The Winnetka Public Schools Superintendent (and New Trier alum), Dr. Kelly Tess, and New Trier High School Superintendent, Dr. Peter Tragos, reflect upon the joys and complexities of leading for the next generation in public schools.  Dr. Tragos reflects, “We are producing and preparing good people for the world.” “We are all temporary stewards of a long rich history and our job is to make it better,” emphasizes Dr. Tess.

Season 4 of the “Winnetka Voices,” kicks off with a conversation on how new teachers are equipped to succeed in a robust two-year Mentorship program in The Winnetka Public Schools. Superintendent Dr. Kelly Tess and special guests Jeff Knapp, Assistant Superintendent of Professional Learning and Human Resources and Ruthie Helmer, 5th grade math and science teacher and Mentorship Coordinator, reflect on the District’s commitment to supporting new teachers so they are best equipped to tend to their students’ academic, social and emotional needs. “We want them to feel like this is home and in turn make it “home” for our kids,” says Mr. Knapp. Ms. Helmer reflects, “We really are making an impact on future generations…Being a teacher is a true calling and Winnetka is a special place. Everyone here has that same calling.”

A Filter-Free Conversation on Parenting the Digital Generation

In this special book club edition of the podcast, The Winnetka Public Schools Superintendent Dr. Kelly Tess and Dr. Devorah Heitner, bestselling author of Growing Up in Public: Coming of Age in a Digital World, have a candid conversation about helping kids navigate today’s complex digital landscape. From privacy and 'cancel culture' to AI, sexting, going viral, and the nonstop cycle of sharing and comparing, Dr. Heitner offers practical, research-backed advice to guide children toward thoughtful, responsible use of technology.

Dr. Tess and Dr. Heitner explore Chapters 7–9, tackling how to manage social media missteps, the lasting impact of digital footprints, and the crucial role of teaching children conflict resolution and social skills. They discuss preparing kids for high school—and beyond—in an ever-changing digital landscape. Dr. Heitner highlights the importance of fostering independence while recognizing the joy and opportunities technology offers. She emphasizes using tech with empathy and intention to ensure we’re living a balanced life. As Dr. Tess says, “Moderation is an important practice to model for our kids.”

A Filter-Free Conversation on Parenting the Digital Generation

In this special book club edition of the podcast, The Winnetka Public Schools Superintendent Dr. Kelly Tess and Dr. Devorah Heitner, bestselling author of Growing Up in Public: Coming of Age in a Digital World, have a candid conversation about helping kids navigate today’s complex digital landscape. From privacy and 'cancel culture' to AI, sexting, going viral, and the nonstop cycle of sharing and comparing, Dr. Heitner offers practical, research-backed advice to guide children toward thoughtful, responsible use of technology.

Are you overwhelmed by the constant stream of performance data about your child? Do you find yourself tracking their every move and wondering where to draw the line? In this episode, Dr. Kelly Tess and Dr. Devorah Heitner explore Chapters 3–6 of Growing Up in Public, focusing on how to navigate conversations around online safety, the risks of sexting explicit image sharing, and the fine balance between freedom and privacy in the digital age.

Special Summer Series, Episodes #1-3:

A Filter-Free Conversation on Parenting the Digital Generation

In this special book club edition of the podcast, The Winnetka Public Schools Superintendent Dr. Kelly Tess and Dr. Devorah Heitner, bestselling author of Growing Up in Public: Coming of Age in a Digital World, have a candid conversation about helping kids navigate today’s complex digital landscape. From privacy and 'cancel culture' to AI, sexting, going viral, and the nonstop cycle of sharing and comparing, Dr. Heitner offers practical, research-backed advice to guide children toward thoughtful, responsible use of technology.

This episode centers on Chapters 1–3 of Growing Up in Public, unpacking how our culture became obsessed with going viral, building personal brands, unboxings, “Get Ready With Me” videos, and more. Dr. Heitner explores how these digital trends shape kids’ social lives—creating space for both connection and anxiety. What does it mean to 'sharent' in an age where children are growing up in the public eye? The key takeaway: 'You have to know your kid,' says Dr. Heitner.

