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…

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• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

I’ve long been an advocate for fundraisers to be better partners with our database colleagues because they can make or break your success. And after decades of working closely with our data buddies, I can say that they often get frustrated with us because we send emails like this:

“Can you pull a list of major donors?”

That’s it. No timeline. No parameters. No context.

When data requests go off the rails, it’s usually not because anyone’s trying to be difficult. It’s because we’re talking past each other.

Fundraisers are focused on goals. Database folks are focused on parameters. You’re thinking: “I need a list of lapsed donors for a postcard.” They’re thinking: “Define lapsed. Which years? Which exclusions? What fields? What format?”

When those details don’t get nailed down up front, your request sits in the queue. Or it bounces back with more questions. Or worse – it gets filled, but it’s wrong, and now you’re scrambling.

That back-and-forth burns time and goodwill. And in fundraising, timing matters.

But – there’s no judgment here. Most fundraisers aren’t trained in how to “speak database.” You know what you need, you just might not know how to say it in a way your CRM or advancement services team can use.

That’s what this post is about. Whether you’re a frontline fundraiser, a VP, or a one-person shop trying to wear all the hats – if you rely on data to do your job (and you do), you need to know how to make a clean, effective request.

​I can help you there.

Taking five extra minutes to complete a thoughtful data request could save you five days of email ping-pong – or five weeks of waiting for a fix when something gets pulled incorrectly.

And if your project is time-sensitive? It could cost you five big gifts. Or more.

Maybe a solicitation gets delayed because someone forgot to specify an exclusion. An important donor gets left out of an event invite because the list was pulled in a rush. The details matter.

You don’t have to become a database expert. But you do need to learn how to frame your request clearly. That means giving enough context for your advancement services or CRM colleagues to:

• Understand the goal
• Identify the correct records
• Exclude the ones you don’t want
• Deliver it in a useful format
• Hit your timeline without a panic button

That’s why I created a Data Request Template, and it’s all at the end of this post. But before you copy and paste, let me walk you through the thinking behind it.

Here’s what should go into every data request you make:

Date Needed
Start with the date you want to review the file. If you have a final send date – like to a printer, email platform, or gift officer – include that too. Build in review time and ask for it at least a week ahead.

Purpose
Be specific. Are you mailing a solicitation? Sending a digital campaign? Calling for event follow-up? This helps determine the right segments and delivery method.

Overview
Write two or three sentences describing the project. This gives your colleague a mental model of what you're aiming to do and why it matters.

Prior Pull
Have you asked for a similar file before? If yes, when? If it went well, that helps them repeat the success. If it didn’t, they’ll know how to make adjustments.

Report Criteria
This is where you define who should be in the file. What makes someone eligible? Think about giving history, affiliation, geography, or whatever criteria match your goal. Think of this as a net you are throwing around the prospects you want to see.

Exclusions
Who should not be in this file? Don’t assume standard exclusions. Spell them out: Deceased, Do Not Contact, Current Students, Faculty/Staff, Current Year Donors – whatever applies. Be clear. Think of this as a boundary keeping records out that you don’t want to see.

Format
Excel, CSV, PDF? Match your needs. If you’re importing into an email platform or using it for a mail merge, say so.

Fields Needed
Don’t just say “name and address.” Think through what you actually need: email, phone number, last gift date, last gift amount, salutation lines, grad year, etc. The more precise you are, the fewer follow-ups you’ll have later.

For instance, when I request a file and I want to see giving information, I ask for the file to include: last gift date, last gift amount, last gift fund, greatest gift date, greatest gift amount, greatest gift fund, and sometimes first gift date, first gift amount, and first gift fund. Sometimes I also like to see total lifetime giving and total number of lifetime gifts too. That list is a far cry from “giving history.”

Notes
If you’re estimating 5,000 records, say so. If this is part of a campaign with other moving pieces, mention that too. Context helps your colleagues prioritize and prepare. If you already have a draft of the specific message, you can attach that. Data folks love having the whole vision.

Want to copy it straight into your next email? Here’s a quick version:
​
Date Needed:
Purpose:
Overview:
Prior Pull?:
Report Criteria:
Exclusions:
Format:
Fields:
Notes:

Clear requests build better relationships. When you send thoughtful, complete data requests, you become someone your CRM team can trust. And when they trust you, they’re faster. More responsive. More likely to go the extra mile when you’re in a crunch.

