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.
​
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.
​
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…

• National Estate Planning Awareness Week
• Cut Through the Clutter
• Planned Giving Leads Don’t Generate Themselves
• How to Talk about Death and Taxes
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

This week, gratitude has been on my mind even more than a normal November.
​
One of my favorite professors from undergrad, Dr. Stanley Hauer, passed away recently. He was incredibly smart, deeply generous with his knowledge, and so precise in his thinking and teaching that decades later, I can still draw the entire Indo-European language family tree from memory. Because of him, I could once recite the opening of Beowulf in Old English and The Canterbury Tales in Middle English.

​Two nights ago, I pulled out my old British Studies binder (I studied The Legends of King Arthur with him in London) and I flipped through page after page of notes, careful outlines, maps, diagrams, and lecture handouts. I could practically hear his voice. He was meticulous. He expected a lot. And what he gave all of us was a kind of training in how to think clearly, how to care about language, and how to carry knowledge forward.

He’s been on my mind so much lately.

And it got me thinking about the gifts we’re given that don’t show up on transcripts or diplomas. The ones we carry long after the exams are over.

I was a scholarship recipient at The University of Southern Mississippi. Donor support made it possible for me to study abroad, to intern in D.C., to attend conferences at places like Princeton. I heard lectures from world-class scholars because someone gave to our University Forum series. I graduated with minimal student debt and a wide-open sense of possibility.

But what those scholarships really bought me wasn’t just travel or resume lines.

They bought me the chance to sit in classrooms like Dr. Hauer’s. To learn how to make connections across centuries. To feel my brain stretch around ideas I wouldn’t have encountered any other way. That’s the kind of education no one can ever take from you.

And here’s what I know now, after years in fundraising: somewhere, a donor (probably many donors) made that possible. Someone gave to the Honors College. Someone gave to the Annual Fund. Someone gave to international programs. Someone gave to make sure a curious kid from Alabama could see Van Gogh’s Starry Night in person – and come home thinking differently about the world.

That’s why I do this work. That’s why I believe in it so deeply.

Donors often never meet the people they impact. But that doesn’t make the impact any smaller. It might make it bigger. Because it means we give not just to people we know – but to a future we believe in.

This Thanksgiving, I’m holding deep gratitude for the education I received, for the donors who made it possible, and for the professors – like Dr. Hauer – ​who shaped the way I see and think and live.

May we all honor the people who taught us well. And may we keep passing that knowledge on.
​
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…

• Thoughts for Thursday: From a Scholarship Recipient, Me
• Planned Giving Leads Don’t Generate Themselves – But They Can Be Sparked
• Decision Styles in Fundraising: It’s Not About What Moves You – It’s About What Moves Them
• Nonprofit Branding: How to Make Your Mission Memorable​
• Motivation Monday: Who are Your Grateful Patients?

So let’s talk about a fundraising skill that never makes the slide deck – but affects every single donor conversation: your ability to receive.

Receiving: the skill of accepting with grace – no strings, no scrambling, no shame. If you can’t accept a compliment without brushing it off, if you downplay a gift or reflexively offer something back the second someone does something kind for you… it might be time to take a closer look at your receivership muscle.

Yes, I said receivership. As in, the ability to simply receive.

Not barter.
Not apologize.
Not prove you’ve earned it.

Just receive.
​​
Now, I know this might sound like a soft skill or a personality quirk. But hear me out. This is mindset work. And for fundraisers, it matters.

Most fundraisers I know didn’t get into this work because they wanted attention or praise. We’re here to serve. We advocate for missions we believe in. We lift others up. But too often, that servant mindset gets twisted into something smaller: self-neglect, chronic under-earning, burnout, or quiet insecurity that whispers you’re not doing enough no matter how much you give.

And if you’re carrying that around – if you’ve internalized the message that your worth is tied to your productivity or output – donors will pick up on it.

Not consciously. But it seeps in.

You’ll hedge your asks.
You’ll downplay your case.
You’ll lead with scarcity instead of confidence.

​You’ll make it harder for them to give.

