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…
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 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…
 Planned Giving Leads Don’t Generate Themselves – But They Can Be SparkedI used to think donor interviews for our legacy giving newsletter were just good stewardship – a warm thank-you to generous folks who’d already made a planned gift. Back then, part of my “gal Friday” role at the university was to call these donors, hear their stories, and write up little features for our newsletter. It felt like we were shining a light on their kindness and leaving it at that. Then something surprising happened. After a few issues, my inbox started filling with messages:
Planned giving can feel awkward to talk about – it’s wrapped up in big questions about life, death, and legacy. But when donors see someone just like them, sharing why they chose to leave a gift, it shifts the conversation. Suddenly it’s not about confronting mortality – it’s about hope for the future. And when those leads came in, the follow-up conversations weren’t awkward at all. I wasn’t “convincing” anyone; I was simply giving them the tools they’d already decided they wanted. If you have even one donor who’s named your organization in their will, you have a powerful story to tell. And those stories can spark more conversations – and more commitments – than any brochure or website copy ever could. Here are five simple, effective ways to start generating planned giving leads right now, starting with the most important one… 1. Collect and share meaningful donor testimonials.Start with real people who’ve already made a legacy commitment. Interview them, ask thoughtful questions, and tell their story with heart. These five questions help bring their motivations to life:
2. Build a simple landing page to support the conversation.You need a place to send people who want more info – don’t make them hunt for it. This doesn’t have to be complicated. Just make sure it includes:
3. Use National Estate Planning Awareness Week (October) to shine a light.This is your annual window to talk openly about legacy giving – especially with donor stories. Tie them to helpful content like estate planning tips, FAQs, or “3 Easy Ways to Leave a Legacy” guides. Light, approachable, and packed with value. 4. Reinforce with your own “Legacy Giving Week” in the spring.Don’t let October do all the heavy lifting. Bring it back around with a spring campaign using your existing content – maybe add a new testimonial, or reframe the messaging. Familiarity builds comfort. 5. Add a 30-second legacy survey to your direct mail reply cards.Flip that reply device over and include a quick checkbox survey: ☑ I’ve already included [Org Name] in my estate plans ☑ I’d like more information ☑ Please send me sample bequest language This low-lift tweak has sparked real results for many nonprofits – and costs zero extra to implement.  If your nonprofit does just these five things, you’ll be light years ahead of most organizations in planned giving marketing. And the best part? None of them require new dollars in the budget. That’s a win for your donors – and a big step toward your organization’s long-term financial stability. 🎉 Ready to make it even easier? Grab the Celebrate National Estate Planning Awareness Week Bundle – just $84.99! 🎉 Planned giving is one of the most powerful ways to future-proof your mission – and October is the perfect time to talk about it. This digital bundle is packed with tools to help you celebrate, educate, and inspire your supporters to leave a lasting legacy. Here’s what’s inside:
💡 Total value: $114.95 – You pay just $84.99. That’s 26% off. And here’s the kicker:
📥 Once you purchase, you’ll receive a downloadable PDF with links, setup instructions, and a tutorial video to walk you through the whole process. 👩💼 Made by me – Jessica Neno Cloud, CFRE – with 20+ years in the field helping fundraisers like you take real, doable steps toward long-term success. 👉 Ready to roll? Get your bundle now and make this October count. Cheers!  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 Questions Donors Ask About IRA Rollover Gifts (and How to Answer Them)IRA rollovers are the best of both worlds. They let donors give from their assets, not their income – so these gifts are often larger than what someone could give from their checkbook. And here’s the best part: the funds can be put to use immediately by the nonprofit. Still, many fundraisers hesitate to talk about Qualified Charitable Distributions (QCDs) – also known as IRA rollover gifts – because they don’t feel confident answering donor questions. But here’s the truth: donors rarely ask complicated questions. They just want to understand the basics. If we want to receive these powerful gifts, we need to be ready with clear, simple answers. Here are the top three questions I hear most often – plus how to respond in a way that builds trust and inspires action. 1. “Will this affect my taxes?”Yes – in a good way. If you're 70½ or older, you can give directly from your IRA to a qualified charity without increasing your taxable income. For donors over 73, that gift can count toward your Required Minimum Distribution (RMD). So you're meeting a federal requirement and supporting a cause you love – without taking the tax hit. 2. “How hard is this to do?”Honestly? It’s very doable. If your IRA account includes check-writing privileges, you can write a check directly to the nonprofit. If not, a quick call to your broker or account manager will do the trick. Just make sure the funds go directly from the IRA to the charity. If they hit your personal account – even briefly – they become taxable. 3. “How much can I give this way?”In 2025, the annual QCD limit is $108,000 per individual, indexed for inflation. If both spouses have IRAs, a household can give up to $216,000 in a single year. Keep in mind: this is the total giving limit per IRA account per tax year. So if you've already made other QCDs this year, you’ll want to keep a tally toward that annual cap. Donors Are Asking – Are You Ready to Answer?If you’re not already promoting IRA rollovers, this is the time to start. And no – you don’t have to start from scratch. ✅ Grab the IRA Rollover Promotion Bundle – Everything You Need to Promote QCDs This $99 bundle includes:
