 How to Ask for Donor Lists Without Delays or DramaI’ve long been an advocate for fundraisers to be better partners with our database colleagues because they can make or break your success. And after decades of working closely with our data buddies, I can say that they often get frustrated with us because we send emails like this: “Can you pull a list of major donors?” That’s it. No timeline. No parameters. No context. When data requests go off the rails, it’s usually not because anyone’s trying to be difficult. It’s because we’re talking past each other. Fundraisers are focused on goals. Database folks are focused on parameters. You’re thinking: “I need a list of lapsed donors for a postcard.” They’re thinking: “Define lapsed. Which years? Which exclusions? What fields? What format?” When those details don’t get nailed down up front, your request sits in the queue. Or it bounces back with more questions. Or worse – it gets filled, but it’s wrong, and now you’re scrambling. That back-and-forth burns time and goodwill. And in fundraising, timing matters. But – there’s no judgment here. Most fundraisers aren’t trained in how to “speak database.” You know what you need, you just might not know how to say it in a way your CRM or advancement services team can use. That’s what this post is about. Whether you’re a frontline fundraiser, a VP, or a one-person shop trying to wear all the hats – if you rely on data to do your job (and you do), you need to know how to make a clean, effective request. I can help you there. Five Minutes Now Saves Five Days (or Five Gifts)Taking five extra minutes to complete a thoughtful data request could save you five days of email ping-pong – or five weeks of waiting for a fix when something gets pulled incorrectly. And if your project is time-sensitive? It could cost you five big gifts. Or more. Maybe a solicitation gets delayed because someone forgot to specify an exclusion. An important donor gets left out of an event invite because the list was pulled in a rush. The details matter. The Good News: This Is FixableYou don’t have to become a database expert. But you do need to learn how to frame your request clearly. That means giving enough context for your advancement services or CRM colleagues to:
That’s why I created a Data Request Template, and it’s all at the end of this post. But before you copy and paste, let me walk you through the thinking behind it. The Anatomy of a Clean Data RequestHere’s what should go into every data request you make: Date Needed Start with the date you want to review the file. If you have a final send date – like to a printer, email platform, or gift officer – include that too. Build in review time and ask for it at least a week ahead. Purpose Be specific. Are you mailing a solicitation? Sending a digital campaign? Calling for event follow-up? This helps determine the right segments and delivery method. Overview Write two or three sentences describing the project. This gives your colleague a mental model of what you're aiming to do and why it matters. Prior Pull Have you asked for a similar file before? If yes, when? If it went well, that helps them repeat the success. If it didn’t, they’ll know how to make adjustments. Report Criteria This is where you define who should be in the file. What makes someone eligible? Think about giving history, affiliation, geography, or whatever criteria match your goal. Think of this as a net you are throwing around the prospects you want to see. Exclusions Who should not be in this file? Don’t assume standard exclusions. Spell them out: Deceased, Do Not Contact, Current Students, Faculty/Staff, Current Year Donors – whatever applies. Be clear. Think of this as a boundary keeping records out that you don’t want to see. Format Excel, CSV, PDF? Match your needs. If you’re importing into an email platform or using it for a mail merge, say so. Fields Needed Don’t just say “name and address.” Think through what you actually need: email, phone number, last gift date, last gift amount, salutation lines, grad year, etc. The more precise you are, the fewer follow-ups you’ll have later. For instance, when I request a file and I want to see giving information, I ask for the file to include: last gift date, last gift amount, last gift fund, greatest gift date, greatest gift amount, greatest gift fund, and sometimes first gift date, first gift amount, and first gift fund. Sometimes I also like to see total lifetime giving and total number of lifetime gifts too. That list is a far cry from “giving history.” Notes If you’re estimating 5,000 records, say so. If this is part of a campaign with other moving pieces, mention that too. Context helps your colleagues prioritize and prepare. If you already have a draft of the specific message, you can attach that. Data folks love having the whole vision. Grab the TemplateWant to copy it straight into your next email? Here’s a quick version: Date Needed: Purpose: Overview: Prior Pull?: Report Criteria: Exclusions: Format: Fields: Notes: Make Their Job Easier – and Yours, TooClear requests build better relationships. When you send thoughtful, complete data requests, you become someone your CRM team can trust. And when they trust you, they’re faster. More responsive. More likely to go the extra mile when you’re in a crunch. This isn’t about being perfect. It’s about being respectful of their time – and protecting your outcomes. So yes, it might take five extra minutes on the front end. But that could save you five days of delays or five missed opportunities. And those gifts? They’re worth it. Want smoother workflows and faster data pulls? Or just want a second set of eyes on your advancement strategy? Let’s connect. Cheers!  P.S. Like this kind of insight?
