 What Worked for Us on Giving Tuesday 2025: Real Strategies, Real ResultsEach 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:
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:
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
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 Scripts to Bring Up Planned Giving Without Feeling Weird About ItWhen 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. What to Say When You Want to Bring It Up (Without Sounding Morbid)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:
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. Why It’s Worth Getting ComfortableYou 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) Shift the Framing, Not Just the PhrasingThese 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. Don’t Wait for the Perfect Moment – Create OneYour 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:
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.
Decision Styles in Fundraising: It’s Not About What Moves You – It’s About What Moves Them9/10/2025  Decision Styles in Fundraising: It’s Not About What Moves You – It’s About What Moves ThemWhen 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. My Journey to StorytellinG 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. Why I Went Looking for a FrameworK 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: The 4 Donor Decision Styles – and How to Speak to EacH There are two axes: • Emotional → Unemotional • Linear → Freeform Put those together, and you get four types of decision-makers:  1. The Data Scientist (Unemotional & Linear)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. 2. The Closer (Unemotional & Freeform)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. 3. The Director (Emotional & Linear)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. 4. The Storyteller (Emotional & Freeform)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. So What Does This Mean for Fundraisers? 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.
Bottom Line: Write to Reach Them All 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:
Fundraising is communication. And great communication connects. Need help building appeals that speak to all four styles?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…
 The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About MoneyWhenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.” He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves. This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence. But here’s what I’ve learned: Your mindset matters more than your pitch. How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose. Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing. Let’s walk through them. 1. Reciprocity: Giving isn’t taking. One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes. That’s not what’s happening. Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves. That’s not taking. That’s inviting them in. I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up. Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction. 2. Receivership: Get good at receiving. Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke? That matters more than you think. If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift. Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent. You’re not just asking for money. You’re offering someone the chance to invest in something meaningful. Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence. 3. Reframing: The ask is not the problem. I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time. The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out. There’s an old joke in our field about someone like that: “How is <<that fundraiser>> like a 7/11 store?” “They never close.” Funny – but also kind of painful. Because many of us have been that person. I know I have. We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask. And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step. Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird. So, what does this mean for you? If you want to grow as a fundraiser, start by checking your mindset.
Fundraising isn’t begging. And it’s not manipulation. It’s invitation. It’s partnership. It’s a shared pursuit of something that matters. My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it. Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are. Cheers! Jessica  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
 The Magic Formula for Making a Confident Fundraising AskLet’s talk about a moment that strikes fear into the hearts of even the most seasoned fundraisers: the ask itself. Not the stewardship. Not the cultivation. Not the coffee chat or the tour. The moment when it’s time to name a number and ask a question. I’ve trained hundreds of folks, from student callers to major gift officers and presidents, and this is where so many otherwise capable fundraisers freeze. They hedge. They mumble. They talk around the gift instead of actually asking for it. That hesitation is what sinks so many proposals—because if you don’t ask clearly, the donor doesn’t know how to answer. Or worse, they walk away unclear on what you needed from them at all. The good news? Asking well isn’t about being fearless or charismatic. It’s about structure. It’s about using a reliable, repeatable framework that gives you confidence and helps the donor have clarity. Here’s what I call my Magic Formula for Making the Ask—and it works whether you’re asking for $100 or $1,000,000. 