Bessie Speers: New Head of School

What is Bessie’s past and what does she want for the future of Middlesex?

The Anvil editorial staff sat down with new Head of School Bessie Speers to discuss her goals for the future of Middlesex and her background as an educator and administrator over the years. 

Starting from the beginning, Mrs. Speers described always “knowing that [she] wanted to be a head of school” and how she worked several posts in admissions offices and other administrative posts before being selected for her first headship at The Ethel Walker School in Connecticut. She then moved on to the Tower Hill School, continuing in her role as Head of School before coming to Middlesex.

Having worked over several decades in the boarding school world, Mrs. Speers comes to Middlesex with a towering reputation. In an interview a year ago with a previous long-time Taft Head of School, Lance Odden, he described Mrs. Speers as “fantastic” and a “great win” for the school. Additionally, it has long been rumored that Mrs. Speers was the hand-picked successor of Head of School Kathy Giles. 

When asked about the beginning of her tenure, Mrs. Speers said, “every school is different,” but stressed how welcoming the Middlesex community was to her and her family, and how impressed she has been by the Middlesex students and faculty whom she describes as “gritty and hungry” for success. 

Mrs. Speers has been remarkably enthusiastic about meeting and supporting Middlesex students and alumni, often hosting students in her office for coffee as well as being a mainstay on the sidelines. No one can doubt her dedication to immersing herself in the Middlesex community.

Looking towards the future, Mrs. Speers frequently mentioned her excitement about the upcoming “strategic vision process” that will evaluate Middlesex from a variety of viewpoints and position Middlesex to succeed in a changing educational environment. Mrs. Speers describes the process as a chance to answer the question “Why does Middlesex matter.” Meanwhile, she hopes “to listen, to learn, to observe, to be a part of things” while working on the next strategic plan for the school. 

Certainly, the next few years will likely challenge and grow Middlesex in many ways. There are plans in varying stages of development for a new athletic field house and Dining Hall, as well as needed renovations to the current Athletic Center and Elliot Hall. The proliferation of generative AI programs will also apply new stress to the task of keeping students’ work honest. Additionally, Middlesex continues to think about how to best meet the needs of students struggling with stress from academics and the social challenges that living away from home often incurs, as well as pushing students to “buy-in” to school culture in the same way they did prior to COVID. These situations all present Mrs. Speers with an opportunity to leverage her experience in planning and leadership as well as her ever-growing understanding and knowledge of the Middlesex community to guide the school.

Luke Power and Nick Costantino