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 Giving Tuesday is a Launchpad, Not a One-Day EventIf you’re treating Giving Tuesday like a one-and-done campaign, you’re missing the point – and the potential. I want you to think of it differently. Think of Giving Tuesday as your momentum builder. The snowball at the top of the year-end giving hill. Not just a date on the calendar, but the kickoff to your most generous season of the year. When you plan it right, Giving Tuesday becomes the moment your donors start paying attention again. The moment they re-engage, make that first gift, and feel the energy behind your mission. It gives you stories to tell in December, a list of donors to follow up with, and progress to build on. This isn’t about chasing trends. This is about strategy. And if you want it to work, you’ve got to start now. Give your donors a real reason to act.My friend, Jake Strang said it best: “As fundraisers, we need to ask ourselves what our donors are asking themselves: ‘Why today?’” That question is everything. Your donors want to make a difference – not just by giving, but by giving on a day that matters. Giving Tuesday answers that question. It creates urgency. It offers momentum. It taps into a global spirit of generosity and focuses it on your mission. But only if you’ve done the work to meet them there. If the messaging isn’t clear, if the plan is rushed, if it’s just another email in the inbox… you’ll miss the moment. The magic is in the lead-up. And the lead-up starts now. Here’s what to focus on while you still have time: 1. Line up your challenge match now. A matching gift is one of the strongest incentives you can offer on Giving Tuesday. But the kind of donors who fund matches – your board, your loyal givers, your major donors – need time. Time to understand the impact. Time to coordinate logistics. Time to feel ownership of the campaign. Don’t treat your match as a checkbox on a planning list. Build it as a strategic asset. Ask now, while there’s room to shape it well. 2. Invite your major donors into the campaign early. Don’t just ask them for money. Give them a role. They can:
Major donors want to be part of something bigger. Giving Tuesday gives you a clear “why now” to help them say yes. 3. Pre-load your pledge list. Here’s one I swear by: Take pledges before the day. Use events, meetings, or board gatherings to ask for early commitments. Then, on Giving Tuesday, your team has a clear list to follow up with. These aren’t cold calls – they’re reminders. “Today’s the day.” That kind of focused effort drives real results. 4. Plan for analog tactics (they still work). Want to send handwritten postcards? Want to use the phone effectively? Want to get a thank-you letter in the mail before year-end? You need to start now. Donors are inundated with email. But the mailbox? That’s a quieter space. A handwritten note cuts through. A real phone call builds connection. These tactics take time, and that’s exactly why they work. 5. Build your multi-channel plan early. When you start now, you don’t have to rely on one message in one channel. You can actually coordinate email, social, print, phone, and even live events with intention. That’s how you stand out. You can code your appeals. Track what’s working. Share updates in real time. You have space to think like a strategist, not a last-minute firefighter. 6. Leave a little space for improv. You’re not planning to control every detail. You’re planning to give yourself room to respond. Maybe a donor offers a surprise match. Maybe a social post gains traction. Maybe the campaign falls just short at midnight, and you need to extend. When your plan isn’t packed too tight, you can adjust with ease – and sometimes those pivots are what make the day feel alive. Stop treating Giving Tuesday like a checkbox. Treat it like what it really is: your launchpad. The starting line for your most generous season. The moment your donors start leaning back in. The energy surge you’ll need to carry you through December. And the best part? You don’t need to overhaul your shop to make this happen. You just need to start early, plan with purpose, and stay connected to why it all matters in the first place. If you’re looking for a sign to start working on Giving Tuesday 2025… this is it. Get your match lined up. Draft that pledge form. Sketch out your outreach plan. Then get ready to make this the year your Giving Tuesday becomes more than a day – it becomes a difference-maker. Cheers,  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
