I was fortunate in my role at the University of Southern Mississippi. My VP made space for me – literally – on every board agenda. I had a standing spot to update the USM Foundation board on annual giving, and I could use that time however I saw fit.

Sure, I gave them numbers. But I didn’t stop there.

I used that time to give them the narratives beyond the numbers. Histories. I pulled the giving records of donors they already admired – the names they knew from building dedications and big announcements – and traced them back to their beginnings. Because almost all of them started small.

I wanted the board to see what I saw every day: Annual giving isn’t just about this year’s total. It’s about long-term trust. It’s how major donors begin. The large gifts you are getting today started with trust-building 10 or more years ago. And how you are treating your $50 donors today is how you are treating your future major and planned giving donors of tomorrow.
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This post is about how I helped shift board thinking – from shrugging at $50 gifts to recognizing them as the first step toward six-figure support.

At every board meeting, I brought receipts. Literally.

I’d share two or three donor stories. Not headline gifts. Origin stories. I’d pull the giving history of a well-known benefactor – the kind of donor whose name was etched on a building or whose estate gift had changed our endowment – and I’d start at the very beginning.

Turns out, the beginning wasn’t glamorous. No gala. No VIP treatment. Just a reply card in the mail or a quick online donation. Often $50, sometimes $100. Inspired by a direct mail piece or a phone call from a student caller.

I told the story of how that first gift came in. How we acknowledged it. How we followed up. What kind of communication they received. How they were stewarded over time. And then I showed the leap: four-figure giving. Five. Sometimes more.

By the third or fourth board meeting, it started to click.

Annual giving isn’t just about dollars this year. It’s a pipeline. And more than that – it’s a vetting process. Donors with real capacity don’t show their full hand right away. They start small. They're testing your systems. They’re watching your stewardship. They want to know: Will my gift make an impact here? Can I trust this organization to be a good partner?

And the truth is, annual giving is the only system robust enough to keep that door open over time. It keeps your data clean. It helps you stay in touch when someone changes jobs or cities. It gives you cues about life changes that might signal major or planned giving potential.

It’s not just donor acquisition. It’s donor cultivation in slow motion.

When I layered in real data – about how much of our major gift pipeline had once started with a $25 or $50 gift – something shifted. Board members started asking about the annual giving numbers. They started taking the appeal letters home. A few even gave leadership annual gifts themselves.

The modest gifts didn’t seem so modest anymore.

And that’s the whole point.

If you want major and planned gifts tomorrow, you have to care deeply about annual giving today.
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Cheers!

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

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Each year, I get a little more reflective about what actually moves the needle on Giving Tuesday. It’s one part adrenaline, one part strategy, and one part relationships – the same ingredients that fuel fundraising the rest of the year, just turned up a few notches.

This year? We hit our match. We saw strong donor response. And we learned a few things worth carrying into the next big push.

Here’s what worked:

1. The Match Game, with a Twist

Last year, we had a $20,000 match and hit it – barely. It took extending our deadline to pull it across the finish line. This year, with our donors’ permission, we split that ask into two: two $10,000 matches from two separate donors. One for Giving Tuesday. One saved for Calendar Year-End.

It created a sense of focus. One target, one day. And we met it.

Now we can head into December with some real momentum. “We hit the match on Giving Tuesday” makes a great line in every follow-up email. It tells a success story that donors helped write – and that builds confidence for the next ask.

2. Direct Contact Beat the Megaphone

Most of our gifts came through personal outreach. Not social media. Not big email blasts. Just me and my annual giving staffer reaching out by phone and plain emails from our Outlook inboxes.

That’s where the action happened. That’s where the giving happened.

I’m not knocking digital strategy – it plays its role. But, for us, Giving Tuesday was won in the inbox and on the phone. This reinforces my observations I wrote about earlier this fall about digital burnout and the reprise of analog communications.

3. Board Engagement Started Early

More than half of our board gave on Giving Tuesday. That didn’t happen by accident.

We start talking about Giving Tuesday in September. By November, they’ve heard the plan, seen the goal, and received a cheat sheet with sample language and graphics to share on social. The week before Giving Tuesday, we send that cheat sheet again.

And this year, they showed up. Not just with gifts, but with pride – and we’re closer to hitting 100% board giving for the year because of it.

4. Targeted Appeals to Past Giving Tuesday Donors and LYBUNTs

We made it easy on ourselves this year. Instead of trying to inspire everyone on our list, we reached out to the people who’ve already shown us they like giving on Giving Tuesday.

We pulled two lists:

• Calendar year LYBUNTs (gave in 2024, but not yet in 2025)
• Anyone who has ever given on Giving Tuesday before

When the subject line says, “I know you like to give on this day…” it doesn’t feel like a cold call. It’s a reminder. And it works.

5. Monthly Donors and Pledgers Want to Participate, Too

This one surprised me last year and held true again.

Donors who already give monthly or have pledge commitments still want to be part of Giving Tuesday. They like seeing the school hit a goal. They like contributing to a match. So, they give again.

That meant a few extra gifts came in from already-committed supporters. Nothing huge – but meaningful.
Here’s how we handled those emails:

"I hope you are doing well! I wanted to reach out today to let you know that it is Giving Tuesday and Starr King School for the Ministry has a goal of raising $10,000 to reach a challenge match of $10,000 (for a total of $20,000 for this beloved school).

