Giving Tuesday and Major Gifts: The Matching Gift Opportunity

 Giving Tuesday is coming!

And I think it's wonderful that we have a day dedicated to celebrating generosity.

Organizations are preparing their emails, social media campaigns, matching challenges, and all the excitement that comes with a day focused on giving.

But I want to talk about something that can get lost in all that activity. 

Giving Tuesday isn't how most major gifts happen.

Think about your major gift donors. Are they sitting at home scrolling through Instagram, waiting for your organization's Giving Tuesday post to inspire them to make a $50,000 gift?

Probably not! That doesn't mean they aren't generous. Or that they won't participate in Giving Tuesday.

But significant philanthropic decisions are usually more thoughtful than that. They grow out of meaningful conversations. Shared values. A genuine understanding of what matters to the donor and what their generosity can make possible.

Someone may see your campaign and spontaneously give $100. Or even $1,000. Wonderful!

But a donor considering a significant investment in your mission is often having a very different conversation. And that's where major gift fundraisers need to keep their attention.

Giving Tuesday Has a Job. So Do You.

Giving Tuesday can be terrific for annual giving, broad participation, bringing new supporters into your mission, and celebrating generosity. I'm all for those things!

But your major gift work is different.

You've been investing time in getting to know individual donors, understanding their interests and values, and exploring opportunities for their philanthropic giving. Those conversations don't suddenly become less important because a national giving day is on the calendar. 

And I worry when major gift fundraisers are pulled away from those conversations to focus on a one-day campaign.

There is, however, one particular opportunity I think major gift fundraisers should consider.

Matching gift opportunities. Not simply because your organization needs one, but because a matching gift can be a wonderful opportunity for an existing donor to inspire generosity in others.

Could a Major Donor Inspire More Giving?

Let's think about what your organization has accomplished on Giving Tuesday in previous years.

How many donors participated last year? How much did you raise?

Maybe it was $7,000. Perhaps it was $70,000.

If your organization has participated for several years, look at those results together. How many donors typically participated? What's your average gift size? And how much revenue does Giving Tuesday usually generate?

Now, sit down with your annual giving or communications team and discuss what might be possible with a matching gift.

For example, if your organization typically raises $70,000 on Giving Tuesday, imagine having a donor willing to match gifts up to $100,000. If your campaign inspires $100,000 in qualifying donations, that $100,000 match could bring the total to $200,000!

Or perhaps your Giving Tuesday campaign typically raises $7,000. A donor might be excited about providing a $10,000 matching challenge to help you reach a new goal.

The numbers will be different for every organization.

But before you start looking for someone who can make the gift, think about WHY a donor might want to offer a match.

Perhaps they're passionate about encouraging more people to support your mission. Maybe they want to help a particular program reach more people. Or they love the idea that their generosity could inspire others to give, creating an even greater impact than their gift alone.

Those are the conversations worth having.

What About Matching Gifts From NEW Donors?

Here's another possibility I particularly like.

Rather than matching every gift received on Giving Tuesday, what if a major donor offered to match gifts from new donors? For some major donors, that is enticing.  Your organization can focus on introducing new people to its work, while your matching donor helps inspire their first act of generosity.

This could be especially appealing to a major donor who cares about growing the community of supporters around your mission. The team might even explore a challenge that encourages existing supporters to invite friends, family, or colleagues to participate.

Of course, you'll want to agree on the details. What constitutes a new donor? What's the maximum matching amount? When does the match begin and end?

Those decisions should be clear before the campaign launches. But the larger opportunity is about more than doubling the dollars.

It's about inviting more people into the mission and giving your matching donor the opportunity to inspire that generosity.

My First Matching Gift Was $40,000

The first time I asked a donor to provide a matching gift, it wasn't for Giving Tuesday. It was for our annual year-end fundraising campaign.

I approached a donor couple who was already giving at the $40,000 level and asked whether they would consider making that year's gift a matching challenge.

And they said yes!

What I loved about that experience wasn't simply securing the $40,000 commitment. It opened up an entirely different conversation about their giving. Instead of thinking only about the annual support they would offer, we were talking about how their generosity could encourage other people to participate and support the work.

It introduced new possibilities for how they could partner with our organization, and it opened the door to broader conversations about their philanthropic interests. Their gift wasn't just about what they could give. It became an opportunity to inspire what others might give, too.

That's what I want you to consider when thinking about a matching gift. Not simply how much money you could raise, but how the opportunity might align with what matters to the donor.

And I've seen this work in other circumstances, too. I've had coaching clients successfully invite donors to make a second gift in the same year to support a Giving Tuesday match.

Don't assume someone who's already given this year wouldn't consider another gift. And don't assume they will, either. You won't know until you have the conversation.

How Do You Approach a Major Donor About a Match?

Start with the relationships you already have.

Think about donors who have demonstrated a strong belief in your mission, who enjoy encouraging others, or who have expressed interest in helping your organization reach more people. Perhaps you've discussed matching gifts with them before. Or maybe this is an entirely new idea.

