The Trends Shaping Independent School Leadership

Grounded in insights from our 2026 Voice of the Head of School Survey, this series will bring together school leaders for structured, discussion-based sessions to deepen understanding of the most pressing trends across their communities.

These sessions are not traditional research briefings. Rather than focusing on sharing insights alone, each session is designed as a facilitated conversation—where participants engage with emerging findings, react to early themes, and help shape how we interpret the findings.

Each session will focus on one or two key themes from the survey. Together, participants will explore what these trends mean for their schools and communities and contribute perspectives to guide deeper research and future engagements.

What to expect:

• A brief overview of select survey findings to ground the discussion
• A structured, facilitated conversation designed to gather participant perspectives
• Opportunities to react to emerging themes and challenge early interpretations
• A chance to directly inform future research priorities and areas of focus

Sessions

Select your sessions and click Register to sign up.

Attendance is limited to Heads of School. Registration for each session is limited to one attendee per institution.

• Wednesday, June 3, 2026 | 2:00 p.m. – 3:00 p.m. Eastern Time
  • Navigating Shifts in Community and Faculty Engagement: As community engagement evolves and expectations for digital-first, highly personalized experiences grow, schools are navigating new challenges in building relationships and sustaining strong communities. At the same time, broader workforce pressures are adding complexity to faculty recruitment and retention. This conversation will focus on how heads are working to strengthen engagement, relationships, and the faculty experience.
• Tuesday, June 30, 2026 | 1:00 p.m. – 2:00 p.m. Eastern Time
  • Evolving Expectations for the School Experience: Changes in college admissions, the growing influence of youth athletics, and increasing demand for services and support are reshaping how families evaluate schools and what they prioritize. Advances in technology, particularly AI, are also prompting schools to rethink teaching and learning, staffing models, and the use of digital tools, while raising new questions about their impact on student learning. This conversation will focus how schools are interpreting these shifts and rethinking the design and delivery of the student and family experience.
• Wednesday, July 22, 2026 | 2:00 p.m. – 3:00 p.m. Eastern Time
  • Financial Sustainability Amid a Tightening Landscape: Rising labor and facilities costs are tightening the financial landscape for independent schools, while widening income gaps are increasing pressure on tuition affordability, enrollment, and financial aid. At the same time, philanthropy is becoming more critical and more complex as giving becomes increasingly concentrated. This conversation will focus on how schools are approaching sustainability, including how they are thinking about managing costs, revenue, philanthropy, and capital investments.
• Tuesday, August 25, 2026 | 1:00 p.m. – 2:00 p.m. Eastern Time
  • AI in Schools: Early Approaches and Learnings: Continuing last year’s conversations about AI’s impact on learning, this session will explore how schools are approaching their use of AI, including emerging use cases, early experimentation, and areas of uncertainty. It will create space to share with one another what they are trying, what they are learning, and how they are thinking about opportunities, risks, and next steps.