In this special series, The Winnetka Public Schools Superintendent, Dr. Kelly Tess, and guests, Dr. Tom Flemma, Head of North Shore Country Day; Dr. Becky Mathison, Assistant Superintendent of Innovation, Teaching and Learning; and Dr. Luke Livingston, Principal of Carleton Washburne School, embark on a deep dive into the history and impact of Progressive Education, including how neuroscience informs current teaching practices. Their conversations touch on themes in the book Loving Learning: How Progressive Education Can Save America's Schools by Tom Little and Katherine Ellison.

Dr. Kelly Tess, Superintendent, and Dr. Becky Mathison, Assistant Superintendent of Innovation, Teaching and Learning; discuss how educators design experiences that encourage curiosity through project-based learning. From studying bugs to folktales to Pioneers, Progressive Educators equip students to connect with the world beyond their classroom walls. Hear more about how Winnetka educators bring Progressive Education to life in our schools.

In this special series, The Winnetka Public Schools Superintendent, Dr. Kelly Tess, and guests, Dr. Tom Flemma, Head of North Shore Country Day; Dr. Becky Mathison, Assistant Superintendent of Innovation, Teaching and Learning; and Dr. Luke Livingston, Principal of Carleton Washburne School, embark on a deep dive into the history and impact of Progressive Education, including how neuroscience informs current teaching practices. Their conversations touch on themes in the book Loving Learning: How Progressive Education Can Save America's Schools by Tom Little and Katherine Ellison.

As a Chicago Public Schools educator, Carleton Washbune School Principal, Dr. Livingston, recalls developing a hands-on way for students to learn about the postal system, while Superintendent Dr. Kelly Tess remembers organizing a replica Oregon Trail activity as a fourth-grade teacher. In this conversation, these leaders reflect on the enduring legacy of Carleton Washburne’s research on experiential and meaningful learning as well as how Winnetka educators effectively infuse creative practices into learning. 

In this special series, The Winnetka Public Schools Superintendent, Dr. Kelly Tess, and guests, Dr. Tom Flemma, Head of North Shore Country Day; Dr. Becky Mathison, Assistant Superintendent of Innovation, Teaching and Learning; and Dr. Luke Livingston, Principal of Carleton Washburne School, embark on a deep dive into the history and impact of Progressive Education, including how neuroscience informs current teaching practices. Their conversations touch on themes in the book Loving Learning: How Progressive Education Can Save America's Schools by Tom Little and Katherine Ellison.

The Winnetka Public Schools Superintendent, Dr. Kelly Tess, and guest, Dr. Tom Flemma, Head of North Shore Country Day, chat about the history of Progressive Education in the Winnetka community. Learn more about how educators create environments that allow students to pursue their passions and develop a love of learning, ultimately building the skills they need to be engaged citizens and strong leaders.

In this summer bonus episode, Dr. Kelly Tess, Superintendent, introduces Ms. Anna Trilla, who is the new Principal at Crow Island School as of July 1, 2025. Ms. Trilla shares why she pursued a career in public education (fun fact: she had a brief stint studying meteorology at the University of Illinois prior to shifting to education). Ms. Trilla reflects on how experience gleaned in leadership roles at Walt Disney Magnet School provided her with the groundwork to serve as the next Principal at Winnetka’s historic Crow Island School. 

Dr. Kelly Tess, Superintendent, interviews The Skokie School students Andrew, Anya, and Sawyer about the middle school experience in 2025. This candid conversation ranges from what students wish adults understood about today's tweens, strategies to manage busy schedules and homework, how personal technology impacts communication (i.e. it is apparently no longer socially acceptable to ring a friend's doorbell to see if they are available to play), what it really means to be a well-rounded student, and reflections on how the adults in their lives best support them. As Sawyer shares, “In this generation, this is not really what kids do: kicking a tire, throwing a rock or playing hopscotch in the street.” Don’t miss this special episode!