You’ll get a downloadable PDF with links to every template, setup instructions, and a short tutorial video. Created by me – Jessica Neno Cloud, CFRE – after 20+ years in fundraising, this bundle is built to help you raise more, with less stress and guesswork. From 2019 to 2021, giving through IRAs jumped 390%. This isn’t a trend – it’s a tidal wave. Let’s make sure your nonprofit is riding it. Want a free way to get started? Download my free resource, Calendar of IRA Rollover Promotions – a simple tool to help you map out smart, strategic outreach across the calendar year. 👉 Download the Free Calendar Cheers!  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. IRA Rollover References Resources If you liked this…
 “Wait, Am I Supposed to Fundraise Now Too?” A Department Chair’s Guide to Getting StartedPop Quiz: A beloved faculty member retires, and your department wants to honor them with a named scholarship. Should you: a) Hit up that top donor at the tailgate b) Meet with Advancement and make a plan c) Launch a GoFundMe and post it to the department's social media If you picked B, congratulations – you’ve passed. If you're scratching your head, you're not alone. (And yes, every one of those quiz options I have witnessed personally.) Far too often, faculty are either sprinting ahead trying to do it all themselves or sitting it out because the maze of advancement feels too intimidating. Neither of these extreme approaches do justice to your students, your honorees, or your own standing as a leader on campus. Here’s the thing: most faculty don’t go into academia thinking they’ll ever be responsible for raising money. Then one day, they step into a department chair role and suddenly, fundraising is on the job description – but no one handed them a manual. It’s a lot to take on, especially when you’re already juggling budgets, personnel, and curriculum. Though I’m an Advancement professional, I’ve worked directly with faculty on fundraising since the 20th century – and I’ve seen plenty of ways fundraising efforts can go sideways. These are the things that work to make you the Advancement team’s favorite faculty collaborator. When you know who to call and how to work together, you not only raise more money, you build momentum, respect, and resources. Let’s talk about how to work effectively across campus. Development Most of the folks in Development departments actually aren’t major gift officers who play golf all day. In reality, it’s the researchers, database managers, gift processors, accountants, and annual giving folks who are the real MVPs and can be your best resource as a department chair. Development offices thrive when faculty help connect academic work to donor dreams. They’re looking for faculty who can paint a clear picture of how gifts support teaching, research, and student success. Want to get off on the right foot? Here are three things you can do:
Alumni Association Your former students aren’t just Facebook friends. They're potential mentors, donors, and champions for your department. The Alumni Association wants your help making those connections stick. Want to build better relationships with alumni staff and support your grads? Here are three ways to start:
Campus Politics Around Giving Yes, it can get political. Departments can get territorial. Your college or university will have its own fundraising priorities which may not match yours. Donors get pulled in ten directions – and when everyone goes rogue with fundraising, everybody loses. Instead of guarding your turf, try building bridges. Focus on what the donor wants and how multiple units might work together. A shared proposal doesn’t dilute your message – it strengthens it. It shows you’re working as a team, which donors love. Collaboration isn’t just a buzzword. It’s a strategy. And when faculty, development, and alumni relations team up, the results are bigger, better, and more sustainable. Truly, everyone working together advances the institution. So, the next time someone announces their intention to retire and you want to honor them with a scholarship, don’t wing it or walk away. Partner up. Think long-term. Be the faculty leader who understands how things get done – and gets them done with heart and strategy. Ready to take the next step?If this post hit home, I’ve got something that’ll really help: a free 35-minute webinar called Building Fundraising Confidence for Department Chairs. It’s practical, empowering, and designed to help you stop second-guessing and start asking with clarity. You’ll get access immediately—and it’ll subscribe you to my newsletter where I share more strategies, stories, and insights for academic leaders who are learning how to fundraise without losing their minds. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you!
