Fundraisers love numbers – but we don’t always slow down to read them.

When I look at donor giving histories, I’m not just tallying lifetime value or calculating retention. I’m looking for inflection points. Clues. Moments that tell me a donor is thinking differently about their relationship with the organization.

You can spot those moments – if you know what to look for.

In my last blog post, I revealed my strategy for connecting annual giving to major and planned giving for board members. Through this process of telling the long version of donors’ origin stories, I saw patterns that repeated. I kept seeing similar types of gifts that signaled the donor had deepened in their connection to the organization’s mission.

Once you know them, you’ll be able to spot these in the gift histories of your current major donors. After a while, you’ll be able to see these gifts when they happen and optimize your systems to steward these donors to the next level!

Here are three gift types I always flag in donor bios:

1. The “Kick the Tires” Gift

This is the donor’s very first gift. It’s usually modest – $25, $50, maybe $100. But don’t let the size fool you.

This gift is a test. They’re watching how your organization responds. Do you acknowledge quickly? Do you give thanks personally? Do you make it easy to give again? Do they feel seen?

Most board members don’t realize that your largest donors often start right here. Not with a gala. Not with a campaign. But with a small, quiet gift and a lot of curiosity.

Track this gift like it matters – because it does.

By reframing first time gifts as “kick the tires” gifts, organizations leverage their systems to make sure every new donor has an exceptional experience and feels appreciated.

Ask yourself: Do you have any special communication or benefits that help first-time donors feel recognized? How I can I use email, phone, volunteer/board outreach, and mail to have this donor feel the love and their impact?

2. The “Hand-Raising” Gift

You’ve got a donor who’s given $100 a year for a decade. Then suddenly – boom – a $1,000 check shows up.

That’s not random. That’s intentional.

The exact numbers matter less than the jump. A $25 dollar donor jumps to $500. A $1,000 donor jumps to $5,000.

All of these are donors signaling interest. They’re re-evaluating what your work means to them. And they’re inviting you to respond.

When you see this kind of jump, drop everything and make a call. Not to ask for more – but to listen. What changed? What are they excited about? Who or what inspired the new level of giving?

This is your chance to deepen the relationship before they drift away.

Ask yourself: Do I have a notification system that will let me know when “hand-raising” gifts happens? What’s my process when I learn about them?

3. The “Breakthrough” Gift

Here’s where it gets exciting. You see a donor move into five- or six-figure territory, or they’ve set up a multi-year pledge. Maybe they’ve reached out about leaving a bequest.

This donor is no longer an annual donor – they are in the pipeline.

Yes, these bumps happen with personal visits and cultivation, but sometimes the donor decides to make the leap.

When I see this move, I bring them into a different lane. Personal stewardship. Custom impact reports. Invitations to help shape the vision, not just fund it. Because at this level, they’re not just giving – they’re investing.

This is where cultivation becomes partnership.

Ask yourself: How can I make sure I don’t miss any of these breakthrough gifts? What’s my plan to meet this donor and find out what their philanthropic goals are for the long-term?

In conclusion…

Make sure these three moments show up in your reports. More than data points, these three gift types represent real shifts in mindset. Catching them early and responding with intention is how you build a stronger, smarter pipeline.

Because fundraising isn’t just about chasing dollars. It’s about listening to the story those dollars are trying to tell you.

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…

• From $50 to Six Figures: How I Got Board Members to Care About Annual Giving
• Scripts to Bring Up Planned Giving Without Feeling Weird About It
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• What is Gracious Receivership and why Fundraisers Need to Practice It
• How to Ask for Donor Lists Without Delays or Drama

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.

If you liked this…

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• Rethinking Board Recruitment: The 4 Ws That Really Matter
• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• How to Build a Philanthropy Calendar That Drives Digital Donations
• How to Ask for Donor Lists Without Delays or Drama

In fundraising, we’ve spent decades perfecting donor-centered language – polished, warm, affirming. And there’s value in that. But as we lean further into equity, honesty, and shared power, we’re realizing something: partnership requires candor. Community centric fundraising built on that sort of trusting partnership is the future.