💬 The Magic Formula: Questioning Opener + Mission Moment + Dollar Amount + Silence Let’s break each part down so you can feel grounded the next time you find yourself sitting across from a donor (or dialing the phone or typing an email, for that matter). ✅ 1. Questioning Opener This is one of the biggest giveaways that a fundraiser isn’t comfortable asking: they frame their “ask” as a statement instead of a question. ❌ “We’d love it if you’d help out with a gift this year.” ❌ “It would be wonderful if you supported us again.” ❌ “We’re hoping you’ll get involved this year.” None of these are technically wrong, but they leave the donor hanging. They don’t invite a response. And they definitely don’t feel like the moment of decision that a real ask should be. Compare that to: ✅ “Would you be willing to make a gift of $5,000 to support undergraduate research?” ✅ “Can we count on you for support at the $25,000 level this year?” ✅ “Will you help our students with a $1,000 gift to the Dean’s Fund?” These are direct. Respectful. And clear. By ending your ask with a question, you’re signaling that it’s now the donor’s turn to speak. That subtle shift sets up a healthy, balanced fundraising conversation. ✅ 2. Mission Moment + Dollar Amount This is where you tie the ask to purpose. Don’t just ask for money—anchor the ask in something that matters. This is what moves the donor from “How much?” to “What for?” Instead of: ❌ “Would you consider a gift this year?” Try: ✅ “To help provide book scholarships for every student in the program, would you make a gift of $10,000?” Instead of: ❌ “We’d love your support.” Try: ✅ “To allow faculty to attend national research conferences this year, would you be willing to give $2,500?” You are the bridge between the mission and the donor’s capacity to make something good happen. That’s your role. You’re not begging. You’re inviting them into something meaningful—with clarity. And don’t shy away from being specific. A donor can always say no to a number. That’s okay. But if you ask, “Would you consider helping us out?” and they say “No,” you’ve left yourself no room to move. When you name a number, you create the chance for a real conversation. They might say, “That’s higher than I was thinking,” and now you can respond: “What would feel more comfortable for you?” or “Would you like to stretch that over a multi-year pledge?” Specificity unlocks possibilities. Vagueness shuts them down. ✅ 3. End. Pause. Listen. This is the part that makes or breaks it. Once you’ve made the ask—STOP TALKING. I know. It’s awkward. It feels like an eternity. But it’s crucial. The silence after the ask gives your donor time to process. It allows them to think. It gives them space to share what’s really on their mind. And what you learn in that silence? That’s gold. Maybe the timing’s off: “I just paid my kid’s tuition bill.” Maybe they need buy-in: “I’d have to talk it over with my spouse.” Maybe they’re passionate—but about something else: “I’d rather support the scholarships instead of the building fund.” If you rush in to fill the silence, you will miss all of that. You’ll speak from your own nervousness instead of their reality—and you’ll never know what part of the ask didn’t work for them. Practice the pause. Get comfortable sitting in it. It’s where the most honest parts of the conversation live. Bringing It All Together: Here’s a strong ask, built using the Magic Formula: “To help us provide every student in our department with book scholarships, would you be willing to make a pledge of $25,000—$5,000 a year for five years?” [PAUSE] If they say yes—celebrate and affirm it. Then let them know next steps to document and facilitate the gift payment. If they say no—that’s your cue to start the conversation. “Would it help to spread the gift out?” or “Is there a specific area you’d like to support instead?” But don’t jump ahead. Let them answer first. Want More on What Amount to Ask For? I’ve got a whole system for deciding how much to ask for—based on donor history, capacity, engagement, and more. If you'd like me to write about that next, leave a comment or shoot me a message. I'm happy to dig into that in a future post. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
 Why Most Fundraising Plans Fail (and How to Build One That Doesn’t)Let’s be honest: a lot of “fundraising plans” aren’t really plans. They’re a collection of ideas scribbled in the margins of a notebook. A to-do list that gets buried under meeting notes. Or a spreadsheet no one has opened since last fiscal year. And when things feel uncertain or urgent, even the most well-intentioned plan gets abandoned. So why do most fundraising plans fail? After 20+ years of working in and coaching nonprofit teams, here’s what I’ve seen over and over again: 1. The plan is not aligned with real capacity. Too many plans are built for imaginary versions of our organizations. You know the ones: the org with unlimited time, a full development team, and a budget for days. In real life, you’ve got a stretched-thin staff, a volunteer board, and one printer that jams every third sheet. The best fundraising plans start where you are. They work with your current capacity – not against it. They help you make choices, not just lists. Staff turnover is one of the biggest challenges that can set you back in fundraising and burnout is often the cause. If you build your plan around the staff you have and use technology to leverage that plan, you can mitigate burnout and turnover. 2. The plan is disconnected from results. If your plan doesn’t tell you how much money you can expect to raise – and from which methods – it’s not a plan. It’s a wish list. A strong fundraising plan includes projections based on past data, average gift sizes, and realistic conversion rates. This lets you set expectations, allocate resources wisely, and make the case for investments when needed. I did an entire blog post showing you how to build those projections so you know what you are able to raise, not just what you wish you would raise. No more spaghetti-on-the-wall fundraising. Just clear goals with measurable outcomes. 3. The plan doesn’t assign real accountability (Or backup).Even when a plan exists, it often fails at the handoff: no one knows who’s doing what – or worse, everyone thinks someone else is handling it. That’s why the final step of a good plan is assigning each task to a specific person. And then assigning a backup person to be cross-trained. This keeps your plan running when life happens – vacations, sick days, job changes – and builds resilience into your team. That’s why I wrote about building a responsibility calendar to protect your plan and ensure it becomes real. No more scrambling. Everyone knows their role, and the show goes on. So what does a successful fundraising plan look like? It’s clear. It’s doable. And it starts with what I call the MVPPP Framework, which is part of my Smart Start Fundraising System course:
