 Listening Is a Skill: How Silence Wins Big GiftsThere is a moment in every donor conversation that tells you almost everything you need to know about a leader’s fundraising readiness. It happens immediately after the ask. You’ve prepared. You’ve built the relationship. You’ve connected the donor’s values to the work. You’ve stated the opportunity clearly and named the amount. And then you stop talking. That pause is not a gap. It is the moment where partnership is either strengthened or unintentionally weakened. And it is one of the hardest disciplines to master. The Pause Is Where the Truth EmergesWhen I teach proposal meetings, I walk leaders carefully through the structure. Frame the impact. Name the investment. Make the invitation. And then I say three words: End. Pause. Listen. That silence will feel longer than it is. It may feel like something has gone wrong. Your brain will search for ways to soften the ask, clarify the number, or add “just one more thing.” That impulse is human. It is also the exact moment where you must manage yourself. If you jump in and speak first, you forfeit your opportunity to hear what the donor is actually thinking. You begin responding to your own anxiety instead of their reality. And anything you say in that moment is likely driven by assumption. Assumption is the enemy of clarity. Silence Is DiagnosticWhen you allow the donor to speak first, you gain something invaluable: information. You learn whether the hesitation is about timing, amount, priorities, or something entirely different. In major gift fundraising, it is rare to hear a definitive, final no. More often, you hear nuance. A different number, timeline, or focus. But you can only respond effectively if you actually hear it. If you rush to fill the silence, you influence the response. You steer it. You muddy it. And then you lose the ability to diagnose what truly needs adjusting. Fundraising, at its best, is thoughtful negotiation rooted in shared values. Silence is what makes that negotiation honest. Silence Is a Team DisciplineIf you are a board member sitting in the room as a peer or partner, this applies to you too. It does not matter who delivered the ask. Once the invitation has been made, the room belongs to the donor. Sometimes a well-meaning board member will derail momentum by jumping in too quickly. They clarify. They soften. They add context. They attempt to “help.” What they are often doing is relieving their own discomfort. And that discomfort can fracture the unity of the moment. If you are present in the room, your job is to protect the pause. Let the donor speak. Even if the silence stretches. Even if your instinct is to rescue. Even if you are certain you know what they are thinking. You do not. Only they do. When a leadership team holds steady together, the donor experiences confidence and alignment. That steadiness builds trust. And trust deepens generosity. Why This Feels So HardLet’s name what is happening beneath the surface. The pause feels vulnerable because you have just placed a proposal on the table. You have stated what the mission requires. You cannot control what happens next. Leadership in fundraising is often about managing your internal response before managing the conversation. The silence shows your composure. When you hold steady, you communicate confidence in both the mission and the donor. That confidence matters. Practice Before You Need ItIf you want your board to handle donor meetings well, rehearse the silence intentionally. In practice sessions, say the ask out loud. Then count slowly to five before speaking again. Notice the urge to jump in. Let it pass. The more you rehearse the silence, the less your body treats it like a threat. The more familiar silence becomes in rehearsal, the less intimidating it feels in real conversations. Listening is not passive. It is disciplined presence. The Quiet That Builds PartnershipFundraising is about alignment, not about winning. When you ask and then truly listen, you communicate respect. You give the donor room to process and respond honestly. Respect builds trust. And trust is what sustains generosity long after a single gift is made. Silence, handled well, strengthens the partnership. Ready to Strengthen Donor Conversations at the Leadership Level?If you would like help scripting and rehearsing donor conversations so your board feels steady and prepared in the room, let’s talk. Book a complimentary Board Fundraising Alignment Call and we'll work through proposal meeting strategy together. The pause will always feel longer than it is. Hold it anyway. That quiet space is often where generosity begins. Cheers!  P.S. This post is part of an ongoing series for nonprofit leaders and Board Chairs who want to build confident, fundraising-positive boards. If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. My goal is to give you practical tools you can use at your next board meeting. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level. If you liked this…
0 Comments
