By Sam Uzwack, Head of School

It would be easy to say the only reason we chose empathetic dialogue as the theme for the current school year is because there was a presidential election, and certainly that was part of it. But what we’ve come to learn is that the ability to truly engage in empathetic dialogue is one of the most important, long-lasting skills we can foster. Take the rapid developments resulting from the proliferation of AI, for example. The immediate and drastic changes are necessitating that we step back and say, “What are we teaching our students that in ten to fifteen years will persist?”

Certainly, empathetic dialogue and civil discourse are two of those skills. That’s not to say it’s an easy task. These are a complex series of skills that must be brought together in real time, with real people, tackling challenging topics. It would certainly be more simple if there were no “spicy topics,” no gray areas to navigate. But if we’re only talking about something we already agree on and you never have conflict, are you really learning how to have civil discourse, how to bridge perspectives? That’s not the point. The point of healthy conflict is to generate new ideas, new possibilities, not to reinforce existing ones

A Diverse Group of People Solving Novel Problems

Imagine putting fifteen eleven-year-olds—or even fifteen sixteen-year-olds—in a room without teaching them directly how to engage in civil discourse, how one “is” in a challenging conversation. You’re not going to get anywhere. Eastside Prep is a place founded on the notion of gathering together a diverse group of people to solve novel problems, so empathetic dialogue may in fact be the most important skill we can teach.

These are foundational skills that should be everywhere in our school. What’s been really great about this year’s series of Insightful Questions podcasts is exploring how empathetic dialogue shows up across all disciplines, from science to athletics to math. It’s understandable that a lot of people assume this is the purview of our Social Science faculty. And frankly, a lot of it does fall to them. But it needs to fall to all of us because empathetic dialogue is necessary everywhere. Civil discourse may look different if you’re in the theatre or on the basketball court, but the principles remain the same. When I think about this complex set of topics, I realize what we’re doing is preparing students for college and beyond. We’re teaching a life skill. If we’re able to equip them and they learn this well, what a gift for their next chapter to be able to engage—to be practiced and have the confidence and capacity to do so. This is exactly the kind of work that matters.

Bridging Perspectives

I heard something recently that really resonates with me: all perspectives are valid but are also incomplete. This reminds us of the power of coming together to talk about anything. There are certainly some perspectives that I don’t feel are valid. But in general, if I’m thinking about an issue or topic, I have a perspective that’s mine, but it’s only my perspective. It might be a rich perspective based on experience and based on research, but I can only benefit from hearing more perspectives on the same issue to deepen and complexify my understanding.

At Eastside Prep, we focus not on speed but on depth and complexity. Engaging with different perspectives—shaped by people’s backgrounds, identities, and lived experience—helps us gain a fuller picture. This is the kind of intellectual rigor that empowers students to think critically and empathetically. That’s powerful.

I REALIZE WHAT WE’RE DOING IS PREPARING STUDENTS FOR COLLEGE AND BEYOND. WE’RE TEACHING A LIFE SKILL.

Breaking the Car in a Safe Space

Empathetic dialogue and civil discourse are not easy to learn, and they’re certainly not easy to teach. One way to teach these skills is through modeling. Students are watching the adults in our community constantly. They see how we interact with each other. We model playing with ideas every day and how we talk with one another. How we converse at the lunch table is also observed. And so we need to remember to engage in empathetic dialogue with one another. Another tool for teaching is not starting with the spiciest topics first. When I was teaching my daughter to drive, we didn’t start on I-5 during rush hour. We started in a completely empty parking lot. We still broke the car, by the way, but we did that in a safe space.

So when you’re bringing students into the teaching and learning of these skills, you need scaffolding and you need to build in the intensity of the topics over time while still making it real for the students. I was recently involved in a lively debate with Middle Schoolers about whether a hot dog is a sandwich. This allowed a platform for discussion without worrying too much about pushing on someone’s deeply held feelings or family beliefs. We need these milder topics in order to be able to ramp up into more intense or personal topics.

Common Ground

Empathetic dialogue is hard because it’s fifteen different things all at once, and you need to tease out each separate skill and put them together in the moment. This may all seem like a pretty tall order, especially when speaking about ten to eighteen-year-olds. But as is true with many things, I believe we start with intentionality if we want to be able to engage students in challenging conversations. We need to provide the “off-ramps” when a topic becomes too personal and create spaces where students can debate ideas without attacking each other’s identity or humanity. By structuring conversations thoughtfully, we can ensure that students are equipped to be able to really dig into the tough stuff.

Most importantly, we need to ensure that our students leave those conversations feeling positive about their peers and about themselves. The more we work at this, the better we’ll all get at it. And who knows, along the way we may find that we have more common ground than we initially realized.