Around with Randall

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 communication. And when done longitudinally, it becomes the foundation for trust, loyalty, and transformational giving.

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 organizations that understand how people actually make giving decisions will be the ones that thrive.

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, effective board that owns its success.

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 strikes. Rebuilding trust takes time, but protecting it starts with awareness, clarity, and steady leadership. Don’t wait for a storm—build your umbrella now.

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 sustainability. By reframing unrestricted giving as mission fuel, nonprofits can help donors see that trust, not just passion, drives meaningful change. Restricted gifts show commitment. Unrestricted gifts show belief in leadership.

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 philanthropy belongs to those willing to adapt, engage, and make giving effortless.

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 and empathetic leadership, the path is clear: taking care of your team is both a moral and strategic imperative.

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 quiver of fundraising, deepening impact and building authentic connections in a digital-first world.

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 reframes calling from a chore into a challenge and makes progress fun again.

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 communication strategies and a reminder that philanthropy is about hope and connection, Randall shows how to keep relationships strong, even when opinions differ.

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 from resilience, consistency, and understanding that small wins compound into lasting donor relationships.

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 stewardship, showing appreciation, and listening with humility, they created space for generosity to grow naturally into something truly transformative.

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 deeper loyalty, larger gifts, and lasting impact. At its core, philanthropy should be about self-determination and joy, not obligation and pressure.

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, when needed, from outside voices) to keep the mission front and center.

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 static—it’s dynamic, personal, and ongoing.

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.

Too many fundraising shops operate in silos, each department focusing solely on its own priorities. This separation creates friction—between donor communications, programming, events, and stewardship—hurting both efficiency and donor experience. A truly successful fundraising operation breaks down these walls and works collaboratively across teams. When everyone aligns around donor impact, not just department goals, the entire organization wins.

Fear is natural—but in fundraising, it's often the silent barrier to real relationship-building. Whether it's a new gift officer hesitating to make a thank-you call or a seasoned professional dreading the ask, fear can shrink our actions and paralyze our potential. But reframing these moments as invitations, not transactions, changes everything. This episode explores how small shifts in language and mindset can turn fear into forward motion—both professionally and personally.

What if everything we know about building donor relationships is backward? In this episode, we flip the script—looking at fundraising not from the fundraiser's lens, but from the donor's experience. From curiosity to trust to continuity, we explore the eight emotional stages a donor navigates before and after making a gift. When you understand how donors feel at every step, you unlock deeper relationships, better communication—and better results. It’s not about what we want to say; it’s about what they need to hear.

When crisis hits—whether it's a struggling department or the entire organization—your response defines your future. This episode explores how to talk about financial distress without sounding desperate, and how to frame fundraising efforts as strategic, not survivalist. The difference? Donors don’t want to save a sinking ship—they want to fuel a mission with momentum. If you can communicate change, trust, and a path forward, you’ll do more than survive—you’ll transform.

Great fundraising, like the growth of bamboo, begins with unseen groundwork. The first five years may show nothing above the surface, but beneath lies a strong, intentional root system—just like the quiet outreach, relationship-building, and resilience fundraisers must invest before major gifts emerge. Today’s donor landscape demands more patience, personalization, and persistence than ever. When we stop chasing instant metrics and start cultivating trust, consistency, and collaboration, we prepare for the kind of exponential growth that surprises everyone—except the one who’s been doing the root work all along.

Right now, too many nonprofits are frozen in place—boards and CEOs so paralyzed by funding cuts and political chaos that they’ve stopped thinking strategically altogether. When organizations stall, donors lose confidence, talented development staff grow frustrated, and transformational gifts slip through the cracks. In this episode, we unpack four practical ways fundraising professionals can respectfully ‘manage up’—from reframing strategy as a leadership duty to enlisting donor voices and phasing in focused roadmaps. You’ll hear real-world examples of how anonymous donor feedback and targeted feasibility studies have reignited momentum and unlocked six- and seven-figure gifts. Tune in to discover...