 What Do I Even Say to That? How to Handle Donor Curveballs with ConfidenceIn fundraising, we’ve spent decades perfecting donor-centered language – polished, warm, affirming. And there’s value in that. But as we lean further into equity, honesty, and shared power, we’re realizing something: partnership requires candor. Community centric fundraising built on that sort of trusting partnership is the future. You can’t build trust on flattery. You build it on clarity. That’s what my new resource is really about. It’s not a script. It’s not a list of ways to smooth over discomfort. It’s a toolkit for having honest conversations with donors – without losing connection, mission, or respect. I’ve lost count of how many times I’ve been asked this question: "What do I even say when a donor asks [fill in the awkward, unexpected, or slightly skeptical question here]?" If you’ve worked in fundraising for more than five minutes, you’ve felt that moment. Someone hits you with a curveball – maybe it’s well-intentioned, maybe it’s a little tense – and suddenly your mind goes blank. You want to respond with confidence and kindness, but your brain’s still trying to find the first word. That’s why I created The Real Deal Fundraiser’s Quick Guide to Donor Questions. It’s a free resource packed with clear, kind, mission-centered answers to the questions we all get asked – and sometimes dread. Whether it’s “Why do you need my gift if you already got a big one from [another donor]?” or “Can I trust you’ll use my money wisely?”, this guide helps you find your footing and keep the conversation moving in the right direction. the framework that grounds it allUnderneath it all is a simple framework I first learned in phonathon and have used ever since: Listen. Acknowledge. Support. Continue. It’s not a script – it’s a mindset. And it works.
This isn’t about avoiding tough topics. It’s about having the tools to meet them head-on – with empathy, strategy, and the kind of language that invites real partnership. Here’s an another example: Donor: “What percentage of my gift actually goes to the mission?” You: "Totally fair question. 100% of your gift supports our mission. That includes the people, infrastructure, and tools that keep programs going strong. We believe in full transparency, and you can always review our IRS Form 990 to see how resources are stewarded." Pro Tip: Don’t shy away from the unglamorous parts of nonprofit work. They’re essential. Want to see the rest of the answers in the freebie? It’s loaded with examples. You’ll see how to apply this framework in real situations, with real donor language, and keep things moving forward without losing the heart of the conversation. Every answer in this guide is rooted in respect for donor autonomy and full transparency – two values that keep relationships healthy and real. Think of it as a conversational compass – something you can adapt to your voice and situation – rather than a one-size-fits-all speech. You’ve got the passion and the instincts. This will help you put it into words – quickly, confidently, and with the clarity today’s donors (and communities) deserve. 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…
 “Jobs Where I Don’t Go to Bed Anxious”: The Search History of a Burnt-Out FundraiserLet's pretend the TikTok comment section is a search history. This was a meme engagement prompt circulating around Tiktok, so I adapted it for nonprofit fundraisers. And the results were funny but also a bit depressing.
