The Art of the Ask: Turning Giving Tuesday into a Season of Yes
December 2, 2025
Today - Giving Tuesday - kicks off what is essentially the Super Bowl of fundraising. Donors are already in a generous mindset, inboxes are buzzing with philanthropy, and people are thinking about the impact they want to make before the year wraps up. It’s the perfect moment to reach out—but not with the old “mass email and hope it lands” approach. The most effective year-end solicitations blend smart prospecting with genuine, human connection.
A great place to start is looking at who’s most likely to respond this time of year. That’s where capacity and affinity come in. Capacity tells you can they give? Affinity tells you do they care? When both are strong, you’ve got a high-potential prospect. Using data—past giving, event participation, volunteer engagement, even email interactions—helps you decide who merits a personal call, who might respond to a warm note, and who needs some cultivation first.
Once you’ve identified your best prospects, thoughtful stewardship becomes your secret advantage. People want to feel valued, and showing appreciation before making an ask can set the tone for a positive response. One colleague of mine actually baked small banana breads decoratively wrapped and hand-delivered them to donors at their home, unannounced. With a friendly smile and freshly baked bread - who can turn you down? It wasn’t complicated, but it was real—and the follow-through was outstanding. That’s what cultivation can creatively look like, and those small gestures ended up showing our whole team just how impactful a thoughtful touch can be when solicitation season arrives.
When it is time for the actual ask, keep it personal. Refer to something they supported before or something they told you matters to them. Year-end solicitations work best when they feel relevant, timely, and sincere. Even a short phone call or handwritten card can cut through the season’s digital clutter. And don’t hesitate to invite someone out for a cup of coffee at their favorite spot—it's a great chance to share the past year’s wins and preview the big goals ahead for 2026, and to successfully make that well-timed solicitation.
Ultimately, year-end fundraising—especially in the glow of Giving Tuesday—is about more than landing a gift (although that should be high on your priority list). It’s about nurturing donor relationships. Mix intentional prospecting with heartfelt stewardship and a bit of creative cultivation (homemade baked goods optional but highly effective), and you’ll create an environment where giving feels easy, appreciated, and genuinely joyful.
~J. Mulcahy
