5 Strategies for Turning Smaller Major Gifts into Larger Ones

What’s the only thing better in fundraising than a major gift?
A bigger major gift.
If you’ve been reading this blog for a while, you already know that major gifts provide the bulk of funding for most large and mid-size nonprofits. If recent trends continue, that’s only going to increase. So in your quest to grow your major and planned giving fundraising, ask yourself what’s easier and more cost-effective:

A: Inspiring a new major gift from a new donor
B: Motivating an existing major gift donor to give more

Neither should be considered ‘easy,’ and your organization is probably trying to do both. But consider this: if you have a repeat donor with whom you have a personal relationship who has signaled that they’d like to give $25,000, what might it take to help them seriously consider moving up to $30,000 or $35,000?

And maybe you have another repeat donor who is ready to give $10,000. Isn’t it likely that you might be able to help them recognize the value they’d gain from moving up to $15,000?

Think of it this way…
If your major gifts fundraising department was able to consistently close gifts at slightly higher amounts, it could mean hundreds of thousands or even millions in additional revenue every year for your organization.

Consider the cost of doing that in relation to the cost of attracting new donors — especially low-dollar donors.

Cost of attracting new donors = $ ?
Cost of increasing the size of a major gift in the decision-making stage = $ ?

Plus, remember that my Fundraising Report Card’s benchmarks found that only about 16% of new low-dollar donors acquired in 2020 gave again in 2021.

With all that in mind, let’s look at five ways to increase the size of your major gifts among previous donors. These are ways to inspire past donors and surprise donors, techniques to motivate larger giving amounts, and a solution for that evergreen question, “How much do I ask for?”

1. Follow Up With Value
Dr. Russell James explained the following in his Fundraising Myth & Science Series: If fundraising were like a movie, then failing to follow up would be like rolling the end credits right after the hero accepts the challenge and begins their quest. Wait! The movie isn’t over yet!

In fundraising, deciding to make a gift isn’t the end of the story. It’s merely a major decision a person has made in their journey to change the world as they develop their personal hero story by giving to your organization.

If you don’t follow up, you aren’t letting them continue their story. You aren’t giving them a chance to relish their victory and enjoy the part of their identity they enhanced for themselves when they gave.

Unfortunately, it seems like too many fundraisers are taught that getting the gift is the end of the story. For them (or, more likely, their leaders and administrators), closing the gift concludes their quest to raise money. That’s why they often drop the ball when it comes to following up with donors after the gift is made.

Sending thank-you cards, having a board member or volunteer or even the founder/CEO make a quick thank-you call, mailing letters detailing the impact their gift will have — these are powerful ways to keep the donor engaged and make them feel extra happy about their donation. They work because they provide value.

And when someone decides to make a planned gift, follow-up is even more crucial, because it might be 10, 20, or 30 years before you receive that planned gift. If you don’t follow up, what are the chances that person will alter their plan later and take your organization out of it?

Pretty high.

The fortune is in the follow-up — especially if you deliver value.

2. Invite Supporters to Fill Out a Questionnaire After an Unsolicited Gift Is Made
It happens all the time. Someone on your list unexpectedly sends in a significant gift. When that happens, consider responding with much more than a thank-you note and a receipt for tax purposes. Send them a questionnaire by mail and email, or pick up the phone and ask the questions yourself.

Of course, this is yet another way to follow up. But make no mistake, it’s an especially powerful one! Your supporter will appreciate your interest if you ask questions such as these:

  • What inspired you to make the gift you just made?
  • How did you come to learn about our mission or cause?
  • I can help you stay connected or get involved more. If you could wave a magic wand to get what you want, what would that be?

These might not suit your approach perfectly. But I hope you get the idea. The bottom line is this: a question or two like these provides additional value to your donor. It shows that you care, and you want to help them find even more meaning from their giving (assuming you continue to follow up after they answered your questions).

They also build trust and position you as a helper, potential counselor, or engagement facilitator. When you combine trust with added value, your relationship with your ‘surprise donor’ will have a chance to grow much further.

Think of it like this. Your questionnaire is a conversation-starter. Or more accurately, it’s a way to re-start and deepen the conversation you didn’t realize you had going with them before they made their initial gift.

3. Steward Past Donors
You already know that stewardship is the ongoing process of nurturing and engaging with a previous donor in ways that make them feel like you care about them and you’re using their money appropriately. It’s more than follow-up, because now you are actively proving that you and your organization are trustworthy.

