Around with Randall

Planned giving won’t grow if we keep rewarding gift officers as if it doesn’t exist. When incentives focus only on cash and pledges, we unintentionally steer MGO’s away from the very conversations that unlock transformational wealth. This episode tackles the internal challenge head-on: how nonprofits can count planned gifts (without violating accounting rules) in ways that motivate the right behav...

Uncertainty has become the backdrop of modern philanthropy. Volatile markets, shifting interest rates, political noise, and a massive transfer of wealth all colliding at once. In moments like these, donors aren’t pulling away from generosity; they’re searching for it. Clarity, flexibility, and reassurance. Planned and estate giving offers exactly that: options to solve real concerns while aligning...

It’s time once again for Randall’s highly anticipated yearly predictions. As many know, the nonprofit landscape in 2026 won’t be defined by doing more, it will be defined by doing different. As donor bases continue to shrink, a smaller group of donors will drive a larger share of giving, forcing organizations to rethink cultivation, stewardship, and board engagement. Donor-advised funds, non-cash...

Looking back on 2025, the real story isn’t which predictions landed, it’s what they exposed about modern philanthropy. Strong markets and record giving mean a deeper shift: fewer donors, rising inequality, and growing dependence on a shrinking pool of major and mega givers. Donor-advised funds surged, AI gained traction, and consolidation quietly accelerated. The year proved philanthropy isn’t fai...

Should a nonprofit create its own foundation? The answer is surprisingly simple and at the same time, relentlessly hard: will it raise more money? Foundations only make sense when organizational complexity, donor access, privacy, or governance limitations are actively holding philanthropy back. Done well, a foundation creates focus, opens doors, and frees leadership to pursue deeper donor relation...

Endowments are the engine that keeps nonprofits strong—not just today, but decades from now. Yet, the fine print matters: overly restrictive funds can choke impact, while flexible quasi-endowments help organizations adapt as needs and missions evolve. The key is striking a balance between donor intent and long-term usefulness. Smart documentation, thoughtful donor conversations, and mission-aligne...

The greatest opportunity in philanthropy today isn’t just the transfer of wealth, it’s the transfer of values across generations. With trillions set to move from silent, high-capacity families into foundations and DAFs, nonprofits must build relationships that go far beyond the matriarch and patriarch. The organizations that thrive will be the ones mapping families, engaging heirs early, personali...

Gratitude isn’t just a warm feeling, it’s a physiological, psychological, and relational reaction that reshapes how we live and lead. Research proves that it lowers stress, improves heart health, helps with sleep, and strengthens resilience. Yet, we rarely slow down long enough to notice its impact. Thanksgiving gives us permission to pause, but the real transformation comes when we choose gratitu...

Donor salons are small, intimate gatherings designed to deepen relationships without asking for money. If you focus on conversation, curiosity, and shared values, you spark authentic engagement that leads to stronger long-term giving. These experiences feel exclusive, personal, and meaningful, more powerful than email, phone calls, or large fundraising events. When executed with purpose, thoughtfu...

One-time stories inspire emotion; longitudinal stories build transformation. The most successful fundraisers don’t just tell what happened, they connect the dots over time, showing progress, growth, and real impact. When donors see themselves within the story—woven into its chapters—they move from giving out of urgency to giving out of identity. Storytelling isn’t about communication; it is commun...

Annual giving programs across every sector are struggling—and the old tactics no longer work. To re-engage donors, fundraisers must borrow from behavioral economics: reduce friction, offer clear defaults, and frame choices that inspire action. Subtle “nudges,” simplified giving options, and immediate impact stories can transform inertia into generosity. In a noisy, overloaded world, the organizati...

Great boards don’t just meet—they measure. When boards track their own performance, they shift from opinion-driven debate to data-informed decisions. Transparent metrics build trust, align strategy, and keep every member accountable to the mission. Start small, stay consistent, and let dashboards reveal where progress is thriving—and where course correction is needed. The result? A more engaged, e...