If you would like to participate, as you have so generously done in the past, your gift would again be matched 100%. Just visit www.sksm.edu/givingtuesday TODAY and you can make your gift online.

Also, we know and appreciate ALL you have done for Starr King as sustainers this year so please don’t feel obligated to give more. I just know you have given to matches in the past and wanted to make sure you knew!"

​No pressure. Just an invitation to be part of something they’ve supported before.

Giving Tuesday doesn’t have to be a guessing game. It’s a day to do what already works in your shop – just more of it, with a little more urgency and clarity.

We focused on:

• Real relationships
• Targeted outreach
• Simple, achievable goals
• And donor behaviors we already knew from our data

It paid off. Not just in dollars, but in board engagement, team morale, and a strong hand to play as we close out the year.

And that’s the kind of success worth repeating.

Cheers!

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads

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When I taught my first graduate-level course this summer – Ethical and Community-Centered Fundraising – I expected good questions. What I didn’t expect was just how much anxiety would surface around one specific topic: planned giving.

These were smart, values-driven future leaders. People already thinking in terms of justice, legacy, and long-term impact. But the minute we shifted into planned giving, the energy changed.

It wasn’t the concept they struggled with. It was the conversation.

How do you bring up wills and estate plans without making it weird?
What if you say the wrong thing?
What if it feels morbid – or worse, transactional?

At their request, I created a simple guide: real phrases, grounded in real situations, to make legacy conversations feel natural, honest, and even hopeful.

Turns out, it’s not just my students who need this.
So if you’ve ever felt that same hesitation – this post is for you.

Because here’s the truth: Planned giving conversations don’t have to be awkward. They can be inspiring. They can even be joyful.

You don’t need to be a tax expert. You just need to know how to bring it up – gracefully and confidently.

Let’s start there.

Sometimes you’ll have donors reaching out first – through your website, a legacy giving survey, or in response to a donor story. Those are the easiest planned giving conversations because the interest is already there.

​But when you need to be the one to raise the topic, here are some ways to bring it up without making it feel heavy:

• “I know how deeply you care about our mission. Have you ever thought about how you’d like that impact to continue in the future?”
• “We’ve been talking a lot about your commitment to this cause. Some donors choose to include a gift that lasts beyond their lifetime – has that idea ever crossed your mind?”
• “Can I ask – have you done any estate planning? Sometimes people like to include a charitable gift, and I always make sure our most loyal supporters know that’s an option.”
• “You strike me as someone who thinks ahead. I wonder if you’ve ever explored including causes you care about in your long-term plans?”
• “You’ve done so much for this organization already. If you ever want to talk about ways to make your impact last, even after your lifetime, I’d love to be part of that conversation.”

​You’re not pushing. You’re not being morbid. You’re simply opening a door – letting them know that this kind of giving is possible, meaningful, and available to them.

You do need to have these conversations. Here’s why:

🟢 Planned gifts are huge. On average, they’re 200–300x the size of an annual gift. That’s because they’re made from lifetime assets, not income. (Source: National Estate Planning Awareness Week)

🟢 They’re already in your database. The donors who are most likely to leave you in their will? They're not wealthy strangers. They’re the consistent supporters who’ve given every year for the past decade. (Source: How to Talk About Death and Taxes)

🟢 You’ll never know unless you ask. A $25-a-month donor might be planning a six-figure bequest and never mention it unless you give them a reason to.

🟢 There’s $12 trillion on the move. The Great Wealth Transfer is projected to move $84 trillion by 2045, with $11.9 trillion going to charitable causes. That wave is already building. (Source: How to Talk About Death and Taxes)

🟢 Peer stories work. When donors hear from others like them who’ve made legacy commitments, your inbox starts filling up with questions – not awkward ones, but warm, intentional ones like: “Can I do this too?” (Source: Planned Giving Leads Don’t Generate Themselves)

🟢 You don’t need to overcomplicate it. Bequests and beneficiary designations are all most donors need to know. These are simple, flexible tools that don’t require financial wizardry or legal acrobatics. (Source: Cut Through the Clutter)

These conversations become easier when you stop thinking of them as talking about death and start thinking of them as talking about legacy.

“What if your annual support could live on forever? By including [Your Nonprofit] in your estate, you could turn your yearly gift into a lasting endowment.”

This is about continuity. It’s about making their values stretch beyond a single lifetime. It’s not about dying – it’s about staying connected to something they believe in.
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And when you position it that way, it doesn’t feel grim. It feels good.

Your donors won’t bring this up on their own unless they’ve already made a decision. Your job is to create the conditions where that decision becomes possible.

And that starts with language – gentle, honest, open-ended questions that let the donor lead, but make it clear that legacy giving is an option you believe in and value.

So don’t be afraid to ask.
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And when they say yes? Be ready with the next step: a landing page, sample language, a checklist, or a simple conversation about how to make it happen.

📌 Want a quick win? Use these same phrases in:

• Your direct mail acknowledgments
• Thank-you calls to long-time donors
• Conversations with board members and volunteers
• Email or social media content during National Estate Planning Awareness Week

Planned giving isn’t about “the ask.” It’s about the invitation.

When you know how to extend it with confidence and care, the whole conversation shifts – from something to avoid… to one of the most meaningful parts of your work.

​Cheers!

P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.

If you liked this…

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