You can’t build trust on flattery. You build it on clarity.

That’s what my new resource is really about. It’s not a script. It’s not a list of ways to smooth over discomfort. It’s a toolkit for having honest conversations with donors – without losing connection, mission, or respect.

I’ve lost count of how many times I’ve been asked this question: "What do I even say when a donor asks [fill in the awkward, unexpected, or slightly skeptical question here]?"

If you’ve worked in fundraising for more than five minutes, you’ve felt that moment. Someone hits you with a curveball – maybe it’s well-intentioned, maybe it’s a little tense – and suddenly your mind goes blank. You want to respond with confidence and kindness, but your brain’s still trying to find the first word.

That’s why I created The Real Deal Fundraiser’s Quick Guide to Donor Questions.

It’s a free resource packed with clear, kind, mission-centered answers to the questions we all get asked – and sometimes dread. Whether it’s “Why do you need my gift if you already got a big one from [another donor]?” or “Can I trust you’ll use my money wisely?”, this guide helps you find your footing and keep the conversation moving in the right direction.

Underneath it all is a simple framework I first learned in phonathon and have used ever since:

Listen. Acknowledge. Support. Continue.
It’s not a script – it’s a mindset. And it works.

• Listen – Really listen. Not just to the words, but to the tone and subtext.
  If someone says “I’m retired,” don’t assume what that means. Are they joyfully gardening between river cruises, or feeling anxious on a fixed income? Same phrase, very different needs.
• Acknowledge – Show them they’ve been heard.
  “Sounds like you’ve had a big transition recently,” or “You’ve earned some rest after working hard for so long.”
• Support – Make your case with warmth and clarity.
  “We have donors in all life stages who support the mission in different ways.”
• Continue – Bring it back to the goal of the conversation.
  “I know you really care about [cause/mission]. We’d love to have you involved in a way that works for you – let’s discuss some options.” Then offer monthly giving, IRA Rollover gifts, etc.

This isn’t about avoiding tough topics. It’s about having the tools to meet them head-on – with empathy, strategy, and the kind of language that invites real partnership. Here’s an another example:

Donor: “What percentage of my gift actually goes to the mission?”

You: "Totally fair question. 100% of your gift supports our mission. That includes the people, infrastructure, and tools that keep programs going strong. We believe in full transparency, and you can always review our IRS Form 990 to see how resources are stewarded."

Pro Tip: Don’t shy away from the unglamorous parts of nonprofit work. They’re essential.

​Want to see the rest of the answers in the freebie? It’s loaded with examples. You’ll see how to apply this framework in real situations, with real donor language, and keep things moving forward without losing the heart of the conversation. Every answer in this guide is rooted in respect for donor autonomy and full transparency – two values that keep relationships healthy and real.

Think of it as a conversational compass – something you can adapt to your voice and situation – rather than a one-size-fits-all speech. You’ve got the passion and the instincts. This will help you put it into words – quickly, confidently, and with the clarity today’s donors (and communities) deserve.
​
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…

• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• Discovery Visits Demystified: Tips for Effective Donor Meetings
• The 3 Questions Donors Ask About IRA Rollover Gifts (and How to Answer Them)
• What to Say to Donors in Uncertain Times: The Near, Dear, Clear Fundraising Framework
• Leveraging National Estate Planning Awareness Week for Planned Giving Success

Whenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.”

He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves.

This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence.

But here’s what I’ve learned: Your mindset matters more than your pitch.

How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose.

Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing.
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Let’s walk through them.

One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes.

That’s not what’s happening.

Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves.

That’s not taking. That’s inviting them in.

I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up.

Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction.

Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke?

That matters more than you think.

If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift.

Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent.

You’re not just asking for money. You’re offering someone the chance to invest in something meaningful.
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Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence.

