 Read Between the Dollars: 3 Gifts to WatchFundraisers love numbers – but we don’t always slow down to read them. When I look at donor giving histories, I’m not just tallying lifetime value or calculating retention. I’m looking for inflection points. Clues. Moments that tell me a donor is thinking differently about their relationship with the organization. You can spot those moments – if you know what to look for. In my last blog post, I revealed my strategy for connecting annual giving to major and planned giving for board members. Through this process of telling the long version of donors’ origin stories, I saw patterns that repeated. I kept seeing similar types of gifts that signaled the donor had deepened in their connection to the organization’s mission. Once you know them, you’ll be able to spot these in the gift histories of your current major donors. After a while, you’ll be able to see these gifts when they happen and optimize your systems to steward these donors to the next level! Here are three gift types I always flag in donor bios: 1. The “Kick the Tires” Gift This is the donor’s very first gift. It’s usually modest – $25, $50, maybe $100. But don’t let the size fool you. This gift is a test. They’re watching how your organization responds. Do you acknowledge quickly? Do you give thanks personally? Do you make it easy to give again? Do they feel seen? Most board members don’t realize that your largest donors often start right here. Not with a gala. Not with a campaign. But with a small, quiet gift and a lot of curiosity. Track this gift like it matters – because it does. By reframing first time gifts as “kick the tires” gifts, organizations leverage their systems to make sure every new donor has an exceptional experience and feels appreciated. Ask yourself: Do you have any special communication or benefits that help first-time donors feel recognized? How I can I use email, phone, volunteer/board outreach, and mail to have this donor feel the love and their impact? 2. The “Hand-Raising” Gift You’ve got a donor who’s given $100 a year for a decade. Then suddenly – boom – a $1,000 check shows up. That’s not random. That’s intentional. The exact numbers matter less than the jump. A $25 dollar donor jumps to $500. A $1,000 donor jumps to $5,000. All of these are donors signaling interest. They’re re-evaluating what your work means to them. And they’re inviting you to respond. When you see this kind of jump, drop everything and make a call. Not to ask for more – but to listen. What changed? What are they excited about? Who or what inspired the new level of giving? This is your chance to deepen the relationship before they drift away. Ask yourself: Do I have a notification system that will let me know when “hand-raising” gifts happens? What’s my process when I learn about them? 3. The “Breakthrough” Gift Here’s where it gets exciting. You see a donor move into five- or six-figure territory, or they’ve set up a multi-year pledge. Maybe they’ve reached out about leaving a bequest. This donor is no longer an annual donor – they are in the pipeline. Yes, these bumps happen with personal visits and cultivation, but sometimes the donor decides to make the leap. When I see this move, I bring them into a different lane. Personal stewardship. Custom impact reports. Invitations to help shape the vision, not just fund it. Because at this level, they’re not just giving – they’re investing. This is where cultivation becomes partnership. Ask yourself: How can I make sure I don’t miss any of these breakthrough gifts? What’s my plan to meet this donor and find out what their philanthropic goals are for the long-term? In conclusion… Make sure these three moments show up in your reports. More than data points, these three gift types represent real shifts in mindset. Catching them early and responding with intention is how you build a stronger, smarter pipeline. Because fundraising isn’t just about chasing dollars. It’s about listening to the story those dollars are trying to tell you. Cheers!  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
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 From $50 to Six Figures: How I Got Board Members to Care About Annual GivingI was fortunate in my role at the University of Southern Mississippi. My VP made space for me – literally – on every board agenda. I had a standing spot to update the USM Foundation board on annual giving, and I could use that time however I saw fit. Sure, I gave them numbers. But I didn’t stop there. I used that time to give them the narratives beyond the numbers. Histories. I pulled the giving records of donors they already admired – the names they knew from building dedications and big announcements – and traced them back to their beginnings. Because almost all of them started small. I wanted the board to see what I saw every day: Annual giving isn’t just about this year’s total. It’s about long-term trust. It’s how major donors begin. The large gifts you are getting today started with trust-building 10 or more years ago. And how you are treating your $50 donors today is how you are treating your future major and planned giving donors of tomorrow. This post is about how I helped shift board thinking – from shrugging at $50 gifts to recognizing them as the first step toward six-figure support. At every board meeting, I brought receipts. Literally. I’d share two or three donor stories. Not headline gifts. Origin stories. I’d pull the giving history of a well-known benefactor – the kind of donor whose name was etched on a building or whose estate gift had changed our endowment – and I’d start at the very beginning. Turns out, the beginning wasn’t glamorous. No gala. No VIP treatment. Just a reply card in the mail or a quick online donation. Often $50, sometimes $100. Inspired by a direct mail piece or a phone call from a student caller. I told the story of how that first gift came in. How we acknowledged it. How we followed up. What kind of communication they received. How they were stewarded over time. And then I showed the leap: four-figure giving. Five. Sometimes more. By the third or fourth board meeting, it started to click. Annual giving isn’t just about dollars this year. It’s a pipeline. And more than that – it’s a vetting process. Donors with real capacity don’t show their full hand right away. They start small. They're testing your systems. They’re watching your stewardship. They want to know: Will my gift make an impact here? Can I trust this organization to be a good partner? And the truth is, annual giving is the only system robust enough to keep that door open over time. It keeps your data clean. It helps you stay in touch when someone changes jobs or cities. It gives you cues about life changes that might signal major or planned giving potential. It’s not just donor acquisition. It’s donor cultivation in slow motion. When I layered in real data – about how much of our major gift pipeline had once started with a $25 or $50 gift – something shifted. Board members started asking about the annual giving numbers. They started taking the appeal letters home. A few even gave leadership annual gifts themselves. The modest gifts didn’t seem so modest anymore. And that’s the whole point. If you want major and planned gifts tomorrow, you have to care deeply about annual giving today. Cheers!  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