 Authenticity and Vulnerability: Why Alignment Changes EverythingI open my board fundraising workshops with this quote from Brené Brown: "Vulnerability is not winning or losing; it's having the courage to show up when you can't control the outcome." Every time I share it, I watch the room shift just slightly. Because fundraising is exactly that. It is showing up when you cannot control the outcome. You cannot control whether the donor says yes or the timing of their decision or what is happening in their financial world that day. You can only control how you show up. And how you show up begins with authenticity. Fundraising Is Personal — Whether You Admit It or NotWhen any nonprofit leader makes an ask, they are not simply delivering information. They are putting belief on display. They are saying, in effect: I believe this work matters. I believe it deserves to grow. I believe it is worthy of investment. There is exposure in that moment. If you are not fully aligned with the mission, that exposure feels risky. You may hedge your language. You may soften the request. You may speak in generalities instead of conviction. Donors can feel that. They may not articulate it, but they sense when someone is reciting talking points versus speaking from lived belief. Years ago, I worked for a leader who has raised billions of dollars in his career. At one point he told me he could never work for a university he did not attend. At first, I thought that was unnecessarily restrictive. Surely skill and strategy are transferable. It took me years to understand what he meant. He was talking about authenticity. Because he had personally benefited from the kind of institution he represented, he never had to manufacture enthusiasm. He never had to convince himself the mission mattered. He had lived it. When he spoke about scholarships or research or student opportunity, he was not delivering a pitch. He was telling the truth. That alignment reduced vulnerability. It strengthened confidence. You do not have to draw your lines as narrowly as he did. You do not have to be an alum, a former client, or a beneficiary to serve with integrity. But you do need to ask yourself a harder question: Am I fully aligned with this mission? Not casually supportive. Not intellectually persuaded. Aligned. Confidence Comes From Congruence — And That Congruence Is LeadershipBoards often assume confidence in fundraising comes from mastering scripts or memorizing the right phrasing. Those tools help. Preparation matters. But true confidence comes from congruence. And for a nonprofit CEO or Board Chair, that congruence is not just a personal asset. It shapes the entire culture around you. When your values and the organization's mission match, your voice steadies. You are not performing. You are advocating. You can speak honestly about the need, describe the vision without exaggeration, make a clear request, and then sit quietly, trusting the process. That steadiness is contagious. Fundraising also requires you to say, "This is what it will take," without knowing how the story ends. That is vulnerable. But it is also powerful. When leaders are transparent about where the organization stands, clear about where it is going, and honest about what is required, donors feel respected. They feel invited into something real, not manufactured. If leadership approaches fundraising as an uncomfortable obligation, the board will treat it that way. If leadership approaches fundraising as an expression of mission, the board will begin to see it that way too. Tone travels. You cannot control the outcome. You can control your integrity. And integrity builds trust faster than polish ever will. A Practical Reflection for CEOs and Board ChairsIf you want to strengthen authenticity in your fundraising culture, begin here:
Write the answers down. Not for publication. For your personal clarity. When you take the time to articulate your connection to the mission, your fundraising voice becomes clearer. Your language becomes simpler. Your conviction becomes visible. And when that conviction is visible, it gives your board permission to show up the same way. Not performatively. Sincerely. Vulnerability, as Brené Brown reminds us, is about showing up when you cannot control the outcome. Fundraising will always require that. When it is rooted in alignment, it feels less like exposure and more like leadership. Ready to Build A deeply authentic culture of philanthropy?Fundraising culture starts at the top. When the CEO and Board Chair are aligned, that clarity travels. When they're not, the whole team feels it. If you want to examine how leadership alignment is shaping your board's engagement in fundraising, a complimentary Board Fundraising Alignment Call is a good place to start. We'll look honestly at where things stand and identify practical next steps to build the kind of confidence that carries through your whole organization. Fundraising does not require perfection. It requires alignment. And when that alignment is present, generosity follows. Cheers!  P.S. This post is part of an ongoing series for nonprofit CEOs and Board Chairs who want to build confident, fundraising-positive boards. If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. My goal is to give you practical tools you can use at your next board meeting. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level. Next week’s piece tackles one of the most misunderstood parts of board fundraising. If you liked this…