I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time.

The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out.

There’s an old joke in our field about someone like that:
“How is <<that fundraiser>> like a 7/11 store?”
“They never close.”

Funny – but also kind of painful. Because many of us have been that person. I know I have.

We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask.

And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step.

​Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird.

So, what does this mean for you?

If you want to grow as a fundraiser, start by checking your mindset.

• Do you believe there’s value on both sides of the conversation?
• Are you willing to receive, not just facilitate?
• Can you honor the relationship by being direct about the opportunity?

Fundraising isn’t begging. And it’s not manipulation.

It’s invitation. It’s partnership. It’s a shared pursuit of something that matters.

My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it.

Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are.

Cheers!

​Jessica

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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My grandfather wasn’t a big donor. He only gave to a handful of causes in his lifetime. But there was one organization that always stood out: St. Jude Children’s Research Hospital. He gave faithfully – moved by the emotional weight of their television commercials. The stories got him every time.

But even though he was already giving, they kept sending him address labels. Over and over again.

At the time, I didn’t get it. Why send him stuff he didn’t ask for when he was already clearly connected?

Years later, working in fundraising myself, I learned what was going on. Those labels weren’t a thank-you. They were part of the ask. A fundraising tactic. A subtle nudge rooted in the psychology of reciprocity: we gave you something, now give something back.

And while it might work once, that kind of giving rarely sticks.

The truth is, these built-in freebies – address labels, calendars, stickers – don’t deepen connection. They dilute it. They train donors to expect something with every letter, and more importantly, they shift the focus away from the mission.
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I still wonder: would my grandfather have kept giving without the commercials? Maybe not. But I know this for sure – it wasn’t the address labels that made him care.

Let’s get practical. Including giveaways in your appeals may seem harmless, but it creates three major problems:

1. It sets the wrong tone.
You’re not building connection – you’re mimicking a subscription box. That’s not what we’re here to do.

2. It costs more than you think.
Printing, shipping, design, fulfillment – it adds up fast. Those funds could go straight to your mission.

3. It attracts short-term, low-retention donors.
This is the biggest problem. Donors who give because of a trinket are less likely to renew, upgrade, or become champions for your cause. You want committed supporters, not one-time transactions.

And There’s a Legal Catch, Too
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Let’s talk taxes. When you include a premium with your appeal, you risk turning that gift into a quid pro quo contribution – where only part of the donor’s gift is tax-deductible because they received something in return. To avoid that, the item has to be of “insubstantial value” – meaning so cheap it’s practically worthless. And if the gift is that insignificant, why bother sending it at all? You’re adding printing, packaging, and postage costs for something that can’t carry real meaning or message weight. It’s a logistical headache with no lasting return.

Here’s what’s wild: Most donors don’t even want the stuff. They want to be moved. They want to know their gift means something.

That’s where Near, Dear, and Clear comes in:

• Near: They feel close to the cause.
• Dear: The mission matches their values.
• Clear: They understand what their gift will do.

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No label sheet in the world can deliver that. But a compelling story can.

This isn’t a full-on war against every branded item. There’s a time and place – but intention matters.

• Give tokens in stewardship, not acquisition.
• Let them be surprises, not bait.
• Make sure they reflect your mission, not just your logo.

A bookmark made by a student in your afterschool program? That’s beautiful.
A bulk-ordered mug with your fiscal year slogan? Probably unnecessary.
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Would you give your best friend a water bottle to say thank you?
Or would you write them a heartfelt note of thanks?

If you’re stuck in a cycle of sending “stuff” or trying to break the premium habit, here’s where to begin:

1. Lead with stories.
Make your appeal emotionally rich and mission-focused. Don’t let a keychain carry the message.

2. Map the full donor journey.
Gifts shouldn't unlock access to your best content. Welcome everyone into the story, not just your VIPs.
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3. Test it.
Try a premium-free version of your next appeal and track the results. You might find your message carries more weight on its own. And don’t forget to track retention of those new donors acquired (with premiums and without) in the next year of giving.

