I want to begin with a statement that may feel simple, but it carries more weight than most boards realize:
​
Fundraising is a noble endeavor.

If you are a nonprofit CEO or Board Chair, your internal reaction to that sentence matters. It shapes how you speak about fundraising. It influences how your board experiences it. It quietly determines whether your culture approaches fundraising with confidence or hesitation.

Belief comes first. Always.

This is where we must be honest with ourselves.

You either believe deeply in your mission, or you don’t.

If you believe your organization changes lives, strengthens families, advances justice, expands education, heals, protects, or restores something that matters, then you already know the work deserves resources. You know it deserves to grow. You know it deserves to be sustained for the long term.

If that belief is strong, you can work through discomfort around money. You can practice the language of invitation. You can sit in a donor meeting and speak clearly about funding needs.

If that belief is shaky, fundraising will always feel heavy. You will delay conversations. You will hedge language. You will hope someone else handles the “hard part.”

If leadership belief wavers, board engagement follows, donor conversations shrink, and revenue eventually reflects that hesitation.
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Belief is not emotional fluff. It is operational fuel.

Early in my career, I worked in political fundraising. I was taught that fear and guilt were powerful motivators. Create urgency. Highlight threats. Push emotional buttons.

And it worked, at least in the short term.

Later, when I returned to my alma mater, I began raising money for education. Our beloved president emeritus who led the university through decades of growth, Aubrey K. Lucas, met with the new development officers. He shared something that stayed with me.

Negative fundraising is rarely truly successful.

We were raising money for education. Education is a universal good. It is something to be proud of. That effort should not be rooted in pressure or fear. It should be rooted in conviction.

That conversation reframed my entire understanding of fundraising.

If education is good, then raising resources for education is good.

If your mission serves a real human need, then securing funding for that mission is honorable work.

That realization has guided my work ever since.

When board members hesitate, the hesitation is rarely about the mission. It is about money.

Money carries history. It carries stories. It carries personal experiences that shape how we feel when we talk about it. But giving is not really about money.

Giving is about shared vision and shared values.

When a donor gives, they are not simply transferring dollars. They are aligning themselves with a cause they believe matters. They are choosing to participate in change. They are saying, “I see this work, and I want to be part of it.”

Money is simply the mechanism that allows that alignment to take tangible form.

When you internalize this truth, something shifts in your posture. You stop speaking about fundraising as if it is separate from the mission. You recognize that it is the engine that fuels the mission.

And that changes your tone.

Culture does not begin in the development office. It begins in the boardroom.

If you speak about fundraising as an obligation, your board will experience it as a burden.

If you treat fundraising as something uncomfortable that must be endured, your board will mirror that discomfort.

But if you speak about fundraising as mission work, as advocacy, as an opportunity to invite others into meaningful impact, your board will feel that shift.

You do not have to eliminate all discomfort. Most of us were not raised discussing money openly. That hesitation is normal, but how you frame the work matters.

When you believe fundraising is noble, you approach it with clarity. You talk about funding needs without apology. You connect dollars to outcomes without shrinking your language. You model confidence.
​
Boards take their cues from leadership. If you approach fundraising with pride and purpose, your board has permission to do the same.

If your board is reluctant, start here. When was the last time your board discussed fundraising as shared leadership responsibility rather than an agenda item?

Have an honest conversation about why your mission matters. Revisit the lives changed. Revisit the transformation you are pursuing. Revisit the gap between where you are and where you need to be.

Then ask this question: If this work truly matters, why would we hesitate to invite others to fund it?

When that belief becomes shared, fundraising stops feeling transactional. It begins to feel aligned.
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And alignment is powerful.

If any of this sounds familiar:

• Your board supports the mission but avoids fundraising conversations.
• You feel like you’re carrying development alone.
• Giving is flat and no one wants to address it directly.
• Board members say yes to serving but hesitate to ask.

It’s time to take a serious look at whether your board’s leadership tone and fundraising expectations are truly aligned. If fundraising feels like a source of stress rather than shared responsibility, this is the work that shifts it.

I’m opening three complimentary Board Fundraising Alignment Calls this month. You can reserve a time here.

P.S. This post is the first part of an ongoing series for nonprofit CEOs and Board Chairs who want to build confident, fundraising-positive boards.

If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level.

If you liked this…

• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Rethinking Board Recruitment: The 4 Ws That Really Matter
• Culture of Philanthropy Check-Up
• The Magic Formula for Making a Confident Fundraising Ask
• The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About Money

When I came back to work at my alma mater in 2011, they had just celebrated the Centennial the year before. The mailing they sent out for the 100-year mark was gorgeous – vintage photos, heavy cardstock, elegant fonts. You could see the pride in every detail.

But there was one big problem.

It cost more to send than it brought in.

When I ran the numbers, the cost to raise a dollar on that piece was $1.40. For every dollar it generated, it cost us $1.40 to get it. We weren’t raising money – we were losing it. It was like we were throwing money overboard and missing a once in a century opportunity!

The issue wasn’t just the over-the-top production. The package was confusing. Too many ask amounts, too many gift designations, and other options. Donors didn’t know where to focus. And when a donor doesn’t know what to do, they don’t give.

The next year, we simplified. One letter. Points of pride on the back. Clear ask string. That mailing had a cost to raise a dollar of 43 cents.
​
Same donor base. Better strategy.

Cost to raise a dollar is exactly what it sounds like. It’s a measure of efficiency. You take your total expenses for a campaign or fundraising channel and divide it by the amount raised.

Formula:
Cost to raise a dollar = Total Expenses ÷ Total Dollars Raised

If you spent $10,000 and brought in $25,000, your cost to raise a dollar is $0.40. That means it cost you forty cents to raise one dollar. Good.

