Heads & Trustees Week 2026

OPPORTUNITIES TO LEARN:

MONDAY: CONFERENCE KEYNOTE:

Understanding Generational Mindsets:  Building Stronger Schools through Connection

Dr. Unnatti Jain, Lifecoach/Speaker

Every generation sees the world differently. In schools, those differing perspectives converge daily among students, parents, faculty, and boards. This keynote explores how understanding generational mindsets can transform institutional challenges into opportunities for connection. By recognizing values, communication styles, and motivations across ages, Heads of Schools and Trustees can foster trust; enhance decision-making; and align their communities. In doing so, they will honor school traditions while preparing students for the future, upholding their mission to champion excellence in teaching and learning.

TUESDAY:

Families Perceptions of Value and Affordability

Allison Davis, Associate Director of Domestic Membership & Business Development, Enrollment Management Association

Independent schools are navigating a complex landscape where families’ perceptions of value and affordability are directly shaping enrollment decisions. Drawing on findings from EMA’s 2025 member-exclusive report, An Independent School Education: Family Perceptions of Value and Affordability, this session will share large-scale research into how families across the socioeconomic spectrum perceive independent schools. Participants will gain a deeper understanding of the critical factors influencing enrollment decisions, including expectations around value, return on investment, financial realities, and the trade-offs families consider. This session is designed for heads of school, trustees, enrollment leaders, and school business officers seeking data-driven strategies to strengthen their enrollment pipeline and sharpen their institutional positioning.

WEDNESDAY:

Financial Vital Signs: How to Measure Sustainability

Brenda Stonecipher, Principal, Stonecipher Consulting

Financially sustainable schools share core practices and financial habits that set them apart. This session explores the “vital signs” of school financial health: a practical checklist of indicators across key areas, including tuition strategy, revenue, budgeting, staffing, reserve and asset management, financial reporting, and other aspects of resiliency. Built on fieldwork and grounded in data from independent schools, this framework helps Heads and Trustees assess their current status, track progress over time, and take corrective action to realign with sustainability goals. School leaders will leave this session with a heightened understanding of their school’s status on the sustainability spectrum, a practical checklist of success indicators, tools for internal assessment, and steps to realign when needed.

THURSDAY:

So You’ve Adopted a Strategic Plan. Now What?

Carla Silver, Executive Director & Co-Founder, and Greg Bamford, Co-Founder & Partner, Leadership + Design

Congratulations on adopting your new strategic plan! But your work isn’t over – it’s just entered a new phase. Effective implementation requires more than clear goals. It calls for flexibility, collaboration, shared language, protocols that fit school culture, and the ability to turn aspirational language into concrete action. Every stakeholder—Head, Trustees, Leadership Team, Faculty, and Staff—must understand their role in bringing the plan to life. And because schools and the world shift over the span of a multi-year plan, strategy may need adjustment, refinement, or even sunsetting along the way. We’ll explore how to: unpack squishy goals; build an evolving committee structure; set committees and chairs up for success; use ecocyle planning; distinguish technical vs adaptive challenges; and navigate human emotions. This session is for heads and trustees seeking practical steps to launch or re-energize implementation, whether their plan is new, just wrapping up, or already underway.

FRIDAY:

What Our Donors Need From Us Now: 6 C’s to Your Fundraising Success Tesha McCord-Poe, Founder & CEO, Joy-Raising

In today’s rapidly changing philanthropic landscape, donors are seeking more than just a compelling cause — they want the right kind of connection. In this dynamic session, Tesha McCord Poe, Founder & CEO of Joy-Raising, will share six essential qualities that every fundraising office or effort can cultivate to inspire trust, deepen engagement, and drive lasting impact.