 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…
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 The CFRE Credential: What I Got Right, What I Got Wrong, and Why It Was Worth ItOf all my blog posts and TikTok videos, some of the most popular have been when I’ve talked about becoming a Certified Fundraising Executive (CFRE). Every time I share about it, I get a flood of DMs and emails with questions like:
So I decided it was time to pull everything together – my real-world experience applying, what I learned the hard way when I took the exam (spoiler: I failed the first time), and why I still believe the CFRE is one of the most valuable credentials in our profession. Here’s what I got right, what I got wrong, and why I’m so glad I did it. Step One: The Application Process is (Actually) User FriendlY Here’s the good news: applying for the CFRE is easier than you think. You just go to www.cfre.org, create a login, and begin your application. Even if you don’t plan to apply right away, you can start tracking your experience and education in the system. It’s like a running professional development journal. Pro tip: You don’t need those little CFRE credit certificates from every session. If the program was hosted by a reputable organization (AFP, CASE, Academic Impressions, etc.), just record the title, sponsor, and date. Bonus – recent changes mean that all your volunteer and service work now counts under “Education.” You’ll also track:
For example, I received credit for a building campaign I directed – even though I didn’t personally ask every donor – because I managed the campaign from the ground up. For my management project, I submitted a policy document I drafted that improved how naming opportunities were documented and proposals were generated. It counted. Once you’ve entered enough qualifying experience, the system will literally give you a green light in each section. That’s when you can pay the exam fee and move forward. Step Two: Don’t Make My Mistake with the ExaM Here’s where I blew it. I decided to take the CFRE exam cold. No prep. No studying. And even though I had 10+ years of experience… I failed by just a few points. The CFRE exam isn’t just a knowledge test – it’s a judgment test. It won’t ask: “Why should you start a donor relations program?” It’ll ask: “What is the first step you should take to build a donor relations program?” And several answers will be technically correct. You have to pick the best one, in the right sequence, based on what a seasoned, ethical professional should do. After my initial disappointment (and, okay, a little self-pity), I registered again for the next testing window. I bought the AFP CFRE Review Guide (worth every penny), and I practiced with sample questions to get a feel for the exam’s structure. If you’re preparing, my advice is this:
Why the CFRE Was Worth IT Earning my CFRE made me a better advancement professional. Period. But it also gave me something more – credibility, confidence, and clarity about what kind of fundraiser I want to be. Here’s why I believe the CFRE is a valuable credential: 1. It signals real expertise. Fundraising isn’t (yet) an academic discipline. The CFRE is shorthand that you know your stuff. It’s like a degree that speaks directly to your skillset and experience. 2. It shows your commitment to ethics. The CFRE requires – and enforces – a high standard of fundraising ethics. That matters. It matters to your employer, to your donors, and to the reputation of the entire nonprofit sector. 3. It demonstrates your dedication to continual growth. In a field that’s always evolving, this credential shows you’re serious about your craft. That you’re not just working hard – you’re working smart and staying sharp. Want to Earn CFRE Credits Right Now? My new course, The Smart Start Fundraising System, offers 5 CFRE continuing education credits and gives you a complete, strategic system to build your annual fundraising plan. Whether you’re already certified and need credits, or you’re planning to apply soon, this course is a great way to invest in your professional development and build a plan you’ll actually follow. And if you have questions about the CFRE process or exam – hit reply or leave a comment. I’d love to hear your story. Are you thinking about applying? What’s holding you back? Let’s talk about it. 💬 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…  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…
