Difficult Fundraising Conversations

Many years ago, I was working at a university that was just starting its foray into a capital campaign. We had spent many months cultivating one of our most loyal donors with the goal of getting her to make the lead gift for the campaign—a gift of several million dollars.  Finally, she said YES.

I don’t need to describe the excitement and sense of accomplishment.  Several weeks later, the president and I went to get the papers signed, and as we handed her the gift agreement, she hesitated before taking it in her hand, sighed deeply, put the agreement on the table, pushed it away and said, “I don’t know.  This is an awful lot of money.  I really need to think more about this gift.”

You are kidding, were the words that went through my mind.  But, of course, I didn’t say anything.  My president, however, did

“Yes, it is an awful lot of money,” he agreed mildly.  “And that is what makes it such a transformative gift.  Remember when we talked about how this gift will not just fund some programs, but will also be the impetus for others to also make stretch gifts?  Our university will be forever changed because of your generosity.  You will be positively impacting our students and our programs.  None of that has changed—this gift says yes to the future, yes to your vision and yes to your leadership.”

And then he did the hardest thing imaginable.  He kept eye contact with her, kept smiling….and kept silent.

Difficult conversations come in all shapes and sizes.  For me, first as a fundraiser and now as a consultant, the most difficult ones are those where I think I have a yes only to watch it turn into a maybe or a definite no. You’re kidding, still comes to mind, but if I am to successfully turn things around, I have to make sure that those words never leave my mind and get said out loud.

So what happened with our suddenly elusive lead donor?

She sat still for a very long moment.  Then she slowly started nodding her head.

My gift will allow you to go public with the campaign, right? She asked.

She was assured it would indeed.

And it will ensure that the Student center—her main interest–will be built?

Oh yes.

She continued in this vein, making the case to us as we had made it to her over many meetings and many months. And finally she pulled the gift agreement back to her….and signed.

What did my president do that turned the tide?


  1. He agreed with her concern, saying in effect, you are correct.
  2. Then, he reminded her why the gift was so large and what it would do.
  3. He showed her how the gift supported what mattered to her—impacting students, transforming the school, and yes, being seen as a leader.
  4. And, while he didn’t specifically ask her again to say yes, he showed her what saying yes meant.
  5. Finally, he kept his mouth shut, and let her close the deal all by herself!

Of course, not all conversations are so straightforward, nor is it always so easy to get a situation back on track!

That was the situation one of my clients recently dealt with.  Let’s call him Joe, my client’s donor.  He had seemed enthusiastic about the project she told him about.  He appeared interested in what she was saying. He hadn’t shrunk back or looked aghast when she put a price tag to the project and talked about the size of gifts that would be required to get the project going.  And at the end of their meeting, he took the prospectus she had prepared and said that he would share this with his wife.

But when she called to set up a meeting with him and his wife, Joe told her that “would not be necessary.”

For a nanosecond, my client was cautiously happy.  She thought perhaps he might say “We love this project and we are going to make a gift of …..” But, of course, that is not how things played out.

A meeting would not be necessary, Joe said because they weren’t going to support the project

My client was unprepared for this.  And so, instead of having that difficult conversation right then and there—and at the very least, starting to move it back to a better place—she simply thanked him for his time and hung up.

But the truth was, he was a great prospect and she couldn’t afford to simply let it go.  With great trepidation, she called him back and asked for a meeting—to which he said no.  So she took a deep breath, and dove directly into a difficult conversation.

Joe, she said, I heard loud and clear that you and your wife are not interested in supporting our project, and I’m hoping that you will be willing to share with me why. And then she stayed silent.  Her job right now was to find out if this was:

  • A no forever or just for now.
  • A no to the organization or just to the project
  • A no to a gift or just to a gift of this size

Joe finally answered.  “It just didn’t seem right for us,” he said. And then HE remained silent.

My client took a deep breath and asked Joe if he could tell her a bit more.  “I really want to do a good job for my organization and, especially, for you and your wife.  And so I need your help in order for me to understand what might be right for the two of you.”

I’m not going to paint a pretty picture here—Joe didn’t immediately open up and tell my client the words she wanted to hear.  What he did say was words to the effect of “I don’t know.”  Which sounds a lot like “I need to know more about you, your organization, this project, and what my gift will mean beyond you reaching your goal.”

On the plus side, Joe did agree that she could stay in touch.  Before she reaches out again, my client needs to find a peer who can influence Joe and his wife, a project person who can show them how their gift will be spent, a story about how another gift of the size she asked Joe for has been used (or is being used).  In other words, she needs to go back two steps and get Joe and his wife both interested and involved with the work they do.

Difficult conversations often occur because difficult situations occur.  I’ve had donors tell me that they won’t give a dime until “so and so is no longer the board chair.”  And then there was the time I took over as ED from a gentleman (I use that word very loosely here) who embezzled over a $100,000.  My board tried to hide this fact, but as will always happen, word got out. For about 7 months, fundraising was anything but fun.  I didn’t want to have conversations with our donors, but these were conversations I had to have.

Here is a list of Seven Steps to Framing a “better” difficult conversation.  I’ve stolen these from a variety of sources—and given the similarity of the lists I’ve “borrowed from”, I suspect that I am not the first or the last thief.

  • Name the issue—Clearly and directly. Don’t start the conversation by saying, “Hi, how’s it going?”  Do start by saying why you are having this conversation.  This has been a very difficult time for our foundation; learning that the executive director embezzled from us—from you!—has been devastating.
  • Specifically illustrate the behavior of the situation you want to change. The board wants to make sure a situation like this can never happen again. I want you to feel that this will never happen again.
  • Describe your emotions about the situation. It has always been important to me that I work transparently and that my donors always know how their generosity is being used. I accepted this job with a commitment from our board that our highest values are honesty and integrity.
  • Clarify what is at stake. I know that you and other donors feel that your trust has been abused.  This impacts our students and I know that what all of us want is that they get the very best education possible.
  • Identify your contribution to this problem. My work is cut out for—I have to regain your trust.
  • Indicate the wish to resolve the issue My hope is that over the next several months I will be able to do that.
  • Invite your partner to respond I would very much like to hear from you what I need to do to ensure that our students can continue to benefit from your support.

Yes, it was hard.  Difficult conversations ARE hard.  But, truthfully, they become most difficult when you don’t have them.

When you do, your difficult situations will become more manageable, and you will be able to get things back on track and heading in the right direction


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