The weird fundraising question that helps you raise a surprising amount of funds

Hold on to your hat, because here’s a fundraising proposition that may look like a hot mess — but it can help you raise a lot of extra money from donors you never knew had the capacity to give large donations. Here’s the Question:

In the coming months, we will have a major push to [do something that the donor is likely to consider worthwhile]. We are looking for leaders to make gifts of $1,000 and up to create a matching fund that will encourage others to donate. Are you able to consider such a gift in the coming months?

That $1,000 is variable, based on each donor’s previous giving — the important thing to know is that it’s an extraordinary amount. Several times higher than the donor has ever given before.

It’s not asking the donor to give now, as we typically do in fundraising. That’s might be why it gives you the willies. It scared me the first time I saw it. It’s asking the donor to consider giving this large amount in the future. The donor has this range of answers to the question:

  • Yes. Please tell me more.
  • Maybe, but send me more information.
  • I’d love to! But not this year.
  • I can’t do this now, but I would be interested in talking about how else I can contribute.
  • Not now.

If you are a direct-response person, you might be breaking out in a nervous sweat right now. Isn’t it a cardinal rule to always go for immediate action?

Not in this case. The strategy here is to give the donor a chance to consider making an unusually large gift. That’s a much easier request than, Please send a really gigantic donation right now! The answer to that one is overwhelmingly NO — but the “think about it” question gets a handful of people willing to think about it.

And you now have two very valuable pieces of information:

  1. Some donors who have the capacity to give larger gifts than you knew about…
  2. … and also care enough to maybe increase their giving to a new level.

Here’s the thing: it works.

When you later get back to the people who answered that question with anything other than “Not now,” and specifically ask them for that large donation, you get an amazing number of large donations. Many of them from people you had no idea they had the capacity.

And many of those people continue as donors at that new higher level.

But that’s not all. Did you notice how the question said the purpose of the large donation as to “create a matching fund that will encourage others to donate”?

When you do this, you now have a Matching Gift Fund.

And that’s gold. When you properly apply a match to an already strong fundraising offer, you improve revenue by anywhere from 10% to 50%.

Bottom line: That strange question I told you about leads to a surge in revenue.

I’ve watched it happen many times. Often a record-breaking jump in fundraising results. And not just during the pandemic, when I say records breaking all over the place.

Most of what it takes to lift your fundraising to a new level is a host of complex and often difficult things. That’s life.

But here’s something that gets you there quickly.

Are you interested in applying this magic to your fundraising program?

I know how you can get there. This year.

The easy and almost foolproof path is to talk to the world’s expert on this exact topic, my friend and colleague Sean Triner.

And for the next couple of weeks, Sean is opening his calendar to people like you to talk about this fundraising powerhouse. For free.

Just click here to on Sean’s schedule.

This is super easy. You’ll end up with direct access to Sean’s calendar, and you can find a time that works for you. Then you’ll have a zoom meeting with him. He’ll ask you a few questions, and show you the way toward putting the Question to work.

It will cost you nothing, and you won’t be obligated or pressured to do anything. Just a quick conversation with a fun-loving guy Down Under who knows a lot about fundraising, especially this tool.

Give it a try. Talk to Sean. You have nothing to lose, but a lot to gain for your organization.


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The future of fundraising is not about social media, online video, or SEM. It’s not about any technology, medium, or technique. It’s about donors. If you need to raise funds from donors, you need to study them, respect them, and build everything you do around them. And the future? It’s already here. More.

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Jeff BrooksJeff Brooks has been serving the nonprofit community for more than 35 years and blogging about it since 2005. He considers fundraising the most noble of pursuits and hopes you’ll join him in that opinion. You can reach him at jeff [at] jeff-brooks [dot] com. More.


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The future of fundraising is not about social media, online video, or SEM. It’s not about any technology, medium, or technique. It’s about donors. If you need to raise funds from donors, you need to study them, respect them, and build everything you do around them. And the future? It’s already here. More.

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About the blogger

Jeff Brooks has been serving the nonprofit community for more than 30 years and blogging about it since 2005. He considers fundraising the most noble of pursuits and hopes you’ll join him in that opinion. You can reach him at jeff [at] jeff-brooks [dot] com.

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