Philanthropy Engagement Techniques

Your gala just ended. You raised $125K. Everyone's exhausted. So you send a thank you email with photos. Just like every other nonprofit. And just like every other nonprofit, you watch those attendees disappear until next year's event. Here's what actually works: Your guests don't need another generic thank you. They need to see what their money did. The nonprofits converting event attendees into year-round donors follow a 10-day impact workflow: Day 1: Text thank you (personal, brief, sets the tone) Day 2: Email with photos and a single impact metric ("Your $50K will provide 200 families with...") Day 5: Impact story (one beneficiary, real name, what changed because of Saturday night) Day 7: Second impact story (different angle, reinforces the mission) Day 10: The ask (specific, tied directly to the stories they just read) But here's the part most people miss: not everyone gets the same sequence. Who bid? Who bought raffle tickets? Who was a first time attendee? Use that data to trigger different follow-ups: Bidders get a call from your ED before the email sequence even starts. Raffle participants get SMS nudges on Day 8 ("You bought raffle tickets. Would you consider a monthly gift of $20?") First-time guests get a longer nurture sequence focused on education, not asks. The workflow isn't complicated. But it requires two things most nonprofits skip: reviewing your event data and planning the sequence before the event ends. Stop treating your gala like the finish line. It's lead gen. And the real fundraising starts the moment your guests leave.

1 Fundraising Stat: Only 2.3% of household wealth is held in cash and checkable accounts. Stop ignoring the other 97.7%. Wealth is not held in cash. It’s held in noncash assets. Real wealth is held in real estate, stocks, bonds, business interests, and retirement accounts. Fundraising tends to fight over the 2.3%. It focuses on cash gifts, cash conversations, and cash asks. Why? Because it’s easy. We don’t have to learn anything to ask for cash. Psychologically, there is a big difference between disposable-income conversations and wealth-sharing conversations. Disposable income is held in cash. Cash conversations lead to disposable-income decisions. Wealth is held in noncash assets. Asset conversations lead to wealth-sharing decisions. These two conversations create two different mindsets. Each creates a different set of reasonable or possible outcomes. Wealth is a large reference point. It makes a big gift feel reasonable. Disposable income is a small reference point. It makes a big gift feel ridiculous. Reminding people of their wealth holdings also makes them feel wealthier. This feeling increases giving. Of course, people know they can turn assets into gifts. But without an asset conversation, they won’t consider that option. If you get a cash bonus of $200 today, it might affect which restaurant you choose tonight. If the shares in your brokerage account go up by $200, it won’t. In accounting, these are identical results. In psychology, they’re different. The brokerage account is a different “mental account.” Assets simply don’t apply to a disposable-income decision. There’s also an immediate penalty for selling the asset: capital gains tax. But having asset-giving conversations can change this mindset. There is no tax for giving an asset. In fact, we can get a double tax benefit (a deduction + avoiding capital gains), all without changing the portfolio. You may not be a financial professional, but you can share stories of what others like the donor have done before. You can be a source of valuable ideas. And unlike some advisors, you aren’t just trying to maximize assets under management. So, you can share ideas the donor might never hear otherwise. And remember, you are the expert. You’re the expert on your organization. You know what it can do and what it can’t. You know when it works for the donor’s philanthropic goals and when it doesn’t. You are a valuable part of the donor’s wealth management conversations. And there’s good news. You won’t have much competition from other nonprofits. Cash and checkable accounts are like a kiddie pool on the beach. Nonprofits are all desperately fighting over the kiddie pool while ignoring the ocean. It takes work, but the learning is free. EncourageGenerosity .com has free videos, slide decks, audiobooks, and digital books on this topic, like: -Visual Planned Giving: Law and Tax -The Storytelling Fundraiser (Ch. 6) -The Socratic Fundraiser (Ch. 6, 7) -The Biblical Fundraiser (Ch. 4)