This isn’t about being perfect. It’s about being respectful of their time – and protecting your outcomes.

​So yes, it might take five extra minutes on the front end. But that could save you five days of delays or five missed opportunities.

And those gifts? They’re worth it.

Want smoother workflows and faster data pulls? Or just want a second set of eyes on your advancement strategy? Let’s connect.

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…

• What Worked for Giving Tuesday 2024
• How to Build a Philanthropy Calendar That Drives Digital Donations
• 31 Ways to Hit the Refresh Button on Your Direct Mail
• Culture of Philanthropy Check Up
• Spring Cleaning for Fundraisers: Organizing Planned Giving Documentation

If you’re treating Giving Tuesday like a one-and-done campaign, you’re missing the point – and the potential.
​
I want you to think of it differently. Think of Giving Tuesday as your momentum builder. The snowball at the top of the year-end giving hill. Not just a date on the calendar, but the kickoff to your most generous season of the year.

When you plan it right, Giving Tuesday becomes the moment your donors start paying attention again. The moment they re-engage, make that first gift, and feel the energy behind your mission. It gives you stories to tell in December, a list of donors to follow up with, and progress to build on.

This isn’t about chasing trends. This is about strategy.

And if you want it to work, you’ve got to start now.

My friend, Jake Strang said it best:

“As fundraisers, we need to ask ourselves what our donors are asking themselves: ‘Why today?’”

That question is everything. Your donors want to make a difference – not just by giving, but by giving on a day that matters.

Giving Tuesday answers that question. It creates urgency. It offers momentum. It taps into a global spirit of generosity and focuses it on your mission.

But only if you’ve done the work to meet them there. If the messaging isn’t clear, if the plan is rushed, if it’s just another email in the inbox… you’ll miss the moment.
​
The magic is in the lead-up. And the lead-up starts now.

1. Line up your challenge match now.

A matching gift is one of the strongest incentives you can offer on Giving Tuesday. But the kind of donors who fund matches – your board, your loyal givers, your major donors – need time.

Time to understand the impact.
Time to coordinate logistics.
Time to feel ownership of the campaign.

Don’t treat your match as a checkbox on a planning list. Build it as a strategic asset. Ask now, while there’s room to shape it well.

2. Invite your major donors into the campaign early.

Don’t just ask them for money. Give them a role.

They can:

• Make their own gift early to seed momentum
• Participate in challenge matches
• Help recruit other donors or ambassadors
• Share their own giving story on video or social

Major donors want to be part of something bigger. Giving Tuesday gives you a clear “why now” to help them say yes.

3. Pre-load your pledge list.

Here’s one I swear by: Take pledges before the day. Use events, meetings, or board gatherings to ask for early commitments.

Then, on Giving Tuesday, your team has a clear list to follow up with. These aren’t cold calls – they’re reminders. “Today’s the day.” That kind of focused effort drives real results.

4. Plan for analog tactics (they still work).

Want to send handwritten postcards? Want to use the phone effectively? Want to get a thank-you letter in the mail before year-end?

You need to start now.

Donors are inundated with email. But the mailbox? That’s a quieter space. A handwritten note cuts through. A real phone call builds connection. These tactics take time, and that’s exactly why they work.

5. Build your multi-channel plan early.

When you start now, you don’t have to rely on one message in one channel. You can actually coordinate email, social, print, phone, and even live events with intention.

That’s how you stand out.

You can code your appeals. Track what’s working. Share updates in real time. You have space to think like a strategist, not a last-minute firefighter.

6. Leave a little space for improv.

You’re not planning to control every detail. You’re planning to give yourself room to respond.

Maybe a donor offers a surprise match. Maybe a social post gains traction. Maybe the campaign falls just short at midnight, and you need to extend.
​
When your plan isn’t packed too tight, you can adjust with ease – and sometimes those pivots are what make the day feel alive.

Treat it like what it really is: your launchpad.

The starting line for your most generous season.
The moment your donors start leaning back in.
The energy surge you’ll need to carry you through December.
​
And the best part? You don’t need to overhaul your shop to make this happen. You just need to start early, plan with purpose, and stay connected to why it all matters in the first place.

If you’re looking for a sign to start working on Giving Tuesday 2025… this is it.

Get your match lined up.
Draft that pledge form.
Sketch out your outreach plan.

