Leading Through the Shift: What New Heads Need to Know (But Don’t Always Hear)
Leadership transitions can be emotionally overwhelming for a school community. Whether you’re stepping into your first headship or transitioning into a new school after years of experience, the early days are filled with expectation, pressure, and that tricky dance of learning while leading.
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.
Slowing Down to Speed Up
Davis described his second headship as noticeably more intentional than his first. With a year-long runway and growing self-confidence, he was able to pause, reflect, and be more discerning about where to focus his energy. “I used to think I had to know everything. Now, I give myself permission not to,” he shared. That shift—from urgency to intentionality—is something every school leader can learn from.
Relationships Are the Real Curriculum
From meet-and-greets with parent groups to informal student conversations, Davis emphasized how every encounter is a chance to build credibility and connection. “People don't get to know you from one headline—they know you from how you show up, consistently, in big moments and small ones.” Hill-Gill reinforced this point, adding that being vulnerable and sharing a bit of yourself (even your favorite music or what books you’re reading) can make a big difference in establishing trust.
Transition Committees That Work (and Last)
Both leaders discussed the crucial role of transition committees. These groups help new heads navigate sacred cows, regional context, and stakeholder dynamics. However, Hill-Gill added a clever twist: the committee should not dissolve after July 1. Consider a second-phase transition team that helps the head get through the full school-year cycle. Who better to help the new head understand how things really work?
Make It Safe to Ask Why
Hill-Gill introduced the concept of the “Jumpstart Exercise” to surface all the questions staff have but might not feel comfortable asking. From policies to personalities to past decisions, making space for curiosity on both sides goes a long way. Davis echoed the power of simply asking, “Why was this done this way?” and resisting the urge to change things before understanding them.
Advice for Boards: Don’t Wing the Welcome
One key audience that came up often: the board. Hill-Gill encouraged schools to invest in preparing trustees for the transition, especially if the incoming head represents a milestone (first woman, first person of color, etc.). Boards should think about:
Appointing a transition committee early
Hosting an installation event that symbolically marks the change
Separating goodbye moments for the outgoing head from the welcome moments for the new
Supporting introductions to donors and key constituents
Know the Fires, But Don’t Fan Them
What if your new head is walking into a tough situation? Hill-Gill’s advice: Be honest about the challenges, but resist overwhelming the incoming leader with unrealistic expectations. Give them space to do their own discovery and prioritize thoughtfully. As Davis reminded us, “Sometimes, you just have to be still.”
Bootcamps, Coaches, and the Power of Planning
Davis shared his plans for a two-day leadership team bootcamp—a deep dive into every department before the new year begins. With mentors, executive coaches, and lots of listening built in, he’s modeling what it means to lead with intention, not ego. Hill-Gill pointed out that the transition can ripple through all leadership levels, not just the headship, and school communities need to be ready for that.
Want the Full Conversation?
This recap is just a taste of the powerful insights our guests shared. From board relations to team morale to the importance of pacing and trust, the full Huddle recording dives deep into what makes or breaks a leadership transition.
If you're a school leader, trustee, or part of a transition committee, this conversation is a must-watch. Grab the recording and hear exactly how two experienced leaders navigated their most high-stakes moments—and how you can do the same.
Stay tuned for our next Huddle season with more candid conversations and real-world advice from inside the world of independent schools.