I've seen so many nonprofits wait until the last minute to collect stories they need for their next fundraising campaign. You’re a week or two away from launching your next big campaign, and your marketing director sends the team an email. “Anyone have any stories to illustrate…?” Suddenly, everyone is scrambling. Someone remembers a client who said something powerful… but it was 6 months ago. Mayyyyybe there’s a photo somewhere. The staff member who oversaw that really cool project? They’ve left. It doesn’t have to be this hard. If storytelling is one of your most powerful fundraising tools, then you need a system to capture stories all year long – not just when you need them. My recommendation? 1️⃣ Set up a shared “Story Bank” CRM. This is a central place where everyone can drop in client stories, donor quotes, Board anecdotes, or milestones as they happen. Use something like Airtable or Notion where the information can be searchable by program, date, and theme. 2️⃣ Create a routine rhythm of having your team add to the Story Bank on a monthly basis. This doesn’t have to be full-blown stories – just moments & emotions that can be fleshed out later. 3️⃣ Commit to sharing stories. A Story Bank that just collects stories and is never used isn’t of much value. You need to actually tell the stories you collect. Commit to sharing a story at least once or twice per month. The truth is, your nonprofit is already creating plenty of meaningful moments and success stories. You just need a system to collect & share them. What is your organization doing to collect Impact Stories?  What tools do you use to aid in the process?

How philanthropy can find its future by relinquishing control 800 years ago, Maimonides wrote that the highest form of giving is to make charity itself unnecessary. That wisdom feels newly relevant as wealth and power converge in modern philanthropy. Laurene Powell Jobs recently warned that too often wealth becomes a substitute for participation. “Giving that expects control,” she said, “is anything but generous.” When benefactors decide what matters and who belongs, philanthropy drifts from love of humanity toward a contest for influence. MacKenzie Scott offered an image of a murmuration of starlings, millions of birds moving as one without a leader. Their direction, she noted, emerges from constant response to one another’s movements. Her metaphor captures what the next evolution of philanthropy might look like—decentralized, adaptive, and animated by trust. Both women describe a shared transformation. Powell Jobs warns against power disguised as generosity; Scott imagines generosity as shared participation. Each challenges the notion that change flows downward from donor to recipient. Both echo what frontline leaders have long known: real progress happens through proximity, not prescription. Philanthropy rarely lacks compassion, but its systems remain transactional. Short grant cycles, risk aversion, and a fixation on measurable outcomes shape. Transformation is rarely linear; it unfolds through learning and trust. Scott’s “seeding by ceding” approach replaces oversight with faith in those closest to the problems. Unrestricted gifts have enabled groups to hire staff, pay fair wages, and rest. Many say that what was strengthened most was not programs, but dignity. That dignity links all three perspectives. Powell Jobs argues that true generosity builds capacity, not dependency. Scott reminds us that care ripples outward in ways that can’t be counted but are real. And frontline organizers measure success by staying power—the ability to keep showing up. Seen from that view, the challenge is not to give more but to govern differently. Money alone rarely shifts power; the governance of money does. A more resilient model would treat funding as a relationship, underwriting the unglamorous foundations of endurance and accepting that some efforts will fail in ways that teach. Scott’s imagery applies here too: each participant adjusting to others in real time. No single actor directs the course, yet the movement coheres. Philanthropy’s future may depend less on innovation than humility—on returning to its original aim, the love of humanity. When funders move from control to accompaniment, they make space for others to lead. Perhaps real generosity lies less in the power to direct than in the willingness to belong: to a community of exchange where the roles of giver and receiver blur with time, and where the measure of impact is not what it buys but what it builds—a culture of trust and solidarity that outlasts any single fortune.