Never forget that major donors often make gifts to test you. They want to see how you’ll treat them so they can determine whether to give more. That’s why you need to think of each gift as an audition. If you deliver a valuable experience, they’ll be back for more of what you provided, and their gifts will grow. If you don’t? You may never see them again.

What are some stewardship strategies? Here are a few:

  • Send fresh updates on how their first gift is being used
  • Tell impact stories about specific people who have benefited from their gift
  • Share videos of their dollars being put to good use
  • Show how their gift led other people to give
  • Put their name on a wall of honored donors
  • Call them up now and then just to check in on how they’re doing – no asks
  • Talk like friends – take them out to dinner and catch up on life

The idea with stewardship is to confirm past wins for this donor while deepening the relationship. People like to win. If you help them remember their past wins, they’ll want to repeat those victories. Plus, people want to feel like they matter.

So make sure you report back in ways that focus on them, not you and your organization. Use phrases such as:

  • Because of you…
  • Thanks to you and your generous gift…
  • We couldn’t do this without your generosity…
  • As a result of your thoughtfulness…

If you show them how much their giving matters and help them feel it, they will give again and increase their gift amounts.

4. Use Fundraising Menus
The first three ideas on this list were for after a gift was made. But what about getting a major donor to increase their giving? One of the best tools for achieving this is to use fundraising menus.

Menus help to solve a common fundraising problem: how to determine the perfect ask amount, which invites two conflicting fears:

  • What if I ask for too much and scare them away?
  • What if I ask for too little and miss out on a bigger gift?

In both cases, fundraising menus reduce the fears associated with ask amounts. They also help make gifts bigger because they provide a better donor experience. Menus help supporters make decisions and connect those decisions to impact.

Here’s an example of a menu from Red Bull Theater in New York City:

Red Bull Theater - ways to show how donors can support Red Bull Theater

That menu is a good start. But your menu should do three things:

  1. Provide specific giving options that your supporters can see or at least visualize.
  2. Make clear that other people are giving at each of the menu selection amounts and even higher (Red Bull Theater missed this opportunity).
  3. Include options that encourage dialogue so you can customize a menu item that resonates with specific donors.

Build your menus around the donor’s capacity. If you believe the donor can give $50,000, then make most of the giving options higher than that.

Just be sure to keep the menu simple and easy to digest. Don’t give them ten giving options. That’s too many. And don’t take a whole big paragraph to describe each giving option. Use bullet points, pictures, and graphics or icons. Show impact in societal benefit and value to the donor, not just cost. For instance, $100,000 builds five playgrounds for underprivileged kids, while $10 million endows the building of playgrounds for all time.

5. Ask for More
In a survey of 1,000 major gift officers, 20% of them were found to have raised 75% of the total dollars raised by the organization.


Because those were the fundraisers who boldly challenged donors to give at or above their capacity. The bottom 80% only asked for about 40% of their donors’ capacity ratings.

That proves that the most effective major gifts fundraisers are the ones who make the biggest, most heroic asks. The stretch asks.

They ask with confidence because thanks to meaningful engagement over time, they understand each donor’s connection and motivation. Plus, they position themselves as counselors and guides, not just solicitors.

If they learned through engagement that a donor’s giving capacity is $50,000, they might try asking for $60,000 or $75,000. Something that challenges the donor. Something that makes them seriously consider their gift, so they gain a greater victory and more identity enhancement.

Yes, in this case, thinking is good.

If you can get them to think deeply about their gift before they make it, they will become more emotionally invested in that gift. They’ll press you on it by asking questions or demanding customizations that add value for them.

Think of it this way:

If you asked a very wealthy person for $10,000, they might not even bat an eye. But if you asked for $10 million, they would at least have to consider the decision.

Everyone has limits like that, even people with average amounts of money. You don’t think much about buying a latte, but you’d think harder about buying lattes for your entire fundraising department. Then you’d consider the value of such a purchase. You’d look at it as a relational investment instead of just a transaction.

And if you decided to do it, you’d feel pretty strongly that you made a good decision. Otherwise, you wouldn’t have done it.

You want your ask amounts to challenge the donor in the same way.

Still, the amount does need to be attainable, so don’t go too high. This again speaks to the value of using fundraising menus. They help you zero in on the right amount. They help you build value you’ll deliver in exchange for their money.


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