Philanthropy Engagement Techniques

I once worked on an 8-figure gift where the board chair had one job: show up to one meeting and answer one question, "Why do YOU care about this mission?" He wasn’t there to recite program details or run the strategy. He wasn’t even there to make the ask. A team of expert staff did the research and together we set the strategy. Over 18 months, we met with the donor, hosted site visits, reviewed finances, and got to know the donor's whole family. We determined the right ask amount and the right moment. We brought the board chair to the solicitation meeting with one clear role: tell your story. He shared the moment he realized this work mattered and why he chose to join the board. I remember being a little nervous. Would that be enough? Would the donor want more technical details from him? But a board member brings something different to the table, a kind of peer influence that builds on the staff’s work. Board members are not on the payroll. They choose to give their own time and money, and that carries weight when they tell another donor, "Here's why I give. Here’s why I believe in this team.” Staff presented the funding opportunity and made the 8-figure ask. The donor said yes. It worked because of months of preparation, a donor who was ready, and staff and board who trusted each other to do their part. The board chair didn't need to know how to structure a gift of this size or understand cultivation timelines. He didn't even need to be comfortable asking for money. Staff can't manufacture peer credibility or replicate the power of one donor telling another donor, "I believe in this enough to give my time and money. Here's why." That opens doors, builds trust, and helps turn a good conversation into a yes. I've thought about this a lot since then. Board members often ask how they can help with fundraising, and I keep coming back to this: Join a solicitation meeting and share why you care, peer to peer. It's one of the most meaningful things you can do as a #nonprofit board member. Share why this work matters to you. You don't need to have all the answers. You just need to start the conversation. #NonprofitLeadership #MajorGifts #BoardDevelopment #Philanthropy #FundraisingStrategy

I have a fundraising horror story to share… Was recently speaking with a community foundation CEO about the challenges nonprofits face with DAF giving ⚠️ The biggest one is the difficulty stewarding these gifts 😤 DAF gifts arrive weeks after they are initiated, with no or limited donor details, which make a nonprofit’s priority of building relationships with these high value supporters much more difficult 😵💫 In this specific case, the community foundation has a DAF fund holder who has made a generous annual gift to a local charity for a few years… … And never heard from the organization 🙈 So they asked to cancel their recurring grant request. The community foundation then had to reach out and let the organization know they’d be losing this significant support and hopefully educate them on DAF giving so they can do better in the future ❤️ There’s a few things about this story that grind my gears: 1️⃣ Even DAF gifts that aren’t anonymous are not straightforward to process. It might have a fund name you can’t necessarily tie to an individual or an address that doesn’t match your existing records 👀 2️⃣ Education for nonprofit leaders on how DAF works is improving, but still way behind. It’s understandable that someone on this organization’s team that’s opening mailed checks just sees it’s from their community foundation and enters it as such in their database 👉🏼 Or maybe they do get a soft credit in there to a donor, but their system isn’t set up to send separate thank yous to a soft credit entry when it’s a DAF gift 🤷🏼♂️ 3️⃣ These things take time that nonprofits don’t typically have. Especially grassroots ones. Properly processing this transaction is about 10x the work of a credit card gift on their website - assuming they have the knowledge on the correct way to manage it ⌛️ My takeaway? 🤔 While DAFs are a phenomenal tool to hold people accountable to their philanthropic goals and increase their giving, the existing infrastructure is so poor that it can create operational burden on nonprofits and poor giving experiences for donors 🚧 But, DAFs are here to stay and growing fast. So what can we do? 1️⃣ Drastically increase nonprofit education on this topic 📚 I’m ramping up my schedule of teach ins and work shops on this topic, if you’ve got an audience that would benefit, let’s chat! 🗣️ 2️⃣ Make digital DAF giving standard ✅ Getting DAFpay into more donation forms and giving experiences will train DAF donors that there is an easier way to give, that lets nonprofits steward them properly right away (get their email and know the gift was requested immediately) ⚡️ 3️⃣ Keep innovating! 🤩 We are working hard to improve all the steps of this process - and hiring! We have open roles in engineering and compliance (all in person in NYC) 🗽 So excited about the year ahead - let’s stop these horror stories! 🫷 #nonprofit #fundraising #philanthropy 

