Let me be honest with you: I used to dread picking up the phone to talk to donors about gifts in wills. I’m an introvert who doesn’t work well with strangers, and the idea of having these conversations felt overwhelming.

But here’s what changed everything for me: I realized that bequest conversations aren’t really about asking at all. They’re about helping.

Why These Conversations Matter

The truth is, bequest fundraising success lives in the follow-up. When donors express interest and you send information but never follow up, most will simply never get around to it. Not because they don’t care, but because life gets busy and wills get pushed to “someday.”

Your conversations break that inertia. They create action. And most importantly, they help donors do something they actually want to do.

What It Feels Like When You Get It Right

Here’s what surprised me most: these are often the nicest conversations you’ll have with supporters. You’re usually calling people who’ve already expressed interest, which means you’re pushing on an open door. They’re expecting to hear from you.

When you approach these conversations from a place of being helpful rather than extractive, everything becomes easier. You’re not interrupting their day, you’re offering guidance on something they’ve been meaning to sort out.

A Few Things to Say That Make It Feel Natural

You don’t need to be a gifted conversationalist. You just need a few comfortable phrases:

Normalize it: “More and more of our supporters are including gifts in their wills to support causes they care deeply about. Is that something that might interest you?”

Make it relatable: “I’ve just spoken to someone like you about this,” or even “I’ve done it myself.” (Only if you really have)

Remove the pressure: “You don’t have to commit to anything now. Just think about it, and whenever you’re ready, we’re here to help.”

Offer options: “There are lots of ways to support the work you care about – volunteering, donations, and yes, including a gift in your will. Here’s what that might look like…”

The Secret: Questions, Not Scripts

The donors I’ve spoken with don’t want to be read a script. They want to be heard. So ask open questions like “What first made you passionate about this cause?” or “Why is it so important to you to make a difference?”

Then – and this is crucial – wait for the answer. Really listen.

Start Somewhere

You will need courage for your first few calls. I won’t pretend otherwise. But with practice, it gets easier. Much easier.

Remember: you’re offering something valuable. You’re giving donors a chance to create a lasting legacy around something they care deeply about. That’s not intimidating—that’s a gift in itself.

So take a deep breath, pick up the phone, and start the conversation. Your donors – and your organization’s future – will thank you for it.

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