I’ve written about burnout. But this felt different. These aren't just punchlines. They're quiet cries for help disguised as jokes. And they struck a nerve. The comments rolled in: funny, raw, painful, *real*. This wasn’t just a social media prompt. It was a mirror for the nonprofit fundraising sector. Why We Laugh So We Don’t CrY Fundraisers turn burnout into memes because humor is safer than honesty. Because saying "I'm not okay" feels like a risk. Because the system rewards silence and penalizes boundaries. Gallows humor isn't just venting – it's a way our nervous systems regulate under pressure. When enough people laugh at the same joke, it signals: you're not the only one. You're not imagining it. This job is breaking people. Quiet cracking, indeed. The Real Punchline? That the expectations of nonprofit fundraising are structurally absurd:
We joke because naming it plainly would require everything to change. What To Do Instead of Just Laugh
You're not alone. And you're not crazy. We need more honest conversations on LinkedIn and in the workplace. We need to acknowledge that burnout isn’t a personal failure. It’s an occupational hazard. So, if you're a fundraiser trying to find your way back to sanity, find me over on Tiktok or subscribe here to my weekly newsletter. Let’s keep this conversation going! 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…
 When the Inbox Is Full, Go to the Mailbox: Why Analog Fundraising Is Making a ComebackEver open your email and feel like your brain’s going to short-circuit? You're not alone. Seventy-four percent of U.S. adults say they feel overwhelmed by email. More than half of U.S. consumers (56%) say they’ll unsubscribe if they receive four or more marketing messages from the same company within 30 days. And it’s not just Boomers. Eighty-one percent of Gen Z and 78% of Millennials say they wish it were easier to disconnect from digital devices. These are your future major donors asking for fewer pixels and more presence. That’s the opening fundraisers need. The real opportunity isn’t another email subject line tweak or fancy GIF. It’s a return to what’s real: mail and phone. Tangible. Human. Hard to ignore. This isn’t nostalgia talking. It’s data. And it might just be the smartest pivot you make this year. Direct Mail: It Never Stopped Working – We Just Got Distracted In the race to do more, cheaper, we forgot what actually works. Physical mail gets opened 80–90% of the time, while emails land between 20–30%. Direct mail spending has even grown recently – reaching about $39.4 billion in the U.S. in 2023. And here’s the kicker: when mail and digital work together, results jump. In one test, donors who received both mail and email were 60.5% more likely to respond to the mail piece than those who got mail alone. That tracks with what I saw last year. Inspired by the project Postcards to Swing States, my team handwrote and mailed over 200 postcards promoting our Giving Tuesday match. It was a standout success. Part of the magic was the form itself: a postcard is immediate – no envelope, no delay, just message received. Call Me, Maybe? Actually – Yes, Do The phone didn’t stop working. Most programs just stopped dialing. Organizations that add professional telemarketing to their strategy see an average 27% increase in annual donations compared to those relying solely on mail or digital campaigns. Why? Because personalized calling does what algorithms can’t – it builds connection. And that connection drives results. DCM’s 2023 telefundraising trends report found that contact rates have remained stable since the pandemic – holding strong at about 2.5 contacts per hour. Advocacy and political campaigns saw average gift amounts rise by 19% between 2018 and 2023, thanks to high-touch calling models. I’ve seen the impact firsthand. Last year, I worked with a college to rebuild their phonathon from the ground up: stronger management, better scripting, and smart segmentation. In 2022, they raised $134,317. This year? $396,309. And their youngest alumni – graduates since 2020 – are showing a participation rate over 17%. That kind of traction doesn’t come from wishful thinking. It comes from consistent, human contact. Telemarketing gets a bad rap, but it’s still the only channel that delivers personalized conversations at scale. It’s strategic because it’s still deeply personal. So if you think phone is “old school,” think again. It’s working better than ever – for those who use it well. Younger Donors Aren’t as “Digital Only” as You Think Here’s where things get interesting: Millennials and Gen Z aren’t avoiding analog as expected but they are getting burnt out on digital. More than 80% of Gen Z (80%) and Millennials (78%) say they share interesting mail with someone else. That’s a viral loop, but with ink and paper. They’re open to analog – especially when it connects to the digital world. QR codes. Custom URLs. Interactive print. That’s not outdated. That’s modern engagement with real presence. Gen X? They’ll still take your call and they appreciate personalized pieces. Boomers? They’re the MVPs of mail. They read