A bad blog doesn’t just look lazy—it proves it. In the world of planned giving, where trust and credibility matter most, an outdated or lifeless blog can quietly sabotage donor confidence. Learn why showing up halfheartedly online is worse than not showing up at all—and how to fix it before it costs you.
Originally Published September 16, 2010. Updated for January, 2025. Apology Not Accepted: Why You Shouldn’t Beg for Forgiveness in Fundraising A few years back, I was lying on a beach with my wife, margarita in hand, enjoying the sound of the waves and the luxury of ignoring my phone. Naturally, that’s when it rang. On the other end was a client, panic vibrating through his voice like a dentist drilling too close to the nerve. “I’m going to have to apologize to all of them,” he moaned. “In fact, I’m writing the apology letter now.” “To who? About what?” I asked, already mentally preparing to cancel my vacation. We had just designed a planned giving brochure for him, and it was going out to over 22,000 of his prospects. My stomach twisted like a corkscrew—I was sure we had screwed it up. But (thankfully for me), it wasn’t our fault. The mail house had botched the cover letter, addressing it to “Mr. and Mrs.” instead of “Dr. and Mrs.” A capital fundraising mistake (or offense) apparently—especially since this particular mailing was targeting alumni of a prestigious medical school. Cue end-of-the-world music. This fundraiser was convinced that unless he groveled in public, careers would end, reputations would be ruined, and Twitter mobs (okay, mailing list mobs) would descend. So I offered him sympathy. And advice. And another margarita. “Don’t apologize.” Yes, I said it. Don’t. Apologize. (Some people say I’ve perfected the art of not apologizing. Those people aren’t all friends… but they’re not entirely wrong either.) The Apology Industrial Complex I understood why he felt the need to send out a soggy “We’re terribly sorry we didn’t validate your full academic pedigree” letter. After all, we now live in an age where microaggressions get more airtime than macro-accomplishments, and an honest oversight is treated like a hate crime. But here’s the truth: most recipients wouldn’t notice the mistake. An even larger chunk wouldn’t care. And if he sent out an apology? He’d only be highlighting the error—possibly irritating more people than he calmed. “Let it go,” I told him. “If someone really cares, they’ll write in and you can apologize personally. Quietly. Directly. Like a rational adult.” Plot Twist: The ‘Offended’ Gave More So did anyone complain? Sure. A handful. And here’s the punchline: three of the people who complained included donation checks in the same envelope. One for $2,000.One for $4,000.One for $6,000. Yes, really. That little salutation “catastrophe” earned him an extra $10,000. Oh, and the campaign as a whole? 26% response rate. To this day, I can’t explain why it worked so well. Maybe the unintended slight gave it an air of authenticity. Maybe it struck the right balance of formality and fallibility. Maybe—just maybe—people don’t actually want every message sterilized and scrubbed by a committee before reaching their mailbox. Imagine that. When Mistakes Become Marketing This isn’t an isolated case. Another fundraiser once mailed a letter that was supposed to include a brochure. It didn’t. The brochure never made it into the envelopes. Sounds like a disaster, right? Wrong. Just the opposite that created an opportunity. The missing brochure prompted recipients to reach out and ask for one. Which meant the development office got personal interaction with dozens of prospects they would have otherwise never heard from. More connection. More conversation. More donations. You can’t plan this stuff. You can’t predict it. But you can learn something from it: Don’t lead with panic. Don’t amplify problems that most people would overlook. Don’t assume that every mistake needs a groveling public mea culpa. And please—for the love of fundraising—don’t let fear of offending someone with a Harvard M.D. lead you to cripple a good campaign. So What’s the Lesson? Screw-ups happen. You’ll mistype a title, forget a brochure, or trigger someone’s inner grievance committee. Relax. You’re not performing surgery. You’re raising money. And sometimes—brace yourself—a little imperfection works in your favor. Just don’t be so quick to flagellate yourself in public. That’s not leadership. That’s theater. And last I checked, you weren’t running a drama club—you’re running a fundraising program. The next time you’re tempted to hit “send” on that mass apology, ask yourself: Is this about them… or is it about me trying to win points in a game no one’s actually playing? Then go pour a margarita. You’ve earned it. But there are some mistakes that would turn off donors. And you should be aware of them.
