By Treasure Brown

In 2022, Collegiate welcomed interim Head of School Billy Peebles. As he is nearing the end of his second and last year here, I got the opportunity to sit down with him and ask him about his time here, his experience, and what comes next.  

Photo courtesy of Collegiate School.

Peebles and his family came to Richmond from Atlanta, Georgia in 2018, where he had been head of the Lovett School for 15 years. Before this move, Peebles had known of Collegiate for a long time. Some of his cousins had attended Collegiate, alongside his sister’s four children, all of whom had enriching experiences here. As a result, Peebles developed a great sense of respect and admiration for the school. 

In 2019, he helped develop Collegiate’s strategic plan and joined the Board of Trustees the following year, while also doing interim work at a small school in Winchester, Virginia. In 2022, when Collegiate’s former Head of School, Penny Evins, resigned, Peebles was asked to come in on an interim basis and was “honored to be asked” and has “felt it a great privilege to be here the past two years.”

Peebles has spent 41 years working in education and the last 36 acting as a head of school. All 36 years that he has worked as a head of school, he has also taught students in class. Although last year he did not get to teach a class of his own, Middle School history teacher Asher Rolfe and Upper School history teacher Brian Justice (‘85) allowed him to teach lessons a few times in their classes during what he called “visit teaching.” This year, however, he taught two sections (one each semester) of World Religion, a semester-long class required for all Upper School students.  

In the class, students learn about the five major religions in the world: Judaism, Christianity, Islam, Hinduism and Buddhism. They talk about the origins, customs and traditions, and people who had a significant impact or influence on them. Peebles said that his favorite part about teaching is getting to interact with his students, saying that he loves “the discussion” and has “a lot of passion for the material, the ideas, and the people.” Peebles added that he enjoys “the students in that class and their engagement, ideas, and questions,” adding that in every class, he looks forward to their discussions about the content and appreciates the students’ contributions. Ruby Goff (’24) reflected on her time in Peebles’ class, saying “Mr. Peebles is clearly passionate about every book, current news, or religious text he brings to us.” She further commented on Peebles’ character, adding that “he also has an unexpected sense of humor and is not afraid to call any of his students out in a playful manner.”

Between teaching and the responsibilities and requirements that come with being Head of School, Peebles’ daily schedule is quite full. Filled with Zoom and in-person meetings, events, classes, and more. Peebles says that in the midst of the business, he has stayed organized thanks to his team. This includes Amy Verdi, his executive assistant, who manages his schedule. He is extremely grateful for his team helping him “learn and understand Collegiate” and what day-to-day operations look like. Peebles added that although the days are busy, they are enjoyable and never feel as long as one might think.

Peebles’ love of education stemmed from his experience at Episcopal High School, a private boarding school in Alexandria, Virginia. Peebles graduated from the school in 1973 and credits his high school experience with inspiring him to teach and work in schools. He said that as he left school and got ready to attend Princeton University, he knew exactly what he wanted to do thanks to his teachers, even going so far as to write a thank you letter to all of the teachers and administrators. For the past four decades, that particular experience has continued to motivate him to do the work that he does. He added that he feels “very fortunate to have figured it out early and [has] really enjoyed this work.”

When asked about his favorite part of being Head of  School, Peebles immediately responded with “the people.” He takes great pleasure in being able to talk to and interact with students, parents, teachers and faculty, and alumni. In talking and working with others, he says that they are able to exchange ideas and build community with one another, which is something that he finds important.

When it comes to his greatest accomplishments as Head of School, Peebles was quick to state that he “it would not be appropriate to take sole credit” for his work at Collegiate, noting that none of it would have been possible without his administrative team and everyone whom he worked with. However, Peebles finds that one of his greatest strengths that has aided him in his work is his ability to be an active listener. He finds that being able to listen to others “helps get ideas on the table” and “establish a consensus on how to move forward when it comes to different issues.” Peebles added that listening allows him to work to bridge connections and avoid division. He appreciates conversations that he is able to have not only with his team, but with students, parents, faculty, staff, and alumni. Whether it be a casual conversation or a philosophical discussion, he is always open and receptive to what others have to share. While he admits that “some days I am better at it than others,” Peebles values listening and finds that it is extremely important and beneficial. 

During his time at Collegiate, Peebles has attended a wide variety of student-centered and led events that he thoroughly enjoyed. In April, he spent time attending both the Upper and Lower School Art Walks, which displayed various art installations around the school. Peebles said that seeing the artwork inspired him, and he was “in awe of the quality of the work” and extremely impressed with what the students had created. He also said he loved getting to see different athletic competitions, noting that volleyball is his favorite and what he regards as “the quintessential team sport.” One of the events he found most impressive was the robotics competitions. He appreciates team Torch 5804’s engineering knowledge and their ability to problem solve and collaborate with one another, comparing the competitions to watching “a basketball tournament.”

Following his departure from Collegiate at the end of this year, Peebles plans to work less but not fully retire. His plans include consulting with schools to share his own experiences and assist them achieve some of their long and short term goals. Aside from consulting, he also hopes to be able to do some more writing and travel more frequently with his wife, as they are celebrating their 40th anniversary this year. 

As he prepares to part ways with Collegiate at the end of this academic year, Peebles shared some advice to the entire Collegiate community. Having seen the divisions and discourse caused by the 2016 and 2020 elections, Peebles knows the negative effects that these events have had on schools and their communities: “The world can be somewhat complicated, polarized, and divided, and in a big community with different perspectives, we are not immune to that.” As we approach the 2024 elections, he encourages the community to “engage with one another,” come together, and work towards mutual understanding. Although he understands that everyone has their own perspectives, he hopes that we will be able to both “speak up for what we believe in, while also listening to others with respect.” In doing so, we will stay true to Collegiate’s core values of honor, love of learning, excellence, respect, and community. 

Last year, a three-generation Collegiate family established the Penny and Billy Peebles Endowment for Faculty and Staff, an endowment that will “provide support for recruitment initiatives, competitive salary assistance and professional development opportunities,” as well as other mentoring and leadership opportunities. The endowment was developed in honor and recognition of Peebles’ leadership and work as Interim Head of School.