by Haley Limo

I’m going to let you in on a powerful strategy—my ultimate secret weapon in fundraising.

It all revolves around a single, "magic" question. When deployed correctly, it effortlessly steers any conversation straight into a meaningful discussion about giving.

The real magic happens in how you handle their response; that’s where the true art of donor relationship management begins. But first, you have to be willing to ask.

Ready for it? Here is the question:

"How do you make your giving decisions?"

In my experience, this simple, seven-word question consistently delivers incredible results. It’s my go-to because it fits seamlessly into any stage of donor engagement. Whether we're just getting to know each other, following up on a recent gift, making a formal ask, or deep in the stewardship process—it always works.

I often introduce this question right at the beginning of a donor relationship, perhaps during an initial coffee chat or after an unexpected contribution. Its brilliance lies in its versatility. It doesn't just reveal how they give to our organization; it opens the door to understanding how they approach philanthropy across the board. Their answer essentially hands you a roadmap for your next steps.

For example, a donor might reveal that they map out their giving once a year after receiving a bonus, or perhaps during an annual family foundation retreat. Others might give spontaneously, while some have a strict giving calendar.

Asking this question might accelerate your solicitation timeline because you discover they are making decisions right now. Or, you might learn they won't be allocating funds for another ten months—giving you the perfect runway to cultivate a deeper relationship in the meantime.

Understanding a donor's strategy is non-negotiable. Major donors almost always have a method behind their philanthropy, and to successfully secure major gifts, you need a window into that process.

Donors aren’t just going to hand you their giving roadmap on a silver platter. If they did, fundraising would be easy! A great development professional is, above all, a great question-asker. Remember: if you are talking more than the donor is, you’re doing it wrong.

You might even ask this question and hear that a donor simply gives "where they feel led" and strongly dislikes being formally asked. Well, guess what? Now you know exactly what your strategy should be for that specific donor!

But you will never know until you ask.

I’ve seen too many development officers freeze up, genuinely scared to ask questions about money or giving. But honestly, inquiring about their philanthropy is the most natural thing you can do! It’s the entire reason you are meeting—because they gave, or might give, to your cause. Donors know this!

Believe me, it’s only awkward if you make it awkward.

In every personal interaction, our goal should be to put the ball in the donor’s court. This little seven-word question is the perfect "pass."

Practical Tip: Over the next few weeks, identify two people you can ask this question. If you're feeling nervous about discussing giving, start with friendly faces—like a board member or a highly engaged volunteer. Just give it a try!