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A Cautionary Tale: How a Gift Solicitation Goes Wrong

By Andrea Kihlstedt

A Cautionary Tale: How a Gift Solicitation Goes Wrong

Have you ever wondered what the ideal number of people is to solicit a gift?

Is a one-on-one meeting best? Or perhaps you should bring two people… maybe your President and campaign chair? Or perhaps three people would be even better — president, campaign chair and board member.

Sounds reasonable, right? Get a power team to solicit a power gift! But here’s a story that will set you straight.

Spoiler alert: It’s not about how many power players you send to solicit the gift, it’s about how you treat your donor!

Planning the Solicitation of a Gift of $1,000,000

Dan is a major donor. He and his wife made one of the top gifts to the XYZ Organization’s last campaign. He was serving on the board at the time. But his term ended two years ago. The campaign chair of XYZ asked him to serve on the campaign steering committee, but he turned him down, saying that he was too busy.

XYZ is in the quiet phase of a big, $10 million campaign and the leadership has high hopes that Dan will once again make a million dollar gift.

Because the stakes are so high, they decide to put together the best, most powerful solicitation team they have. They gather the President, the Campaign Chair and a current board member who happens to be a close friend of Dan and his wife, Joan.

They schedule a meeting with Dan and his wife, letting them know that they were coming to ask them for a gift to the campaign.

The Solicitation Plan

The three solicitors get together to plan the solicitation. Here’s the plan they came up with:

  1. The president will start the meeting, telling Dan and Joan about XYZ and how it has grown and developed since Dan was on the board.
  2. The campaign chair will tell Dan and Joan all about the campaign. What it’s for and why it matters.
  3. Then the board member will take over. It will be her job to ask Dan and Joan for a gift of $1,000,000.

They all agreed that once the board member asked for the gift, they will all be quiet until Dan responds. Then the Campaign Chair will manage the rest of the conversation, tying down the details of the gift.

What Happened When they Asked for the Gift?

At the appointed time, our power team drove to Dan’s lovely house. Dan and Joan ushered them into the living room. Our three solicitors sat on one side of the coffee table. Dan and Joan sat on the other. After a bit of small talk, they got down to the solicitation.

As planned, the President started and spent about 10 minutes talking about the growth and success. Then, he turned to the Campaign Chair, saying:

“Jeff, why don’t you tell Dan about the campaign.”

And Jeff, the Campaign Chair, launched into his 15-minute description of the campaign. Afterwards, Jeff turned to the board member, and she picked up smoothly, saying:

“Dan, we know you care about our organization. You’ve been one of our most generous donors and we are so very grateful. We are hoping that you will consider a leadership gift of $1,000,000 to this campaign.”

All three people on the solicitation team sat quietly and waited patiently for Dan’s response. After what seemed an interminable amount of time, Dan responded this way:

“We’re in the middle of another project and can’t decide now. Give us a call in six weeks and we’ll let you know then.”

The board member pushed back, telling Dan how important his early leadership gift would be to get the campaign off to a strong start. But Dan wouldn’t budge.

Six weeks later, the campaign chair called Dan with high hopes. Without much fanfare, Dan said:

“I’m sorry to disappoint you, Jeff, but we’ve decided to give you $50,000 this time around.”

And that was that.

What Went Wrong? The Other Side of the Story

On the surface, this sounds like a text book solicitation. They put together a power team. They planned the solicitation carefully. What did they miss?

Dan’s wife happens to be a friend of mine. Here’s what she told me:

Dan had rotated off the board two years earlier. We went to a couple of events there after that, but we really pulled back because we got involved in a big campaign for another organization we support.

No one thought to ask us what we were doing. They didn’t give us a chance to tell them about our new interests. They didn’t ask what we thought of the project their campaign was funding. They simply assumed that we were still as committed as we had been.

They hadn’t done their homework well. And honestly, they put us in an awkward situation.

What was the most galling part was that the only time they stopped talking was after they had asked us for money. It was demeaning. It seemed as if the only thing they cared about was our money — not us.

And honestly, for me, the meeting was infuriating. No one asked me what I thought. No one even looked at me. Everyone assumed that the decisions about our giving were up to Dan. We make our giving decisions jointly and I’m a big part of the process.

Would we have given more had we felt that they were interested in us?

We wouldn’t have given a million dollars this time, but if I hadn’t had such a bad taste in my mouth from that meeting, I probably could have convinced Dan to do a good bit more.

3 Lessons to Learn from this Sad Solicitation Tale

Now that you’ve heard both sides of this gift solicitation gone wrong, there are a number of lessons you can learn — three stand out the most.

1. Talk to your largest donors before you solicit them.

Find out what they are up to. Get a sense of their level of interest and excitement for your project. Ask what’s going on with them and what their current interests are. Don’t wait to talk with them until you are ready to ask for a gift.

2. Don’t make assumptions about who controls the money.

Don’t assume that the man controls the money and makes the giving decisions. When you speak with a couple about making a gift, be sure you pay attention to both of them. If you don’t know how they make their decisions, find out! If you ask, they’ll tell you.

3. Have a conversation rather than a presentation.

When you plan a solicitation, don’t just plan a series of presentations to be delivered one after the other. Instead, plan to ask real and probing questions and let the answers guide your solicitation. The solicitation should be a conversation and not just a presentation.

Are there any other lessons you can learn from this cautionary tale? Share your thoughts in the comments below.

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Filed Under: Major Gifts

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Reader Interactions

Comments

  1. Barbara Gross says

    September 16, 2025 at 2:23 pm

    Andrea – thank you for sharing this cautionary tale, which was cringeworthy!
    So many missteps… the solicitation team viewed it all from the inside-out, not the outside-in; there appeared to be no ‘how’ questions; and there was no pre-amble, no curiosity expressed to explore the donors’ passions and priorities. And so much more…

    And don’t get me started in 2025 on directing the ask only to the husband. Yeesh!! It is so helpful to hear the (potential) donor’s side of the story — I hope the ‘power team’ did a debrief and will learn from this experience. Hearing about and learning from the failures is so valuable.

    Reply

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