Then get ready to make this the year your Giving Tuesday becomes more than a day – it becomes a difference-maker.
​
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… 

• What Worked for Giving Tuesday 2024
• How to Build a Philanthropy Calendar That Drives Digital Donations
• All About Giving Days (Interview with Jake Strang)
• Cut Through the Clutter: Focus on the Two Planned Giving Options That Really Work
• Spoilt for Choice: Why Giving Donors Direction Works

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

Let's pretend the TikTok comment section is a search history.

This was a meme engagement prompt circulating around Tiktok, so I adapted it for nonprofit fundraisers. And the results were funny but also a bit depressing.

• "Free spa day near me."
• "Easy six-figure grant."
• "Jobs where I don’t go to bed anxious."
• "Work from home jobs where no one yells at me."
• "How to plan a gala on $250."

​
I’ve written about burnout. But this felt different. These aren't just punchlines. They're quiet cries for help disguised as jokes. And they struck a nerve. The comments rolled in: funny, raw, painful, *real*. This wasn’t just a social media prompt. It was a mirror for the nonprofit fundraising sector.

Fundraisers turn burnout into memes because humor is safer than honesty.

Because saying "I'm not okay" feels like a risk.

Because the system rewards silence and penalizes boundaries.
​
Gallows humor isn't just venting – it's a way our nervous systems regulate under pressure. When enough people laugh at the same joke, it signals: you're not the only one. You're not imagining it. This job is breaking people. Quiet cracking, indeed.

That the expectations of nonprofit fundraising are structurally absurd:

• Raise millions but don't spend on staff.
• Be warm and authentic but hit your metrics.
• Work for the purpose, but not for the pay.

​We joke because naming it plainly would require everything to change.

• Name it. Share the meme *and* the meaning.
• Don’t confuse burnout with weakness.
• Support each other. Community is armor.

​You're not alone. And you're not crazy. We need more honest conversations on LinkedIn and in the workplace. We need to acknowledge that burnout isn’t a personal failure. It’s an occupational hazard.
So, if you're a fundraiser trying to find your way back to sanity, find me over on Tiktok or subscribe here to my weekly newsletter. Let’s keep this conversation going!

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… 

• How to Spot and Stop Fundraising Burnout Before It Leads to Turnover
• Take Your PTO: Why I’m Logging Off – and Why You Might Need To, Too
• How to Climb Out of Burnout in Quarantine (with special tips for fundraisers)
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• Wear the Suit: Presence starts in your mind, not your closet

Ever open your email and feel like your brain’s going to short-circuit?

You're not alone. Seventy-four percent of U.S. adults say they feel overwhelmed by email. More than half of U.S. consumers (56%) say they’ll unsubscribe if they receive four or more marketing messages from the same company within 30 days. And it’s not just Boomers. Eighty-one percent of Gen Z and 78% of Millennials say they wish it were easier to disconnect from digital devices.

These are your future major donors asking for fewer pixels and more presence.
​
That’s the opening fundraisers need. The real opportunity isn’t another email subject line tweak or fancy GIF. It’s a return to what’s real: mail and phone. Tangible. Human. Hard to ignore.

​This isn’t nostalgia talking. It’s data. And it might just be the smartest pivot you make this year.

In the race to do more, cheaper, we forgot what actually works.

Physical mail gets opened 80–90% of the time, while emails land between 20–30%. Direct mail spending has even grown recently – reaching about $39.4 billion in the U.S. in 2023.

And here’s the kicker: when mail and digital work together, results jump. In one test, donors who received both mail and email were 60.5% more likely to respond to the mail piece than those who got mail alone.

That tracks with what I saw last year. Inspired by the project Postcards to Swing States, my team handwrote and mailed over 200 postcards promoting our Giving Tuesday match. It was a standout success. Part of the magic was the form itself: a postcard is immediate – no envelope, no delay, just message received.

The phone didn’t stop working. Most programs just stopped dialing.

Organizations that add professional telemarketing to their strategy see an average 27% increase in annual donations compared to those relying solely on mail or digital campaigns.

Why? Because personalized calling does what algorithms can’t – it builds connection.

And that connection drives results. DCM’s 2023 telefundraising trends report found that contact rates have remained stable since the pandemic – holding strong at about 2.5 contacts per hour. Advocacy and political campaigns saw average gift amounts rise by 19% between 2018 and 2023, thanks to high-touch calling models.