 Fundraising Is a Noble EndeavorI want to begin with a statement that may feel simple, but it carries more weight than most boards realize: Fundraising is a noble endeavor. If you are a nonprofit CEO or Board Chair, your internal reaction to that sentence matters. It shapes how you speak about fundraising. It influences how your board experiences it. It quietly determines whether your culture approaches fundraising with confidence or hesitation. Belief comes first. Always. You Either Believe in the Mission or You Don’tThis is where we must be honest with ourselves. You either believe deeply in your mission, or you don’t. If you believe your organization changes lives, strengthens families, advances justice, expands education, heals, protects, or restores something that matters, then you already know the work deserves resources. You know it deserves to grow. You know it deserves to be sustained for the long term. If that belief is strong, you can work through discomfort around money. You can practice the language of invitation. You can sit in a donor meeting and speak clearly about funding needs. If that belief is shaky, fundraising will always feel heavy. You will delay conversations. You will hedge language. You will hope someone else handles the “hard part.” If leadership belief wavers, board engagement follows, donor conversations shrink, and revenue eventually reflects that hesitation. Belief is not emotional fluff. It is operational fuel. What Shifted My ThinkingEarly in my career, I worked in political fundraising. I was taught that fear and guilt were powerful motivators. Create urgency. Highlight threats. Push emotional buttons. And it worked, at least in the short term. Later, when I returned to my alma mater, I began raising money for education. Our beloved president emeritus who led the university through decades of growth, Aubrey K. Lucas, met with the new development officers. He shared something that stayed with me. Negative fundraising is rarely truly successful. We were raising money for education. Education is a universal good. It is something to be proud of. That effort should not be rooted in pressure or fear. It should be rooted in conviction. That conversation reframed my entire understanding of fundraising. If education is good, then raising resources for education is good. If your mission serves a real human need, then securing funding for that mission is honorable work. That realization has guided my work ever since. Giving Is Not About MoneyWhen board members hesitate, the hesitation is rarely about the mission. It is about money. Money carries history. It carries stories. It carries personal experiences that shape how we feel when we talk about it. But giving is not really about money. Giving is about shared vision and shared values. When a donor gives, they are not simply transferring dollars. They are aligning themselves with a cause they believe matters. They are choosing to participate in change. They are saying, “I see this work, and I want to be part of it.” Money is simply the mechanism that allows that alignment to take tangible form. When you internalize this truth, something shifts in your posture. You stop speaking about fundraising as if it is separate from the mission. You recognize that it is the engine that fuels the mission. And that changes your tone. Leadership Tone Shapes Board CultureCulture does not begin in the development office. It begins in the boardroom. If you speak about fundraising as an obligation, your board will experience it as a burden. If you treat fundraising as something uncomfortable that must be endured, your board will mirror that discomfort. But if you speak about fundraising as mission work, as advocacy, as an opportunity to invite others into meaningful impact, your board will feel that shift. You do not have to eliminate all discomfort. Most of us were not raised discussing money openly. That hesitation is normal, but how you frame the work matters. When you believe fundraising is noble, you approach it with clarity. You talk about funding needs without apology. You connect dollars to outcomes without shrinking your language. You model confidence. Boards take their cues from leadership. If you approach fundraising with pride and purpose, your board has permission to do the same. The Cultural ResetIf your board is reluctant, start here. When was the last time your board discussed fundraising as shared leadership responsibility rather than an agenda item? Have an honest conversation about why your mission matters. Revisit the lives changed. Revisit the transformation you are pursuing. Revisit the gap between where you are and where you need to be. Then ask this question: If this work truly matters, why would we hesitate to invite others to fund it? When that belief becomes shared, fundraising stops feeling transactional. It begins to feel aligned. And alignment is powerful. Ready to Strengthen Your Board’s Fundraising Culture?If any of this sounds familiar:
It’s time to take a serious look at whether your board’s leadership tone and fundraising expectations are truly aligned. If fundraising feels like a source of stress rather than shared responsibility, this is the work that shifts it. I’m opening three complimentary Board Fundraising Alignment Calls this month. You can reserve a time here. Fundraising is not separate from your mission. Fundraising fuels your mission. And when you truly believe that, you become a stronger advocate, a clearer leader, and a far more confident fundraiser. Cheers!  P.S. This post is the first part of an ongoing series for nonprofit CEOs and Board Chairs who want to build confident, fundraising-positive boards. If this conversation is resonating, I invite you to subscribe so you don’t miss the next installment. Each piece builds on the last, and together they form a practical roadmap for strengthening fundraising culture at the leadership level. If you liked this…
