Tyler Casertano, Head of School, The Haverford School

In an interview with Invest:, Tyler Casertano, Head of School at The Haverford School, said that fostering emotional intelligence, building strong relationships, and preparing boys for a rapidly evolving world are at the heart of the School’s mission. “We want them to discover a new ceiling — one that’s higher than they imagined when they arrived,” he said.

What changes over the past year have most impacted the School, and in what ways?

We’ve been undergoing a strategic visioning and planning process. Our current strategic plan runs through 2025, and over the past year, our Board of Trustees has been working closely with our Leadership Team and the broader community to shape the next Strategic Vision, which will guide us toward our 150th anniversary in 2034. We’ve spent considerable time reflecting on who we are as a school, the current educational landscape, particularly for boys, and who we aspire to become. We’ve identified several core areas that require focus. One is people: ensuring we have the strongest possible community of teachers and learners. We’re examining the current market, the challenges and opportunities in hiring and supporting faculty, and how to attract and retain dynamic, committed educators who want to be at Haverford. Likewise, we’re thinking deeply about how to attract curious, engaged boys and what barriers may currently hinder that growth.

Another key area is resources, particularly our endowment. We’re committed to building an endowment that ensures the School’s longevity so that Haverford remains a thriving institution for the next 50, 100, and even 150 years. The third area is programming. We’re considering what boys need to succeed in today’s world, in college and beyond. That includes both classroom learning and extracurricular opportunities. We’re fortunate to have a strong academic foundation, but our boys also learn and grow in studios, on stages and athletic fields, and through programs like robotics, mock trials, and speech and debate. We constantly think about how these experiences reinforce one another and support the holistic development we aim to cultivate in our students.

Could you expand on the curricular adaptations and how Haverford is evolving its models to meet the changing demands of colleges and employers?

Having worked in boys’ education for nearly two decades, I can say this is one of the most exciting and important times to be in this space. There’s a growing body of research on how boys learn, how the male brain develops, and what kind of environments best support them. At the same time, there’s mounting evidence that boys are struggling academically, socially, and emotionally. That’s why our work is so crucial. We’re creating the conditions that help boys thrive, and that starts with emotional and social intelligence. Many boys form negative associations with school early on because they don’t feel successful there. They may feel stigmatized for not meeting expectations. So, we focus on helping them develop skills like emotional regulation, building healthy relationships, executive functioning, and movement-based learning, especially in the Lower School.

Reading is often an area where boys lag behind, so we’ve invested in a science- and research-backed reading program that helps boys become confident readers. In Middle School, we layer in programs that support psychological wellness and teach them to be emotionally expressive, vulnerable, and authentic — traits boys often resist during adolescence but that are crucial for their development. Our goal is for every boy to feel that he can bring his full self to school and engage fully with the program. When they do, they grow in remarkable ways.

How do you foster belonging and inclusion across the School?

That’s something we focus on constantly. Our students come from a wide variety of backgrounds, but there’s a strong sense of brotherhood and camaraderie. They learn to recognize and appreciate their differences while also embracing their shared humanity and common Haverford experience. Programs like Reflections in our Middle and Upper Schools give students a platform to share personal stories and insights. In the Lower School, our community time serves a similar purpose. These shared moments build connection and empathy, and they strengthen the collective by encouraging individual authenticity.

Could you expand on some of the most compelling programs you offer?

We think of our programming in terms of three A’s: academics, arts, and athletics. These areas have formal requirements depending on the grade or division. We also offer structured extracurriculars like robotics, Model UN, and speech and debate, as well as informal clubs like fishing and chess. Boys are encouraged to create new clubs based on their interests. Our global education program includes both grade-wide and course-specific trips. For example, the entire eighth grade travels to Puerto Rico, while Latin students might go to Rome. We also have a partner school in Barcelona, and we’ve organized non-academic trips to places like Iceland. The goal is to foster global awareness and real-world learning.

How is technology, especially AI, impacting your educational approach?

We approach technology by first understanding how a boy’s brain is developing. We only introduce tools that enhance, rather than impede, that growth. Our aim is to teach boys how to learn, analyze, and collaborate so they can adapt to tools that don’t even exist yet. While some students use AI for prototyping or idea generation, we emphasize the importance of critical analysis and synthesis. The usefulness of AI depends on the quality of the questions asked and the depth of understanding the student brings to it. We want students to see AI as a tool, not the endpoint. Faculty are also exploring how AI can streamline administrative tasks, freeing up time for the human work only teachers can do, such as connecting, guiding, and mentoring.

What are your top goals for the School in the next few years?

Our goal is to build upon our strengths and make Haverford the best version of itself, not to change its DNA. Our focus remains on teachers, learners, and programs. We want each boy to leave with three things: enduring relationships that support him for life, the skills and habits to succeed in an ever-changing world, and a transformed understanding of what he’s capable of. We want students to discover a new ceiling — one that’s higher than they imagined when they arrived.