For independent schools, advancement has always depended on relationships, but the terms of those relationships are changing. Independent school philanthropy remains resilient, but more than ever, donors want to understand how their gifts will be used, what impact they will have, and whether a school’s actions align with its stated values. Generational differences are also reshaping the work, as younger donors tend to look for specificity, transparency, and authentic opportunities to build trust.
In my chapter in the new 2026–2027 NAIS Trendbook, I examine what these changing expectations mean for schools. The following excerpt focuses on how schools can strengthen donor relationships in a more skeptical, choice-filled environment.
The New Advancement Relationship
Philanthropy has always been an act of trust. A donor who makes a gift—particularly an unrestricted one—is extending confidence that the institution will use resources wisely, act with integrity, and deliver on its mission. For much of the 20th century, that trust was largely ambient. Families arrived at independent schools with a presumption of institutional credibility, and alumni gave back to alma maters whose reputations felt settled. The ask was historically straightforward because the foundation of trust was assumed.
That foundation is no longer a given.
The parents who now occupy the center of independent school donor pipelines—Gen X and millennial families—came of age through a sustained erosion of institutional confidence. They watched corporate scandals, political failures, and media implosions unfold in real time. For these generations, skepticism of institutions is not cynicism; it is a reasonable condition, earned through experience. They do not distrust schools specifically; they simply do not extend trust automatically to any organization, regardless of prestige or track record.
As a result, the nature of the fundraising relationship is fundamentally changed. Boomer donors often gave as an extension of identity and loyalty: The institution had conferred something, and giving back honored that exchange. Gen X and millennial donors are less moved by institutional prestige and more attentive to institutional behavior. They ask not only whether a school is excellent but whether it is honest, whether it listens, whether it follows through. They are more likely to give to causes than to institutions, which means that a school must make a compelling case for why it specifically deserves resources rather than simply assuming that affiliation creates inclination.
These donors also expect transparency with feedback loops. When a school communicates only when things are going well, or when an annual fund letter arrives without context about how last year’s gifts were used, younger donors notice the gap. Stewardship that feels one-directional quietly undermines trust.
What builds trust with these generations is specificity, consistency, and voice. Specificity means showing donors what their money makes possible in concrete terms. Consistency means that what a school says about its values is visibly reflected in how it operates and communicates. And voice means that donors—particularly current parents living alongside the institution—feel that their perspective is genuinely sought, not merely collected. For Gen X and millennial parents, philanthropic engagement tracks closely with relational engagement. A family that feels heard is far more likely to give generously; a family that feels like a consumer rather than a stakeholder is unlikely to become a philanthropic partner, regardless of capacity, and may in fact become an enrollment retention risk as well.
The annual fund sits at the center of this challenge. Unrestricted giving requires the highest degree of institutional trust because the donor is explicitly surrendering control over how resources are used. Making the case for flexibility requires making the case for the institution itself—not its history or rankings but its current trustworthiness. That case is best made through relationship rather than marketing. Schools that are transparent about how they use unrestricted funds, that report back in plain terms, and that engage families as genuine partners in mission and culture will find the annual fund ask landing in a very different context. In the current environment, trust is not a background condition for advancement work, it is the work itself.
A Roadmap for What’s Ahead
The advancement landscape is being reshaped by both resilience and recalibration. Schools that make their values visible in daily practice, invite authentic participation, and communicate the case for support with clarity will be best positioned not only to secure gifts, but to build the deeper relationships that make philanthropy possible.
The 2026–2027 NAIS Trendbook is now available for purchase as single copies and convenient packets of 10, an economical way to share these key insights with trustees and staff.