EPS Insightful Questions

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 a...

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...

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 c...

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...

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 hon...

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.

For this episode of Insightful Questions , Science faculty member Krissy Russell and students Batu and Audrey (both Class of 2029) join Head of School Sam Uzwack to discuss the importance of empathetic dialogue in the science classroom. As Krissy Russell notes, “Science is a process, it’s not about right and wrong.”

For this episode of Insightful Questions , EPS senior Jacob Chaney and Literary Thinking teacher and Faculty Development Coordinator Karen Mills join Head of School Sam Uzwack. They discuss leading with empathy and fostering meaningful dialogue in English classes and beyond. As Jacob notes, empathetic leadership includes “not forcing people out of their comfort zones but inviting them.”

For this episode of Insightful Questions , Director of Athletics Kim Eng and student Abby Miller join Head of School Sam Uzwack to discuss the importance of empathy in athletics. As Abby notes, “The best teams succeed when they balance drive with support.”

For this episode of Insightful Questions , two members of the EPS Spanish faculty (Josefa Ruiz Mercader and Malcolm Yates) join Head of School Sam Uzwack to discuss the role of empathy in the Spanish classroom. They discuss their different approach to teaching Spanish given their disparate backgrounds. Regarding empathy among our students, Josefa notes, “They always impress me, the way they care a...

For this episode of Insightful Questions , two members of the EPS math faculty (Sarah Aguiar and Steve Fassino) join Head of School Sam Uzwack to discuss the role of empathy in math classes. They discuss empathetic dialogue in the math discipline and how it has impacted both students and faculty. As Sam noted after recording this episode, “The most exciting thing about recording these podcasts is...

For this episode of Insightful Questions , two members of the EPS fine and performing arts faculty (F&PA Director Ginger Ellingson and drama teacher Lisa Frystak) join Head of School Sam Uzwack to discuss the role of empathy in the arts. They discuss how materials are chosen and the importance of encouraging and modeling risk-taking. Ginger Ellingson notes, “We’re working with the students thr...

For this episode of Insightful Questions , EPS social science faculty members Diana Gonzalez-Castillo and Dan Yezbick reflect on building trust within the classroom setting in order to build on the habits of mind and skills for civil discourse to flourish. As Diana Gonzalez-Castillo notes, “One of the most exciting things about teaching is getting to foster a community within a classroom.”

For the first episode of Insightful Questions Season 2, EPS faculty member Caitlin McLane and Director of Enrollment Management Cheryl Schenk share their experiences from summer professional development opportunities centered on empathetic dialogue, exploring how they are integrating these insights into the campus community and classroom environments. As Head of School Sam Uzwack notes, “You don’t...

For this episode of Insightful Questions , Eastside Prep’s Founding Head of School, Dr. Terry Macaluso, joins Sam Uzwack to discuss leadership and some impactful moments in the founding of Eastside Prep.

For this episode of Insightful Questions, author Michelle Icard joins Head of School Sam Uzwack to discuss her book 8 Setbacks That Can Make a Child a Success and her upcoming visit to Eastside Prep.

  For this episode of Insightful Questions , EPS faculty members Karen Mills and Anne Duffy join Head of School Sam Uzwack to discuss various aspects of teaching and mentorship.

For this episode of Insightful Questions , Nicole Curry (Sam’s wife) joins Head of School Sam Uzwack to discuss their own partnership over the decades as well as Eastside Prep’s partnerships—current and future.

For this episode of Insightful Questions , Max Sheffield (EPS alum from the Class of 2014) joins Head of School Sam Uzwack to reminisce about their shared EPS experiences, the ongoing connections alumni have to our school, and talk about the future.

For this episode of Insightful Questions , EPS fifth and sixth graders were invited to ask their burning questions of Head of School Sam Uzwack. From hot dogs (are they a sandwich?) to the future of Eastside Prep, the questions covered a wide range of topics from serious to silly.   

For our third episode of Insightful Questions and in honor of the Thanksgiving holiday, Sam’s children - MacKenzie Curry Uzwack and Oliver Curry Uzwack – join Sam to discuss their family Thanksgiving traditions and engage in the dressing versus stuffing debate.