John Stegeman: Eastside Prep’s New Upper School Head

By Wendy Lawrence, Contributing Writer

JOHN STEGEMAN KNEW HE BELONGED AT EPS the second the students started grilling him with questions. “The students who interviewed me asked serious questions that were tough but fair, and came from a genuine and authentic student perspective,” Stegeman says. “I’ve always been drawn to places where intellectual curiosity flourishes, and that’s what I saw when I visited EPS.” He was also struck by how much everyone liked each other.

Stegeman is a natural fit for a school leader—he doesn’t just love the students, he loves and admires the adults, too. “Teachers combine the best aspects of humanity, in my opinion—achievers who believe in putting the needs of others before their own,” he says. “Every day in the classroom brings fresh challenges and teachers have to be constantly re-creating their courses. That’s exciting to me, and really fun to be a part of.”

Stegeman joins EPS as the Upper School Head in the summer of 2019, and brings years of experience in a wide variety of educational settings. Early on in his career, he tried both high school and college teaching. “When I found independent schools,” he says, “I found the Goldilocks conditions I was looking for: really smart students who were eager to learn and work hard, and a professional environment where teachers worked together to push the envelope of creative interdisciplinary thinking.”

“Teachers combine the best aspects of humanity, in my opinion—achievers who believe in putting the needs of others before their own.”

With numerous degrees and interests, Stegeman also has a diverse range of his own educational experiences. After studying anthropology and economics at University of Colorado Boulder, he earned a teacher certification at Colorado State, an MA in World History at The State University of New York at Brockport, and finally a PhD, MPhil, and CAS in Latin American History at Syracuse University. He won’t tell you how many nights and weekends he worked to finish his PhD thesis, but will admit that he’s “simultaneously proud of my stick-to-it-iveness and a little embarrassed by my own longevity.”

Stegeman is never afraid of a challenge, whether that’s adding another degree or taking a school to new heights. While leading the Upper School at Manlius Pebble Hill, he helped propel them through a difficult time and the school emerged with an academic program that is stronger than ever and a community tightly committed to a shared purpose.

He’s also ready to challenge others. “I found it too easy to get by in high school and no one ever called me on it. I wish I had teachers who knew me well enough not to accept my second best, and I also wish they had been able to think from a student’s perspective.” He brings both of these goals to his work today. “I recognize the importance of building trust with students so they are willing to push themselves to their limits, and sometimes stumble along the way. I know firsthand the importance of adapting content and learning goals to the student audience.”

“I’ve always been drawn to places where intellectual curiosity flourishes, and that’s what I saw when I visited EPS.”

In the environment that he helps create, Stegeman loves to watch upper-school students grow up. “In the span of four years, high school students transform from goofy and somewhat awkward teens into fully self-sufficient adults. The most transformational classroom experience I had as a student was an undergraduate night class where the adjunct professor treated us like grad students. I’ve had a lot of success structuring upper-school classes like graduate seminars. Upper-school students are astounding in their ability to grasp complex ideas and apply them to their own experience in genuine and meaningful ways.”

John Stegeman, his wife Laura, son Will, and daughter Ruby

As excited as Stegeman is to join the Eastside Prep team, EPS is equally eager to have him aboard. Bart Gummere (current Upper School Head and soon-to-be Associate Head of School for College Counseling and Alumni Relations) says, “John is going to be a great addition to Eastside Prep. In speaking to him during the interview process and since then, I’ve been impressed by his thoughtful comments. I feel very excited to be passing the reins over to such a qualified and good person.”

Stegeman lives with his wife Laura, two children, Ruby and Will, a cat and a dog, and is excited to move closer to western family members for some joint camping and hiking trips. He participates in endurance sports, including cycling, swimming, and running. His mom and four aunts grew up in New Orleans and passed along a love of jazz and funk and a good crawfish boil. He also loves the Latin American culture he studied for his PhD. “The coming together of European and native societies in America raises all sorts of interesting questions about cultural, racial, and national identities. They are good questions to think with.”

Stegeman will arrive on the Eastside Prep campus in July, ready to ask and receive even more challenging and engaging questions.

The Search

By Dr. Terry Macaluso, Head of School

The search that led to the hiring of Dr. Stegeman was a lengthy and involved one, as, I think, is appropriate for such an impactful position. A search committee was formed and was composed of students, faculty, and parents.  This hardworking group reviewed dozens of resumes from highly qualified candidates, hosted eight semi-finalist candidates for on-campus interviews, and then invited four finalists to visit Eastside Prep for a full day.  Each candidate observed classes, interviewed with faculty and staff, lunched with students, and met with parents in informal afternoon receptions.

A senior leadership position demands this kind of inclusive process. It’s important for both the school and the candidates, because it’s indicative of a school’s values. As has been observed often, the most important decisions we make at Eastside Prep are offering contracts for employment and inviting families to enroll.  Many thanks to the members of the committee who invested substantial time and thought in his effort.


Bill Conquergood, parent of Grady (’18) and Ethan (’20)
Sharon Kasel, parent of Kaitlyn (’23) and Mera (’26)
John Tardif, parent of Egan (’22) and Gavin (’26)


Millan, Class of 2019
Rhea, Class of 2019
Subi, Class of 2021
Sydney, Class of 2020


Shelly Allen, Upper School Administrative Assistant and Registrar
Jonathan Briggs, Chief Innovation and Technology Officer
Ginger Ellingson, Music Faculty
Steve Fassino, Math Faculty
Adam Kruger, Science Faculty
Terry Macaluso, Head of School
Karen Mills, English Faculty
Verity Sayles, English Faculty
Sam Uzwack, Middle School Head

About the Author

Wendy Lawrence was one of the four founding faculty at Eastside Prep. She started as a science teacher and three years later became the Head of the Middle School. Wendy has moved to Ann Arbor, Michigan but remains connected to Eastside Prep through her work on this magazine.