Here’s the truth I come back to, again and again: Worthiness is inherent. Not earned. Not measured by campaign goals or gift totals. It’s your birthright. Mine too.

But most of us weren’t raised to feel that in our bones. And let’s be honest, nonprofit culture doesn’t always help. We celebrate hustle and sacrifice. We glorify being “lean.” We wear our under-resourced status like a badge. And then we wonder why our donors hesitate.
​
That energy – of not-enoughness – clashes with the generosity we’re asking for. If we want donors to see our missions as worthy of investment, we have to believe that ourselves. And that starts with how we show up in everyday life.

Let someone buy your coffee without rushing to get the next round.

Accept a compliment without shrinking or deflecting. Just say thank you.

Take a breath when someone helps you, instead of jumping into apology or explanation.

These are small things. But they add up. They rewire your nervous system to believe: I can receive. I don’t have to hustle for every drop of goodness in my life.

And that’s the same belief you need when you sit across from a donor and ask for a major gift. It’s the belief that says: This work is worthy. This mission deserves support. And I am a trustworthy guide for your generosity.

That doesn’t come from a script. It comes from the inside out.

If this resonates with you, I’d love to hear how you’ve worked on receiving in your own life. Or where you’ve struggled with it. It’s tender work – but it’s the kind that changes everything.

Let’s stop shrinking. Let’s stop scrambling to prove ourselves. Let’s remember what was true all along: You’re worthy. Your mission is worthy. And it’s okay to receive.
​
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…

• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money
• The Magic Formula for Making a Confident Fundraising Ask
• Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every Time
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

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

When I worked at the University of South Carolina from 2005 to 2010, I was proud of the cases I built. I wrote compelling scripts and talking points for our phonathon team – clear, detailed, airtight.

I led with numbers, and they were good ones. I talked about the decline in state support, the rising importance of a college degree in the job market, and the long-term economic impact of thriving public universities. I knew the statistics on student loan debt inside and out. I framed the problem clearly and gave donors a chance to be part of the solution.

And it worked. To a point.

​Looking back, those appeals were sharp – but they leaned heavily on logic and numbers. That clicked with some donors. But others? Not so much. Those appeals weren’t wrong. They were just incomplete for the wide range of minds we’re trying to reach.

Fast forward to 2012. I was at The University of Southern Mississippi, learning how to write copy for direct mail. I started ghostwriting letters for different deans, department chairs, and students. At first, I stuck to what I knew: the stats. But it didn’t feel like enough.

I needed a broader emotional range.

So I started interviewing the letter signers, weaving in their voices and their vision – what this place meant to them, not just what they wanted donors to do. That’s when I started seeing the power of storytelling.

When I came to work at Starr King School for the Ministry in 2015, I had to stretch again. The usual notes in higher ed fundraising – nostalgia, school pride, career outcomes – didn’t resonate with a justice-minded, largely layperson donor base. These were Unitarian Universalists who cared deeply about their values and how the school perpetuated those values in the world.

I needed to connect the dots with emotion, shared purpose, and a clear sense of what their giving could do.
​
That meant telling stories that didn’t just inform – they moved people.

Somewhere along the way, I realized this shift wasn’t just about moving from stats to stories. It was about recognizing how different people make decisions.

One person might want the spreadsheet. Another wants the story. A third just wants the ask – clear and bold. And someone else? They want to feel like they’re part of something bigger before they commit to anything at all.

That’s when I remembered a model I’d seen back in 2007, from Mark Murphy at Leadership IQ. It mapped out the four main persuasion styles – and it helped me understand why my old appeals worked for some and left others cold.
​
Here’s the gist:

There are two axes:
• Emotional → Unemotional
• Linear → Freeform

Put those together, and you get four types of decision-makers:

This is where I naturally live. I want the stats. I want the logic. I want the argument that makes sense.

If you're reading this post and wondering, “Where’s the ROI?” – you might be here too.
​
That’s the kind of appeal I built early in my career. And it worked with people like me. But that’s not most donors.

Think of the board member who scans your whole appeal in 14 seconds and writes the check anyway.

