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 roadmap
- How Longwood became a place of healing, stability, and lifelong connection
- The shift from athlete and coach to impactful educational leader
- What it means to humanize leadership while maintaining accountability
- How mentorship, relationships, and community shape lasting success
- Why true leadership starts with investing in people, not power or position
Ebony’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 Cherry
Subscribe to Longwood GradCast: Beyond the Degree to hear more stories of alumni whose journeys prove the lasting power of people, connection, and opportunity.
Creators and Guests
Host
Dr. Sarah Tanner-Anderson
Dr. Sarah Tanner-Anderson serves as Associate Dean of the College of Graduate and Professional Studies, as well as Associate Professor and Program Director of Educational Leadership. A former principal, assistant principal, middle- and high-school English teacher, department and grade-level chair, high-school coach, and club sponsor, Dr. Tanner-Anderson has spent nearly two decades serving and supporting public education in the Commonwealth. A proud Longwood Lancer, Dr. Tanner-Anderson obtained her Bachelor of Arts in English ('02) and Master of Arts in English, Education, and Writing ('07) from Longwood University. She earned her Post Master's Administrative Certification ('11) and Doctor of Education in Educational Administration and Policy Studies ('14) from The George Washington University. Her research interests include women's educational leadership, social justice in education, and literacy leadership.
Guest
Ebony Cherry
Ebony Cherry is a two-time alumna whose Longwood journey has come full circle. As an undergraduate, she balanced athletics with leadership roles in the Mortar Board. That experience shaped her commitment to service and excellence, and that same passion led her back to earn her graduate degree. It also helped her transition into an educational leader focused on making an impact through personal growth and student success. For the past 20 years, she has dedicated her career to teaching art, special education, and English before stepping into administration. She has had the privilege of serving at both the middle and high school levels. Her approach to leadership is rooted in the same team-first mentality she developed as a student-athlete, focusing on building strong relationships, developing people, and creating environments where students and staff can thrive. Coaching has always been a huge part of who she is, and she believes in using that foundation to teach life lessons, resilience, and the power of teamwork. She is also a motivational speaker and professional development facilitator, having spoken at several conferences across Virginia. She brings energy, authenticity, and real-world experience to every session. Her goal is that participants leave not only inspired to be change agents, but also equipped with tangible strategies they can implement immediately in their classrooms. At the end of the day, her greatest roles are at home. She is married to a coach, and together they are raising a teenage daughter who keeps them grounded, motivated, and inspired to be better every single day.
Producer
Jamie Eacho
Jamie Eacho holds the title of Director of Marketing and Recruitment in the College of Graduate and Professional Studies (CGPS) at Longwood University. Starting out five years ago as the Marketing Specialist for CGPS, Jamie has grown her love for Longwood and her desire to help prospective students find the graduate program of their dreams. While her marketing journey started as the Marketing Manager for Campus Recreation at Roanoke College, and took her to Washington D.C. marketing for the Washington Nationals, and then out to the Eastern Shore of Maryland, marketing for a hospital, she has always held a special place in her heart for working with and for students. As an alumna of Roanoke College, having obtained her Bachelor’s of Business Administration with a concentration in Marketing in 2017, her passion for small Virginia schools and the value that they can add to students’ lives runs deep.
Producer
Madison Hommey
Health and Physical Education Teacher, Jefferson Forest High School (BS’21, MS’22) Health & Physical Education M.S: Maddie Hommey, an adept educator and enthusiastic athlete, currently serves as a Health and Physical Education teacher at Jefferson Forest High School in Bedford County, VA. Her journey as an educator and her active engagement in various roles reflect her commitment to education and community involvement. Maddie is a proud Longwood University alumna, holding a Master of Science in Health and Physical Education (May 2022) and a Bachelor of Science in Liberal Studies with a concentration in Elementary and Middle School Mathematics Education (May 2021). As a student-athlete she received many awards and recognitions, for academics, athletics, leadership, and service. Now, she proudly serves on the Longwood Graduate Alumni Collaborative. With a robust work background, Maddie has excelled in roles such as Marketing Assistant at Longwood College of Graduate and Professional Services (formally Marketing Graduate Assistant), Social Media Manager for FC Frederick, Remote Teacher at Elevate K12, Camp Counselor at Camp Augusta, Longwood Athletics Compliance Assistant and Marketing and Communications Student Worker, Substitute Teacher, NCAA Soccer Referee, and beyond. Maddie's leadership roles, including serving as the Big South National SAAC Representative and Student Athlete Advisory Committee President at Longwood University, showcase her commitment to student welfare and advocacy. She actively engages in service activities, volunteering for Autism on the Seas, formerly Special Olympics, Alternative Breaks, and other community events, embodying her dedication to making a positive impact beyond the classroom or field.