 Microwave Fundraising vs. Crockpot Fundraising: Why the Slow Simmer Wins Every TimeA few years back, I worked with a team that was stuck in microwave fundraising mode. If there was a quick-cash tactic out there, they were doing it: golf tournaments, raffles, sponsorship deals heavy on the benefits, you name it. It kept the lights on, but it wasn’t building anything lasting. I gave a presentation about crockpot fundraising – relationship-building, long-term strategy, donor engagement – and it started to click. I wanted to challenge them to try something new and to move out of their "microwave" comfort zone. I promised them that if they could do that, it would pay dividends down the line and make fundraising easier and more enjoyable. I've been in rooms full of nonprofit leaders who are scrambling to make payroll, stressed over budget gaps, or just plain overwhelmed by the pressure to "do more with less." And in those moments, it's tempting to reach for the quick fix – a car wash, a 5K, a golf tournament, a donut sale, a last-minute sponsorship deal. These microwave fundraising tactics can bring in a little fast cash, and I won't pretend they never have a place. But let's be honest: they're not going to carry your mission for the long haul. Microwave fundraising is all about urgency. It's transactional. It gets warm fast, but it cools off just as quickly. These events are often labor-intensive, draining your staff and volunteers. The ROI is usually modest. They’re familiar, easy to organize, and feel reliable. But they’re not always the healthiest choice for your organization. They only feed a few folks, and they don’t build connection to your mission or long-term sustainability. Here's a side-by-side breakdown that captures the heart of the metaphor:  Caption: Microwave vs. Crockpot Fundraising: A visual comparison of quick, transactional tactics vs. slow, relationship-centered strategies. Then there's crockpot fundraising. It takes longer to get cooking, no doubt. And yes, there’s a learning curve. But it’s healthier for your mission in the long run. These strategies usually involve more “vegetables” – meaning thoughtful, nourishing activities like donor conversations, stewardship touches, and consistent storytelling. It takes time. You can’t flip a switch and expect results tomorrow. But when you commit to it – when you really let it simmer – the flavor builds. The connections deepen. The nourishment multiplies. Crockpot fundraising feeds a crowd. You’re not just generating one-time gifts – you’re building community. It’s transformational. It deepens loyalty. It keeps donors connected to the mission. It gives your work staying power. It means investing in consistent donor communications, one-on-one conversations, thank-you calls, stewardship, and strategic asks. First-time donors become recurring givers. Recurring givers become advocates. Advocates become legacy donors. Is it slower? Yes. But it is sustainable. It doesn’t burn you out or box your organization into lopsided agreements just to chase a check. It feeds your mission in a way that microwave tactics never will. It keeps your team grounded and your donors inspired. So when you're weighing your next move, ask yourself: Are we microwaving or crockpotting this? One will keep you hustling for scraps. The other will feed your mission for years to come. Let it simmer. You'll be glad you did. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 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!
 Your Board Wants to Help with Fundraising – They Just Don’t Know HowLet’s bust a myth right now: “Our board won’t help with fundraising.” That’s almost never the full truth. Most board members want to help. They believe in your mission. They want your organization to succeed. What they don’t have is clarity or support. They don’t know what to do, where to start, or how to help in a way that feels comfortable and meaningful. In other words: this is usually a training problem, not a motivation problem. If you want board members to engage with fundraising, you have to give them a roadmap. That’s why I created a “Board Fundraising Menu” – an easy, low-pressure way to show board members that fundraising is more than just asking for money. (Full transparency: this is an idea inspired by Andy Robinson, who has great books about how to train your board to raise money.) It’s about helping create the conditions where giving is more likely. I used this with a higher education Board of Trustees and told them it was an “All You Can Eat” menu but they had to pick at least one from each category: Appetizers, Entrees, and Desserts. I walked them through filling it out in the meeting and left with a list of folks who could write notes, open doors, make calls, and host events! Here are 3 specific actions your board members could take today: Appetizer: Sign and personalize donor letterS If picking up the phone makes them queasy, that’s fine. Start here. A short handwritten note or a personally signed appeal letter makes a huge difference – and helps board members feel included without the pressure of a direct ask. Entrée: Host a house party or donor touR This one’s for your connectors. Board members don’t have to ask for money – they just need to open the door. Hosting a gathering where staff shares impact stories or tours a program site is a powerful way to build trust and widen your prospect funnel. Dessert: Make thank-you calls to donorS No one is ever mad about a thank-you call. And hearing directly from a board member? That’s memorable. It boosts donor