If your cost to raise a dollar is over $1, you’ve got a problem – if you’re not executing a donor acquisition strategy where you expect to lose money upfront to gain long-term donors who’ll give again and again for less.
​
But if you’re not acquiring or upgrading donors – and your cost to raise a dollar is that high? You’re hemorrhaging money.

Recently I was teaching a webinar and got asked whether you should track staff time on any particular fundraising effort in the total expenses when calculating cost to raise a dollar. My answer is no.

I’ve never met a fundraiser who’s sitting around wondering what to do next, and I don’t think tracking every minute of your working hours is a good use of that valuable time.

Staff salaries are in your normal budget. Consider them a constant. Don’t tie yourself in knots trying to figure out if you spent 20 hours on the gala last week or 22 hours.

Examples: For a mailing, count printing, postage and processing costs (if using a mailhouse or other paying part-time folks to stuff mailers). For an event, expenses would include catering, décor, invitations (printing, postage, and processing), printings programs, etc.
​
Keep it simple and you’ll be ahead of the game.

Fundraisers talk a lot about leaky buckets – usually in terms of donor retention. But there’s another leak that’s just as costly: spending more to raise a dollar than you get back. That’s what this metric uncovers.

Most fundraisers are trained to focus on total dollars raised or number of donors who give. And yes, those are crucial. But cost to raise a dollar gives you clarity at the tactical level. It shows you where your fundraising machine is humming – and where it’s grinding your budget into dust.

Cost to raise a dollar is especially helpful when:

• You’re evaluating different channels (direct mail vs. email vs. phonathon)
• You're preparing for a budget meetings and need simple, apples-to-apples comparisons
• Leadership is asking to cut costs, and you need to defend what’s working
• You’re trying to argue against flashy design choices or work-intensive events that don’t move the needle

That Centennial piece taught me something I’ve never forgotten: Beautiful isn’t always effective. Impact matters more than gloss.

It also gave me a compelling number to take into conversations. I could walk into meetings and say, “This mailing costs us $1.40 to raise a dollar. Last year’s only cost 43 cents. Which one do you want to fund next year?”
​
I didn’t need to yell. I just needed to know my numbers.

Some channels will have higher cost to raise a dollar – and that’s okay. Phonathons, acquisition campaigns, certain events – they often cost more. But if you’re tracking those donors and seeing strong retention and future giving, that higher initial cost might be justified. But do that deliberately, for strategic reasons.

In higher ed, campaigns like student philanthropy programs or senior class gifts often have an “upside-down” cost to raise a dollar. That’s not a failure – it’s intentional. We spend more than we bring in because we’re focused on something bigger: starting the donor relationship early, before students graduate, move away, and scatter.

While they’re still on campus, their connection to the institution is at its peak. That’s the right time to invite them into giving – not just for dollars today, but for loyalty tomorrow.

Just don’t confuse “tradition” or “looking nice” with effectiveness. Know what each dollar is doing for you. Make that a habit. Teach it to your team.

And please – for the love of fundraising – don’t let your best-looking piece be your worst-performing one.

If you’ve never calculated your cost to raise a dollar, start now. Pull your last three mailings or campaigns. Be honest about all the expenses, minus staff salaries.

Run the numbers. Then start making decisions that build toward efficiency – and impact.

This metric gives you the insight you need to be smart with the resources you’ve been trusted to steward.
​​
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…

• Read Between the Dollars: 3 Gifts to Watch
• From $50 to Six Figures: How I Got Board Members to Care About Annual Giving
• Six Ways to Show Gratitude to Donors in 2026
• Scripts to Bring Up Planned Giving Without Feeling Weird About It
• 4 Power Questions to Ask Donors That Build Rapport and Lead to Major Gifts

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

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

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

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

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

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

1. The “Kick the Tires” Gift

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

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

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

Track this gift like it matters – because it does.

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

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

2. The “Hand-Raising” Gift

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

That’s not random. That’s intentional.

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

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

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

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

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

3. The “Breakthrough” Gift

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

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

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

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

This is where cultivation becomes partnership.

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

In conclusion…

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

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

Cheers!

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

If you liked this…

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

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

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

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

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

At every board meeting, I brought receipts. Literally.

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

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

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

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

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

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

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

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

The modest gifts didn’t seem so modest anymore.

And that’s the whole point.

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

• Your Board Wants to Help with Fundraising – They Just Don’t Know How
• Rethinking Board Recruitment: The 4 Ws That Really Matter
• Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling Donors
• How to Build a Philanthropy Calendar That Drives Digital Donations
• How to Ask for Donor Lists Without Delays or Drama

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

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

Here’s what worked:

1. The Match Game, with a Twist

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

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

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

2. Direct Contact Beat the Megaphone

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

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

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

3. Board Engagement Started Early

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

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

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

4. Targeted Appeals to Past Giving Tuesday Donors and LYBUNTs

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

We pulled two lists:

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

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

5. Monthly Donors and Pledgers Want to Participate, Too

This one surprised me last year and held true again.

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

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

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

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

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

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

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

We focused on:

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

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

And that’s the kind of success worth repeating.

Cheers!

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

If you liked this…

• What Worked for Giving Tuesday 2024
• How to Build a Philanthropy Calendar That Drives Digital Donations
• When the Inbox Is Full, Go to the Mailbox: Why Analog Fundraising Is Making a Comeback
• All About Giving Days (Interview with Jake Strang)
• Don’t Add Another Event Until You Read This

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

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

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

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

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

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

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

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

Let’s start there.

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

So don’t be afraid to ask.
​
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.

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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.

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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.

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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.

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