Want to build your best fundraising plan yet? My new course, The Smart Start Fundraising System, is officially here! It’s designed for nonprofit leaders who are tired of spinning their wheels and ready to raise more – strategically, confidently, and without burnout. 🎯 Inside, you'll learn how to craft a compelling message, choose the right methods, identify and engage donors, mobilize your board, and build a plan you can actually execute – all using my proven MVPPP framework. ✅ 5 Pre-approved CFRE credit hours available ✅ Four high-impact bonus trainings included ✅ A 21 page workbook plus tools, templates, and spreadsheets you can plug and play 💻 Enrollment is open now! Price is $549 Take a look, see what’s inside, and get started at your own pace: 👉 Take a closer look here. Because passion doesn’t build a fundraising plan. But clarity? That’ll take you the distance. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…  How To Build a Recurring Gift Program from Scratch: A Step-by-Step Guide for Nonprofit FundraisersI learned the power of recurring gifts when I ran a faculty/staff giving campaign. I saw how quickly even $5 payroll deductions added up across the year when dozens upon dozens of donor participated. When I arrived at a much smaller institution that really needed unrestricted gifts, I knew they needed a strong monthly giving program that would help us reach our annual goals. Recurring giving is a powerful strategy that can transform your nonprofit’s fundraising model. A successful recurring gift program provides steady, unrestricted income and builds a loyal donor base that supports your mission long-term. Here’s how to build a thriving recurring gift program from scratch. What is a Recurring Gift Program and Why Start One? A recurring gift program allows donors to give smaller, automated contributions on a monthly basis, typically via credit/debit card or bank draft. These "set it and forget it" donations make giving simple and budget-friendly for donors, while providing nonprofits with reliable revenue. Why You Should Launch a Recurring Gift Program:
Why Donors Love Monthly Giving Monthly giving resonates with donors for several key reasons:
8 Steps to Launch Your Recurring Gift PrograMHere’s a step-by-step approach to creating a sustainable recurring gift program that will drive long-term success. Step 1: Explore Technical OptionS Choose a donation platform that securely stores donor payment information and processes automated monthly contributions. Key features to consider include:
Step 2: Build Internal SupporT Engage your team and leadership early. Present a clear case for why a recurring gift program is a strategic priority using data and examples:
Step 3: Create an Identity for Your PrograM Develop a unique brand identity for your recurring giving group to create a sense of community. Consider naming the group and designing a logo (e.g., "The [Organization] Sustainers"). This branding helps build a strong identity and a feeling of belonging among donors. Examples: Step 4: Start Small with Personal OutreacH Begin by reaching out personally to a select group of 25-50 loyal donors, volunteers, or board members. These individuals are likely to be early adopters and provide valuable feedback for refining your program. Action Steps:
Step 5: Launch a Broader CampaigN Once you’ve piloted your program, it’s time for a full launch. Use a multi-channel approach to reach your audience:
Step 6: Offer Meaningful PerkS While your main goal is sustainable support, offering small perks can enhance donor loyalty without significantly increasing costs:
Step 7: Steward, Maintain, and Upgrade DonorS Ongoing maintenance is key to the success of your program. Be proactive about updating expired credit cards and follow up with donors whose payments fail. In January, send timely letters for tax purposes covering all of the gifts the donor made in the previous tax year. I’ve always liked to send monthly donors a sticker and/or car decal for every year they are in the program. Upgrade Strategy:
Step 8: Conduct an Annual Recurring Gift PusH Persistence is crucial when building a recurring gift program. Plan an annual campaign to recruit new donors and replace any who have lapsed. Case Study: When we started "The Starr King Sustainers" program in 2016, we had just 11 donors giving under $1,000 monthly. By 2024, we grew to over 110 monthly donors contributing nearly $6,000 each month, providing a stable base of support for our mission. Conclusion: Start Your Recurring Gift Program TodaY Building a successful recurring gift program takes time and effort, but the payoff is substantial. With a thoughtful approach and consistent stewardship, you’ll create a loyal base of donors who are passionate about supporting your mission month after month.  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
