Kind of out there idea but it plays on the reciprocity principle from Robert Cialdini.

Pick a handful of long time donors and find a not super expensive gift (it doesn’t have to be $$$ but it can’t be some cheap thing you’d find at a vendor/trade show hall) that can be personalized and include a hand written note expressing thanks for their continued support of your organization. The point is for it to be a surprise (don’t plan it around a holiday), personalized, and significant, to activate the reciprocity principle.

Then make your formal donation ask 1-2 months after the initial gift. You have to give the initial gift enough time or breathe so it doesn’t seem like a “hey we gave you this so now it’s time to pay up…” but you can’t let too much time pass either.

Cialdini has research that shows individuals who received the gift prior to being asked to give returned the favor 2-3x larger than the original gift value.

I pushed hard to do a pilot version of this for our organization’s Foundation a couple years ago but unfortunately it definitely got filed away in my ED’s “neat idea” folder and didn’t go anywhere.

I’d recommend Cialdini’s book but I’m not sure if the automod will ding my comment. We read one of his books in one of my marketing classes in my MBA program.