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[ASK AN EXPERT] How to Engage Major Donor Prospects Who Blow Hot, then Cold

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Our Ask An Expert series features real questions answered by Claire Axelrad, J.D., CFRE, our very own Fundraising Coach, also known as Charity Clairity.

Today’s question comes from a fundraiser who wants advice on ways to stay in touch with potential donors who have major donor potential. 

Dear Charity Clairity,

Do you have advice on ways to stay in touch with a possible donor who has indicated an interest in making a major gift? They approached me regarding a gift of property, but they seem wishy-washy whenever I approach. 

I’ve had several conversations with him, and he says I can stay in touch. However, when I call, I don’t know what to say, and he’s not a big talker. I just don’t know how to proceed. 

I presented a mock-up brochure showing how we would use the property and promote the associated services, but I don’t feel I’m moving the needle at all. Any ideas?

— At a loss

Dear At a loss,

It can be tricky to get someone to enter into a relationship with you, especially if they’re at all ambivalent about doing so. With folks who haven’t donated to you before and who are primarily motivated by their own desires—be it unloading a hard-to-sell property, leaving a legacy gift, or some combination thereof—it can be even more complicated.

I don’t know if your donor is known to you or not, but sometimes donors will approach more than one charity simultaneously with the same offer. They’re essentially “shopping” for the best deal. In this case, it’s important that you don’t begin by bending over backwards to please them. 

There are two reasons for this:

1. You don’t really know them well enough yet, so you’re shooting in the dark.

When you showed him your brochure, you made assumptions about what the donor most cares about. Before doing so, it would’ve been better to ask some open-ended questions that invite the donor to elaborate on why making this gift would mean a lot to them. 

You can’t offer them something of value until you truly know what they value. So before getting to the solution, try sussing out the problem. What does the donor want to accomplish by making this gift? For donors with a charitable intent, this is pretty straightforward. 

It’s harder if they don’t have a charitable intent, but you can lead them there. Try asking questions like:

  • What caused you to become interested in this, and why is it important to you?
  • What is it about our vision and mission that most resonates with you? 
  • What part of our work do you find most inspiring?
  • How would you rank your philanthropic priorities?
  • What would you like to know about us that you don’t already know? 
  • If you had to pick one thing that our organization should never stop doing, what would it be? 
  • What can you tell me about your family?
  • If you had a family slogan, what would it be?
  • Who were your heroes and mentors growing up? 
  • What are the most important things you learned from your parents?
  • What do you want to teach your children and grandchildren? 
  • How would you describe your personal mission?
  • If people remember one thing about you, what would you like it to be?
  • What philanthropic gifts (time or resources) have been the most meaningful to you, and why?
  • What makes you hopeful, and why?

2. You don’t want to lose sight of whether the gift’s purpose truly aligns with your mission.

One human services charity I know was approached by a donor wanting to give their city residence so the nonprofit could use it as a shelter for children with disabilities. The donors had their personal reasons, including (1) they had a niece with a disability and wanted to help other children like her, and (2) they wanted to avoid capital gains taxes on the appreciation in their property, while also receiving a sizable tax deduction. Both are reasonable objectives. 

However, while the proposal aligned with the nonprofit’s mission, it was not central to it. The residence would house a maximum of four children at a tremendous annual operating cost. This would be out of whack with other programs operating at a lower cost and serving much greater numbers of people.

Bending over backwards to please these donors might ultimately mean robbing future children, families, and seniors of essential resources because you’re diverting funds to sustain other needs. This was not an insurmountable problem, but it was something that needed to be authentically raised with the prospective donors. 

In order to do so, you can ask questions like:

  • What do you think we should do?
  • Do you have suggestions about ways we might approach this issue?
  • Are there others you would recommend we contact you to brainstorm this idea?
  • How would you approach next steps if we want to bring this project to fruition?
  • Can you tell me more about that? This is one of the best open-ended questions I know.
  • What’s the best philanthropic decision you’ve ever made? Why? This keys you into information about what type of impact your donor is hoping to have and how they evaluate opportunities. 

Instead of making statements or asking yes/no questions, you should ask open-ended questions. And don’t ask leading questions or questions with an agenda or a particular idea in mind. Those could sound like: “Don’t you think you should…?” Or “Here’s my brilliant idea; what if we were to try this?”  

Questions that assume things and questions that fall into preaching mode—these are no-nos. Try to really stay in listening mode. Be fully present to suss out the donor’s agenda before thinking about yours.

My best advice is simply to try different tactics. And, finally, maybe if he won’t respond to you, he’ll respond to someone else. Put your ego aside, and ask if he’d like you to put him in touch with your executive director, board president, a specific program director, or anyone else you think he’ll perceive as a VIP. Sometimes “no” simply means “not you.”

Hope this helps you to no longer be at a loss and to move on to a big win,

— Charity Clairity

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