In today’s digital world, one false post can damage a nonprofit’s reputation faster than any press release can repair it. False information spreads up to six times faster than truth—and small organizations often lack the resources to respond effectively. The key is preparation: monitor social platforms, respond calmly and transparently, and have a crisis protocol ready before misinformation strike...

Nonprofits often face a silent crisis: they can’t fund the very infrastructure that keeps their mission alive. While donors love to support visible programs, few realize that unrestricted gifts – the ones that cover salaries, compliance, and basic operations – are what make real impact possible. When organizations underfund their “overhead,” they enter a starvation cycle that weakens long-term sus...

Nonprofits must learn to meet Millennials and Gen Z where they live—online, mobile, and driven by values. These generations demand immediacy, authenticity, and easy digital giving experiences, from QR codes to Apple Pay to thank-yous turned in 24-hours. Their gifts may start small, but their potential as future major donors is enormous if organizations invest in them now. The future of philanthrop...

Nonprofits can’t afford to ignore mental wellness. Stretching employees too thin leads to burnout, turnover, and lost donor trust—costs that ripple across mission, fundraising, and community impact. Leaders who invest in staff well-being not only do the right thing but also protect retention, efficiency, and donor relationships. From normalizing mental health conversations to flexible workspaces a...

Once seen as an invasion of privacy, texting is now one of the most effective tools for donor engagement. With open rates as high as 98%, texts dramatically outperform email and can strengthen relationships when used thoughtfully for outreach, stewardship, and even giving. The key is to keep messages short, timely, and personal—never spammy. When done well, texting becomes another arrow in the qui...

Getting in front of new prospects is harder than ever—but sitting back and waiting isn’t an option. This episode introduces a creative solution: gamifying the dreaded phone call. By turning outreach and even rejection into a points-based game, fundraisers can build camaraderie, reduce fear, and spark real momentum. From scoring voicemails to celebrating “rejection of the week,” this approach refra...

Donor conversations aren’t always smooth - especially when political or social issues enter the mix. In this podcast, Randall Hallett unpacks how fundraisers can navigate divisive topics with civility, professionalism, and focus on shared values. He stresses the importance of staying agnostic, listening first, and reframing discussions around mission and impact rather than ideology. With practical...

Building a strong donor portfolio isn’t magic. It’s math, persistence, and mindset. In this piece, we break down the real metrics behind qualification calls, revealing how many dials it takes to land conversations and turn those into meaningful meetings. It’s not just about picking up the phone, but about embracing follow-ups, leveraging multiple channels, and tracking every step. Success comes fr...

Transformational philanthropy doesn’t happen overnight—it’s the result of patience, humility, and deep trust built over years. Too often, organizations focus on immediate needs and campaign timelines instead of donors’ passions and timeframes. This story highlights how a client took the long view, nurturing a relationship with one of the rare 0.1% capable of extraordinary giving. By personalizing...

Too often, nonprofits treat donors as if they are obligated to give—out of duty, guilt, or long-standing expectation. This mindset not only diminishes donor joy but also undermines the potential for transformational gifts. True philanthropy is rooted in passion, where giving aligns with a donor’s values, identity, and sense of purpose. By shifting from obligation to passion, nonprofits can foster...

When a nonprofit’s founder or small group wields too much influence, mission drift can quietly erode trust, credibility, and board strength. The result? Confusion among donors, disengaged board members, staff turnover, and even reputational risk. The cure lies in proactive governance: clear roles, term limits, strong bylaws, intentional recruitment, and the courage (both from inside the board and,...

For decades, annual reports were the gold standard of nonprofit transparency—but today’s donors want more. They expect real-time updates, emotional stories, and a visible impact that doesn’t wait 12 months. Whether through dashboards, video messages, or live virtual briefings, organizations that communicate continuously build deeper trust and engagement. The future of donor communication isn’t sta...

Nonprofits can no longer afford to wait for 100% certainty. In a world moving at the speed of chaos, inaction is a decision, and often the costliest one. It's time to lead with agility, clarity, and a bias for action. Let’s talk about what effective decision-making looks like now, and why our old models might be holding us back.