power of People that shaped her path: professors who showed up, literally and figuratively, during her hardest seasons, mentors who pushed her to see her own leadership potential, and a Longwood community that became a place of stability, belonging, and transformation.Now a noteworthy assistant principal, Ebony is redefining what leadership looks like in education by balancing high expectations with humanity, and ensuring every person in her building feels seen, valued, and supported.In this episode, listeners will explore:The realities of entering college as a first-generation student without a roadmapHow Longwood became a place of healing, stability, and lifelong connectionThe shift from athlete and coach to impactful educational leaderWhat it means to humanize leadership while maintaining accountabilityHow mentorship, relationships, and community shape lasting successWhy true leadership starts with investing in people, not power or positionEbony’s story embodies the heart of Season 3 by demonstrating how resilience, mentorship, and meaningful relationships can transform not only individual lives, but entire communities.“I'm gonna hold you accountable, yes, but I'm also gonna love you through the process.” — Ebony CherrySubscribe to Longwood GradCast: Beyond the Degree to hear more stories of alumni whose journeys prove the lasting power of people, connection, and opportunity.