Is Your Donor Ask Too Aggressive—Or Just Bold Enough?

By Kate Jaeger-Thomas

We coach a lot of our clients to aim higher when approaching a donor with a solicitation. As someone who spent decades fundraising for arts institutions, I know where that hesitation comes from. In the moment, you worry about overdoing it and scaring off the donor—possibly forever.

That fear is real. We’ve all heard (or experienced!) stories about an ask that went sideways, or a donor who dropped their support when their expectations met the reality of the cost of bringing a new program to life. In one of my own first big solicitations, the donor seemed incredibly offended, and I was sure I’d missed the mark.

But a week later, they came back. Not only did they agree to the gift in full, but they wanted to make two payments instead of the four I suggested.

What Is Too Aggressive, Anyway?

One faith-based client recently shared that “aggressive is in the eye of the beholder” and I couldn’t agree more. There are some examples that we know go too far, like making a multimillion solicitation with no context or sending a message to your entire membership asking them to donate $20,000.

For those of us who have been at this for a while, however, defining an aggressive ask is subjective—and finding that line between discomfort and aggressiveness is all about doing your homework. In most cases, I’ve found that an ask was seen as an overreach because the fundraiser was trying to fit a donor into their timeline rather than meeting the donor where they are.

Lead with Curiosity, Not Assumptions

To avoid that situation, I try to build several strategic questions into donor conversations. Asking a donor, “When would be an appropriate time to talk about giving?” or “Where do you see yourself in this campaign?” or “How do you and your family approach philanthropic giving?” can yield a lot of helpful information that can shape your solicitation strategy down the road.

For instance, you may find out that a donor needs more information about the goals and costs of a program before they’re ready to sign on. Maybe there’s a board member or organization leader who, with a little coaching, would be better suited to make the solicitation. Or maybe your gut is telling you that their expectations are misaligned and you need to spend more time understanding the donor’s goals.

Give the Donor Space to Digest

If you’ve done that prep work and feel confident about your approach but the donor still reacts with uncertainty, it’s OK to acknowledge that and give them time to consider. I’ve seen new philanthropists who aren’t used to being asked and don’t know what to expect, as well as long-time donors who don’t understand the nuances of what you’re trying to accomplish. The way forward in either situation is giving them space to take in the information.

Discomfort is Where Transformation Happens

In the end, I’m not sure there’s such a thing as an aggressive ask. We need to be curious and listen, we need to slow down and make sure we’re all on the same timeline. And in my experience, being assertive—even if it’s not exactly the right moment—never ends a relationship. 

However, discomfort is a necessary part of this work—sometimes the hardest part. When you run a major capital campaign or you set a big goal for your organization, you’re undergoing a change and that can be uncomfortable for anyone. But when you do big things, you have to put yourself out there in big ways. That discomfort is where the transformation happens.

Are you worried that your approach is too aggressive? Or worse—that you’re holding yourself back? Our team can help you make sense of your donors, data, and goals to develop a plan for transformational giving. Schedule a free strategy session to get started.

Learn more about Heller Kate Jaeger‑Thomas, Consulting Services Director, on our Team Page.