Unlock Bigger Gifts – 3 Types of Questions that Position Major Donors for Maximum Generosity

Why do too many major donor prospects not give, or give far less than their giving capacity?

One of the main reasons is because they have not been helped to see and feel the connection between their identity and making a gift to your nonprofit. Identity is the most powerful motivation for giving, because that turns the gift into an expression of who the donor is as a person.

No longer are they just giving to ‘help out.’ When giving as an expression of self-identity, they are now advancing their personal hero story through their gift. They are changing the story of their life, and making it closer to the one they want told about them even after they’re gone.

As a major gift officer, part of your job is to help donors in your caseload advance their hero story through giving.

Asking questions – the right questions – is your best approach for unlocking bigger and more impactful gifts.

What Comes Before This

Bear in mind that what you’re about to read doesn’t happen in isolation. As you know, the major gift cultivation process can take months, sometimes years.

What you’re about to read is not something you would use early in that process. This is best used after you have already established a relationship with a donor. They have already expressed interest in your organization, and they have begun to connect their identity with giving.

The questions you’re about to see are designed to be used after all that has happened.

In sales terms, these questions are more like ‘closing’ questions. The gift is in sight, and the issue here is how to make that gift bigger, and given with great enthusiasm.

For a start-to-finish exploration of major gifts fundraising from a donor story perspective, and to get hundreds more questions to use at specific moments within the cultivation process, sign up for Donor Story: Epic Fundraising, our groundbreaking online course, based on decades of research from Dr. Russell James.

Here are three types of questions you can start using in your later conversations with major gift prospects.

1. ‘How’ Questions

Once a donor prospect understands and believes that their identity is linked with giving to your cause, your goal at that point is to help them feel how incredible their gift really is, and how it enhances that identity. These ‘how’ questions enable the donor to reflect and come to terms with what has brought them to this point, so they follow through with making the biggest possible gift.

Why do these questions work?

Because stories are about journeys and quests. Overcoming obstacles. Pushing through challenges. ‘How’ questions ask the donor, how did you get here? How did you do this?

Here are some examples:

  • You’ve done so much for Charity Name. What allows you to be so generous?
  • How were you able to make such wonderful gifts?
  • What makes it possible for you to make this generous cash gift?

These first three questions attempt to get the donor to realize that their past gifts and their current gift say something truly amazing about them.

The idea is, other people could do this too, but they don’t. What makes you different? You want them to appreciate the journey they’ve already traveled, because it will make them that much more excited to complete the trek and finish with a bang – the biggest gift they can give.

Here are two more that take a different approach:

  • Have you ever given something other than cash to charitable organizations?
  • Are you planning to sell something this year that is worth more than you paid for it?

With these, you’re exploring the donor’s capacity to give gifts of assets, rather than cash. And you want to do this, because most wealthy people possess far more of that wealth in assets such as property, business equity, stock options, insurance, and retirement accounts.

These questions help the donor expand their paradigm of what constitutes a charitable gift. Where does that gift come from? How can you give way more than you had originally envisioned, and still feel great about it?

2. ‘Reverse’ Questions

A reverse question isn’t actually a question. It’s a statement that triggers a question from the other person. The idea with a reverse question is to get them to ask you a question that gives you the opportunity to share something you already wanted to share.

Now that you have their permission to share it, they will be far more interested.

Two of our favorite examples relate to how you describe your work as a major gift officer:

  • I help people give weird assets to Charity Name.
  • I help donors to Charity Name give in smarter ways.

If someone made either of these statements to you, what would you naturally say in reply? You’d want to know what defines a weird asset. What makes it weird, and how do you help people give them? What are some examples of weird assets other donors have given?

Likewise, how do you help donors give in smarter ways? You mean there are smart ways and dumb ways to give? What makes one way smarter?

See how that works? When you make statements like those to a prospect, their curiosity will compel them to ask you questions like these in response. And that gives you an opportunity to talk about gifts of assets. You can tell stories of smart ways other donors have given, and why it was smarter for them to do it that way.

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You can reveal your expertise, and expand the donor’s mind about what’s possible when it comes to charitable gifts.

That can only result in better outcomes for you.

3. ‘Follow-up’ Questions

Follow-up questions can be used in all sorts of conversations with donors, not just in the context of this article. This is true because following up demonstrates interest. It shows you’re listening, and that you care about what the other person is saying. You want to know more.

In this article’s context, following up increases the chances that you’ll get to talk about the sorts of topics that lead to bigger gifts, such as wealth planning, estate planning, and other methods.

Suppose you ask a donor if they have ever made any unusual investments. This could be art, real estate, baseball memorabilia – anything. If the donor says yes, then employ a simple follow-up question:

  • What’s the story on that?
  • How did you do it?
  • That must mean you’re good at investing. What happened next?

Keep the conversation going. Help the donor feel smart and important. Make them feel good about how they handle money. In doing this, you can also position their major gift as a smart investment.

These are just some of the benefits of good follow-up questions. Here are 10 more follow-up questions you can use in almost any donor conversation.

Bonus 4th Question Type – Collaboration Questions

In story language, your job is like that of the Sage, a common character archetype that plays a key role in the donor’s fundraising story.

Sometimes, a donor might express confusion, uncertainty, or frustration with the process of giving. So, maybe they’ve expressed a desire to give, but the nuts and bolts intimidate or annoy them.

Collaboration questions position you as a helpful guide who can walk with the donor through that process so they can fulfill their desired end goal – making a gift.

Some collaboration question examples include:

  • What’s holding you back from reaching your charitable giving goals?
  • What if it was possible to make a gift and still accomplish your financial goals? Would you mind if I shared some options with you?
  • You mentioned that you are going to be [passing the business on to your kids / selling your practice]. Would you be interested in charitable options that may save you money on your transaction?
  • You have been so generous to this cause in the past. Would you be interested in learning how to give more at a lower cost by using better assets?

When there’s a problem preventing the donor from making their gift, collaboration questions help address whatever that problem is. If you don’t know the problem, use the first question. The other three, and other ones you could develop, work for more specific situations.

Want more insights into donor story-based fundraising?

See 3 key elements of a good fundraising story


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1 year ago

Loved this post. Greg Warner is very likely both the most generous and also insightful high donor fundraising expert around, and I’ve been following several.

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