I’ve seen the impact firsthand. Last year, I worked with a college to rebuild their phonathon from the ground up: stronger management, better scripting, and smart segmentation. In 2022, they raised $134,317. This year? $396,309. And their youngest alumni – graduates since 2020 – are showing a participation rate over 17%. That kind of traction doesn’t come from wishful thinking. It comes from consistent, human contact. 
​
Telemarketing gets a bad rap, but it’s still the only channel that delivers personalized conversations at scale. It’s strategic because it’s still deeply personal.

So if you think phone is “old school,” think again. It’s working better than ever – for those who use it well.

Here’s where things get interesting: Millennials and Gen Z aren’t avoiding analog as expected but they are getting burnt out on digital.

More than 80% of Gen Z (80%) and Millennials (78%) say they share interesting mail with someone else. That’s a viral loop, but with ink and paper.

They’re open to analog – especially when it connects to the digital world. QR codes. Custom URLs. Interactive print. That’s not outdated. That’s modern engagement with real presence.

Gen X? They’ll still take your call and they appreciate personalized pieces.

Boomers? They’re the MVPs of mail. They read it, they act on it, and yes – they still pick up the phone when the number’s familiar.

We’re in the relationship business, not just the metrics business. Somewhere along the way, digital promised us scale and forgot to tell us we’d lose connection.

If you want your message to stand out, don't just add to the digital pile-up. Get in someone’s mailbox. Pick up the phone. Make it personal. Make it human.

Analog hasn’t vanished – it’s been waiting. And right now? It’s the cleanest path to cutting through.

This isn’t a call to throw out your digital playbook. It’s a nudge to rebalance. To layer your strategy. To stop thinking in either/or.

You don’t need to call everyone or mail every donor. Segment. Experiment. Pair analog with your digital. Measure. Adjust.

I’ve been doing this long enough to tell you: this is where fundraising is heading next.

I’m betting on analog. Because I’ve seen the numbers. I’ve seen the results. And I’ve seen how a phone call or handwritten postcard can do what a hundred emails never could.
​
Let’s go back to what works. Not because it’s old – but because it still moves the needle.

This isn’t a blip or a nostalgia play. The signs are clear: digital fatigue is rising, mail spend is climbing, and younger donors are just as responsive to tangible, personal outreach as their parents and grandparents.

We’re not at the plateau. We’re on the upswing.

That’s why the institutions that recalibrate now – layering mail and phone back into their strategies for all generations – will see the payoff not just in annual giving but in the major gift and planned giving pipelines for decades to come. Early engagement drives loyalty, and loyalty drives legacy.

The inbox is saturated. The mailbox and the phone line are open. The organizations willing to seize that opening today are the ones who will own the donor relationships of tomorrow.

Fundraising’s next edge won’t come from squeezing another 0.2% out of your email subject line. It’ll come from showing up where people are actually ready to listen.

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…

• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• 31 Ways to Hit the Refresh Button on Direct Mail
• Kickstart the Year: Setting Annual Giving Projections for Success
• Spoilt for Choice: Why Giving Donors Direction Works
• 10 Traits All Former Phonathon Callers Share

Works Cited:

• GlockApps – Email Fatigue and Overload
• GetApp – Why Users Unsubscribe
• Quad + Harris Poll – Gen Z & Millennial Digital Disconnect
• Postalytics – Direct Mail Stats
• Winterberry Group – 2023 Direct Mail Performance
• NextAfter – Mail + Email Synergy Study
• Callin.io – 27% Giving Increase via Telemarketing
• DCM Telefundraising Trends – Contact Rates + Gift Growth
• Lob – 2025 Direct Mail Consumer Insights
• USPS Delivers – Generational Preferences for Mail & Phone

In 2018, I sat in a conference room during a session led by executive presence coach Eda Roth. She broke down executive presence into three components: communication, appearance, and gravitas. She shared that the impact of your presence comes across in three ways:

• 55% through visual cues – your appearance and body language
• 38% through vocal cues – tone, pacing, and volume
• Only 7% through your actual words

That stuck with me. As a fundraiser, I’d been taught to focus on what I was saying: the pitch, the story, the ask. But this shifted something. I started to think more about how I was being – not just what I was saying.
And the more I worked with fundraisers in the years that followed, the more I came to believe this: Gravitas isn’t one-third of executive presence. It’s the result of the other two (communication and appearance) – plus something extra.

It’s what makes someone feel grounded, trustworthy, and clear – even before they speak. And here’s the good news: you don’t have to act like someone else to cultivate it.