10 years ago, I thought fundraising was about working harder. I was wrong. It's about working smarter. Here are 10 cheat codes I wish I knew then: 1. The 48-Hour Rule: Thank donors within 48 hours. No excuses. 2. The Calendar Rule: If it's not on your 12-month plan, it's a distraction. Say no with confidence. 3. The Second Ask Timing: Ask first-time donors again at 90 days, not 12 months. The window closes fast. 4. The Specificity Rule: "$5,000 funds one classroom" beats "$50K for our program" every time. 5. The 80/20 Audit: 80% of your revenue comes from 20% of donors. Spend your time there. 6. The Phone Call Multiplier: A 3-minute thank-you call = 5x retention vs. email alone. 7. The Question That Closes: "What questions do I need to answer for you to feel good about this?" Then stop talking. 8. The Handwritten Note: One handwritten sentence beats a templated email every time. 9. The Upgrade Path: Move donors up 50% at a time, not double. $100 → $150, not $200. 10. The Board Accountability Hack: Give board members ONE specific action per month. Not vague "help with fundraising." None of these require budget. None of these require permission. All of them work. Which one are you ignoring right now?

When I took on my role as Chief Corporate Citizenship Officer at PMI, I set a handful of parameters for myself and my team: 1. Don’t fall into the trap of arm’s-length checkbook philanthropy: One-off cash infusions can help nonprofits in the immediate term, but they don’t get at the issue of sustainable growth. 2. Focus, focus, focus: Diffusion is the enemy of progress. There are an endless number of worthy causes and charitable organizations, but our greatest impact will come from identifying a small number of causes that are intrinsically tied to our values and vision and making those causes priorities. (In our case, this is U.S. military veterans, women’s equity and empowerment, and hyperlocal activations.) 3. Empower—and learn from—those already in the trenches: We’re not going to dictate what happens at the community level. We’re here to listen and learn and find ways to support and expand the good works already underway. 4. Give a “hand up” instead of a handout: Band-Aid solutions may make us feel good in the short term, but they don’t get to the root problem. The cash infusions we give our community-based partners are meaningful, but their value grows exponentially when paired with our business expertise and insights. 5. Offer employees a chance to contribute to change: We polled PMI’s U.S. workforce earlier this year about our plans to support military veterans. An astonishing 97 percent of employees raised their hands to get involved. There’s a hunger out there for making a positive difference in local communities and the broader world. Find ways to connect your people to the issues that matter most to them. It turns out that this is the way the next generation of philanthropists is thinking about their impact as well. A recent article (I’ll share the link in comments) shares interesting insights into how our younger generations—millennials and Gen Z—are embracing a more comprehensive approach to philanthropy focused on measurable impact and deeper connections. They’re also showing a greater tolerance for the “long game,” willing to take risks in the short term to lay the groundwork for greater gains down the road. As the next generation of philanthropists takes the reins and starts investing more than money in the causes they care about, let’s make sure our organizations are prepared to do the same.