 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
 Don’t Add Another Event Until You Read ThisI get it – events feel like momentum. They’re visible. They’re exciting. And if your board or staff is worried about revenue, the first suggestion is often: “What if we did another fundraiser?” But here’s the thing I wish more nonprofits understood: More events aren’t always the solution. Sometimes, they’re the problem. Events are expensive – even when they "make money"Sure, your spring gala might net $12,000 after expenses. But how many staff hours did it take to plan? How many other fundraising activities were delayed or abandoned in the lead-up? Did it bring in new major donors or long-term monthly supporters? Or was it mostly your usual crowd eating chicken and bidding on a silent auction basket? I’m not saying you should never do events. But I am saying you need to know what each one is actually doing for your mission – and at what cost. I have strong feelings about 5Ks and golf tournaments – and here’s whY Because they trick you into thinking you’re fundraising, when what you’re really doing is facilitating a transaction. Participants are there to run, or to play golf. They’re not connecting to your mission. They're not hearing stories of impact or seeing their role in your work. They’re getting a t-shirt and a swag bag – and then they’re gone. You might as well be selling donuts on the street corner. So how do you know if an event is actually worth it? Ask yourself:
What if we have an event and I can’t cancel it? Now, if you’ve got an event that’s locked in – maybe it’s tradition, or there’s a sponsor you don’t want to lose – make it count. Infuse as much mission into that event as you possibly can. Don’t just entertain – connect. I once went to a Broadway revue fundraiser for a group supporting teens in foster care, and in between each number, they played short audio clips of the teens sharing their stories. It was powerful. I still remember those voices. That’s what sticks. And that kind of emotional resonance is what opens the door for deeper engagement. Pair that with a strong follow-up plan – something that nurtures those attendees beyond their ticket or entry fee – and you can turn one-time guests into long-term donors who truly understand and care about your work. The Hidden Cost No One Talks AbouT Every event on your calendar takes time – time your team could be spending building real relationships with major donors, deepening stewardship, or crafting a compelling campaign that brings in five- or six-figure gifts. That’s the real opportunity cost. It’s not just the hours spent on centerpieces or silent auction items – it’s the connections you didn’t make, the asks you didn’t have time to prep, the impact that got delayed because your best energy was tied up elsewhere. If you want transformational gifts, you need the bandwidth to pursue them. Events rarely give you that. A smart plan does. How to Stop Letting Events Run Your StrategY In my Smart Start Fundraising System, we assess your fundraising “vehicles” – the methods you use to reach donors. Events are just one of many vehicles. And often, there are smarter, leaner options with better ROI. But the real magic happens when you zoom out and create a Plan – one that aligns your fundraising activities with your goals, capacity, and budget. Not every organization needs a gala. Some need a good direct mail strategy. Others need better donor journeys or stronger partner engagement. When your events support your overall plan instead of driving it, everything clicks. Before you plan another event… Ask yourself: Is this the best use of our time, energy, and budget? And if you’re not sure? 💡 That’s exactly what my course, The Smart Start Fundraising System, helps you figure out. We walk through your fundraising menu, evaluate the ROI of each activity, and build a plan that plays to your strengths – without burning your team out. 🎯 Enrollment is open now! You’ll get instant access to the training, tools, templates, and bonuses – plus 5 CFRE credits. 👉 [Click here to enroll today] and start building a smarter, more sustainable fundraising plan. Because you deserve a fundraising strategy that works as hard as you do. Cheers!  PS - I hope you’ll continue the conversation by subscribing to Real Deal Fundraising. When you subscribe, you’ll get my e-newsletter, which includes the best articles on fundraising, productivity, and cool stuff every week. The whole thing is curated awesomeness as well as freebies like webinars, instructional videos, and whatever else I can put together to be helpful to you! If you liked this…
 Why Most Fundraising Plans Fail (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…  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.   New Fiscal Year Approaching – Are You Ready for the Ride?Jessica here! Today, I’m thrilled to welcome a guest post from my friend and colleague, Melissa Derrick Adair, who brings a wealth of experience and insight. I like to introduce Melissa as the most competent person I’ve ever met, especially since she changed my life by teaching me about the “filter by color” function in MS Excel. 😊 Her post below is packed with practical wisdom and actionable tips – I know you’re going to love it. Have you ever thought that annual giving is just a classic roller coaster? You might think I’m referring to thrill you get from the ride – but I’m thinking deeper about the science behind the ride. Roller coasters use a combination of gravity, inertia and momentum to propel riders through the track. If you look closely, the biggest hill is first. This is called the lift hill. The lift hill uses a chain or other mechanism to pull the cars to the top. Take yourself back to your last roller coaster ride. Do you remember the excitement and anticipation you felt slowly creeping towards the top? When you reach the top of the lift hill, the train is filled with potential energy – in fact the height of that hill has a direct impact on the rest of the ride. As the train tips over the top of the lift hill, gravity, momentum and inertia take over. IS YOUR LIFT HILL TALL ENOUGH? For a rollercoaster, the kinetic energy gained from the initial descent dictates how the rest of the ride will go. If the lift hill is too short, there will not be enough energy built up for the cars to make it through the entire ride. In annual giving, the three months before the fiscal year start is our lift hill. This is the time where you should be looking ahead towards the next fiscal year and setting your plan. Setting the plan now allows time to ensure that your strategy can make an impact starting on day 1. Ask yourself:
DO YOU HAVE A GOOD DESIGN? Have you ever noticed how a roller coaster doesn’t just have a series of loops? It has turns, slopes and other elements to ensure that as the train moves through the track it can build up more energy. In annual giving, your plan should be like the rollercoaster and include more than just solicitation.