They don’t need the backstory. They just want the point. What do you need, what will it do, and how much are you asking?
​
Closers are decisive. If you wander, they’re gone. You need to be bold, clear, and fast.

These folks are organized and thoughtful. They care about the story and the structure. Think of the alum who replies with a thoughtful email after every annual report – who joins the volunteer committee and follows up on the agenda.
​
They want a beginning, a middle, and an end. They respond when you connect emotionally but still give them a path to act.

Picture the alum who tears up thinking about the choir trip to Italy in 1983. They’re not interested in bullet points. They’re here for the moment – the meaning.
​
They want to feel something. And if your message is too structured or too clinical, they’ll check out. But if you pull them in with a meaningful quote or a powerful scene, they’ll stay – and they’ll give.

In major gifts, you can tailor every ask. You’re sitting across from one person, learning what moves them, and crafting your pitch accordingly.

But in annual giving? You’re writing to the whole list. That means your appeal has to layer styles – something for each persuasion type.

• Stats and logic for the Data Scientists
• Clear action steps for the Closers
• Warm structure for the Directors
• Emotional storytelling for the Storytellers

Don’t write the appeal that would convince you. Write the one that can meet your donors where they are – all of them.

When you're working on your next appeal, ask yourself:

• Does it have a story?
• Is there data to back it up?
• Is it structured clearly?
• Is there a moment of emotion?
• Is there a clear ask?

​
Fundraising is communication. And great communication connects.

This is one of my favorite things to teach. Reach out – I’ve got frameworks, real-world examples, and plenty of lessons learned the hard way.

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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• How to Build a Philanthropy Calendar That Drives Digital Donations

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.
​
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.
​
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…

• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• The Magic Formula for Making a Confident Fundraising Ask
• Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every Time
• “Wait, Am I Supposed to Fundraise Now Too?” A Department Chair’s Guide to Getting Started

I used to think donor interviews for our legacy giving newsletter were just good stewardship – a warm thank-you to generous folks who’d already made a planned gift.

Back then, part of my “gal Friday” role at the university was to call these donors, hear their stories, and write up little features for our newsletter. It felt like we were shining a light on their kindness and leaving it at that.

Then something surprising happened. After a few issues, my inbox started filling with messages:

• “How do I make a bequest?”
• “Can you send me sample language?”
• “I think I want to do this too.”

That’s when I realized: peer stories are one of the most powerful planned giving lead generators you’ll ever have.

Planned giving can feel awkward to talk about – it’s wrapped up in big questions about life, death, and legacy. But when donors see someone just like them, sharing why they chose to leave a gift, it shifts the conversation. Suddenly it’s not about confronting mortality – it’s about hope for the future.

And when those leads came in, the follow-up conversations weren’t awkward at all. I wasn’t “convincing” anyone; I was simply giving them the tools they’d already decided they wanted.

If you have even one donor who’s named your organization in their will, you have a powerful story to tell. And those stories can spark more conversations – and more commitments – than any brochure or website copy ever could.
​
Here are five simple, effective ways to start generating planned giving leads right now, starting with the most important one…

Start with real people who’ve already made a legacy commitment. Interview them, ask thoughtful questions, and tell their story with heart. These five questions help bring their motivations to life:

• What motivated you to include [Your Organization] in your estate?
• What does this gift mean to you?
• How did you become committed to the work of [Your Organization]?
• What would you say to others considering a gift like this?
• What is your dearest hope for the future of [Your Organization]?

Share those stories in newsletters, emails, social media, and video. These stories are your campaign – they create connection, trust, and curiosity.

You need a place to send people who want more info – don’t make them hunt for it. This doesn’t have to be complicated. Just make sure it includes:

• Sample bequest language
• A downloadable letter of intent
• A list of beneficiary options (retirement accounts, IRAs, life insurance, etc.)
• A contact form or a real name and email for follow-up

This is your annual window to talk openly about legacy giving – especially with donor stories. Tie them to helpful content like estate planning tips, FAQs, or “3 Easy Ways to Leave a Legacy” guides. Light, approachable, and packed with value.