it, they act on it, and yes – they still pick up the phone when the number’s familiar. Fundraisers Need to Think Like Communicators Again We’re in the relationship business, not just the metrics business. Somewhere along the way, digital promised us scale and forgot to tell us we’d lose connection. If you want your message to stand out, don't just add to the digital pile-up. Get in someone’s mailbox. Pick up the phone. Make it personal. Make it human. Analog hasn’t vanished – it’s been waiting. And right now? It’s the cleanest path to cutting through. This isn’t a call to throw out your digital playbook. It’s a nudge to rebalance. To layer your strategy. To stop thinking in either/or. You don’t need to call everyone or mail every donor. Segment. Experiment. Pair analog with your digital. Measure. Adjust. I’ve been doing this long enough to tell you: this is where fundraising is heading next. I’m betting on analog. Because I’ve seen the numbers. I’ve seen the results. And I’ve seen how a phone call or handwritten postcard can do what a hundred emails never could. Let’s go back to what works. Not because it’s old – but because it still moves the needle. The Upswing Is Here This isn’t a blip or a nostalgia play. The signs are clear: digital fatigue is rising, mail spend is climbing, and younger donors are just as responsive to tangible, personal outreach as their parents and grandparents. We’re not at the plateau. We’re on the upswing. That’s why the institutions that recalibrate now – layering mail and phone back into their strategies for all generations – will see the payoff not just in annual giving but in the major gift and planned giving pipelines for decades to come. Early engagement drives loyalty, and loyalty drives legacy. The inbox is saturated. The mailbox and the phone line are open. The organizations willing to seize that opening today are the ones who will own the donor relationships of tomorrow. Fundraising’s next edge won’t come from squeezing another 0.2% out of your email subject line. It’ll come from showing up where people are actually ready to listen. 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… Works Cited:
 Gravitas in Fundraising: Executive Presence Without PretendingIn 2018, I sat in a conference room during a session led by executive presence coach Eda Roth. She broke down executive presence into three components: communication, appearance, and gravitas. She shared that the impact of your presence comes across in three ways:
That stuck with me. As a fundraiser, I’d been taught to focus on what I was saying: the pitch, the story, the ask. But this shifted something. I started to think more about how I was being – not just what I was saying. And the more I worked with fundraisers in the years that followed, the more I came to believe this: Gravitas isn’t one-third of executive presence. It’s the result of the other two (communication and appearance) – plus something extra. It’s what makes someone feel grounded, trustworthy, and clear – even before they speak. And here’s the good news: you don’t have to act like someone else to cultivate it. What Gravitas Really Looks Like in FundraisinG Dr. Lisa Hale, writing for Forbes, defines gravitas as the blend of eight qualities: confidence, composure, credibility, clarity, conviction, connection, decisiveness, and respect. She says it’s the moment you stop asking “Do I belong in this room?” and start asking “What do the people in this room need from me?” That’s exactly the shift fundraisers need to make. Gravitas isn’t about being the loudest or most polished. It’s about having internal calm and external presence – so that donors, board members, and colleagues feel like they’re in steady hands. Eight Traits That Anchor Gravitas for Fundraisers Here’s what gravitas looks like when it shows up in real conversations and real donor meetings:
Your Clothes Can Speak, Too After that 2018 conference session, I found myself in a networking event with other women in higher education leadership. The conversation turned to fashion. I happened to be wearing knee-high black suede boots, small fishnet hosiery, and a red-and-black dress that made me feel powerful and completely myself. So I asked, “Do you think women in higher ed leadership can be successful wearing boots and fishnets?” One woman answered, without missing a beat: “Women in leadership should wear whatever makes them feel powerful.”  That’s stayed with me. We sometimes forget that appearance is part of presence – not because we have to look a certain way to be respected, but because what we wear affects how we carry ourselves. When you feel put together, you stand taller. You smile more easily. You claim your seat at the table. Let your wardrobe reflect both professionalism and personality:
You don’t have to disappear into neutrals to lead with strength. Body Language That Builds TrusT You don’t have to be a body language expert to connect powerfully in a meeting. These small cues can make a big difference:
Vocal Presence That Commands the Room Fundraisers often worry about what to say. But how you say it carries even more weight.