If AI Equity is the goal, Community-Centric AI is one way to practice it. I made this image four years ago — and it still feels relevant. I nerded out on this so deeply because I think community-centric AI can sound abstract until we connect it to actual choices philanthropy is making — or will soon be making. So today I am sharing some context to read these truths (and use them in your conversations): ● 𝐀𝐈 𝐢𝐬 𝐧𝐨𝐭 𝐚𝐧 𝐞𝐧𝐞𝐦𝐲 𝐨𝐫 𝐚 𝐡𝐞𝐫𝐨. I often see AI described in extremes — either as the thing that will save nonprofit capacity, or the thing that will ruin human work. In philanthropy, that kind of language can rush bad decisions. Community-centric AI asks us to speak about it beyond binaries. ● 𝐓𝐡𝐞 𝐜𝐡𝐨𝐢𝐜𝐞𝐬 𝐢𝐧 𝐭𝐡𝐞 𝐬𝐲𝐬𝐭𝐞𝐦 𝐦𝐮𝐬𝐭 𝐛𝐞 𝐞𝐱𝐩𝐥𝐢𝐜𝐢𝐭. For example, if a funder uses AI to summarize grant applications, what choices shaped that tool? What does it define as “clear,” “strong,” “scalable,” or “high potential”? Whose language patterns and communication styles are being rewarded? These choices are never neutral, which is why they need to be named. ● 𝐀𝐈 𝐦𝐮𝐬𝐭 𝐛𝐞 𝐚𝐜𝐜𝐞𝐬𝐬𝐢𝐛𝐥𝐞 𝐚𝐧𝐝 𝐢𝐧𝐜𝐥𝐮𝐬𝐢𝐯𝐞 𝐢𝐧 𝐝𝐞𝐬𝐢𝐠𝐧 𝐚𝐧𝐝 𝐮𝐬𝐞. If nonprofits are expected to engage with an AI-enabled grant portal, chatbot, or reporting system, can they access, afford, and use it institutionally? If not, the AI may appear efficient from tech perspective while creating new burdens on the community. ● 𝐓𝐞𝐬𝐭𝐢𝐧𝐠 𝐦𝐮𝐬𝐭 𝐢𝐧𝐜𝐥𝐮𝐝𝐞 𝐭𝐡𝐞 𝐜𝐨𝐦𝐦𝐮𝐧𝐢𝐭𝐢𝐞𝐬 𝐭𝐡𝐞 𝐬𝐲𝐬𝐭𝐞𝐦 𝐰𝐢𝐥𝐥 𝐢𝐦𝐩𝐚𝐜𝐭. If a nonprofit is piloting AI, testing cannot be limited to consultants or tech vendors. The people who will be affected by the system need to be part of core understanding what works, what confuses, and what needs to change. ● 𝐄𝐯𝐞𝐫𝐲𝐨𝐧𝐞 𝐛𝐞𝐧𝐞𝐟𝐢𝐭𝐢𝐧𝐠 𝐟𝐫𝐨𝐦 𝐀𝐈 𝐦𝐮𝐬𝐭 𝐭𝐚𝐤𝐞 𝐚𝐜𝐜𝐨𝐮𝐧𝐭𝐚𝐛𝐢𝐥𝐢𝐭𝐲. Not just the vendor. Not just the nonprofit using the tool. Not just the funder. Whoever funds, adopts, or benefits from AI use is accountable, together. This tenet exists so that collective as well as individual responsibility does not disappear the moment a tool’s efficiency enters the room. ● 𝐀𝐈 𝐨𝐮𝐭𝐜𝐨𝐦𝐞𝐬 𝐜𝐚𝐧𝐧𝐨𝐭 𝐛𝐞 𝐯𝐚𝐥𝐮𝐞𝐝 𝐨𝐧𝐥𝐲 𝐢𝐧 𝐞𝐟𝐟𝐢𝐜𝐢𝐞𝐧𝐜𝐲 𝐧𝐮𝐦𝐛𝐞𝐫𝐬. This one matters deeply in philanthropy because the sector already lives close to metrics. Even if an AI tool helps process more applications, summarize more reports, or respond more quickly, we still need to know the impact on trust, burden, access, and dignity. These tenets exist to remind us that AI should not only be judged by what it produces for institutions. It should also be judged by how it feels, functions, includes, protects, and redistributes for the people living closest to its effects. For philanthropy, I think community-centric AI is one way of asking a very fundamental question: Who is this really for? #nonprofits #community

"Fundraising is everyone's job." How many times have you heard this well-intentioned phrase? It sounds great in theory but it often leads to confusion and overwhelm in practice. Here's a better approach: "Building a culture of philanthropy is everyone's job." The difference? Instead of turning everyone into reluctant fundraisers, we create an environment where each person understands and supports the mission through their unique role. Imagine a world where your program officer excels at creating amazing initiatives, your finance team ensures fiscal responsibility, and your fundraisers build strong donor relationships. All while working in harmony towards a shared vision. So, how do we build this culture of philanthropy without turning everyone into reluctant fundraisers? Educate: Help all staff understand the role of philanthropy in achieving your mission. Empower: Give everyone tools to talk about your impact and connect supporters to the right team member. Engage: Involve program staff in donor meetings to share frontline stories. Appreciate: Recognize all contributions to the fundraising process, not just closed gifts. Communicate: Share fundraising successes and challenges with the entire organization. When everyone plays to their strengths while supporting a culture of philanthropy, that's when the magic happens. Have you successfully built this culture in your organization? Or are you facing challenges?