Nonprofits did not do well last year, and you wonder why. I recently came across a job listing that read something like this: “[A nonprofit] is seeking a planned giving advisor. This is a junior position for a fundraiser with 3 or so years of experience who wishes to move into planned giving. Focus is on bequests, CGAs, and marketing.” Now, for those of us who have been in the trenches of planned giving for a while, that one little word—junior—jumps off the screen. Not because there’s anything inherently wrong with junior hires (everyone starts somewhere), but because of what that label suggests in the context of planned giving fundraising. In fact, a response I saw to this posting was quite blunt: “Hiring a junior person for a planned giving program is a guarantee of underperforming … a recipe for failure.” Why? Not due to some prejudice against younger or entry-level fundraisers, but rather a legitimate concern about fit—or lack thereof. Planned giving often involves nuanced conversations with financially sophisticated individuals. It’s not an entry-level sport. And yet, some nonprofits seem to think they can start one with an entry-level bench. This brings us to a larger question: Is entry-level nonprofit fundraising—particularly in planned giving—a sustainable model, or a shortcut to mediocrity? “Economy Class” Is Still an Oxymoron What struck me more than the job listing itself was how it reflected a broader trend: the creeping adoption of a business model I’ll call the “entry-level organization.” This is the model where an organization’s entire staffing strategy revolves around hiring people straight out of college, paying them as little as possible, and replacing them just as quickly. These workers are young, cheap, eager, and—let’s be honest—usually expendable. The idea is not new. Take the retail book industry as a prime example. When brick-and-mortar bookstores began facing brutal price competition from online retailers, they responded by gutting overhead. That meant saying goodbye to knowledgeable, experienced sales staff and saying hello to an army of bright-eyed, underpaid 22-year-olds. The result? Sure, the labor costs dropped. But so did the customer experience. You might remember a store called Borders. They perfected this model. And then they flatlined. To a spreadsheet-driven executive, this kind of cost-cutting is a seductive idea. On paper, the math adds up. In practice, however, it fails spectacularly over time—especially in sectors that depend on trust, nuance, and long-term relationship-building. Sound familiar? The Planned Giving Parallel Planned giving fundraising is not retail. You don’t sell CGAs like you sell coffee mugs. You don’t walk a donor through a charitable remainder trust the way you recommend a summer beach read. These are deeply personal, often complex financial decisions involving taxes, legacies, and family considerations. In short, planned giving requires maturity, emotional intelligence, and technical fluency. That’s not to say entry-level nonprofit professionals shouldn’t be involved. Quite the opposite. We need a new generation of fundraisers who are trained, mentored, and equipped to become the future leaders of our sector. But here’s the catch: You can’t hire cheap and expect premium results. Nonprofits that treat planned giving like a low-cost experiment—assigning it to someone with no real training, guidance, or experience—are playing a short-term game in a long-term sport. The Real Cost of “Cheap” In today’s economic climate, it’s tempting to chase short-term savings. Budgets are tight. Boards are cautious. And executives are often pressured to “do more with less.” Running your nonprofit like a (successful) business is imperative. But here’s the inconvenient truth: Under-investing in planned giving talent is a false economy. Hiring an entry-level fundraiser without pairing them with a mentor is not strategic—it’s reactive. It may check a box, but it won’t build a program. Instead of viewing young hires as a way to cut costs, we should view them as assets in training. That means building systems for professional development, mentorship, and long-term growth. Pair your junior staff with a seasoned fundraiser. Allow them to shadow donor conversations. Let them listen, observe, and learn the language of legacy. Think of it this way: In planned giving, the best returns take time. That applies to both donors and staff. So why not align your internal strategy with your external mission? A Smarter Alternative Rather than chasing quick wins through “youth exploitation,” nonprofits should invest in multi-generational skill-building. Mentorship over management: Don’t just assign tasks—offer guidance. Apprenticeship over assumption: Don’t assume your hire knows what a CRUT is—teach them. Long-term vision over short-term savings: Build your planned giving bench like you build your endowment—with patience and purpose. When you invest in your team the way you ask your donors to invest in your mission, you create something sustainable, ethical, and deeply effective. The Future Begins Now This is a concept that every planned giving officer understands: Legacy is built today. The same holds true for your team. Cheap savings today will never match the compound interest of a wise hire, a strong mentor, and a multi-year investment in talent. Yes, fundraisers have to start somewhere. But that “somewhere” should be in a supportive, strategic environment, not a sink-or-swim cost-cutting scheme. You cannot hire an entry-level fundraiser, throw them in the ocean without so much as a life preserver, and then expect success. Let’s retire the myth of the “entry-level organization” in the world of planned giving. The future of fundraising deserves better. And if you’re looking to build that future, start with your people. Key Takeaways Entry-level nonprofit fundraising has its place—but not as the sole strategy for planned giving programs. Treating planned giving as a “junior” role for an entry-level fundraiser sets up programs for mediocrity and failure. The better model is mentorship and multi-generational training that mirrors the long-term mindset of planned giving itself. Organizations that prioritize short-term savings over long-term investment will pay for it in missed opportunities and stagnant results. Want to build a sustainable, high-performing planned giving program? Start by investing in your team like you invest in your mission. Because in fundraising—as in life—the future begins now.