Most first-time donors are testing the waters—curious if your nonprofit delivers on its promise and if a deeper connection is worth their investment. That’s why speed isn’t just a courtesy in stewardship; it’s a strategy. In this episode, I explore how re-qualifying new donors within the first 90 days can mean the difference between a one-time gift and a lifetime of giving. The data is clear: fast, thoughtful follow-up—especially from the right people—dramatically boosts your donor retention and major gift potential.

Today marks a milestone—250 episodes of Around with Randall! This journey has been one of service, storytelling, and sincere gratitude for those unseen moments of influence we have on each other. What started as a simple goal to make a difference in just one life has blossomed into a community of listeners across the globe. I never imagined the reach or the impact, but I am deeply humbled and more inspired than ever to keep showing up, sharing insights, and building this classroom of compassion and purpose. Here’s to the next 250!

Some of our most transformational donors are the ones you’ll never see on a wall or at a gala. They drive up in Hondas, not Bentleys—and they give in silence, often more generously than the loudest names on the marquee. But here's the catch: treating anonymity like invisibility is a critical failure. These quiet philanthropists still crave impact, connection, and trust—they just want it without the spotlight. Ignore them, and you don’t just lose a gift; you risk losing a legacy.

What is the concept of "choice architecture" in nonprofit fundraising? How can organizations better present options to donor and strike a balance between too much and too little information? Learn how to avoid common mistakes like the "Menu of Doom," false equivalency, and overselling, and discover practical strategies for curating meaningful giving opportunities that connect with donors' passions and the mission of your nonprofit. Join us for a thoughtful discussion on refining donor relationships and maximizing philanthropic impact.

With fewer households making charitable gifts, annual giving is under pressure and needs a more strategic approach. Randall argues for evaluating annual giving through three-five year data trends rather than single-year snapshots. If nonprofits focus on trends, they can better allocate resources, elevate donors into major gifts or planned giving, and create lasting cultural shifts. Annual giving isn't just about dollars—it's about building the long-term foundation for transformational philanthropy.

Are you staring at stalled proposals and wondering what to do next? This episode dives into the root causes of donor dormancy—like misaligned timing, a disconnect in perceived value, or inconsistent follow-up—and offers a framework to triage and reengage major gift prospects. Learn how to categorize your dormant proposals, prioritize them by impact, and take practical next steps based on the kind of interaction you last had. It’s time to stop waiting and start prompting. If your portfolio includes “zombie” proposals, this conversation offers the tactics to revive them.

1. Timing is everything — especially when it comes to making a major gift ask. In this episode, Randall explores the psychology behind donor readiness, uncovering the emotional and strategic signals that reveal the right moment to solicit transformational gifts. Learn the four critical feelings every donor must experience and the key questions to evaluate before making your move. If you want to master the art of asking at the perfect time, this episode is a must-listen.

In this episode, we check into the often-overlooked ethical complexities of donor recognition. Randall explores how poorly managed recognition can lead to mission drift, disproportionate acknowledgments, access inequities, problematic associations, and excessive donor involvement. With high-level donors becoming more sophisticated and competitive, nonprofits must be clear and intentional about how recognition aligns with values and long-term strategy. A thoughtful, transparent practice grounded in ethics is essential for sustainable fundraising and donor trust.

Building strong donor relationships goes beyond just securing gifts—it's about creating a meaningful feedback loop that fosters deeper, lasting connections. By listening to donors' perspectives, nonprofits can identify pain points, refine processes, and show that their voices matter. Randall also explores how this approach leads to better retention, upgraded gifts, and risk mitigation, all while building a culture of trust and genuine relationship-building.

