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.
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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…

• 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…

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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.
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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!
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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… 

• 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.