retention (especially for first time donors) and builds board confidence in your development process. But here’s the truth: board members need support. Okay, okay – you’re busy. I know. You’re running events, managing emails, answering the auditor’s questions, and cleaning up after the copier jammed again. But they’re busy too. They’re volunteers. They have full-time jobs, families, responsibilities – and most of them have never done this before. Anyone would feel unsure operating outside their expertise. So when a board member says, “I’ll introduce you to my friend,” the best thing you can do is write a draft email for them to send. Not because they can’t write one, but because it saves them time and anxiety. It gives them something to react to. They can edit it to sound like themselves – but only they can send it. If they offer to make calls, set them up for success with a guide that explains the data set, answers frequently asked questions, and provides scripts and samples. And don’t forget to give them a seamless way to get all that feedback to you so it can be recorded in your database too! Your role? Be their concierge. Their guide. Their teacher. When you hold their hand through these steps, you're not just getting results today – you’re building better, more confident board members for the future. The secret? Board members are your partners. If this kind of clarity and confidence sounds like something your board needs, I’ve built something for you. Tired of chasing your board or getting ghosted after a meeting? Inside the Smart Start Fundraising System, you’ll get a plug-and-play plan to turn passive board members into proactive partners. Because fundraising isn’t a solo sport. It’s a team effort. And your board? They're not just fiduciaries – they’re your fundraising partners. But they need the tools, training, and support to step into that role effectively. Want the full board engagement menu? It’s included in the Smart Start Fundraising System – along with a plan to actually activate it. 💡 You’ll learn how to:
🎯 Enrollment is open now. Click below to get started and download the full board fundraising menu inside: 👉 [Click here to enroll now] Because “they won’t help” can become “they’re amazing ambassadors” – with the right structure in place. 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…
 The Problem with Totes and T-Shirts: Why Freebies Can Undermine FundraisingMy grandfather wasn’t a big donor. He only gave to a handful of causes in his lifetime. But there was one organization that always stood out: St. Jude Children’s Research Hospital. He gave faithfully – moved by the emotional weight of their television commercials. The stories got him every time. But even though he was already giving, they kept sending him address labels. Over and over again. At the time, I didn’t get it. Why send him stuff he didn’t ask for when he was already clearly connected? Years later, working in fundraising myself, I learned what was going on. Those labels weren’t a thank-you. They were part of the ask. A fundraising tactic. A subtle nudge rooted in the psychology of reciprocity: we gave you something, now give something back. And while it might work once, that kind of giving rarely sticks. The truth is, these built-in freebies – address labels, calendars, stickers – don’t deepen connection. They dilute it. They train donors to expect something with every letter, and more importantly, they shift the focus away from the mission. I still wonder: would my grandfather have kept giving without the commercials? Maybe not. But I know this for sure – it wasn’t the address labels that made him care. When Fundraising Starts to Feel Like a Loyalty ProgramWe’ve all seen it – and some of us have inherited files full of it:
These “free” items are anything but free. They come at a cost – not just to your budget and your time, but to your donor relationships. Why These Kinds of Premiums Can BackfirELet’s get practical. Including giveaways in your appeals may seem harmless, but it creates three major problems: 1. It sets the wrong tone. You’re not building connection – you’re mimicking a subscription box. That’s not what we’re here to do. 2. It costs more than you think. Printing, shipping, design, fulfillment – it adds up fast. Those funds could go straight to your mission. 3. It attracts short-term, low-retention donors. This is the biggest problem. Donors who give because of a trinket are less likely to renew, upgrade, or become champions for your cause. You want committed supporters, not one-time transactions. And There’s a Legal Catch, Too Let’s talk taxes. When you include a premium with your appeal, you risk turning that gift into a quid pro quo contribution – where only part of the donor’s gift is tax-deductible because they received something in return. To avoid that, the item has to be of “insubstantial value” – meaning so cheap it’s practically worthless. And if the gift is that insignificant, why bother sending it at all? You’re adding printing, packaging, and postage costs for something that can’t carry real meaning or message weight. It’s a logistical headache with no lasting return. What Donors Actually WanT Here’s what’s wild: Most donors don’t even want the stuff. They want to be moved. They want to know their gift means something. That’s where Near, Dear, and Clear comes in:
No label sheet in the world can deliver that. But a compelling story can. When Thoughtful Tokens Do Make Sense This isn’t a full-on war against every branded item. There’s a time and place – but intention matters.
