Creating Leadership Alignment in Independent Schools
In our latest Huddle, we had the pleasure of speaking with Tyler Casertano, Head of School at Haverford School, about one of the most crucial yet challenging aspects of independent school leadership: alignment. Whether it's keeping the leadership team on the same page or ensuring the board of trustees stays in its governance lane, Casertano shared valuable insights from his experience leading a thriving boys' day school in suburban Philadelphia.
The Constant Work of Alignment
“If we’re not constantly working on creating this alignment, it can very quickly turn into a game of tug-of-war,” Casertano remarked early in our discussion. Without alignment, schools risk different factions pulling in opposing directions, leading to inefficiency and frustration.
For Casertano, alignment starts with the leadership team, which acts as the bridge between the board and faculty/staff. His approach is intentional and structured:
Daily standup meetings keep small issues from becoming big problems.
Weekly strategic meetings allow for deeper discussions on priorities.
Three annual retreats provide dedicated time for reflection and long-term planning.
While meetings can sometimes feel like a necessary evil in leadership, Casertano sees them as the glue that holds the team together. “Being surrounded by a team, to me, is at the end of the day sort of the thing that makes it all work.”
Hiring for Culture, Not Just Competence
A strong leadership team doesn’t happen by accident. Casertano has designed a hiring process that prioritizes not only skill but also cultural fit. Every new leadership hire goes through a collaborative vetting process, involving input from the entire team.
“We want to make sure we’re bringing in people who will enhance our ability to function together,” he explained. By involving multiple voices in hiring decisions, Haverford ensures that new leaders align with the school’s strategic priorities and team dynamics from day one. After receiving multiple inputs from his team, Casertano makes the final hiring decision.
Setting Board Members Up for Success
Board governance can make or break a school’s ability to execute its mission. Casertano has worked hard to prevent operational overreach by establishing a rigorous onboarding process for new trustees.
“Our goal is to clarify roles, responsibilities, and boundaries from the start,” he said. This prevents well-intentioned but misguided board members from micromanaging or interfering in day-to-day operations.
One innovative tool Haverford uses is the Haverford Leadership Council, an “incubator” group that allows potential future board members to engage with strategic issues before officially joining. This approach helps maintain a high-functioning board that understands its governance role from the outset.
Holding the Board Accountable
Even with clear expectations, challenges still arise. Casertano and his leadership team remain vigilant in addressing governance issues head-on. “We can’t ever take our eye off the ball in that type of governance work.”
If a board member starts drifting into operational territory, school leadership—particularly the board chair—steps in to provide a course correction. Having strong relationships and open lines of communication allows these conversations to happen in a constructive, rather than adversarial, way.
Avoiding the Pitfall of Too Many Priorities
One of the more thought-provoking moments in our conversation came when Casertano reflected on the modern tendency to “pluralize priority.”
“For most of human history, you’ve got one priority, and that was your focus,” he said. “And we’ve, at least at Haverford, grown accustomed to pluralizing it in a way that I think can dilute our focus.”
This observation resonated deeply with the group. In an era of constant change and pressure to do more, leaders must be disciplined in maintaining focus on what truly matters.
Final Takeaways
As Casertano enters his fourth year as Head of School, he’s seeing the results of these alignment efforts. “Yes, we’re pushing a boulder up the hill that might roll back down,” he said. “But we’re doing it together.”
Independent school leaders face complex challenges, but the lessons from this Huddle are clear:
Alignment isn’t a one-time task—it’s ongoing work.
A strong leadership team starts with intentional hiring and consistent collaboration.
Boards function best when roles, responsibilities, and boundaries are crystal clear.
Focusing on a few key priorities is more effective than trying to tackle everything at once.
As we wrapped up, one participant asked a great follow-up: How does this approach translate to faculty and staff alignment? Casertano’s response: The principles are the same—clarity, communication, and shared purpose.
What do you think? How do you create alignment in your school? Watch the Huddle here!