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Ready to Ask for a Major Gift? Don’t Make These 5 Mistakes

You’ve done your homework. You’ve built the relationship, learned what matters to the donor, identified common ground, and prepared for your meeting. Now comes the moment you’ve been working toward: asking for a major gift.

Even experienced fundraisers can get nervous at this point. They may hesitate to name a specific amount, rush to fill an uncomfortable silence, or leave the meeting without a clear plan for what happens next.

The good news? These mistakes are avoidable. Here are five common missteps that can undermine an otherwise promising solicitation — and what to do instead.

5 Mistakes to Avoid When Asking for a Major Gift

Here are five common missteps that can undermine an otherwise promising solicitation — and what to do instead.

5 Major Gift Meeting Mistakes to Avoid Before You Make the Ask

A successful major gift solicitation rarely begins when you ask for a gift. It begins well before that — with whom you invite to meet, how you prepare, what you learn about the donor, and the kind of relationship you establish.

Get these things wrong, and even the most compelling case for support can fall flat. Get them right, and you create the conditions for a conversation that feels less like a fundraising pitch and more like an opportunity to explore what you might accomplish together.

Before we get to the five mistakes, I’d like you to try a quick visualization exercise. Think of a donor you’ve been hoping to meet with about a major gift.

Imagine Yourself in the Room with a Donor

Picture the two of you together. What would make this meeting feel comfortable, engaging, and worthwhile for both of you?

So let’s get curious. I’m going to ask you to close your eyes for a minute and imagine a donor you’ve been hoping to meet with about a major gift. Picture the two of you together. Where are you meeting? In your office? At the donor’s home? Over coffee? Or perhaps on a Zoom screen? Choose a setting that feels comfortable and where you could realistically see this meeting taking place in the next month or so.

Okay, do you have your donor and meeting place in mind? Excellent!

Now, before opening your eyes, imagine these four things:

1. You’re in the room together.
2. You smile. They smile back.
3. Someone else is there with you. Imagine you’ve invited this person to join you. Who are they, and how does it feel to have them there to support you?
4. Bolstered by the smiles and good company, what do you say to open the conversation?

SELF-EXERCISE: Ready? Close your eyes and picture your donor, your meeting space, the additional person supporting you, and how you’ll open the conversation. What are you saying? What might the donor say in response? Don’t think in terms of pitching what they can do for you, but of promising what you can do together. Play out the scenario just a bit, until you reach a place of comfort — or discomfort. Then open your eyes.

What did that feel like?

What felt comfortable? Uncomfortable? Did it feel more pleasant than you imagined? Smiling people, committed to the same cause, spending time together in a comfortable space… from such a space can come many good things.

• What did you say to open the conversation?
• How did that feel?
• If it felt good, why?
• If it didn’t, why?
• What might feel better?
• Do you think it might feel better to the donor, too?

REFLECT AND JOURNAL: Take a few minutes to jot down your answers. Whatever comes to mind first is fine; don’t overthink it. This simple exercise can help you shift the energy you bring to your next donor meeting — in real time.

A Mistake is Just a Misjudgment

It’s not fatal; you can correct it. But first you have to recognize it happened!