Over the last year, I've been asked to advise several non-profit organizations that are looking to diversify their funding and pursue non-grant revenue streams. Often the most pressure is coming from their current donors, who are looking to reduce their funding and want the non-profit to find the ever-elusive 'sustainable business model'. Unfortunately, this is a REALLY tough ask, for the following reasons: 1. Mission-market tension: Generating revenue requires tailoring offerings to paying customers — which may not always align with the organization’s core social mission. When your solution and strategy have been optimized for years to deliver impact over revenues, you're typically serving the most vulnerable people in the hardest-to-reach communities with lowest ability to pay. 2. Lack of IP protection: Many non-profits have open-sourced their IP. Often this is required within grant agreements. Without protected IP, it is much harder to find opportunities to monetize their solutions. 3. Market failures: Many non-profits are addressing market failures, where the societal benefits of their solutions outstrip any individual market demand. Remember also that need ≠ demand... or as someone once said to me: 'just because there is a gap in the market, doesn't mean there is a market in the gap'. Many non-profits are solving for a lack of domestic financing to pay for public goods that governments really should (but can't) pay for. 4. Capacity gaps: Many non-profits lack the internal systems, skills, or business models to operate commercially. Financial planning, marketing, pricing, and customer acquisition are often underdeveloped. 5. Cultural resistance: Shifting from a grant mindset to an entrepreneurial one can cause friction within teams or boards used to traditional philanthropic models. 6. Brand identity risk: There’s a fear that pursuing revenue might dilute public trust or make the organization seem less altruistic to donors or communities. 7. Access to growth capital: Non-profits typically can’t raise equity, and most don’t have the financial runway to test or scale new models without flexible funding. Non-profits aren’t broken — they’re solving problems markets won’t. Let’s be realistic about what “sustainability” really means.

After years of looking at donor behavior, one pattern keeps showing up. Fundraisers spend a lot of time worrying about asking too often. Donor fatigue. Too many appeals. When donors talk about why they stopped giving, what they remember is different. They remember not being thanked. They remember never hearing what their gift accomplished. They remember being asked once and then forgotten. This doesn’t mean fundraiser concerns are irrational. Those fears are real and widely shared. But donor attrition research consistently shows that silence leaves a deeper impression than frequency. Fundraiser concerns reflect what practitioners worry about. Donor memories reflect what actually changes behavior. (Practitioner concerns drawn from recurring themes in AFP, Bloomerang, Blackbaud, and M+R surveys and training materials. Donor experience based on donor-reported attrition research from IMPACTS, FEP, and Engage USA.)

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.

A few weeks back, I watched Maggie Hott, GTM leader at OpenAI, confidently navigate her first board meeting at Unify. Having worked with her through Emergence Capital's Operator in Residence (OIR) program, seeing her immediately contribute valuable insights made me think about how most board members receive virtually no training for this critical role. At Emergence, we've built our firm around developing board excellence. We grow all our partners from within and have established a culture of mentorship focused on board service. Junior investors aren't thrown into the deep end—we pair them with senior GPs to observe effective board dynamics firsthand. My initial experience was at DroneDeploy alongside my partner Kevin Spain, where I got great mentorship before taking on independent board responsibilities. We extend this methodology to our OIR program, where operators learn how to be effective board members. Based on my experience mentoring directors, here are the fundamental principles I share with first-timers for how board members can best support founders: 1. Reframe the purpose: Problem-solving, not reporting If your board meeting is primarily reporting, you're wasting your management team's time. Information sharing should happen asynchronously, with board members engaging with materials before the meeting. This enables the live session to leverage collective intelligence on critical challenges. This rarely happens because many directors overextend themselves across too many boards—another reason we maintain a disciplined investment pace. 2. Master the Socratic approach The most valuable contribution often comes through thoughtful questions rather than declarative statements. Your objective is to enhance the decision-making capability of management. I enter each meeting with 1-3 specific areas where I know I can add value, focusing questions on these topics. 3. Follow-through separates professionals from amateurs Diligently document your commitments, establish clear action items, and execute them. It's crazy how just doing this proactively makes a board member stand out. 4. Understand your unique contribution to the board ecosystem A high-functioning board resembles a great basketball team—you need complementary skills, not redundant ones. In every meeting, I stay conscious of my distinct value relative to others in the room, whether that's SaaS expertise, AI knowledge, or a particular relationship dynamic with the CEO. I calibrate my role based on needs—sometimes assertively addressing areas where others have less experience, other times asking probing questions where fellow members have deeper expertise. -- To my knowledge, Emergence is the only VC firm with a formalized program dedicated to board excellence. It's an investment that yields returns where they matter most—in bending the odds of success for our founders. Founders, I'm curious: What board member behaviors have you found most valuable?