Don’t let October do all the heavy lifting. Bring it back around with a spring campaign using your existing content – maybe add a new testimonial, or reframe the messaging. Familiarity builds comfort.

Flip that reply device over and include a quick checkbox survey:
☑ I’ve already included [Org Name] in my estate plans
☑ I’d like more information
☑ Please send me sample bequest language

This low-lift tweak has sparked real results for many nonprofits – and costs zero extra to implement.

If your nonprofit does just these five things, you’ll be light years ahead of most organizations in planned giving marketing. And the best part? None of them require new dollars in the budget.
​
That’s a win for your donors – and a big step toward your organization’s long-term financial stability.

Planned giving is one of the most powerful ways to future-proof your mission – and October is the perfect time to talk about it. This digital bundle is packed with tools to help you celebrate, educate, and inspire your supporters to leave a lasting legacy.

Here’s what’s inside:

1. ✍️ Planned Gift Landing Page Web Copy – $15.99 value
   Pre-written, customizable copy to get your new page up and running fast.
2. ✍️ Planned Gift Letter of Intent – $15.99 value
   A ready-to-go Canva template that makes it easy for donors to document their intentions.
3. 📜 Sample Bequest Language – $15.99 value
   Plug-and-play language your donors can use in their wills.
4. 📅 Digital Marketing Plan for National Estate Planning Awareness Week – $34.99 value
   Your entire week planned out with posting schedules, content ideas, and engagement tips.
5. 📲 Social Media Planned Giving Templates (10) – $24.99 value
   Customizable, scroll-stopping designs for Facebook, Instagram, and X.
6. 🎁 Bonus: Email Headers for Promoting Planned Giving (3) – FREE
   Designed to pair with your planned giving email blasts.

​💡 Total value: $114.95  –  You pay just $84.99. That’s 26% off.

And here’s the kicker:

• Planned giving brings an average return of $56.83 for every $1 spent.
• It often boosts annual giving, not just future gifts.
• And it opens the door to new, deeply loyal donors.

📥 Once you purchase, you’ll receive a downloadable PDF with links, setup instructions, and a tutorial video to walk you through the whole process.

👩‍💼 Made by me – Jessica Neno Cloud, CFRE – with 20+ years in the field helping fundraisers like you take real, doable steps toward long-term success.

👉 Ready to roll? Get your bundle now and make this October count.

Cheers!

If you liked this…

• Why Nonprofits Can’t Afford to Sleep on IRA Rollovers
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• The 3 Questions Donors Ask About IRA Rollover Gifts (and How to Answer Them)
• Leveraging National Estate Planning Awareness Week
• How to Talk About Death and Taxes: Getting Comfortable Having Planned Giving Conversations

IRA rollovers are the best of both worlds. They let donors give from their assets, not their income – so these gifts are often larger than what someone could give from their checkbook. And here’s the best part: the funds can be put to use immediately by the nonprofit.

Still, many fundraisers hesitate to talk about Qualified Charitable Distributions (QCDs) – also known as IRA rollover gifts – because they don’t feel confident answering donor questions. But here’s the truth: donors rarely ask complicated questions. They just want to understand the basics.

If we want to receive these powerful gifts, we need to be ready with clear, simple answers.
​
Here are the top three questions I hear most often – plus how to respond in a way that builds trust and inspires action.

In 2025, the annual QCD limit is $108,000 per individual, indexed for inflation. If both spouses have IRAs, a household can give up to $216,000 in a single year.
​
Keep in mind: this is the total giving limit per IRA account per tax year. So if you've already made other QCDs this year, you’ll want to keep a tally toward that annual cap.

If you’re not already promoting IRA rollovers, this is the time to start. And no – you don’t have to start from scratch.