 The Other Leaky Bucket in Fundraising: Cost to Raise a DollarWhen I came back to work at my alma mater in 2011, they had just celebrated the Centennial the year before. The mailing they sent out for the 100-year mark was gorgeous – vintage photos, heavy cardstock, elegant fonts. You could see the pride in every detail. But there was one big problem. It cost more to send than it brought in. When I ran the numbers, the cost to raise a dollar on that piece was $1.40. For every dollar it generated, it cost us $1.40 to get it. We weren’t raising money – we were losing it. It was like we were throwing money overboard and missing a once in a century opportunity! The issue wasn’t just the over-the-top production. The package was confusing. Too many ask amounts, too many gift designations, and other options. Donors didn’t know where to focus. And when a donor doesn’t know what to do, they don’t give. The next year, we simplified. One letter. Points of pride on the back. Clear ask string. That mailing had a cost to raise a dollar of 43 cents. Same donor base. Better strategy. So what is Cost to Raise a Dollar – and why should you care?Cost to raise a dollar is exactly what it sounds like. It’s a measure of efficiency. You take your total expenses for a campaign or fundraising channel and divide it by the amount raised. Formula: Cost to raise a dollar = Total Expenses ÷ Total Dollars Raised If you spent $10,000 and brought in $25,000, your cost to raise a dollar is $0.40. That means it cost you forty cents to raise one dollar. Good. If your cost to raise a dollar is over $1, you’ve got a problem – if you’re not executing a donor acquisition strategy where you expect to lose money upfront to gain long-term donors who’ll give again and again for less. But if you’re not acquiring or upgrading donors – and your cost to raise a dollar is that high? You’re hemorrhaging money. Tracking Staff Time: Don’t Worry about ThatRecently I was teaching a webinar and got asked whether you should track staff time on any particular fundraising effort in the total expenses when calculating cost to raise a dollar. My answer is no. I’ve never met a fundraiser who’s sitting around wondering what to do next, and I don’t think tracking every minute of your working hours is a good use of that valuable time. Staff salaries are in your normal budget. Consider them a constant. Don’t tie yourself in knots trying to figure out if you spent 20 hours on the gala last week or 22 hours. Examples: For a mailing, count printing, postage and processing costs (if using a mailhouse or other paying part-time folks to stuff mailers). For an event, expenses would include catering, décor, invitations (printing, postage, and processing), printings programs, etc. Keep it simple and you’ll be ahead of the game. Why This Metric Gets OverlookedFundraisers talk a lot about leaky buckets – usually in terms of donor retention. But there’s another leak that’s just as costly: spending more to raise a dollar than you get back. That’s what this metric uncovers. Most fundraisers are trained to focus on total dollars raised or number of donors who give. And yes, those are crucial. But cost to raise a dollar gives you clarity at the tactical level. It shows you where your fundraising machine is humming – and where it’s grinding your budget into dust. Cost to raise a dollar is especially helpful when:
Cost to Raise a Dollar in Action: How It Helped Me Lead SmarterThat Centennial piece taught me something I’ve never forgotten: Beautiful isn’t always effective. Impact matters more than gloss. It also gave me a compelling number to take into conversations. I could walk into meetings and say, “This mailing costs us $1.40 to raise a dollar. Last year’s only cost 43 cents. Which one do you want to fund next year?” I didn’t need to yell. I just needed to know my numbers. A Quick Reality CheckSome channels will have higher cost to raise a dollar – and that’s okay. Phonathons, acquisition campaigns, certain events – they often cost more. But if you’re tracking those donors and seeing strong retention and future giving, that higher initial cost might be justified. But do that deliberately, for strategic reasons. In higher ed, campaigns like student philanthropy programs or senior class gifts often have an “upside-down” cost to raise a dollar. That’s not a failure – it’s intentional. We spend more than we bring in because we’re focused on something bigger: starting the donor relationship early, before students graduate, move away, and scatter. While they’re still on campus, their connection to the institution is at its peak. That’s the right time to invite them into giving – not just for dollars today, but for loyalty tomorrow. Just don’t confuse “tradition” or “looking nice” with effectiveness. Know what each dollar is doing for you. Make that a habit. Teach it to your team. And please – for the love of fundraising – don’t let your best-looking piece be your worst-performing one. What to Do NextIf you’ve never calculated your cost to raise a dollar, start now. Pull your last three mailings or campaigns. Be honest about all the expenses, minus staff salaries. Run the numbers. Then start making decisions that build toward efficiency – and impact. This metric gives you the insight you need to be smart with the resources you’ve been trusted to steward. 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…