 Beautiful on a Budget: How to Design Stunning Fundraising Event Decor for $250 or LessIf you’ve gotten a catering or A/V quote lately, you know: the prices are out of control. Five figures for chicken on a salad and a microphone? It’s enough to make any nonprofit event planner want to cancel everything and cry into a spreadsheet. But here’s the thing: we still need in-person events. We still need beautiful, welcoming spaces that feel right for our missions. We just can’t afford to throw money around. That’s why today I’m sharing how to create stunning event decor for $250 or less – without sacrificing your brand, your sanity, or your goals. Let’s make every dollar count and still wow your donors. Start with Your BranD Before you add anything to your Amazon cart or hit the dollar store, pause. Ask yourself: What should donors feel when they walk into the space? And: What does our mission look like in color, texture, and style? Use your brand colors as your base palette. Add a neutral (like cream or gray) and one metallic (gold, silver, rose gold) for a little pop and polish, especially for more formal evening events. This is how you create cohesion – and it helps you avoid that “Pinterest mishmash” look. 🎨 Need help visualizing? Use Canva to build a simple vision board for your event. Drop in colors, photos, and textures. You don’t need to be a designer – just get the look clear in your head before you start sourcing. (Confession: I might be a bit of vision board addict. I do these for any kind of visual planning, including my kids’ birthday parties.) Fabric Is Your FrienD If you take one thing from this post, take this: there are affordable fabrics that can make any space look expensive. Buy bolts of voile, gossamer, chiffon, or tulle to drape across tables, hang behind a podium, or soften up harsh lighting. It instantly elevates even a basic space. 💡 Pro tip: My favorite is a gossamer/tulle combo. Use your venue-provided tablecloths (usually white or black), layer a strip of gossamer as a runner, and tie a bow on each side in one of your brand colors. Bonus points if it’s an evening event and you pick something with some sparkle in the material! Think in LayerS Don’t just lay everything flat and call it done. Think like a stylist. Use:
Most venues can provide these kinds of risers for food displays but if you are doing a total DIY event, thrift stores are your friend. Layered spaces feel intentional – and they photograph beautifully, too. Here’s an example:  Reuse Is Not a CompromisE If your decor only lasts one night, you’ve overspent. Invest in reusable pieces like:
Also, if your table runners don’t have any food stains, you can reuse them again. Just untie any bows and fold everything neatly, storing for next year. You’ll not only save money long-term but having an “event kit” will make setup so much easier next time around. And it’s a better option for the environment too! Budget Breakdown (Yes, Really!) Here’s an example budget and vision board for an upcoming fundraising luncheon I’m hosting. I’ve used this method for years and know it will look great. Table runners: $143 Tulle: $30 Total: $173 (round up to $200)  💡 Pro tip: Don’t forget about decorating the registration table if you have one. That’s the first impression your guests/donors will see, make sure it’s on brand too. Want another example? Here’s the vision board and budget for an upcoming evening Gala event: Tablecloths for high boys: $60 Tulle: $20 Flameless candles: $22 Fabric: $115 Total: $217 (Round up to $250)  And lastly here’s one more vision board from years past.  And here’s how this vision board actually manifested across several different events with minimal new décor items added:  What about flowers?
 And here are some centerpieces I did with real roses and sunflowers for another event, just tie some of the tulle in your brand colors around the clear glass vase to customize to any color you need.  One of the easiest ways to arrange flowers is to combine roses and hydrangeas. The large hydrangea blossoms take up a lot of space and cover a multitude of sins and the roses elevate the whole piece and add more color.   If you want to know more about DIY floral arrangements, I’ll be doing a whole series on this later this month on my Tiktok channel – follow me @realdealfundraising. (And if you’re not on TikTok, those posts will get reposted to Youtube @jcloudrealdeal.) What’s Your Go-To Budget Décor Hack? I’d love to hear how you create meaningful, mission-centered event spaces without blowing the budget. Drop your favorite tips in the comments or tag me if you build your own inspiration board using these ideas. Let’s normalize great design that doesn’t break the bank. 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!
 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
P.S. If you found this post helpful, be sure to subscribe to my blog so you don’t miss more content like this. And while you’re at it, check out Melissa’s work and sign up for her newsletter too – you’ll want her voice in your inbox.