The X Factor? It’s Trust – in Yourself Imposter syndrome is real. And it’s sneaky. You can be experienced, credentialed, and well-prepared – and still feel like your voice doesn’t carry weight. But gravitas shows up when you shift from proving yourself to trusting yourself. You don’t need to be louder. Or slicker. You need to be more yourself – grounded, clear, and focused on the person in front of you. Let’s Bring It HomE Executive presence isn’t a suit you put on. It’s a muscle you build. Fundraisers with gravitas don’t just ask for money – they inspire trust, connection, and confidence. So go ahead:
You don’t have to act like someone else to have presence. You just have to show up on purpose. What’s one way you’re learning to trust yourself more this year – in fundraising or in life? 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…
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…
 Breaking into Fundraising: Real Talk for New Grads (and Anyone Starting Fresh)I had a long conversation a few days ago with a brand-new college grad who’s hoping to land her first job in fundraising. We covered a lot of ground. Some of what I shared was the usual advice. Some of it was the stuff you only hear when someone’s willing to tell you the truth. So here’s my actual advice for those who want to break into fundraising but feel stuck because they don’t have the experience yet. 1. Know where you’re headed – or you won’t know what direction to take. To paraphrase the Cheshire Cat from Alice in Wonderland: “If you don’t know where you’re going, any road will take you there.” If your long-term goal is Executive Director, Chief Development Officer, or Major Gifts Officer, don’t apply for back-office roles like gift processing. Those positions matter (I’m on record as saying that partnership with these important roles is paramount to fundraising success) but they rarely lead to donor-facing roles, no matter how good you are. The leap from behind-the-scenes to front-line is a hard one, even if you’re in the same department. If your dream job is out front with donors, start out front with donors – even if it’s entry-level. A Leadership Annual Giving or Donor Relations role might not sound flashy, but it will get you in the room with donors and decision-makers. Think long. Think strategically. Your first job should point in the same direction as your dream job. 2. Network like it’s your job – because it kind of is.Front-line fundraising roles have a personal element that doesn’t always come across on a resume. You’re selling your communication skills, your presence, your ability to connect. To put it bluntly, great fundraisers are at least in part personality hires. But, as with many things, if you have to say that you are a personality hire, you probably aren’t one. The best way around that? Don’t rely only on paper. Talk to people. Tell everyone you know that you want to work in nonprofit fundraising. Your neighbor might be on the board of a food bank. Your friend’s aunt might chair the development committee at a local theater. Ask for informational interviews (which is exactly how this new grad got to talk with me for an hour). Join your local AFP chapter. Volunteer at events. These conversations open doors. Sometimes wide. 3. This one is for the girls. Apply like a man. Research shows that women tend to apply for jobs only when they meet all the required and preferred qualifications. Men? They'll throw their hat in the ring even if they don’t check all the boxes. Stop waiting until you’re 100% qualified. There is no one keeping score for jobs you don’t get a callback on (except maybe you). As they say, you can’t win it, if you ain’t in it. Read the job description. If you’re even halfway there, and it aligns with your long-term goals? Apply. Don’t self-select out. You can learn the rest. That’s what I told her. And if I were talking to you, I’d tell you the same. Your career in fundraising won’t be built in a day. But if you start with intention, talk to the right people, and stop waiting for perfect – you’re already ahead of the game. Cheers! Jessica  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
 The 3 Rs of Fundraising Mindset: What It Really Takes to Talk About MoneyWhenever my grandfather was asked what I did for a living, he’d grin and say, “Oh, she’s a professional beggar – and very good at it.” He meant it playfully. But that joke pointed to something deeper: how fundraising is often viewed in American culture – and sometimes, how we as fundraisers view ourselves. This work can feel loaded. Talking about money brings up all kinds of things: values, power, pride, fear of rejection. It’s personal. And when that discomfort goes unchecked, it sneaks into our conversations and undermines our confidence. But here’s what I’ve learned: Your mindset matters more than your pitch. How you feel about money shapes how you talk about it. And that directly affects whether you avoid the big asks – or step into them with clarity and purpose. Over the years, I’ve noticed three mindset shifts that help fundraisers move past the awkwardness and into authentic, effective conversations. I call them the 3 Rs: Reciprocity, Receivership, and Reframing. Let’s walk through them. 1. Reciprocity: Giving isn’t taking. One of the most harmful myths in fundraising is the idea that we’re taking