 Trends & Predictions: Nonprofit Fundraising in 2025I remember the feeling of confidence I had going into 2020. I had been in the fundraising field for over 15 years (full-time), and at the time, I thought I had most things figured out. I would have confidently made broad, sweeping predictions about the future. And, as we all know, I would have made a complete fool of myself. Because everything we thought we knew was turned upside down by the global pandemic just a few weeks later. That humbling experience taught me a critical lesson: predicting the future isn’t about certainty; it’s about curiosity. It’s about studying trends, tracking the breadcrumbs, and embracing flexibility. As we look toward 2025, the nonprofit fundraising landscape continues to evolve, shaped by technology, shifting donor expectations, and global economic conditions. Here are a few trends to watch and how they might reshape the way we fundraise: 1. Highly Personalized Donor EngagemenT Gone are the days when a generic email blast could sustain your donor base. Modern donors expect nonprofits to know their preferences, interests, and giving history. This shift demands a deeper investment in donor data and segmentation strategies. What this looks like in practice:
2. AI and Predictive AnalyticS AI has moved beyond being a buzzword – it’s now a practical tool reshaping nonprofit fundraising. From automating administrative tasks to analyzing donor data, AI is helping fundraisers work smarter, not harder. Emerging applications in fundraising:
By prioritizing ethics, privacy, and authenticity, nonprofits can leverage AI responsibly while maintaining the integrity of their donor relationships. 3. Automation for EfficiencY With limited staff and growing expectations, nonprofits are turning to automation to streamline repetitive tasks. Automation allows teams to focus on what truly matters: building relationships and driving impact. What’s being automated:
4. Emphasis on Mission TransparencY Donors today demand clarity on how their contributions are being used. Organizations that can clearly articulate their impact and demonstrate accountability will stand out in an increasingly competitive philanthropic landscape. How to show transparency:
5. New Channels for Donor EngagemenT The way people consume information and interact with brands (including nonprofits) is constantly evolving. In 2025, expect to see growth in emerging channels like:
FINAL THOUGHTSThe future of nonprofit fundraising is both exciting and daunting. The tools and strategies available today offer incredible potential to engage donors in meaningful ways – but only if we approach them thoughtfully. As we navigate these trends, let’s remember the lessons of the past: stay adaptable, keep learning, and never forget that at the heart of every fundraising effort is a desire to connect people with purpose. What trends are you seeing in your work? Let’s keep the conversation going in the comments! Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
 “The important thing is not to stop questioning. Curiosity has its own reason for existing.” ― Albert EinsteinI can’t remember where I heard it, but it’s a great aphorism. Be relentless about the goal, but flexible about the methods. Another way to say it is: Be relentless about the what and the why. Be flexible about the how. We walk around with these axioms in fundraising. Consider: “Always call to get the visit.” And “Always ask for money in person.” Well, we’ve been presented with an opportunity to question these methods and how we do fundraising. I did a webinar recently about Frontline Fundraising in a Virtual Environment and I shook things up by confessing that I *gasp* didn’t often call to get visits. Folks were very interested in this maverick idea. It’s not really that maverick. It’s efficient. I send individual, personalized emails to the donors I would like to meet with and let those responses come in for 24-48 hours or until I have a full schedule. Of course, those emails are NOT graphics heavy, HTML promotional emails sent in bulk. They are personal notes from me to a specific donor. And if I have some donors who I need to meet with and I know that I don’t have an email for them or that they don’t check email often, I will call them. But, mostly my schedule fills right up without having to drudge through calling a list. I can put my energy and effort into fostering great conversations when I meet with them rather than on getting the visit. And of course, the meaning of the word “visit” has changed drastically in just a few months. So many metrics systems for fundraisers see an in-person visit as the gold standard. Of course, that’s true that in person interactions cement relationships in a special way. But, if we believe that other communication methods don’t have the power to significantly move relationships forward in a meaningful way, we are fooling ourselves. Furthermore, we hamstring our own efforts in this new reality. Even though many states are “re-opening”, the virus is still a real threat, especially to those over age 55. That’s an age group that comprises a mighty portion of our non-profit donors. In-person visits and events will not be a viable, “normal” option for a long time. A commitment to metric systems that reward in-person visits only will cause fundraisers to be frustrated and leave and campaigns to fail. Zoom and other video-conference technologies is only a sliver less effective as an in-person visit. And nearly everyone is open to trying out this new way of connecting right now out of necessity. But, let’s be clear: phone calls are also meaningful too. Personalized video and virtual events are fast becoming highly useful tools in the connection toolkit too. Anything that moves the relationship forward connecting the donor to mission is the goal. The goal is connection. Be relentless about the goal. The medium is the how. Be flexible about that how. Generally speaking, fundraising is not considered a creative profession. I disagree. In fact, I feel maintaining a creative approach to methods is essential as we face new challenges in any profession. We must remain perpetually curious as to what works. Let me know what you think in the comments. And subscribe to my FUNdraising Friday newsletter to keep the conversation going.  PS - If you liked this post, you might also like these:
