How do you arrive at the development goal in your annual budget? If you're like many school leaders, you took last year's number, added 5–10%, and moved on. That's not strategy. That's a placeholder and it's costing you more than you think.
The issue isn't effort. School development professionals work hard. Development directors and heads of school are logging long hours, running events, sending appeals, and genuinely caring about their communities. The issue is the time horizon they've been handed or have inherited without questioning. Most development programs are built to solve this year's budget problem. Fewer are built to fund the school's next chapter.
That distinction matters more than almost anything else in development.
When development is structured primarily around annual events and participation metrics, it optimizes for immediate, smaller dollars and quietly trades away the conditions needed to secure larger, transformational ones. The gala raises $200K. The annual fund hits its participation target. The board sees the numbers and nods. But the major donor who has been giving $5,000 a year for a decade — and could give $500,000 — has never had a real conversation with anyone at the school. Nobody has ever asked.
This isn't negligence. It's the natural consequence of a program built around short-term outputs rather than long-term relationships. When your team's calendar is consumed by event logistics and appeal cycles, there is simply no time left for the slower, quieter, more consequential work of major gift cultivation. You can't do both at full capacity. Something has to give and in most schools, what gives is the work that would have changed everything.
It plays out in two recognizable patterns.
The under-resourced school moves from event to event, afraid to cut anything because each one represents a few thousand dollars the school genuinely needs. The community is divided: half loves the togetherness the events create; the other half feels perpetually solicited. No one on staff has deep major gift experience. The real cost to raise a dollar is obscured by gifts-in-kind and hundreds of volunteer hours no one is tallying. The board sees a lean model and calls it efficient. Meanwhile, the school's most capable donors are wondering why no one has ever sat down with them.
The better-resourced school has a larger team and more polished events, but still only one person, if that, working major gifts in any sustained way. They're proud to raise $2M annually. They've been raising $2M annually for fifteen years. Event costs are buried in separate expense categories. The alumni receptions and golf tournaments at the country club, despite enduring belief to the contrary, have not translated into any transformational gifts. The school's most thoughtful donors are quietly wondering whether they're the only ones holding the program together.
Both models are working hard. Neither is working strategically.
A genuine development strategy doesn't abandon events or annual giving — those play important roles in community-building and in developing the pipeline of future major donors. But it subordinates them to a longer arc. It asks: what does this school need to be financially stable and mission-driven five years from now, and what kind of giving program gets us there?
That question produces a different set of priorities. It means identifying — by name — the donors who have both the capacity and the affinity to make significant gifts and building a sustained cultivation plan around those relationships. It means your head of school carries a portfolio of 10 to 15 major gift prospects she is actively engaging, not occasionally emailing. It means tracking donor journeys the way enrollment teams track prospective families: with intention, with regular touchpoints, and with a clear sense of where each relationship is headed.
Rather than concerning yourself with 100% parent participation or 75% alumni participation in each class or ensuring that every faculty member can attend the gala, deepen your understanding of benchmarks to focus the team (both paid and volunteers) on how development is part of the overall financial strategy of the school.
The same logic applies to events. The question isn't whether to hold them. It's whether you have a clear answer to what happens after each one. What did you learn about the people in the room? Which relationships moved forward? What is the follow-up plan, and who owns it? Events without strategy are expensive community gatherings. Events with strategy are cultivation opportunities.
Here is where many development leaders and heads of school get stuck. Shifting toward a multi-year model requires making deliberate choices to do less of some things and boards, understandably, want to understand why gross revenue might plateau or why the gala is being scaled back. That conversation is not just inevitable; it's essential.
The case to make is this: we have been optimizing for the wrong metric. Annual participation rates and event revenue are easy to count, but they are not the measures of a program building toward its full potential. The measures that matter are the depth of your major gift pipeline, the strength of your top donor relationships, and whether you are creating the conditions for a successful campaign when the school needs one.
Boards respond to that argument when it's made clearly and with data. Show them where your top gifts have actually come from. Show them what percentage of staff time is currently going to event logistics versus direct donor contact. Show them what a realistic five-year model looks like if you redirect some of that energy. The board's job is to steward the long-term health of the institution and a well-framed conversation about development strategy is exactly the kind of thing they should be weighing in on.
None of this changes overnight. Development cultures are deeply embedded, and every school carries a set of inherited assumptions about what fundraising is supposed to look like. But summer — before the calendar fills and the fall urgency takes over — is the right time to ask harder questions.
Start here:
1. When you think about your three largest gifts in the last three years, did they come from a cultivated relationship or from an event or appeal?
2. What percentage of your development staff time goes to event logistics versus direct, one-on-one donor contact?
3. Does your Head of School have a named list of major gift prospects she is actively — not occasionally — engaging?
4. If you cancelled your biggest fundraising event tomorrow, what would you actually risk and what might you gain?
5. Do you have enough closely stewarded relationships right now that you could raise 70% of your next campaign before it is publicly launched?
If those questions are uncomfortable, that's useful information. The goal isn't a perfect program built overnight. It's a program that is consciously moving from optimizing for this year's number toward building something that serves the school for the next decade.
Even if you're crawling right now, the right questions will get you walking. Then running. In a system that actually works.
Jill Goodman, is the founder of Jill Goodman Consulting. She works with independent school leaders to address budget concerns by increasing enrollment retention, building development capacity, and enhancing leadership skills.
Moira Kelly is the president of EXPLO and is the managing partner of EXPLO Elevate. She works in governance, strategy, and leadership.