 Scripts to Bring Up Planned Giving Without Feeling Weird About ItWhen I taught my first graduate-level course this summer – Ethical and Community-Centered Fundraising – I expected good questions. What I didn’t expect was just how much anxiety would surface around one specific topic: planned giving. These were smart, values-driven future leaders. People already thinking in terms of justice, legacy, and long-term impact. But the minute we shifted into planned giving, the energy changed. It wasn’t the concept they struggled with. It was the conversation. How do you bring up wills and estate plans without making it weird? What if you say the wrong thing? What if it feels morbid – or worse, transactional? At their request, I created a simple guide: real phrases, grounded in real situations, to make legacy conversations feel natural, honest, and even hopeful. Turns out, it’s not just my students who need this. So if you’ve ever felt that same hesitation – this post is for you. Because here’s the truth: Planned giving conversations don’t have to be awkward. They can be inspiring. They can even be joyful. You don’t need to be a tax expert. You just need to know how to bring it up – gracefully and confidently. Let’s start there. What to Say When You Want to Bring It Up (Without Sounding Morbid)Sometimes you’ll have donors reaching out first – through your website, a legacy giving survey, or in response to a donor story. Those are the easiest planned giving conversations because the interest is already there. But when you need to be the one to raise the topic, here are some ways to bring it up without making it feel heavy:
You’re not pushing. You’re not being morbid. You’re simply opening a door – letting them know that this kind of giving is possible, meaningful, and available to them. Why It’s Worth Getting ComfortableYou do need to have these conversations. Here’s why: 🟢 Planned gifts are huge. On average, they’re 200–300x the size of an annual gift. That’s because they’re made from lifetime assets, not income. (Source: National Estate Planning Awareness Week) 🟢 They’re already in your database. The donors who are most likely to leave you in their will? They're not wealthy strangers. They’re the consistent supporters who’ve given every year for the past decade. (Source: How to Talk About Death and Taxes) 🟢 You’ll never know unless you ask. A $25-a-month donor might be planning a six-figure bequest and never mention it unless you give them a reason to. 🟢 There’s $12 trillion on the move. The Great Wealth Transfer is projected to move $84 trillion by 2045, with $11.9 trillion going to charitable causes. That wave is already building. (Source: How to Talk About Death and Taxes) 🟢 Peer stories work. When donors hear from others like them who’ve made legacy commitments, your inbox starts filling up with questions – not awkward ones, but warm, intentional ones like: “Can I do this too?” (Source: Planned Giving Leads Don’t Generate Themselves) 🟢 You don’t need to overcomplicate it. Bequests and beneficiary designations are all most donors need to know. These are simple, flexible tools that don’t require financial wizardry or legal acrobatics. (Source: Cut Through the Clutter) Shift the Framing, Not Just the PhrasingThese conversations become easier when you stop thinking of them as talking about death and start thinking of them as talking about legacy. “What if your annual support could live on forever? By including [Your Nonprofit] in your estate, you could turn your yearly gift into a lasting endowment.” This is about continuity. It’s about making their values stretch beyond a single lifetime. It’s not about dying – it’s about staying connected to something they believe in. And when you position it that way, it doesn’t feel grim. It feels good. Don’t Wait for the Perfect Moment – Create OneYour donors won’t bring this up on their own unless they’ve already made a decision. Your job is to create the conditions where that decision becomes possible. And that starts with language – gentle, honest, open-ended questions that let the donor lead, but make it clear that legacy giving is an option you believe in and value. So don’t be afraid to ask. And when they say yes? Be ready with the next step: a landing page, sample language, a checklist, or a simple conversation about how to make it happen. 📌 Want a quick win? Use these same phrases in:
Planned giving isn’t about “the ask.” It’s about the invitation. When you know how to extend it with confidence and care, the whole conversation shifts – from something to avoid… to one of the most meaningful parts of your work. Cheers!  P.S. Like this kind of insight? Subscribe to Real Deal Fundraising and get my best articles, tools, and curated resources every week – including webinars, videos, and free downloads.