something from people. That donors are losing when they say yes. That’s not what’s happening. Giving is about alignment. When a donor gives, they’re not being depleted – they’re investing in meaning. They’re making their values visible. They’re stepping into a story that’s bigger than themselves. That’s not taking. That’s inviting them in. I’ve watched donors light up – not because of tote bags or nameplates – but because they felt connected. When we approach conversations with the understanding that there’s value on both sides, it changes how we show up. Try this: When a donor shares why they give, listen closely. Then reflect it back. Say, “It means a lot to me that this work aligns with your values.” That simple moment of recognition reinforces that this is a relationship – not a transaction. 2. Receivership: Get good at receiving. Let me ask you something: when someone picks up the lunch tab, do you fidget? When they compliment your work, do you wave it off or make a joke? That matters more than you think. If you struggle to receive in small, everyday moments, it’s going to be tough to stand still and grounded when it’s time to receive something much bigger – like a major gift. Fundraising isn’t just about facilitating generosity. It’s about receiving it. That means knowing your own worth, your organization’s worth, and the worth of the mission you represent. You’re not just asking for money. You’re offering someone the chance to invest in something meaningful. Try this: The next time someone compliments you – on your work, your outfit, your presentation – just say, “Thank you.” No hedging. No “Oh, this old thing.” Practicing that kind of presence builds your capacity to receive with grace and confidence. 3. Reframing: The ask is not the problem. I’ve worked with some truly talented fundraisers – smart, strategic, big-picture thinkers – who freeze at the edge of the ask. I’ve done it myself from time to time. The relationship is there. The timing is right. The groundwork has been laid. But when it’s time to actually say the number... they stall out. There’s an old joke in our field about someone like that: “How is <<that fundraiser>> like a 7/11 store?” “They never close.” Funny – but also kind of painful. Because many of us have been that person. I know I have. We hesitate because we don’t want to feel pushy. We worry we’ll mess up the relationship. But here’s the truth: donors – especially high-net-worth donors – know what we do. They expect us to ask. And when we don’t? It doesn’t protect the relationship. It creates confusion. When trust has been built, the ask isn’t a surprise. It’s the next logical step. Try this: Start using this phrase in conversations: “I’d love to talk with you about a way to deepen your impact.” It’s warm. It’s clear. And it helps you move into the ask without making it weird. So, what does this mean for you? If you want to grow as a fundraiser, start by checking your mindset.
Fundraising isn’t begging. And it’s not manipulation. It’s invitation. It’s partnership. It’s a shared pursuit of something that matters. My grandfather may have called me a “professional beggar” – but he wasn’t wrong about the skill it takes to do this work well. He just didn’t know the half of it. Get your 3 Rs in alignment, and you’ll stop feeling like you’re asking for a favor – and start showing up like the professional you already are. Cheers! Jessica  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads. If you liked this…
 Wear the Suit: Presence starts in your mind, not your closet. Back in 2007, I was prepping for a presentation to my peers – young professionals like me, running fundraising call centers across the country. We were mostly in our 20s, ambitious, a little scrappy, and working in a company culture that leaned casual. I was thinking about wearing a skirt suit. It felt like the right thing for the moment. But I was second-guessing it hard. What if they thought I was stuck up? Or trying too hard? Or trying to be something I wasn’t? I asked my husband what he thought. He said, “Wear the suit.” I explained the whole situation again, sure he didn’t get it. He said again, “Wear. The. Suit.” By the third time, I was exasperated. That’s when he clarified: “If you’re going to wear the suit, wear the suit... Stand in it. Own it. Don’t apologize for it. You’re stepping into the authority you already have – but you’ve got to embody it. If you do that, what anyone else thinks won’t matter.” That moment stuck. Because it was never about the suit. It was about how I carried myself in the suit. You can’t control how other people read you. But you can decide how you show up. You can choose to walk into the room with the posture, presence, and clarity of someone who belongs there. You can lead – even when you're still growing. So whatever your “suit” is – your outfit, your opening line, your tone – don’t just put it on. Wear it. Let’s bring it into your world: What’s your version of “the suit”? That thing that helps you stand taller and lead stronger when it counts? Drop it in the comments – I’d love to hear what helps you show up with presence. 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.
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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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