The truth is, you don’t need gimmicks to raise money. When you lead with purpose, your donors feel it. And they’ll stick around.
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Mission-centered messaging doesn’t just build trust – it builds staying power.

The Smart Start Fundraising System will show you how. I break down what motivates giving without resorting to trinkets and help you build a complete plan grounded in what matters.

[→ Get on the waitlist now or check out the course here.]
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Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this…

• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• What With Love, Meghan Can Teach You About Donor Relations
• Culture of Philanthropy Check-Up

As a college freshman, I responded to an announcement on the Honors College listserv (that may give you a clue how long ago this was) for a job talking on the phone to alumni. I thought this was a dream job. All I needed to do was talk to people and make money. As an extrovert who had been trained by her manners-minded Southern mother to “make good conversation” my whole life, I had no qualms about keeping the conversation going and making folks like me on the phone.

After becoming a student supervisor in the call center, I quickly realized that most folks needed more structure and examples of what to say to have success at building rapport in conversation. It was indeed an art. I’ve now spent a couple of decades helping to systematize and teach the process of successfully talking to someone new. Over the years, I’ve learned that the secret to great conversations is the same whether you're a college student, a seasoned fundraiser, or even a 7-year-old girl chatting with her great aunt. It all comes down to asking the right questions.

Questions help us connect and connecting with a donor is essential before you ever ask for a gift. The right questions remove roadblocks and pave the way for a strong, lasting relationship between the donor and your organization. People give to people they like. As a fundraiser, you’re the bridge connecting the donor to your institution. Your goal in a discovery visit is to listen, learn, and understand what truly motivates them.
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Bad rapport-building does more harm than good. Questions should always stimulate a lively back and forth. Think dialog, not monologue. The best questions also extract valuable information, make the donor feel appreciated, and naturally lead to the next step in cultivation.
​
Here are my favorite questions to ask during a discovery visit:

The key to a successful discovery visit isn’t just asking great questions – it’s truly listening to the answers. Take notes, follow up thoughtfully, and use what you learn to deepen the relationship. Building real rapport makes every future conversation easier and more meaningful. When the time comes to ask for a gift, you’ll know exactly how to approach it in a way that aligns with their motivations and values.

What’s your favorite discovery question to ask donors? Drop it in the comments—I’d love to hear what works for you!
​
Cheers!

​PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!

If you liked this… 

• What With Love, Meghan Can Teach You About Donor Relations
• 8 Essential Skills for Success in Fundraising
• Discovery Visits Demystified: Tips for Effective Donor Meetings
• What Makes for Great Rapport Building
• Culture of Philanthropy Check-Up

As we turn the page to a new year, it’s the perfect time to reflect on the incredible impact your donors have made on your organization. Donor appreciation isn't just about wrapping up last year's success - it’s about laying the groundwork for lasting relationships that will sustain your mission well into 2025 and beyond.
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In nonprofit fundraising, donor retention is key. It’s much easier (and more cost-effective) to retain a donor than to acquire a new one, which is why a thoughtful approach to showing gratitude can be a game-changer. Starting the new year on a note of appreciation can make all the difference in keeping those relationships strong. Here are six creative and practical ways to show your gratitude this New Year:

Instead of sending out traditional holiday cards, why not opt for a New Year’s card? It’s a great way to stand out, especially since January mail isn’t competing with the December rush. At my current institution, where we serve a multi-religious community, we steer clear of specific religious holiday cards, but New Year’s cards offer a respectful and inclusive option.

This isn’t just about sending a card; it’s about showing donors they’re valued as you enter a fresh chapter. By sending a message of gratitude and well wishes for the year ahead, you remind them that their support is crucial to your mission’s success.

Why It Works: A New Year’s card avoids the crowded December mailbox, acknowledges diverse traditions, and sets a positive tone for the year ahead.