 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…
 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:
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…
 Nonprofit Branding: How to Make Your Mission MemorableWhen it comes to nonprofit fundraising, one thing is clear: Your mission is the heart of your organization. But while your cause drives everything you do, a strong, memorable brand is what helps you stand out and attract the major gifts that will take your work to the next level. Whether you’re at a large, established institution or running a smaller startup nonprofit, your brand should reflect who you are, what you stand for, and how people can get involved. A polished brand boosts credibility and builds trust, but a memorable one moves people to action. Your Mission Is the Core of Your Brand Before thinking about logos, colors, or marketing campaigns, start with the foundation of your nonprofit brand: your mission. What drives your organization? What problem(s) are you solving? What’s your CEO’s vision for the future? These aren’t just feel-good statements – they should be at the core of every message you share. Example: The Monson Free Library This small library in Maine has embraced its fun and quirky side by creating TikTok videos that showcase the staff’s personality while highlighting their programs. By tapping into the creativity and passion of their team, they’ve built a brand that’s as unique and welcoming as their services. The community now sees the Monson Free Library as more than a place for books – it’s a place to have fun, get involved, and support something bigger than themselves. Learn more. Actionable Tip: Start by asking yourself these questions:
Visual Identity: Be Consistent, But Stay FlexibleWhen you think of branding, visual elements like logos, color palettes, and fonts come to mind. These are crucial for creating a consistent, professional presence. But let’s be real – sometimes, nonprofits get so caught up in the “rules” of branding that they lose the ability to stay nimble. There’s a balance between maintaining brand integrity and being flexible enough to seize opportunities in the moment. Many nonprofits create brand guides with rigid rules for logos, colors, and language. And while I love a good style guide, if these guidelines slow you down or make it harder to engage donors, it’s time to rethink them. A major gift might hinge on a timely, heartfelt social media post or a quick thank-you email. If your guidelines require three layers of approval for every little thing, you could miss your moment. Example: The Trevor Project The Trevor Project underwent a major rebrand in 2019, replacing a formal font and muted colors with a bolder typeface and a vibrant, colorful design. The updated branding, along with fresh messaging and visuals, emphasized inclusivity, hope, and support for LGBTQ+ youth. The change strengthened their identity as a safe, approachable, and supportive organization while making them more visually appealing to young people. See their rebrand. Actionable Tip: If your branding guidelines feel like red tape, ask yourself:
Messaging That Moves People to Action Now, let’s talk about the most important aspect of branding – your story. Whether you’re crafting an email appeal, a social media post, or a campaign landing page, your messaging should inspire action. Major donors don’t just give to organizations; they give to stories they believe in. That’s why it’s essential to center your messaging around the people you serve and the change you’re driving in the world. Storytelling Tip: Showcase Personal StoriesPeople want to feel emotionally connected to your cause. Show them the impact they can have through the eyes of those you help. Example: St. Jude Children's Research Hospital St. Jude’s branding and messaging revolve around powerful, emotional stories of families whose lives have been transformed by their medical care. These stories create a deep personal connection, inspiring donors to give and stay engaged. Explore their storytelling approach. Actionable Tip: Incorporate donor-centered language into your messaging:
Building a Memorable Brand: Flexibility, Authenticity, and Consistency A memorable nonprofit brand is more than a logo or a catchy slogan – it’s a vehicle for connection. It drives donor engagement, cultivates long-term support, and inspires major gifts. To build a brand that resonates, focus on three key principles:
Make Your Brand Matter Branding isn’t about flashy logos or catchy taglines – it’s about making an emotional connection with your supporters. When your brand reflects your mission, values, and unique story, it becomes a powerful tool for attracting major gifts and building lasting relationships. Your nonprofit’s story is powerful. Make it memorable. Make it matter. And don’t be afraid to let your passion shine through. Now – it’s your turn. Have you been through a rebrand? Was the process the transformation you hoped for? Do you feel your branding guidelines and processes support your fundraising work or hold you back? 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...
 Start-of-Year Advice to Stay Organized and ProductivE As a fundraiser, I have never felt like there was enough time to get everything done. I’d often start the day with the best of intentions, focused on raising money and cultivating donor relationships—the "main thing" in our work. But then, other tasks would creep in: emails, scheduling, reports, and urgent but less critical projects. Over time, I learned to shift my approach, adopting strategies that helped me stay focused on what truly matters while keeping everything else under control. Here’s what I discovered that transformed my productivity and mindset. Leveraging Virtual Tools for EngagementOne of the biggest lessons from recent years is how much technology can simplify donor engagement while saving time. Here are my go-to virtual tools and strategies:
Zoom for Donor Meetings
Blast Emails That Feel Personal
|
Jessica Cloud, CFREI've been called the Tasmanian Devil of fundraising and I'm here to talk shop with you. Archives
May 2026
Categories
All
|
RSS Feed