Overview:
Rob Hershey's remarkable 46-year career in independent school education was defined by compassionate, student-centered leadership, an unwavering commitment to teaching, and a lasting legacy of mentoring educators and strengthening schools through integrity, humility, and service.
After leaving Atlanta, GA, and Marist School in 1985, I applied for a teaching position at Durham Academy in Durham, NC, and was hired by Head of School Rob Hershey. The School needed a 5th grade teacher. I’d never taught that grade level before, and, to make matters even more nerve-racking, Rob’s son Will would be in that class.
To my relief, young Will was an excellent young man, well-liked by his peers and all the teachers, well behaved and a solid B student. I learned soon enough that Rob would prefer that his son be an A student. I don’t recall whether parent teacher conferences were in the fall of spring of that school year, but I do recall sweating bullets and losing sleep for nights before my conference with Rob and his wife Kathy. I had met Kathy early in the school year at an opening-of-the-year faculty and staff party at the Hersheys’ home. She was kind and welcoming to me and other new faculty members, but I didn’t know where she landed on her son earning only B’s in my class.
On the day of our fall parent teacher conference, I braced for the question that I knew would come from Rob. What did Will need to do to become an A student? I thought about the happy, laid back, friendly, well behaved young man in my class and didn’t want him to change at all. I said to Rob, “Please don’t try to make him an A student. He’s one of the happiest and most enjoyable students I’ve ever taught, and I don’t want that to change.”
As Rob pondered my response, Kathy, who was sitting just slightly behind Rob, gave me a big smile and two thumbs up. I remember my internal sigh of relief that at least one parent was onboard. I also recall my nervous chuckle. I didn’t yet know Rob well enough, so I wasn’t sure where the conference would go from there. His smile and acceptance of my suggestion as well as Kathy’s endorsement was the first of many examples I could offer of Rob’s willingness to listen to others’ opinions.
Small world story. In my second year (1999) at Blue Ridge School in central Virginia, I learned that Blue Ridge graduate and recently appointed Alumni Relations Director Peter Holland was a childhood friend of Rob’s. Not only that but Peter’s wife Anne and Rob’s sister were also childhood friends. They’d all been raised in Virginia Beach. Lucky for me that Rob and his wife Kathy as well as Peter and Anne were once again living in their home town just a few miles apart. I therefore thought it would be a great idea to get us all together. They agreed!
What a treat it was to share an evening with them at Sorella’s on Wednesday, September 10, 2025. Having explained to them that Chick Donohue’s Greatest Beer Run Ever was one of my inspirations for my tour, the deal was that I would purchase their beverages for them as a gesture of my gratitude. They agreed to these terms but still pulled a fast one on me by paying for my dinner. I’ll mention this joyous gathering again when I pay tribute to Peter next week in The Educator’s Room.
As I retold the story of my teaching Will and the nail-biting (for me) parent conference, Rob grinned. Kathy said, “Will’s been a B student his whole life and just one of the happiest people you’ll ever meet.” They were quick to add that Will is now fifty years old, married with three children, and the CFO for Davenport and Company Investment firm in Richmond, VA. I couldn’t help but tear up a little bit as I heard of Will’s current happiness and success.
Rob Hershey graduated from Collegiate School in 1966. During his senior year at Williams College in Williamstown, Massachusetts, he still wasn’t certain about his career path. As he interviewed for several of the traditional corporate slots and considered applying to Harvard business school, he also recalled his many summers as a camper, then as a counselor.
Several independent schools visited Williams that year to interview prospective teaching candidates. That caught Rob’s attention. He’d truly enjoyed those summers as a counselor – the energy and curiosity those young people brought to summer camp. After his first interview, he knew what he wanted to do with his life. He thought, “What a dream it would be to make a living doing something I loved to do!”
After earning his BA in economics from Williams in 1970, he was hired to teach history and economics as well as coach basketball at Woodberry Forest School in Orange, VA. He’ll be forever grateful to Baker Duncan, an old-line Headmaster who took pride in personally selecting his faculty. “Beyond credentials, Baker looked for other qualities when hiring. If he felt you had great character and were willing to give your all to the students, he’d take a chance on you.” Rob clearly met his criteria.
In his first year at Woodberry, Rob and his wife Kathy lived in an apartment above the gymnasium. On game days, they’d enjoy (maybe tolerate) the sound of the buzzers from noon until early evening. Rob caught everyone’s attention, and in a good way. He clearly had leadership traits. Still in his early twenties, he was named assistant Head of School at Woodberry. As busy as his teaching, coaching and eventual administrating kept him, he managed to earn his M. Ed. from the University of Virginia in 1975. He earned everyone’s respect at Woodberry as he showed clear signs of being ready to take the next step.