From a fundraiser’s point of view, or course, a perfect world would include all prospects coming directly to the fundraiser or her organization for advice on giving. But numbers indicate fewer potential donors are seeking advice from NPOs and their personnel. They are turning instead to legal and financial professionals.
Breaking the Myth: You Don’t Need a Law Degree Let’s dispel one of the biggest myths in fundraising: that planned giving is only for experts with a Harvard Law degree—preferably the kind who believe every problem needs a 20-page policy paper and a new government subcommittee. If you’re a development officer with a strong background in annual or major gifts, and someone has just tapped you to “start a planned giving program,” you might feel the urge to panic. Or worse—you dive into the deep end by attending advanced seminars on charitable lead trusts, gift annuities, and other exotic instruments you’ve never dealt with before. While these technical concepts have their place, they represent only a fraction of what you need to build a successful planned giving program. And too often, this approach leads to “majoring in minors.” We see it all the time: smart, capable fundraisers get overwhelmed by the technical jargon, get distracted by complexity, and miss the big picture. If this sounds like you, take a deep breath. You don’t need to be a tax attorney. You don’t need a decade of experience in estate law. And you certainly don’t need to be a Harvard lawyer. The Core Truth: Keep It Simple Let’s be clear: about 90% of all planned gifts are simple bequests. These are the most common, easiest-to-understand, and most cost-effective gifts for your donors to make. Bequests don’t require trust agreements, actuarial tables, or gift annuity contracts. Whether you’re fundraising for Harvard, the Chattanooga Symphony, or a local soup kitchen, the story is the same—most legacy gifts come in the form of straightforward bequests. Donors want simplicity, and your job is to make that simplicity accessible. So why do so many of our peers gravitate toward the complicated stuff? Because it feels productive. But here’s the hard truth: complexity is the enemy of execution. Start With One Simple Question We’ve coached thousands of nonprofit professionals, and here’s the single most powerful question you can ask a loyal donor: “Have you ever considered including us in your will or estate plan?” That’s it. No Latin phrases. No tax codes. No technical diagrams. Just a direct, thoughtful question that starts a meaningful conversation. This one sentence has resulted in countless bequests. The best part? It respects the donor. It starts where they are. And it opens the door for future conversations without intimidation. When you focus on simplicity and clarity, you increase the likelihood that your message will stick. Planned giving becomes less of a legal puzzle and more of a natural extension of the donor relationship. Leverage What Already Works At PlannedGiving.com, we specialize in making complex things simple. From our turnkey micro-sites to our popular LegacyPlanner™, we’ve proven that success in planned giving is about starting small, scaling smart, and keeping your messaging clear. The LegacyPlanner™ is a simple free will-planner that nonprofits can embed into their donor experience—completely eliminating the “legal intimidation” factor for your prospects. No Harvard degrees required. We also publish GIVING Magazine, a resource that shares strategies, thought leadership, and case studies from the best minds in fundraising. And if you’re new to all of this and wondering how to even begin, our Boot Camp is a great place to start. The Bottom Line: Don’t Overthink It If your job is to raise money—and you’ve been successful with annual or major gifts—planned giving should be your next logical step. You already have the skills. You already know your donors. You just need the right frame of mind. So skip the legalese. Put away the pie charts. Stop majoring in the minors. And start having authentic conversations with your most loyal donors. Because in the end, planned giving isn’t about being smarter than everyone else. It’s about being consistent, clear, and committed.
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