Dr. Lisa Hale, writing for Forbes, defines gravitas as the blend of eight qualities: confidence, composure, credibility, clarity, conviction, connection, decisiveness, and respect. She says it’s the moment you stop asking “Do I belong in this room?” and start asking “What do the people in this room need from me?”

That’s exactly the shift fundraisers need to make.

Gravitas isn’t about being the loudest or most polished. It’s about having internal calm and external presence – so that donors, board members, and colleagues feel like they’re in steady hands.

Here’s what gravitas looks like when it shows up in real conversations and real donor meetings:

• Confidence – You know your worth, your expertise, your impact and the impact of your organization – and you let that knowledge inform your tone, your posture, and your choices.
• Composure – You stay calm when a donor surprises you with a tough question or an emotional story. You don’t rush. You breathe.
• Credibility – You follow through on your promises. You bring the right facts. You become someone they can rely on.
• Clarity – You don’t speak in jargon or try to impress. You say what you mean and ask for what’s needed – directly.
• Conviction – Your belief in your mission is tangible. You’re passionate without being pushy.
• Connection – You listen deeply. You nod. You mirror their energy. You see the person across from you.
• Decisiveness – You steer the conversation. You guide next steps. You’re not waiting for permission to lead.
• Respect – You treat your donors’ time, stories, and values with care – and you treat yourself the same way.

After that 2018 conference session, I found myself in a networking event with other women in higher education leadership. The conversation turned to fashion.

I happened to be wearing knee-high black suede boots, small fishnet hosiery, and a red-and-black dress that made me feel powerful and completely myself. So I asked, “Do you think women in higher ed leadership can be successful wearing boots and fishnets?”
​
One woman answered, without missing a beat:
“Women in leadership should wear whatever makes them feel powerful.”

That’s stayed with me. We sometimes forget that appearance is part of presence – not because we have to look a certain way to be respected, but because what we wear affects how we carry ourselves. When you feel put together, you stand taller. You smile more easily. You claim your seat at the table.

Let your wardrobe reflect both professionalism and personality:

• Tailored pieces with a pop of color or bold pattern
• Comfortable, confident footwear (yes, that includes boots)
• Accessories that feel like you, not like a costume

​You don’t have to disappear into neutrals to lead with strength.

You don’t have to be a body language expert to connect powerfully in a meeting. These small cues can make a big difference:

• Nod as they talk. It shows you’re tracking – and it makes them feel heard.
• Lean in slightly when they share something important. It’s a physical signal of emotional presence.
• Mirror their posture and pace – subtly. People tend to trust those who feel “in sync” with them.
• Slow down if they’re reflective. Speed up a bit if they’re animated. Match their energy with authenticity.

Fundraisers often worry about what to say. But how you say it carries even more weight.

• Match your volume to the space and person. Don’t overpower – or disappear.
• Use pauses to let your words land – and to show confidence in your message.
• Ask a thoughtful question right before you take a bite or sip in a meeting where you are having a meal. It gives the donor the floor and you a moment to regroup.

Imposter syndrome is real. And it’s sneaky. You can be experienced, credentialed, and well-prepared – and still feel like your voice doesn’t carry weight.

But gravitas shows up when you shift from proving yourself to trusting yourself.
​
You don’t need to be louder. Or slicker. You need to be more yourself – grounded, clear, and focused on the person in front of you.

Executive presence isn’t a suit you put on. It’s a muscle you build. Fundraisers with gravitas don’t just ask for money – they inspire trust, connection, and confidence.

So go ahead:

• Wear the dress that makes you walk taller.
• Ask the direct question.
• Let silence do some of the work.
• Show up as the most grounded version of yourself.

You don’t have to act like someone else to have presence. You just have to show up on purpose.

What’s one way you’re learning to trust yourself more this year – in fundraising or in life?

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…

• 21 Ways to Alleviate Impostor Syndrome
• Breaking into Fundraising: Real Talk for New Grads (and Anyone Starting Fresh)
• Wear the Suit: Presence starts in your mind, not your closet.
• Self-Care: The Most Important Thing We All Should Be Doing Right Now (How to Build Your Self-Care Practice)
• Who’s Afraid of Burnout & Turnover? You Should Be.

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…

• Don’t Add Another Event Until You Read This
• Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)
• The Problem with Totes and T-Shirts: Why Freebies Can Undermine Fundraising
• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• How to Build a Philanthropy Calendar That Drives Digital Donations