7 Tips to Ask Friends for Capital Campaign Gifts (Without the Awkwardness)

Every week on our peer support calls, nonprofit leaders from all over the country gather to swap stories, share tips, and tackle thorny campaign questions. During a recent call, Hilary, an Executive Director at a small historical society, leaned in with a compelling question.

Hilary explained that she’s lived in her community for years and has lots of long-standing friendships. Nearly all those friendships predate her role as Executive Director at the historical society.

She now finds herself knee deep in the quiet phase of her campaign and needing to speak with several of her friends about the effort. Some of her friends already give annually to the organization, some don’t, but she thinks they might be interested. And yet, Hilary admitted that she’s been dragging her feet. She confessed:

“It just feels awkward. I’m not sure how to handle asking my friends for money.”

Heads were nodding in sympathy all around the virtual room. Let’s be honest: asking friends for philanthropic support can feel tricky. But in a capital campaign, those conversations are often essential.

7 Tips to Make Asking Friends for Capital Campaign Gifts Less Awkward

The good news is that with the right mindset, you can make the experience feel natural, respectful, and even fun. Here are seven tips to help you get there.

1. Ask for Advice on How They’d Like to Proceed

Sometimes the best way to honor the friendship is to invite your friend into shaping how the ask happens. You can acknowledge the relationship and give them the option to choose a path that feels comfortable. This might sound something like:

“Because we’re friends, I want to be thoughtful about how we approach this. Would you prefer that I be the one to share project details with you, or would you rather someone else from the campaign team reach out?”

This not only reduces awkwardness but also shows that you care about maintaining trust in the friendship first.

2. Ask Permission to Ask

Start by giving your friend control:

“Would you be open to hearing about a project I’m involved in?” or “Can I share something exciting and if you’re interested, invite you to consider supporting it?”

By asking permission first, you’re inviting your friend to answer a low-stakes question before the (far) higher-stakes question of, “Will you give?” Instead of feeling cornered, they can decide whether or not they want to hear more. If they say “yes,” they’ve opened the door themselves, which automatically makes the conversation smoother and more comfortable. And if they say “no,” you’ve avoided the awkwardness of a direct ask and preserved the friendship without pressure. A win-win!

3. Lead with the Mission, not the Money

Start by sharing why the organization matters to you and the difference you believe the project will make:

“I’ve gotten involved in this campaign because I really believe in the impact it will have on our community. It’s one of the most exciting projects I’ve ever worked on, and I’d love to share it with you.”

When friends see your genuine passion, the conversation feels less transactional and more like an invitation into something meaningful.

4. Frame It as an Invitation, not a Personal Favor

Avoid making it feel like you’re asking for a personal favor. Instead, say something like:

“I’m not asking for a personal favor for me. I’d love to invite you to be part of something bigger than both of us, something really meaningful. Your gift would help make this project possible.”

This shifts the focus to shared impact rather than obligation.

5. Call Out the Awkward Feelings

Calling out the elephant in the room can instantly put everyone at ease. Try something like:

“It feels a little awkward to bring this up because we’re friends, but I care so much about this project that I’d regret not exploring whether it’s of interest to you, too.”

6. Acknowledge Your Two “Hats”

Be transparent that you’re both a friend and a volunteer or staff member connected to the organization you represent. Say something like:

“I want to be clear that I’m talking to you right now with my [XYZ Organization] hat on, not just my friend hat. Our friendship comes first, though, and I’ll always be transparent about which hat I’m wearing.”

Naming your roles helps your friend understand the context and builds trust that they’ll never be blindsided.

7. Make Gratitude the Centerpiece

Whether your friend gives a large gift, a modest one, or nothing at all, thank them sincerely for considering it. Gratitude strengthens relationships and leaves the door open for future engagement. Consider something like:

“Thank you so much for considering this project. Whether you decide to give or not, I’m really grateful that you took the time to listen.”

A Real-World Lesson in Asking Friends for Gifts

I’ve been in Hilary’s shoes myself — deeply rooted in a community, navigating a high-stakes fundraising role, and surrounded by friends who cared about the organization, too. I remember how heavy the hesitation felt, but I learned something important:

It’s usually far more awkward for you than it is for your friend.

When you lead from the heart, act with integrity and transparency, and ask permission before diving into an ask, the relationship almost always deepens. More often than not, your friends will appreciate being invited, and they’ll value even more that the friendship doesn’t hinge on their answer.

With these seven strategies, you can approach friends with confidence, knowing your ask is rooted in respect and transparency.