A bookmark made by a student in your afterschool program? That’s beautiful. A bulk-ordered mug with your fiscal year slogan? Probably unnecessary. Would you give your best friend a water bottle to say thank you? Or would you write them a heartfelt note of thanks? So What Should You Do? If you’re stuck in a cycle of sending “stuff” or trying to break the premium habit, here’s where to begin: 1. Lead with stories. Make your appeal emotionally rich and mission-focused. Don’t let a keychain carry the message. 2. Map the full donor journey. Gifts shouldn't unlock access to your best content. Welcome everyone into the story, not just your VIPs. 3. Test it. Try a premium-free version of your next appeal and track the results. You might find your message carries more weight on its own. And don’t forget to track retention of those new donors acquired (with premiums and without) in the next year of giving. Fundraising That Feels Better (and Works Better) The truth is, you don’t need gimmicks to raise money. When you lead with purpose, your donors feel it. And they’ll stick around. Mission-centered messaging doesn’t just build trust – it builds staying power. Ready to ditch the swag and write stronger appeals that actually retain donors?The Smart Start Fundraising System will show you how. I break down what motivates giving without resorting to trinkets and help you build a complete plan grounded in what matters. [→ Get on the waitlist now or check out the course here.] 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…
 Phonathons Are STILL Not Dead – Busting the Biggest Myths About Calling DonorsEvery few months, another university quietly kills its phonathon. And just like that, inboxes everywhere light up:
Let’s set the record straight. Phonathons are not dead. And many of the arguments used to declare their demise are based on myths – not real data, not field experience, and definitely not what’s actually happening on the ground at most institutions. So let’s bust some of the biggest myths I hear over and over again: Myth #1: “Nobody picks up the phone anymore.” Reality: Pick-up rates (contact rates) are absolutely impacted by things like caller ID, time of day, area code, and list segmentation. But even in the post-pandemic world, institutions are still having real, quality conversations with alumni, parents, and friends. When done right, phone outreach still delivers contact, conversation, and conversion. In fact, one partner institution recently doubled their call completion rate within a single year, simply by improving their strategy – things like making more attempts per record, using smart list management, and building trust through clearer caller ID. The problem isn’t that people don’t pick up. The problem is we’ve stopped giving them a good reason to. Myth #2: “We don’t need phonathon anymore.”Reality: This one usually comes from someone who hasn’t worked a call shift or analyzed the pipeline lately. If you’re serious about long-term fundraising success, you need phone outreach. Here’s why:
One institution I advised recently saw a huge bump in average gift size – up over 50% – and their calling center is now on track to exceed their full fiscal year results any day now. You can get great ROI from calling… if you treat it like the professional fundraising channel it is. Myth #3: “The phonathon loses money (or only breaks even).” Reality: It’s supposed to break even – or come close. Phonathon isn’t just about the immediate dollars in the door. It’s about the long game: donor reactivation, new donor acquisition, pipeline building, and massive volumes of updated data. That work fuels years of future fundraising success. If your phonathon is consistently losing money, the issue usually isn’t the channel – it’s the execution. Maybe your manager is under-supported. Maybe you’ve got outdated or clunky software that makes it impossible to track results or process credit cards smoothly. Maybe you aren’t calling enough to make your fixed costs worthwhile. But let’s be clear: the blame doesn’t lie with the callers – or with the channel itself. Myth #4: “Call center manager is just an entry-level gig.”Reality: Running a call center is one of the hardest jobs in advancement. It demands a unique skill set: donor communication, hiring and training, shift logistics, data reporting, budget management, and tech troubleshooting – just to name a few. And yet, too often this role is underpaid, undervalued, and handed off to someone with no real support or path for growth. Here’s the truth: If you want your phonathon to succeed, you need a strategic leader managing it. When that happens, everything gets better – culture, results, retention, and ROI. Myth #5: “We’ll just go multichannel instead.” Reality: I support multichannel fundraising 100%. Donors need options. But cutting your call center with no plan to replace what it actually does isn’t innovation – it’s just short-sighted. If you eliminate phone outreach, here’s what you’re walking away from:
Ask yourself: What’s the plan to make up for all of that? If your phonathon isn’t performing, it’s not because the channel is dead. It’s probably due to low volume of work, poor strategy, clunky systems, undertrained callers, or a lack of clear goals. All of those are fixable. That’s what I help institutions do every day – reset, retool, and rebuild programs that actually work. If you’re ready to stop chasing trends and start making smart decisions about your donor outreach, let’s talk. Whether you need a strategic audit, caller training, or a full-scale turnaround, I’ve got your back. Bottom line: Phonathon isn’t broken. The way it’s managed might be. And with the right approach, calling still works – and it works beautifully. 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! PPS – If you need to freshen up your phonathon, be sure to check out my book Successful Fundraising Calls: A Phonathon Scripting Workshop available through Academic Impressions and my e-book How to Staff Your Phonathon Super-Fast available to download instantly here in the Real Deal Fundraising Store.  |
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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