What does it really mean for a board to be strategic—and why does it matter? In this episode, Randall breaks down how defining strategy is the key to unlocking true board ownership and aligning long-term impact with community needs. It’s not about documents or retreats—it’s about thinking ahead, asking better questions, and creating a shared vision that reshapes roles, meetings, and expectations. If your board is stuck in neutral, this might be the starting point you didn’t realize you needed.

What can we learn from some of the world’s most influential philanthropists? In this episode of Around with Randall, we explore the giving philosophy of Steve and Connie Ballmer—how their approach to philanthropy started at the kitchen table and evolved into a multi-billion-dollar effort to drive economic mobility. Discover how data, trust-based giving, and a deep commitment to impact shape their work, and what nonprofit leaders can take away to strengthen their own fundraising efforts.

Who really owns a nonprofit? Unlike for-profit businesses with clear ownership, nonprofits are technically owned by no one—but that doesn't mean responsibility is absent. In reality, the community is the true owner, and the board of directors serves as its steward. But what happens when boards become passive? CEOs can gain too much control, leading to governance failures, weakened oversight, and long-term risks for the organization. What makes this shift happen? What are the consequences? And—most importantly—how do you restore strong nonprofit governance? Find out more here.

Physicians play a critical role in philanthropy, particularly in health care, as trusted referral agents for grateful patient giving. This episode explores why physician engagement is essential and how their involvement leads to significantly larger gifts. While doctors shouldn't be asking for donations directly, they can recognize moments of gratitude, engage meaningfully, and transition relationships to development teams. The broader nonprofit sector can apply this approach by leveraging board members, executives, or faculty as trusted connectors. In a shifting philanthropic landscape, where fewer donors are giving but at higher amounts, mastering these relationships is vital for long-term fundraising success.

Donor-advised funds (DAFs) are growing rapidly, presenting both challenges and opportunities for nonprofits. While they offer donors tax advantages, investment growth, and simplified giving, they also create barriers between nonprofits and the donors themselves. To effectively engage with DAF donors, nonprofits must proactively promote DAF giving options, retrain gift officers to discuss them, and build relationships with financial advisors and community foundations. By embracing DAFs and integrating them into fundraising strategies, organizations can strengthen donor relationships and unlock new philanthropic potential. The key is adapting to this shifting landscape rather than resisting it.

This episode of Around with Randall explores the concept of upskilling, inspired by Amazon’s billion-dollar investment in workforce development. Randall discusses how acquiring new skills enhances career growth, job security, and personal satisfaction, particularly in the evolving nonprofit sector. He highlights practical ways to upskill—such as online courses, mentorship, and learning new software—while emphasizing the importance of data analytics and cybersecurity knowledge. By continuously improving, nonprofit professionals can increase their value to their organizations and adapt to an ever-changing landscape.

Wealth screening has long been a staple of donor identification, but the future lies beyond wealth—it's about connection and inclination. Let’s explore the evolution of screening, from manual processes to internet-driven data aggregation, and now the rise of artificial intelligence. AI is shifting the focus from static wealth indicators to behavioral patterns, predicting not just who can give but who is most likely to engage. This transformation presents opportunities for deeper donor relationships, it also raises challenges in adoption, ethics, and the role of gift officers. As AI continues to refine donor strategies, organizations that embrace the change will...

In this week’s episode of Around with Randall, we discuss the impact of positive and negative influences in our personal and professional lives, especially in the nonprofit sector. What is the science of emotional contagion, how others' emotions affect our well-being and productivity, and the importance of surrounding ourselves with positive individuals? We end with some practical advice for evaluating potential hires based on their emotional impact, highlighting the value of creating a supportive, uplifting environment for personal and organizational success.

In this week’s episode, we focus on the importance of endowing positions, particularly outside higher education, to create financial stability and attract top talent to nonprofits. Look at universities that have successfully endowed faculty chairs. How much could those endowments help nonprofits manage rising costs and ensure critical roles are funded? The goal is to help nonprofits adopt this model, enabling long-term sustainability and greater impact in their communities.