Message to donors: Go Big or Go Bigger!

“It seems like the more I give the more I get, and that is the way it is supposed to go in life.”
—Dolly Parton
Isn’t it wonderful when donors live by that motto? Even if you’re quite certain your donors enjoy giving to your organization, you’ll still likely be hit with waves of uncertainty from time to time. For instance, a capital campaign, milestone anniversary, major facility project, or other special initiative can create an exciting opportunity to invite your most committed donors to make unusually significant gifts. But it can also create an uncomfortable question for fundraising teams: If we ask a donor to give big now, are we jeopardizing the annual—and perhaps even planned—gifts we hope they’ll make later?
It’s a legitimate concern, particularly as donors navigate a changing tax environment. With the higher standard deduction making it harder for some taxpayers to realize an income tax benefit from charitable gifts in any single year, donors and their advisors may increasingly consider savvy tax planning strategies such as “bunching” multiple years of charitable contributions into one tax year. This can make giving patterns look different from the steady annual gifts nonprofits have traditionally encouraged.
The answer isn’t to shy away from transformational asks. Instead, think of a major gift as one part of a donor’s long-term relationship with your organization—not the finish line.
Here are four ways to do it.
Talk about the donor’s whole giving picture, not just the campaign.
When you’re seeking a significant campaign gift, it is tempting to focus every conversation on the immediate goal: the new building, endowment initiative, anniversary campaign, or other pressing priority.
But your most engaged donors likely care about more than a project. Ask how they envision supporting your mission over the next several years. What programs matter most to them? What do they hope their philanthropy accomplishes? Is creating a legacy important to them?
Those questions can open the door to a broader conversation about annual, campaign, and planned giving. Some donors might make substantial campaign commitments while maintaining annual support, for example. Others might decide that a particularly large current gift means annual giving needs to look different for a few years—but also make commitments through their estate plans.
There isn’t one correct combination. The important thing is to have the conversation.
Don’t mistake a change in giving pattern for a change in commitment.
Tax considerations may influence the timing, amount, and type of charitable gifts donors make. For example, a donor who historically wrote a check every December might instead combine several years of giving into a larger contribution in a single year, potentially using appreciated assets or a donor-advised fund. That means your stewardship systems need to be ready to accommodate these opportunities.
Another example is a loyal donor who pauses giving for a calendar year. Are they no longer interested in supporting your mission? Or perhaps they simply have funded several years of charitable giving at once. Make sure your development team understands the donor’s intentions and records them appropriately so that an intentional change in giving strategy doesn’t accidentally trigger a “lapsed donor” communication.
Most importantly, don’t let a pause in gifts become a pause in the relationship. Continue sharing impact, expressing appreciation, inviting participation, and keeping donors connected to your work.
Keep planned giving in the conversation—even after a very large gift.
One of the easiest mistakes to make after receiving a major campaign gift is assuming you’ve already asked enough of the donor. Planned giving doesn’t have to be another immediate ask. Instead, it can be part of an ongoing conversation about what the donor wants their philanthropy to accomplish over a lifetime and beyond.
A donor who makes a significant campaign gift today may also be an excellent legacy giving candidate, whether they name your organization as a beneficiary of an IRA, include a charitable provision in an estate plan, establish an endowment, or explore another planned giving strategy with their tax, legal, and financial advisors.
Indeed, a major campaign gift may signal something important: This donor cares deeply about your mission. That’s a reason to continue the relationship, not retreat from it.
Think lifetime relationship, not individual transaction.
Campaign fundraising naturally creates urgency. There are goals to meet, deadlines approaching, and perhaps a very large thermometer somewhere that everyone would like to see reach the top. Your donors, however, aren’t campaign transactions.
The strongest fundraising strategy considers how annual giving, major giving, and planned giving fit together across a donor’s lifetime. Ask boldly when the opportunity warrants it, but accompany those asks with thoughtful conversations about the donor’s broader goals. And after the campaign gift arrives, keep stewarding, listening, and talking about the future.
A big gift today doesn’t have to diminish support tomorrow. Handled thoughtfully, it can become another chapter in a much longer story of generosity. Please reach out to Illinois Prairie Community Foundation anytime. We are happy to be a sounding board!
This article is provided for informational purposes only. It is not intended as legal, accounting or financial planning advice.