One voice hijacked the Board meeting. And it almost went sideways. It was a winter morning, and the boardroom felt brighter than the conversations we were about to have. A director with a long history in the company took his usual seat near the head of the table. The early items moved quickly, and then we arrived at pricing and margin, the contentious item on the agenda. The director leaned forward and began to talk about a different issue entirely, something large and adjacent that would have taken up the remaining time. Eyes dropped to laptops, the CEO paused, and the quietest director folded her hands. The room's vibe began to change. I let the director finish his first long arc, and then I gently raised my hand to interrupt the pattern. “I'm mindful we have 20 minutes left on this agenda item. Please can we come back to the decision at hand about the price adjustment?” The sentence was simple, the timeframe was clear, and it returned everyone to the work we were supposed to do. The director pivoted into a broader concern about market share and brand risk, and those were fair concerns. I called on two quiet voices and asked what they were seeing that could change their views on a price change. The meeting shifted to a better pace, and we now had perspectives anchored in data rather than status. We closed the item with a motion to pilot the price change for sixty days, publish a simple weekly dashboard, and return with customer feedback. I thanked the director for identifying a strategic risk and scheduled a separate session for the broader brand question. For me, authority in a boardroom comes from protecting the process and dignity of attendees. That enables good decisions to be made. When finance leads that way, clarity becomes part of the culture. 1. Frame decisions early. Ask the chair and one skeptical director to explain the decision needed and the risks they fear the most. Naming this early reduces the need for speeches. 2. Bring out the quiet voices first. Ask two people who rarely speak to share their observations. This expands the data set. 3. Separate the person from the idea. Acknowledge the value of concerns raised, then relocate them to the right forum. This teaches the room that ideas will be heard, just not everywhere and not at any cost. 4. Close with a clear summary. Explain the choice, the why, the owner, the first deadline, and the measure that will tell you if the decision was right. If you lead rooms where one voice dominates the conversation, try this sequence and watch the energy change. What's your biggest challenge when it comes to Board meetings? ------- ➕ Follow Jonathan Maharaj FCPA for finance‑leadership clarity. 🔄 Share this insight with a decision‑maker. 📰 Get deeper breakdowns in Financial Freedom, my free newsletter: https://lnkd.in/gYHdNYzj 📆 Ready to work together? Book your Clarity Session: https://lnkd.in/gyiqCWV2

Stop pitching, start listening. I lost a $250K gift because I walked into a meeting ready to close. The donor was ready to talk. I was ready to perform. Deck loaded. Budget tight. Impact projections color-coded. I thought this was professionalism. It was just... transactional. Fifteen minutes in I could feel it. The shift. They went polite but distant. "We'll think about it." Never heard from them again. What I figured out: you're not here to convince anyone. You're here to find out what they already care about, then show them how your work connects to that. That donor didn't need a pitch deck. They needed someone to listen. So I rebuilt my whole approach. First meeting? I ask questions and listen. That's it. Second meeting? I share stories, not spreadsheets. Third meeting? I invite them to experience the work firsthand. Fourth meeting? They tell me what they want to fund. The ask becomes a formality. You're already partners by then. My close rate went from 40% to 85%. Not because I got better at selling... but because I stopped trying to sell. People don't fund organizations. They fund visions they co-created with you. What's a mistake that completely rewired how you approach your work? Photo:  Having a deep conversation with Reggie Love, Obama's right-hand man. #DonorRelations #FundraisingStrategy #NonprofitLeadership #ListeningFirst #PhilanthropyTips

Once you get to the point where your company graduates from working sessions to board meetings, there’s an entirely new set of dynamics you have to learn to navigate. Here are my best tips for founders on how to get the most out of your board meetings, based on my time on both sides of the table: 1/ No big surprises. The purpose of a board meeting is to set the direction and priorities for the company, grounded in the context of what’s going well and what’s not — and none of that background information should be a surprise to your board members during the meeting. If you have news to share, whether it’s good or bad, do it in real time with quick phone calls in between board meetings. This builds trust and allows you to use the meeting time more effectively. I’m also a fan of the pre-wire call a few business days before the board meeting. Set up 30 minute 1:1’s with each board member to run through the agenda and any pertinent business updates before the meeting. Give space for each individual to air any concerns or asks they may have. It helps you get ahead of any hot topics to better manage the time in the board meeting. 2/ Leave room for discussion. There’s always excitement to share a lot of info during board meetings, but you want to avoid having it feel like you’re presenting a book report. No matter how good the materials are, it’s disappointing if you walk away without learning from the viewpoints of your board members. Leave enough time for discussions, questions, and follow ups to create a two-way conversation, rather than just talking at your board. Set the timing for this in the agenda upfront and keep an eye on the clock to make sure you shift to discussion time promptly. You’ll get a lot more value out of your board members this way. 3/ Figure out the right balance between execution and vision. You have to hit multiple notes during your meeting. On one hand, you need to be able to talk about execution and operational precision. On the other hand, you need to be able to speak to your high-level vision and remind your board of the bigger picture and long term goals. The best founders can strike a balance between both. It takes time and iteration to find the sweet spot. One tactic to help accomplish this is to always set the table by recapping the company mission and vision at the start of the meeting. Another way to ground everyone is to include a couple customer anecdotes and stories before you dive into the metrics and performance data. Bookend the meeting the same way, by touching on the company mission and thanking the folks around the table for their roles in that journey. I have a lot more thoughts on navigating board dynamics, so keep an eye out for Part 2 of this post.