In this special season finale of Insightful Questions, Head of School Sam Uzwack takes a seat on the other side of the desk as four seniors— Piper Belfiore, Anhat Bhutani, Andrew Ma, and Cass Megiddo—step into the studio. The script was flipped, with students asking Sam questions about leadership at EPS, decision-making, EPS traditions, and the impressive qualities of the Class of 2026.

In this episode of Insightful Questions, Head of School Sam Uzwack is joined by EPS faculty member Gaylynn Lynch, Jamie Andrus, Associate Director of Student Well-Being, and Dr. John Stegeman, Head of Upper School. They discuss ensuring that every EPS student feels seen and supported and how clarity in expectation, communication, and care helps create a more connected school environment.  They also discuss finding balance at school. As Dr. Stegeman notes, “If we can center the student, the human being, in the conversation about balance, it’s a way of reducing the complexity of the conversation…We want to have all parts of our experience and identity validated.  And when it is, the equilibrium appears.”

In this episode of Insightful Questions, Head of School Sam Uzwack is joined by EPS parents Bengu Bostanci, Polina Mokshina, and Hao Song to discuss how the partnership between parents/guardians and Eastside Prep helps build a more caring and connected school.

In this episode of Insightful Questions, Head of School Sam Uzwack is joined by two Eastside Prep alums: Josie Kranick and Lorenzo Da Fieno, both EPS Class of 2024. They discuss lessons learned at EPS including accountability and working with others. They also discuss advice they would give to their younger selves. Josie’s advice to her junior- and senior-year self includes, “Be where my feet are planted…be a bit more present.”  

In this episode of Insightful Questions, Head of School Sam Uzwack is joined by student Alyson (Class of 2027), faculty member Burton Barrager and Marinn Carpenter, a resource specialist for King Conservation District for a conversation about caring for the environment with intention. They discuss how EPS can help students grow into environment stewards and reflect on a place each of them feels connected to the environment. As Alyson notes, “Nature connects everything.”

In this episode of Insightful Questions, Head of School Sam Uzwack is joined by student Victoria (Class of 2028), School Counselor Amy Sanchez, and Trustee Dr. Habib Rahbar for a rich conversation about responsible use of technology tools, digital boundaries, and growing up in the age of artificial intelligence. Together, they reflect navigating the nuances of our digital age and on shared values. As Habib notes, “AI is going to make us all more efficient, but how are we all going to learn to be better human beings through that…I love how EPS has kind of always been focusing on those things.”

In this episode of Insightful Questions, Head of School Sam Uzwack speaks with students Javier and Roya as well as Director of Student Well-Being Paul Hagen and Student Life Coordinator Karla Harris about what leadership looks like at Eastside Prep. Together, they explore how care and clarity guide their experiences as student leaders—whether in classrooms, clubs, or community events. Through honest reflection and shared stories, they reveal how leadership at EPS is less about titles and more about collaboration, communication, and making space for others to thrive.

In this episode, Head of School Sam Uzwack is joined by Associate Head of Upper School Verity Sayles and Middle School Head Sarah Peeden to engage in a thoughtful dialogue about their perspectives, experiences, and efforts for clear communication within the Eastside Prep community.

For this episode of Insightful Questions, Head of School Sam Uzwack is joined by four EPS students (seniors Addie and Anvika and eighth-graders Axel and Solena) to discuss their perspectives on compassionate leadership. As Addie notes, “What stands out to me about leading compassionately is really listening compassionately.”

For this episode of Insightful Questions, Director of Strategy, Technology, and Innovation Jonathan Briggs and co-founder of Colleague.AI Dr. Min Sun join Head of School Sam Uzwack to discuss both the future and 'the now' of technology and artificial intelligence.