Either way, begin by thinking about what you know about the donor.

What might make this opportunity interesting to them? Then make a personal invitation to explore it.

You might say: 

"You've mentioned how much you'd like to see more people become involved in supporting our work. We're exploring a matching gift opportunity for Giving Tuesday, and I immediately thought of you. Would you be open to a conversation about how your generosity could inspire others to participate?"

Or, if you already have a strong relationship and have discussed their giving:

"Last year, we raised $70,000 through Giving Tuesday. This year, we're hoping to build on that success, and we're considering a matching gift challenge of up to $100,000. Knowing how important this work is to you, would you consider offering a match that could encourage others to give?"

Notice that you're not simply asking for money because your organization needs to reach a campaign goal.

You're inviting the donor to consider an opportunity that may be meaningful to them. And you're being elegantly direct about what you're requesting.

Of course, you should also be prepared to discuss the details: the matching amount, whether the match is dollar-for-dollar, the types of gifts that qualify, and how the donor would like to be recognized.

Some donors may love being publicly acknowledged as the inspiration behind the challenge. Others may prefer to remain anonymous.

Don't assume. Ask.

Is It Too Late to Ask for a Matching Gift This Year?

Giving Tuesday is December 1, and we're already well into November. I'll be the first to tell you that this conversation would ideally have happened weeks, or even months, ago.

But that doesn't necessarily mean you've missed the opportunity.

If you have a donor who typically gives toward year-end, someone with whom you have an established relationship and who is comfortable having giving conversations with you, it may be worth exploring.

Especially if you have good reason to believe a matching challenge might appeal to them.

But please don't start calling every wealthy prospect in your portfolio hoping someone will agree to a $100,000 match in the next couple of weeks. That's not the approach I'm suggesting.

Look at what you already know about your donors. Consider their interests, their previous giving, and the conversations you've been having. And if there's someone who might genuinely be interested, invite them into a conversation.

And before making the invitation, make sure your annual giving and communications colleagues have the capacity to put a matching campaign together in the time remaining.  This may be a plan that you activate for next year. 

If the answer is "Not Yet," or the timing isn't right, that's useful information. Perhaps you've opened up an opportunity for next year's Giving Tuesday or another campaign.

Not every meaningful conversation needs to result in a gift by December 1.

Don't Let Giving Tuesday Distract From Your Major Gifts

Here's where I want to return to my original point.

Giving Tuesday can be wonderful. And a thoughtful matching gift can be an excellent opportunity for a major gift donor to inspire broader generosity.

But don't let the excitement surrounding a one-day campaign pull you away from the donor relationships you've been cultivating all year.

Your major donors may receive campaign emails, see social media posts, or participate in Giving Tuesday themselves. That's fine! Just make sure you know what communications they're receiving, particularly if you're already discussing a significant gift with them.

And don't set aside important donor conversations simply because everyone in your organization is focused on December 1. You still have donors considering year-end gifts. You have proposals to follow up on, visits to schedule, and relationships that need your attention.

Giving Tuesday has a job. So do you.

And for major gift fundraisers, that job is to continue building the meaningful connections that lead to significant philanthropy.

Your Assignment This Week

Here's what I'd encourage you to do if your organization would like to consider major gift support for Giving Tuesday:

1. Have your team analyze your Giving Tuesday history. How many donors participated last year? How much did you raise? What's been typical over the last few years?

2. Talk with your team about matching gift opportunities. Would matching all gifts or encouraging new donors be especially meaningful for your organization?

3. Identify one or two major donors who might be interested. Think about their motivations, previous giving, and the relationship you've built. If there's a natural fit, invite them into a conversation.

And while you're doing all of this, keep your other major gift conversations moving forward.

A matching gift can be an exciting opportunity. But it's not a substitute for the thoughtful, connection-based fundraising you do throughout the year.

Because meaningful gifts usually begin with meaningful conversations.

 The Year-End Major Gifts Series | Part 2 of 6

Part 1: Year-End Giving: Less Frenzy, More Focus

Coming next: Part 3 — That Donor You Haven’t Called? They Probably Aren’t Thinking What You’re Thinking.

Q: Can Giving Tuesday be part of a major gift fundraising strategy?

A: Absolutely! One of the best opportunities is inviting an established major donor to provide a matching gift that encourages others to participate. Start by considering the donor's interests and motivations. Some donors may enjoy inspiring broader participation, while others may be particularly interested in helping your organization attract new supporters.

A Giving Tuesday matching gift should grow out of a meaningful donor relationship, not simply the organization's need to reach a campaign goal.

Q: How do you ask a major donor to provide a Giving Tuesday matching gift?

A: Begin by reviewing your organization's previous Giving Tuesday results and identifying a realistic matching opportunity. Then consider which existing major donors might be interested in encouraging others to give.

Approach the donor personally, explain how the match could inspire additional generosity, and ask whether they'd be open to discussing the opportunity. Be clear about the potential matching amount, the purpose of the challenge, and what participation would involve.

Most importantly, connect the opportunity to what you already know matters to the donor.