Last May, we brought together two seasoned leaders to discuss this moment of change candidly. Barry Davis, incoming Head of McLean School and outgoing Head of St. Ann’s Episcopal School, joined Yanni Hill Gill, President of ADVIS and former head of Atlanta Girls School, for a rich conversation about what really matters when preparing for (and successfully leading) a leadership transition.

In February, we welcomed Sean Brown, Chief Advancement Officer at St. Andrew’s School in Boca Raton, Florida to The Huddle. With a decade of experience at The Frederick Gunn School in Connecticut, Brown shared his firsthand insights on assessing and strengthening an internal team—an essential skill for school leaders navigating transitions and seeking to foster a high-performing culture.

Last April, we explored how Emma Willard School, a historic girls’ school in upstate New York, embraced a student-driven approach to branding and marketing. By focusing on authenticity and engagement, the school saw a rise in applications, inquiries, and enrollment.

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.