I once watched a major gift officer spend ninety minutes in a couple's living room and barely mention the organization he represented. He asked about their lives. Their careers. Their family. What kept them up at night. What gave them hope. The conversation wandered through one donor's childhood – growing up poor in rural Appalachia, a teacher who changed her trajectory by believing in her when no one else did. She talked about education with the kind of passion that only comes from lived experience. He didn't learn any of this from a wealth screening report or a donor database. He learned it by listening. Six months later, she made a transformational gift to fund scholarships for first-generation college students from rural communities. The ask wasn't hard. He simply invited her to do what she already wanted to do – in a way that aligned with what he'd learned about her values. That's what listening does. It creates the foundation for everything else. In the immortal words of Jerry Panas, "The true art of asking lies in listening." I've been in this work for more than thirty-five years. And over those decades, one pattern has become unmistakable: the major gift officers who consistently produce results – not one-time wins, but sustained, long-term generosity – share a common set of instincts. Chief among them is this: they lead with questions, not asks. But here's the uncomfortable truth. Most of our fundraising systems are designed to do the opposite. We assume we know what donors care about and broadcast it back to them through one-way messaging. We build systems for efficiency and scale – not for listening. And donors can tell. They know when they're being heard and when they're being sold. The difference is visceral. When you listen, donors lean in. When you talk at them, they pull away. This isn't just good fundraising technique. It's the donor's return on investment. When people ask "what's in it for the donor?" – this is part of the answer. The feeling of being valued. Of mattering. Of genuine connection. For many donors, that experience is as meaningful as the impact their gift creates. Listening is one of a fundraiser's most important skills. It's one of what I refer to as the Seven Behaviors – disciplines that define exceptional major gift work and that I believe must become the foundation of all fundraising. Not just for the top one percent. For every donor. These seven behaviors are at the heart of my upcoming book, 𝗔 𝗕𝗲𝘁𝘁𝗲𝗿 𝗪𝗮𝘆 𝘁𝗼 𝗙𝘂𝗻𝗱𝗿𝗮𝗶𝘀𝗲: 𝗧𝗿𝗲𝗮𝘁 𝗘𝘃𝗲𝗿𝘆 𝗗𝗼𝗻𝗼𝗿 𝗟𝗶𝗸𝗲 𝗮 𝗠𝗮𝗷𝗼𝗿 𝗗𝗼𝗻𝗼𝗿. The book argues that the technology now exists to operationalize these seven behaviors at scale, and that the future belongs to organizations that commit to extend these behaviors across their donor base and begin treating every donor with the dignity and respect they deserve – or, to put it simply, to treat every donor like a major donor. More to come... #aBetterWay

I recently had the pleasure of interviewing Chet Jainn, the founder of Crowdera, who shared his profound insights on the differences between charity and philanthropy for The Mohua Show. Chet explained that while charity is a reactive response to immediate needs, philanthropy is all about creating long-term, systemic solutions to address root causes. He emphasized how understanding this distinction is crucial for anyone involved in effective fundraising and driving real impact. Here are some key highlights from our inspiring conversation: ✅ How Chet transitioned from a teen entrepreneur to a visionary philanthropist: His journey began with a simple yet powerful question, leading to the birth of Crowdera. ✅ Vision behind Crowdera: How the platform evolved to become a leading force in philanthropy, offering innovative solutions for effective fundraising. ✅ The digital transformation of Indian charities: Chet sheds light on how technology is revolutionizing the way charities operate, making fundraising more accessible and transparent. ✅ Crowdera’s cutting-edge fundraising models: Learn how Crowdera is reshaping traditional models and bringing a new wave of innovation into philanthropy. ✅ Key advice for new entrepreneurs and philanthropists: Chet shares invaluable tips on how to balance passion with strategy to create lasting impact. Tune in to the full episode for more insights and inspiration: https://lnkd.in/g-FkkMu7 #Philanthropy #Charity #ImpactEntrepreneur #FundraisingInnovation #Crowdera #DigitalTransformation #IndianCharities #StartupJourney #Entrepreneurship #Podcast #TheMohuaShow