​✅ Grab the IRA Rollover Promotion Bundle – Everything You Need to Promote QCDs

This $99 bundle includes:

• 🖥️ Web language to launch your IRA Rollover landing page
• 📽️ Three video scripts to educate and inspire donors
• 📱 Nine social media templates for Facebook, Instagram, and Twitter
• 💌 Three plug-and-play email templates for key seasons
• 🖋️ A 12-slide presentation deck for board meetings, webinars, or donor events

You’ll get a downloadable PDF with links to every template, setup instructions, and a short tutorial video. Created by me – Jessica Neno Cloud, CFRE – after 20+ years in fundraising, this bundle is built to help you raise more, with less stress and guesswork.

​From 2019 to 2021, giving through IRAs jumped 390%. This isn’t a trend – it’s a tidal wave. Let’s make sure your nonprofit is riding it.

Want a free way to get started?

Download my free resource, Calendar of IRA Rollover Promotions – a simple tool to help you map out smart, strategic outreach across the calendar year.
​
👉 Download the Free Calendar

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.

IRA Rollover References Resources

• Qualified charitable distributions allow eligible IRA owners up to $100,000 in tax-free gifts to charity (IRS)
• What is a qualified charitable distribution? (Fidelity)
• New reporting requirement for Qualified Charitable Distributions (Wolters Kluwer)

If you liked this…

• Why Nonprofits Can’t Afford to Sleep on IRA Rollovers
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• How to Build a Philanthropy Calendar That Drives Digital Donations
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

Pop Quiz:

A beloved faculty member retires, and your department wants to honor them with a named scholarship.

Should you:
a) Hit up that top donor at the tailgate
b) Meet with Advancement and make a plan
c) Launch a GoFundMe and post it to the department's social media

If you picked B, congratulations – you’ve passed. If you're scratching your head, you're not alone. (And yes, every one of those quiz options I have witnessed personally.)

Far too often, faculty are either sprinting ahead trying to do it all themselves or sitting it out because the maze of advancement feels too intimidating. Neither of these extreme approaches do justice to your students, your honorees, or your own standing as a leader on campus.

Here’s the thing: most faculty don’t go into academia thinking they’ll ever be responsible for raising money. Then one day, they step into a department chair role and suddenly, fundraising is on the job description – but no one handed them a manual. It’s a lot to take on, especially when you’re already juggling budgets, personnel, and curriculum.

Though I’m an Advancement professional, I’ve worked directly with faculty on fundraising since the 20th century – and I’ve seen plenty of ways fundraising efforts can go sideways. These are the things that work to make you the Advancement team’s favorite faculty collaborator.

When you know who to call and how to work together, you not only raise more money, you build momentum, respect, and resources. Let’s talk about how to work effectively across campus.

Most of the folks in Development departments actually aren’t major gift officers who play golf all day. In reality, it’s the researchers, database managers, gift processors, accountants, and annual giving folks who are the real MVPs and can be your best resource as a department chair.

Development offices thrive when faculty help connect academic work to donor dreams. They’re looking for faculty who can paint a clear picture of how gifts support teaching, research, and student success.

Want to get off on the right foot? Here are three things you can do:

1. Meet with the donor research officer and ask for a list of the top 10 donors (or potential donors) to your area. Write all 10 a nice note with an update on the department.
2. Meet with the annual giving director about ways you can partner. Come prepared with a list of points of pride about your department, faculty, students, and research.
3. Anytime you send communication or meet with an alum or donor, find out how to relay that back to be added to the database. Most shops have a web form or a dedicated email address for this purpose.

Your former students aren’t just Facebook friends. They're potential mentors, donors, and champions for your department. The Alumni Association wants your help making those connections stick.
​
Want to build better relationships with alumni staff and support your grads? Here are three ways to start:

1. Be a database darling! If you find out that someone has a new email or got divorced and they are a graduate, relay that information to be updated in the alumni database. There's always a disconnect if the faculty member is emailing them but then they don't get an email inviting them to homecoming from the institution.
2. If you find out about an alum receiving a big honor or award, relay that to the editor of the alumni magazine. The alum will feel honored and the alumni staff will love you.
3. Meet with the staffer planning homecoming and ask how your department can help get more of your grads there. Perhaps offer to host a tent for the tailgate.

