Recently, I helped a client prepare for a donation ask in the millions. Before we talked about the amount, we worked through the opportunity, the donor’s connection to it, and what that gift would accomplish.

The number needed a reason behind it.

With year-end giving approaching, consider this: Some of your donors may give $500 to your organization and $5,000 or even $50,000 to another.

Is that organization doing better work? Showing more impact?

Not necessarily. They may be making a better ask.

You cannot control a donor’s priorities or finances. But you have more influence over the size of the gift than you might think.

Sending everyone the same generic appeal with three giving options can leave significant support on the table. For donors with greater giving potential, consider these five moves:

1. Stop letting their last gift set your next ask.

A $500 gift tells you what someone gave. It does not tell you everything they could give or what would inspire them to do more.

Review giving history, involvement, interests, and what you actually know about their capacity. Build a short list of people who deserve a personal conversation.

2. Find out what matters to them.

Before you present your priorities, understand theirs.

“What part of our work means the most to you?”

That simple question can tell you more than another round of guessing in a staff meeting. Their answer should help shape the opportunity you bring them.

3. Give the larger gift a specific job.

“We need your help reaching our year-end goal” puts the focus on your budget.

A stronger ask connects a specific amount to a clear result: expanding a program, serving additional families, or funding a defined project.

Show what the gift will make possible and how you will report back. Make sure the numbers hold up.

4. Make an actual ask.

“Anything you can do would help” leaves the donor to figure out what you need.

Try: “Would you consider a $10,000 gift to help us accomplish [specific outcome]?”

Explain why you thought this opportunity would matter to them. Then pause. Give them room to think, ask questions, and respond.

5. Start the conversation before the December rush.

A larger gift may require several conversations. Give donors time to understand the opportunity and consider their involvement.

Reach out now. Share the vision. Agree on a next step. Follow up personally.

Here’s the leadership challenge: Do not let your discomfort with asking decide the size of someone else’s generosity.

You are responsible for presenting a thoughtful, credible opportunity. The donor gets to decide how they respond.

Before your year-end appeal goes out, choose ten donors who warrant a more personal approach. Build an intentional ask for each.

Need help turning your year-end appeal into a strategy for larger gifts? Reply, and let’s talk.