ARE YOUR PROSPECTS READY TO RIDE? Another key part of any roller coaster ride is ensuring that all the passengers are ready for the ride. Amusement park attendants do final checks to ensure passengers are secure. As you look ahead to the next fiscal year, be sure that your prospects are ready for your outreach. Studies continue to show that fundraising campaigns utilizing multiple channels of outreach create more opportunities for potential donors to connect with your organization and have higher rates of conversion. Now is a great time to ensure that your prospects will be able to receive your omnichannel outreach.
When I started out in annual giving, the running joke was that once the fiscal year flips, you wipe the slate clean and start all over again. But after two decades of leading annual giving fundraising strategy, I’ve learned that it is far from the truth. What you do in the final quarter of your fiscal year has a direct impact on the next year’s results. So, as you are looking ahead to next year, remember the importance of a good design. Have a strong initial climb with a mixture of loops, turns and slopes throughout the path. And always ensure your passengers are ready for the ride! Melissa Derrick Adair
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 How to Build a Philanthropy Calendar That Drives Digital DonationsEvery year in November, National Philanthropy Day would roll around and I’d sigh and say to myself: “Next year, I’m going to be ready.” I’d swear that I would plan ahead, write the emails, prep the social media graphics, and really celebrate the day with our donors. Then February would roll around and I’d see adorable Valentine’s Day posts from other schools – “We ❤️ our donors!” – and then again on St. Patrick’s Day – “We’re lucky to have you!” And I’d think: Next year. Definitely next year. Finally, last summer, I had had enough. We blocked time, pulled out the project management software, and started building a full philanthropy calendar – complete with stewardship moments, giving day content, and awareness-based messaging. And now? We don’t miss those chances to talk about philanthropy. We show up with intention. And the best part? Once this year is done, we’ll already have an entire year’s worth of content ready to refresh and reuse next time around. Honestly – it’s one of the best things we’ve done. Why every nonprofit needs a philanthropy calendar If you’re in higher ed advancement (and especially if your fiscal year starts July 1), now is the time to build your calendar for the next year – before you're juggling events, campaigns, and year-end appeals. When you plan your giving-focused content in advance, you give your team the time and space to tie fundraising to moments that matter – national observances, cause-based awareness days, and your own institutional milestones. You stop scrambling. You start seeing results. Digital fundraising isn’t just about being visible. It’s about being intentional. What kinds of dates belong on your calendar?Start with the obvious ones: your founding date, commencement, homecoming, or the birthday of a beloved former president with a named scholarship fund. Then build out from there. Here are a few ideas to get you thinking:
The more your calendar reflects your organization’s story, the more it will resonate with your community. These aren't throwaway posts – they’re meaningful messages that reinforce your mission and make giving feel timely and personal. Tools to make it happen Use scheduling tools like Buffer, Later, or Hootsuite to plan ahead. Build Canva templates you can reuse year after year. And make sure someone on your team is tracking which content types drive engagement – not just likes, but actual clicks, gifts, or email signups. Once you get into the rhythm of planning ahead, the content starts to build on itself – and pretty soon, you're not starting from scratch every year. You’re refining, reusing, and getting stronger with every cycle. You don’t need a massive team or a fancy agency. Just a plan, a few tools, and a commitment to showing up for your donors in meaningful ways. Need a head start? I’ve done the heavy lifting for you – get your free Year-Round Philanthropy Calendar with dates organized by theme and by month and ideas for implementation. This curated list of dozens of dates is tailor-made for fundraising, stewardship, and storytelling – including giving days, mission-aligned observances, and the quirky holidays that make for surprisingly great donor content. Just drop your email, and you’ll be able to download it instantly. Easy. One calendar. A year’s worth of opportunities to show up, connect with your donors, and tell the story of your mission.  What dates are important for your messaging and content throughout the year? Let me know 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! 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!
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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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