Yes, it can get political. Departments can get territorial. Your college or university will have its own fundraising priorities which may not match yours. Donors get pulled in ten directions – and when everyone goes rogue with fundraising, everybody loses.

Instead of guarding your turf, try building bridges. Focus on what the donor wants and how multiple units might work together. A shared proposal doesn’t dilute your message – it strengthens it. It shows you’re working as a team, which donors love.

Collaboration isn’t just a buzzword. It’s a strategy. And when faculty, development, and alumni relations team up, the results are bigger, better, and more sustainable. Truly, everyone working together advances the institution.
​
So, the next time someone announces their intention to retire and you want to honor them with a scholarship, don’t wing it or walk away. Partner up. Think long-term. Be the faculty leader who understands how things get done – and gets them done with heart and strategy.

If this post hit home, I’ve got something that’ll really help: a free 35-minute webinar called Building Fundraising Confidence for Department Chairs. It’s practical, empowering, and designed to help you stop second-guessing and start asking with clarity.

​You’ll get access immediately—and it’ll subscribe you to my newsletter where I share more strategies, stories, and insights for academic leaders who are learning how to fundraise without losing their minds.

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…

• A Practical Primer on Endowments
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A few years back, I worked with a team that was stuck in microwave fundraising mode. If there was a quick-cash tactic out there, they were doing it: golf tournaments, raffles, sponsorship deals heavy on the benefits, you name it. It kept the lights on, but it wasn’t building anything lasting. I gave a presentation about crockpot fundraising – relationship-building, long-term strategy, donor engagement – and it started to click. I wanted to challenge them to try something new and to move out of their "microwave" comfort zone. I promised them that if they could do that, it would pay dividends down the line and make fundraising easier and more enjoyable.

I've been in rooms full of nonprofit leaders who are scrambling to make payroll, stressed over budget gaps, or just plain overwhelmed by the pressure to "do more with less." And in those moments, it's tempting to reach for the quick fix – a car wash, a 5K, a golf tournament, a donut sale, a last-minute sponsorship deal. These microwave fundraising tactics can bring in a little fast cash, and I won't pretend they never have a place. But let's be honest: they're not going to carry your mission for the long haul.

Microwave fundraising is all about urgency. It's transactional. It gets warm fast, but it cools off just as quickly. These events are often labor-intensive, draining your staff and volunteers. The ROI is usually modest. They’re familiar, easy to organize, and feel reliable. But they’re not always the healthiest choice for your organization. They only feed a few folks, and they don’t build connection to your mission or long-term sustainability.
​
Here's a side-by-side breakdown that captures the heart of the metaphor:

Caption: Microwave vs. Crockpot Fundraising: A visual comparison of quick, transactional tactics vs. slow, relationship-centered strategies.

Then there's crockpot fundraising. It takes longer to get cooking, no doubt. And yes, there’s a learning curve. But it’s healthier for your mission in the long run. These strategies usually involve more “vegetables” – meaning thoughtful, nourishing activities like donor conversations, stewardship touches, and consistent storytelling. It takes time. You can’t flip a switch and expect results tomorrow. But when you commit to it – when you really let it simmer – the flavor builds. The connections deepen. The nourishment multiplies.

Crockpot fundraising feeds a crowd. You’re not just generating one-time gifts – you’re building community. It’s transformational. It deepens loyalty. It keeps donors connected to the mission. It gives your work staying power.

It means investing in consistent donor communications, one-on-one conversations, thank-you calls, stewardship, and strategic asks. First-time donors become recurring givers. Recurring givers become advocates. Advocates become legacy donors.

Is it slower? Yes. But it is sustainable. It doesn’t burn you out or box your organization into lopsided agreements just to chase a check. It feeds your mission in a way that microwave tactics never will. It keeps your team grounded and your donors inspired.

So when you're weighing your next move, ask yourself: Are we microwaving or crockpotting this? One will keep you hustling for scraps. The other will feed your mission for years to come.

Let it simmer. You'll be glad you did.
​
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…

• Why Most Fundraising Plans Fail
• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Don’t Add Another Event Until You Read This
• The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising
• Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or Less