This December, four of the five major world religions celebrate miracles, revelation, and light. Whether a spiritual moment or a secular observance, this time of year offers us opportunities for joy, reflection, and community. And as the calendar year comes to a close, many people seek to strengthen their communities by making year-end philanthropic gifts. When you think about the Greek roots of the word philanthropy––philos, meaning loving, and anthropos, meaning humankind––it seems fitting that people would want to honor our schools with a year-end gift to express their love for the institutions that shaped their or their children’s humanity.
December is also a time of chaos for heads of school and other school leaders, despite the fact that every year during calendar-setting and planning exercises, senior leadership teams the world over swear they will have fewer things on the schedule at this time next year. (If anyone manages that, please do let us know!) There’s a lot going on in schools right up until winter break, but amid the holiday concerts and parties and end-of-year traditions, you need to remember your duty as advancement officers at this crucial moment.
While many heads of school have traditionally entered their roles without advancement office experience, this trend is gradually shifting. Increasingly, new heads are bringing at least some background in fundraising to the position. For those who lack significant fundraising experience, it can be tempting to focus on other year-end responsibilities or to avoid fundraising altogether. However, leading fundraising efforts is a vital aspect of the head’s role. According to NBOA, philanthropy, including annual funds, restricted gifts, and endowment draw, constitutes roughly 10% of school operating budgets in the U.S.
Making time for year-end fundraising is possible, however, even for heads who haven’t yet planned for it. It helps to start by remembering that personal outreach, words of gratitude, appeal, and encouragement can make the difference between an average gift and an extraordinary one. From there, you can maximize the time left in the year with a three-point action plan.
1. Check in.
You should collaborate closely with their chief advancement officer to review donor lists together and ask:
Who has given and needs a personalized thank you from the head?
Who hasn’t yet given and needs an ask or a reminder?
Who has never given but has the capacity to make a meaningful gift?
Working together, you and the CAO can identify major donors or potential donors who would value direct outreach. If you’re having a hard time prioritizing, narrow your list down to those whose gifts are exceptional given your advancement program and goals, or those whose gifts could be exceptional, based on your wealth indicators in your database. If your window of time is narrow, focus on just 10 individuals or families, but if you have more time, open the list to the top 25 donors and prospects. If you’re in a campaign, use campaign data to make these choices; if you’re not in a campaign, base your choices on annual fund behavior or other recent restricted giving. With the changes to tax laws that will go into effect in 2026, it’s especially important to cultivate leadership donors now to ensure continued support in the future.
2. Map out a plan.
Nothing happens without a plan. And for those of you with already-full plates who might now also have to dress up as Santa, hand out treats, and read at a multi-faith holiday celebration, fundraising calls might never happen. Which is why you need to set aside time now.
Here’s the good news—it’s still November, and there is still time to create a manageable and thoughtful outreach plan that can have a significant impact. It can start today with an email: Ask your executive assistant to block off two full days or four half days in early December dedicated to fundraising efforts, which should include phone calls, voicemails, and handwritten notes.
3. Reach out.
Once you have the list of donors with whom you want to connect, create space for that connection. That means shutting the office door or going off campus for a bit to reach out to key donors or potential donors. Whenever possible, these should be real-life phone calls, not just texts or emails. Take the extra time to make this connection personal. Don’t forget to express continued gratitude and always have a call to action:
“Thank you for your time; I’m happy to speak with you and I want to share …”
“We hope we can count on your support this school year.”
“We hope you’ll consider a first-time gift.”
“We are grateful for your past contributions; our students are benefiting as I speak. I hope we can count on your continued partnership.”
Fundraising is a joyful endeavor, and heads of school are in a unique position to truly inspire giving. You have the great privilege to be able to share stories about the school you love and celebrate the joy that is watching young people become better versions of themselves. Genuine enthusiasm inspires support; when leaders are passionate, funding will follow.
To achieve meaningful results, however, heads can’t rely solely on inspiration and hope. You must set time aside for outreach and make joy and celebration central to the approach. When you do, you not only encourage gifts but also strengthen relationships with parents and alumni, fostering a lasting sense of community and partnership.