2026-27 New Governance Realities for Heads and Boards

Tuesday, October 13, 2026 | 12:00-1:00 PM

Shadow Dockets and Succession Planning:

When Boards Already Have a Replacement in Mind

This session will explore one of the more sensitive and increasingly common dynamics in independent school governance: what happens when boards begin thinking about leadership transition long before a head’s contract is nearing completion.

Drawing on real case studies, we will examine how informal conversations, shifting alliances, and behind-the-scenes succession planning can affect trust, transparency, and the board-head relationship. Participants will consider the difference between responsible long-term succession planning and governance practices that can unintentionally destabilize leadership or create division within a school community.

Tuesday, October 27, 2027 | 12:00-1:00 PM

Managing Conflicts Within Boards and Among

Board Members: A Disciplinary Issue

In the AI era, fabricated images can be posted online, creating wide-ranging challenges for boards, heads, and schools to navigate. The situation is particularly difficult when students deploy these tools against one another, and especially fraught when the children of board members are either the perpetrators or the victims of such activity.

How do boards and heads manage these situations effectively?

How do leaders make sound decisions and facilitate appropriate outcomes that protect children while preventing damage to the school, its reputation, and its enrollment?

We will use a case study approach to illuminate the issues and draw insights from these types of leadership challenges.

Monday, November 16, 2026 | 12:00-1:00 PM

Managing the Head of School and Compensating

the Head Fairly and Competitively

Boards and schools are asking more and more of their heads of school, and the mounting pressure shows up everywhere: in conversations between heads and board chairs, between heads and full boards, and even within heads' own families.

Genuinely supporting a head means getting contract renewal and compensation benchmarking right, and yet too many boards either skip this work entirely or start it far too late. This session unpacks what boards need to know to get the timing and process right, before it becomes a problem.

John Littleford served as teacher, trustee, and head of school in his 25 year independent school career. Since 1994 he has been a full-time consultant to over 3,000 independent and international schools as well as corporations, foundations, universities, and a range of medical and arts oriented non-profit organizations. As Senior Partner of Littleford & Associates, John's expertise includes: governance, strategic planning, executive and faculty compensation and evaluation, executive searches, marketing, fund raising, managing change, crisis management, school climate, organizational review, institutional and financial audits, and team building.

John has been a speaker, presenter, workshop leader and keynote on several continents and is the author of a highly popular book on faculty salary systems in independent schools. His firm's newsletter goes out five times a year to 25,000 trustees and school leaders and is circulated and read worldwide.