In 1978, again at the very young age of 29, he was named Head of School at Durham Academy. Perhaps because he was so young, he became known for hiring a slew of young teachers during his tenure that lasted until 1988. Several of those young teachers, including former colleagues and dear friends Steve and Teresa Engebretsen and Chuck Roser (all three to whom I also pay tribute), remained at Durham Academy for many years. They each put Rob at the top of their lists of the mentors they’d visit if they were on their own gratitude tours.
During our conversation at Sorella’s, I learned not only that Rob was Peter Holland’s childhood friend but that he also knew Hatcher Williams, another Blue Ridge School legend. As Head of BRS beginning in 1963, Hatcher is credited for developing the school’s core philosophy and being a giant among its leaders. As Hatcher neared retirement in 1984, he called Rob at Durham Academy to ask if he’d consider applying for the Head of School position at Blue Ridge. Rob respectfully declined as he wasn’t at that point ready to leave the Durham Academy community.
During his ten years at Durham Academy, Rob was so admired by colleagues, parents, students and board members that the F. Robertson Hershey Distinguished Faculty Award was established in 1988 to provide an annual cash prize to that year’s recipient. That same year, Rob returned to Collegiate to be Head of School until 1998. He was then named Head of School at Episcopal High School in Alexandria, VA, where he remained until his retirement in 2016.
Rob had given forty-six years to education. Even after becoming an administrator early in his career, he is proud to have taught a class in each of those forty-six years. I’ve known other heads of school to teach a class here and there, but it’s rare, and it speaks a great deal to Rob’s love for working with young people and to his values. “It was always clear to me that faculty are the lifeblood of any school. They are truly the creative and enduring strength of education. One of the responsibilities I most enjoyed as headmaster was recruiting and hiring. I worked very hard to bring outstanding faculty to the institutions I served.”
Early in his retirement as Rob began consulting, additional recognitions soon followed. He is proud that Collegiate dedicated the Arts Center in his honor and that Episcopal High School dedicated the athletic complex in his name at about the same juncture. It drove home to him that a true independent school education immerses students and faculty in all realms of human endeavor. In 2019, he was presented with the Sally K. Boese Distinguished Service Award at the VAIS annual conference. He also earned the Ruzicka Compass Premier Leadership Award, presented by TABS, in 2020. This award is given annually to “an extraordinary individual who has dedicated his/her life to the advancement of boarding schools.” Of the many honors bestowed upon Rob for his dedication to education, this is his most cherished recognition.
Rob is grateful to the many school leaders who mentored him in various ways. At Durham Academy, the Board Chair Dr. Fred Brooks, who was chairman of the computer science department at UNC at the time, had a sensitivity for people as well as extremely strong foundational values and a very clear philosophy of education. “It is not an understatement to say I learned at the knee of a giant!” Mrs. Margaret K. Woods, Head of Lower School at Durham Academy, also had a lasting impact on him. Her care of the children and her devotion to her faculty modeled the very best of educational leadership and established a loving culture. When he went to Collegiate, he was mentored by Board Chair Mr. Wallace Stettinius, who was a successful corporate leader but, in his heart, was truly an educator. There were many occasions in which Rob sought Mr. Stettinius’ counsel. He always enlightened Rob’s perspective and helped him see the way forward.
Though Rob was educated in independent schools and taught and led in independent schools, he cares about education in public schools as well. He’s overwhelmed by the challenges currently facing public education and dismayed over the lack of our nation’s priority and leadership devoted to public education. If public education fails, independent schools suffer as well. He sees the hurdles facing independent schools through an administrator’s eyes. “With so many competing alternatives for young people today, the challenge to attract and keep great teachers grows. Both public and independent schools must continue to explore how to capture the interests and enthusiasm of their students. This is made more difficult when fewer young people are interested in the profession.”
When Rob looks back on the many responsibilities that came with his position as Head of School, he realizes he didn’t have the luxury to dwell on what he liked and didn’t like about his job. In every situation, he cared enough to celebrate successes and to find solutions to difficulties. He knew that was his job on a daily basis.
Rob is also fully aware that he was blessed in his career. In trusting his instincts, he surrounded himself with dedicated educators and made it a priority to continue to teach even after he moved into administration. He was also wise enough to seek the advice of others and then make critical decisions on behalf of students and his colleagues. Given the chance, he’d start it all over again tomorrow.
My time spent with Rob at the same school was only from 1985 to 1988. However, when I moved to Virginia in 1993, I began hearing his name over and over again. I learned that Rob’s start in life, his start in education, and his remarkable impact on multiple high schools outside North Carolina all happened in Virginia. I followed his career from a distance as I settled in at Blue Ridge School. I admired him. I never heard a cross word about him. On the contrary, anyone who ever worked with him spoke of his firm belief in education, his ability to support what was already effective and change what was ineffective, and his kindness. I witnessed that kindness once again during my visit to Virginia Beach. It was a delightful evening filled with gratitude all around.
