Newly appointed Head of Upper School, Jonathan Oglesbee walked into the Bistro with a friendly presence and immediately gave a warm smile as he took his seat. Even before beginning the interview,  he took a great interest in me, asking how I am and what grade I am in. We began by discussing where he worked before applying for the Middle School head position at Sandy Spring.  Before coming here he was at the Key School in Annapolis. He was there for six years teaching humanities to middle schoolers. He was also involved in working with students as they transitioned from 8th to 9th grade. Then he decided to work at Sandy Spring where he has been for three years.

Oglesbee was persuaded by many colleagues to look into Karen’s position when it was announced that she was leaving. He started to become intrigued with the idea while being clear that it is no negative reflection on the Middle School.   He understood his cohesive sense and vision and that he can relate to students, parents, and faculty. He mentioned how he cares about the school being successful. Before going into education, Jonathan worked with as many as sixty to seventy high school students as a Presbyterian Church minister. He also worked in many conferences with high school students. He feels that high schoolers are already empowered and, therefore, his role is more about providing them the resources. High schoolers are at a point in their lives where they can reflect with a level of maturity. He stated that high school students are able to achieve significant accomplishments through such activities as Torch and our variety of clubs.

Oglesbee said he is excited to build on an environment where the classroom is “ours” and the learning is mutual between the students and teachers.  Once he takes his new position as Head of the Upper School,  he looks forward to seeing what new ideas are generated from within the community and what students want to see started. He sees these initiatives coming from the students and faculty, while his job will be to see what the obstacles are and what we need to do to implement the initiatives.  Oglesbee also has programmatic changes that he wants to start, but isn’t ready at this point to discuss without deeper explanation. He wants the community to be able to share their ideas, as well.

When asked why he likes working at Sandy Spring, he responded that he continues to be drawn to “the community” and “the honest exchange of ideas.”  He believes that while Sandy Spring is leaning political and socially to the left, it is open to hearing voices of people that we disagree with and is able to disagree without being disagreeable. He believes that Sandy Spring is continuing to become not static but rather more authentic and dynamic. While Sandy Spring holds certain traditions it is not bound by them.

At the end of the interview, I asked him if there was anything he wanted to add.  Oglesbee responded that he hopes that once he takes his position as Head of Upper School, he will be able to say yes to ideas and, if he can’t say yes right away, to work with an idea to figure out how we say yes, giving it a “noble effort.” He hopes and expects his ideas to be challenged but he comes to the position looking to “seek the answers together.” He also added that with the unique circumstances right now and the political stance of our country, everybody is on edge for different reasons and that we have to be mindful of that so we don’t tear each other apart.  

Finally, he mentioned his deepest respect for Karen as an authentic person, funny, smart, and compassionate. He senses that students love her, and that he has big shoes to fill. He’s looking forward to bringing his ideas to the table.