 4 Power Questions to Ask Donors That Build Rapport and Lead to Major GiftsAs a college freshman, I responded to an announcement on the Honors College listserv (that may give you a clue how long ago this was) for a job talking on the phone to alumni. I thought this was a dream job. All I needed to do was talk to people and make money. As an extrovert who had been trained by her manners-minded Southern mother to “make good conversation” my whole life, I had no qualms about keeping the conversation going and making folks like me on the phone. After becoming a student supervisor in the call center, I quickly realized that most folks needed more structure and examples of what to say to have success at building rapport in conversation. It was indeed an art. I’ve now spent a couple of decades helping to systematize and teach the process of successfully talking to someone new. Over the years, I’ve learned that the secret to great conversations is the same whether you're a college student, a seasoned fundraiser, or even a 7-year-old girl chatting with her great aunt. It all comes down to asking the right questions. Questions help us connect and connecting with a donor is essential before you ever ask for a gift. The right questions remove roadblocks and pave the way for a strong, lasting relationship between the donor and your organization. People give to people they like. As a fundraiser, you’re the bridge connecting the donor to your institution. Your goal in a discovery visit is to listen, learn, and understand what truly motivates them. Bad rapport-building does more harm than good. Questions should always stimulate a lively back and forth. Think dialog, not monologue. The best questions also extract valuable information, make the donor feel appreciated, and naturally lead to the next step in cultivation. Here are my favorite questions to ask during a discovery visit: 1. How did you become involved with our organization (or mission)?This simple yet powerful question invites the donor to share their personal story. Did they have a life-changing experience? Was a loved one impacted? Did they connect with your work through a friend or colleague? Understanding their “why” gives you insight into what matters most to them and helps tailor your approach moving forward. 2. What are your philanthropic priorities, and where does our organization fit in?This question helps you understand where you stand among the causes they support. Are you a top priority, or do they view your organization as one of many they give to? It also gives you a glimpse into their overall generosity and what drives their giving decisions. 3. Who else should I be talking to?Your donors often have strong networks of like-minded individuals. Asking this question uncovers potential new prospects and champions for your cause. It also signals that you respect their influence and see them as more than just a financial contributor. 4. How do you prefer to communicate and stay involved?Some donors want regular updates, while others prefer to give quietly without much engagement. Some enjoy receiving physical mail, while others prefer a quick email or social media updates. Understanding their preferences ensures you’re communicating in a way that resonates with them, making cultivation and stewardship more effective. The key to a successful discovery visit isn’t just asking great questions – it’s truly listening to the answers. Take notes, follow up thoughtfully, and use what you learn to deepen the relationship. Building real rapport makes every future conversation easier and more meaningful. When the time comes to ask for a gift, you’ll know exactly how to approach it in a way that aligns with their motivations and values. What’s your favorite discovery question to ask donors? Drop it in the comments—I’d love to hear what works for you! 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!
 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…
 Cut Through the Clutter: Focus on the Two Planned Giving Options That Really WorkMost fundraisers hesitate to talk about planned giving because they feel like they need to be experts in trusts, annuities, and tax law. The good news? You don’t. You just need to focus on two simple, flexible options that work for nearly everyone. Planned giving is a powerful way for donors to leave a lasting legacy, but the sheer number of options can create confusion and hesitation. Each option comes with its own set of benefits and complexities. While these options certainly have their place, trying to promote all of them can dilute your message and overwhelm your supporters. In today’s post, I’m making a case for simplicity. Instead of trying to master every planned giving option, focus on the two that are most common, simplest, and most flexible for donors: bequests and beneficiary designations. The Two Simple, Flexible Options After years of experience, it’s clear that the majority of nonprofit organizations would benefit most from sticking with two straightforward approaches: bequests and beneficiary designations. 1. Bequests Bequests are perhaps the simplest form of planned giving. They allow donors to include a gift to your nonprofit in their will. Not only are bequests easy for donors to understand, but they also require minimal ongoing effort on your part once the gift is in place. Why Bequests?
2. Beneficiary Designations The second option, beneficiary designations, is equally compelling. This approach is often used for individual retirement accounts, pensions, 401(k)s, and life insurance policies. By naming your nonprofit as a beneficiary, donors can provide significant support without having to alter their wills. Why Beneficiary Designations?
In my store you’ll find social media templates for planned giving, which include a template Beneficiary Designation Checklist and pre-written Web Copy to create a planned giving focused landing page on your website. Keep It Simple, Keep It Effective By narrowing your planned giving strategy to these two options – bequests and beneficiary designations – you create a clear, focused message that resonates with donors. Not only do these methods simplify your messaging, but they also provide the flexibility that many donors are looking for when planning their legacies. Instead of overwhelming your supporters with a menu of complex options, concentrate on making it as easy as possible for them to learn about and pursue these two powerful tools. Whether it’s through offering a handy sample bequest language template or leveraging engaging digital content to promote beneficiary designations, a focused approach is key. final thoughtsWhen it comes to planned giving, less is often more. Focusing on just these two options will make your planned giving efforts clearer, easier to promote, and ultimately more successful. Keep it simple, and you’ll see results. What planned giving opportunities does your organization focus on? Where will you focus your efforts for the rest of 2025? 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…
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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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