PPS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my FUNdraising Friday emails, which includes the best articles on fundraising, productivity and cool stuff every week. The whole thing is weekly curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!  The legendary fundraiser, Jerold “Jerry” Panas, passed away in July 2018. I feel so tremendously lucky that I got to hear him speak in 2014 at a statewide Association of Fundraising Professionals event here in Mississippi. He had a salt-of-the-earth, no-nonsense style that was very attractive and inspirational. His books are wonders of pith and restraint. My favorite is “Asking: a 59-Minute Guide to Everything Board Members, Volunteers, and Staff Must Know to Secure the Gift”. It’s a 108-page crash course in fundraising, easy to read, and highly quotable. As the fundraising world adjusts to the new reality of the pandemic, I asked myself what Jerry would be advising us to do right now. Wondering how he might approach it, I flipped through my much highlighted and underlined copy of "Asking" to find out. I felt I should remind all of us of these timeless truths from a master of our profession. Here are 8 amazing quotes about the practice of fundraising that I found highly relevant to our current situation: “What I’ve discovered in all my years of fundraising is that it almost doesn’t matter how you ask . . . what is important is that you ask. Just do it” (p. 11)I’ve already answered the question of “To Ask or Not to Ask?” in this post. I love that Jerry agrees with me. Fundraisers are not hired to raise money. We are hired to ask for money. So, we must find effective ways to do that and not let our discomfort or ego get in the way. “Keep in mind that men and women don’t want to give money away. They want to invest in great causes, in bold and exciting dreams.” (p. 12)Don’t Jerry’s quotes make you want to whoop and shout “Amen!”? Fundraisers can only go so far if there is not a bold and inspiring vision coming from the very top visionary leadership of the organization. Create something folks want to invest in. Right now, that may mean emphasizing how important your mission still is, despite coronavirus. Or you may need to switch to relief fundraising to help those you serve directly. “Integrity is the mightiest weapon in the fundraiser’s arsenal – more important than the campaign literature or anything that is said. Its power is explosive. Integrity alone is no assurance of getting the gift. But without it, you can’t even begin the journey.” (p. 20)I’ve written about integrity as an essential quality for a fundraiser last week and back in 2017. Find your deep connection to the mission of your organization or, by golly, go work somewhere else. That belief in mission will radiate realness from you and your donors will feel it and respond to it. “Work hard at putting people completely at ease and making them feel important.” (p. 48)This is the essence of quality cultivation conversation in one brief sentence. (Didn’t I tell you Jerry was pithy?) This advice can apply as easily to Zoom and telephone conversations as it applies to in-person visits. “People don’t care how much you know until the know how much you care.” 55Lead with care for people. Start with inquiring about the health and welfare of your donors and their family. Then move to expressing your care and concern for those your organization serves. If that caring is communicated effectively and with integrity, you are only millimeters away from a gift. “Lucky you. You are a fundraiser. Some shy away. Some are afraid. Some say they don’t like it. You know better. You are, in your own special way, helping to change a corner of the world.” (p. 77)We must remember the worthiness of fundraising as an endeavor if we are to survive and thrive in the non-profit world during this difficult time. Connect to that broader mission and be proud of it. I wrote a similar post here. “Giving up is the ultimate tragedy. Failure is not the crime – low aspirations are.” (p. 79)When I think about all the challenges that history has brought to those going before us (wars, disease, genocides, massive social change, etc.), I connect to the fact that we must endure. The first organized capital campaign (for the YMCA) happened during World War I and the Spanish Flu Pandemic. Harvard University embarked on their first endowment campaign in 1919, just after those two pivotal events. The American Red Cross had their first successful multi-million campaign during World War II. We can do this. “In all you do, act as if it’s impossible to fail.” (p. 88)Amen, Jerry! Our mindset largely determines how far we can go. What I see right now is a firmly 20th century mindset is dying, and organizations are being forced into a fully 21st century mindset. Organizations who have a scarcity mindset are already cutting revenue-generating staff at the mere anticipation of challenges. Institutions that have truly made the switch to a 21st century, abundance-oriented mindset will find a way to function in this new reality, as Jerry says, “as if it’s impossible to fail.” What's your take? Do you agree with Jerry or feel his lessons aren't applicable to the current moment? What's your favorite book of his? Comments and questions are, as always, welcomed and encouraged! Cheers, PS - If you liked this post, you might also like these: PS - If you liked this post, you might also like these:
PPS - There's only 12 Days left to join my new course, All-Star Annual Giving. Registration is open! All-Star Annual Giving is a fully online 12-week course with 9 modules covering all areas of annual giving strategy and execution. If you want to roll into the semester with a fully-fledged plan to raise more money than you've ever raised before in your annual giving programs, you need to be in this course. |
Jessica Cloud, CFREI've been called the Tasmanian Devil of fundraising and I'm here to talk shop with you. Archives
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