Dr. Josephine Diemond, Head of Upper School

Head of Upper SchoolDr. Josephine Diemond

EdD, Educational and Organizational Leadership, University of Pennsylvania

MA, French Literature, New York University

BA, Biology, Princeton University

My Story

Josephine Diemond holds a special place among the divisional heads guiding McLean School’s future: she is the veteran member of the team. Josephine has been the Head of Upper School for 13 years.

Raising teenagers, parents know, is an art, a delicate balancing act between the fostering of autonomy and supplying of boundaries. As Head of Upper School, Josephine can be seen as “raising”—academically, socially, and emotionally— more than one hundred of them.

How does she do it? What has educational leadership at McLean meant to her? What is special about her experience at McLean School?

On a quiet summer afternoon—strangely devoid of the hustle and bustle that characterizes the Upper School hallways during the school year—Diemond sits back and thoughtfully considers these questions, before offering her replies. Choosing her words carefully, she displays a characteristic that defines this leader known for her equanimity and calm.

Day in and day out, Diemond explains, her work is driven by one overarching question: Is my decision “mission appropriate?”

Clearly, her every move is filtered through the school’s mission statement: “McLean School’s mission is to make education accessible, stimulating, and meaningful to a broad range of learners.”

Serving a broad range of learners is the essence of the McLean School. Describing the diversity of the McLean student body, Diemond says that some parents are drawn to the school because they want their children, primarily, to benefit from a small, supportive community with rich extra-curricular programs. Other parents are drawn to the school’s teaching practices, where teachers employ differentiated learning methods in order to serve students with learning differences such as ADHD, dyslexia, anxiety, or executive function issues.

McLean students succeed because, in Diemond’s words, “teachers just don’t stop. They don’t give up on students. It’s not a cliché to say that we are a warm, caring, and nurturing community and through these qualities, students thrive.”

When Diemond gets talking about her corps of Upper School teachers, her rhetoric soars. When she observes classrooms, this is what she sees: “Teachers trying to be as creative as possible to reach all the students. Teachers who live and breathe a nurturing approach to education each and every day. Teachers who genuinely care about the kids and will literally do anything to help them.”

A self-described opponent of pessimism toward teenagers’ ability to achieve, Diemond recoils when she hears a student say, “I can’t.”

“Yes, they can,” she insists.

“I don’t take these words lightly,” she explains. “It’s where we set the expectations. If you set the bar low, that’s where they’re going to reach. If you set the bar high, even students with learning differences will be successful. I have seen our students go on to be valedictorians, be admitted to elite colleges, and go on to graduate school. Because I have seen it, I believe it.”

Making sure her point has been understood, she emphasizes, “You must have the perseverance and creativity to try different methods. If “x” doesn’t work, you try “y” and “z,” because eventually something will work.”

Perhaps what defines Josephine Diemond more than anything else is her identity as a believer in McLean students. “Yes, they can” and “we never give up” are the central motifs in her commentary and the foundation of her school philosophy.

Diemond’s personal history reflects this same spirit of perseverance. Having received a bachelors of arts degree from Princeton University in biology, she decided as a graduate student to follow her passion and pursue a masters degree in French literature at New York University. Her parents did not immediately warm to her decision to give up a medical career for one in education, but she stood by her calling. She silenced some of the opposing voices around her with the question, “Who do you want teaching in your children’s classrooms, the best and the brightest or the bottom third?” Her commitment to education led to her receiving a doctorate in educational and organization leadership from the University of Pennsylvania.  

Diemond began her career as a French teacher at Millbrook School, a boarding school in upstate New York. Once relocated to Washington, DC, she made a gradual shift into other administrative roles, serving as Assistant Academic Dean at The Madeira School and head of grades eleven and twelve at The Field School.

With many years now under her belt as Head of Upper School at McLean, Diemond plans to continue to realize her vision for McLean: “To be,” she says, “the best little school around.”

She has already made clear the means through which she plans to proceed: “We believe in our students. We don’t give up!”