Around with Randall

Great leaders are often hired to create change but organizations want transformation without the discomfort that comes with it. In this episode, Randall explores the “familiarity trap” and why boards, teams, and leaders unintentionally pull change agents back toward the status quo. Learn six practical ways to stay focused on transformation, build trust, distinguish resistance from wisdom, and accept that meaningful leadership rarely comes without some discomfort.

The next great shift in philanthropy may not be about younger donors. It may be about who makes the decisions. Women increasingly influence financial decisions and are positioned to inherit (and ultimately direct) enormous amounts of wealth. Fundraisers need to rethink how they build relationships with couples, surviving spouses, and families.

The difference between a good gift and a transformative one is not a donor’s generosity, it is the way we help them see what is possible. This episode explores how a fundraiser helped a donor move beyond a narrow view of giving and consider a broader funding strategy rooted in values, timing, business identity, and community impact. When we present thoughtful options instead of assumptions, we may unlock a better path for the donor and a deeper outcome for the mission. It is a reminder that meaningful philanthropy often begins with better questions.

What happens when a trusted gift officer leaves and someone new inherits the portfolio? Too often, new fundraisers worry they're replacing a beloved relationship when, in reality, they're continuing a donor's commitment to a mission they already believe in. Why are donors more connected to organizations than individuals? Understanding these five practical strategies will make portfolio transitions seamless, donor-centered, and successful.

There is a tension many nonprofit leaders feel but rarely name: when a mission statement remains sacred, even after the organization’s work has evolved. Mission change should be rare, careful, and rooted in identity rather than opportunity. It’s not about finding new language. The most important statement should accurately reflect who they are, what they do, and why their work matters now. For leaders navigating strategy, donor trust, and community need, consider this thoughtful framework for knowing when a mission is still guiding the work and when it may be holding the organization back.

What do the Seven Deadly Sins have to do with fundraising? More than you might think. Pride, greed, envy, wrath, sloth, and the others quietly find their way into nonprofit leadership, donor relationships, and fundraising strategy. This limits an organization's ability to fulfill its mission. Let’s dive in and find out how these timeless human tendencies show up in philanthropy and look at a practical framework for recognizing and overcoming them.

Most fundraising challenges don't stem from a lack of generous donors. They stem from never extending the right invitation. Organizations stay trapped in endless cultivation meetings, updates, and tours because they haven't uncovered what truly motivates a donor to give. The best solicitations are never surprises. Discovery should replace persuasion and six practical strategies can help donors accomplish the impact they already want to make.

As America celebrates its 250th birthday, it's worth reflecting on something even bigger than our nation's history: the enduring value of freedom. In this special episode we explore how freedom has shaped civilizations, why it requires constant stewardship, and how philanthropy is one of its greatest expressions. From the Declaration of Independence to today's nonprofit leaders, choosing to serve others is one of the highest forms of freedom.

Artificial intelligence and predictive analytics are transforming fundraising, but better technology does not automatically create better decisions. Let’s look at how bias, incomplete records, flawed assumptions, and overreliance on data models can lead organizations to overlook promising donors and opportunities. Fundraisers need to think critically about the information feeding their systems. Data should inform decisions, not replace human judgment, relationships and thoughtful strategy.

Many fundraising conversations focus on the donor sitting across the table, but rarely are major philanthropic decisions made by one person alone. Spouses, children, attorneys, financial advisors, and trusted friends often shape the timing, confidence, and ultimate outcome of a gift. This episode explores how understanding those influence networks can remove hidden obstacles, strengthen donor relationships, and help donors make the decisions they already want to make. The best fundraisers aren't asking for gifts, they're helping donors navigate the people and dynamics that surround every significant decision.

Fundraising is relationship building, but too many donor conversations feel disconnected, repetitive, and transactional. Enter the “Donor Waltz”. A three-step sequence of conversations designed to move donors from discovery to alignment, to meaningful commitment. Donors experience philanthropy emotionally, not operationally, and organizations that fail to find the emotional journey risk losing momentum, trust, and transformational opportunities. When fundraisers learn to sequence conversations, donor relationships begin to feel less like a checklist and more like a partnership.

Andrew Carnegie did not believe philanthropy was simply about relieving immediate need. He believed it was about creating opportunities that could create generational change. In this special episode, we look at how Carnegie’s philosophy shaped modern giving through libraries, education, research, and long-term investment in human potential. Challenging nonprofits to think beyond short-term charity and ask a harder question. Are we only responding to problems, or are we helping people escape them? A reflection on wealth, responsibility, and the deeper purpose of philanthropy.

Fundraisers often spend enormous amounts of time pursuing prospects who will never make a gift. Not because they lack capacity, but because nobody properly qualified their intent. In this episode, we look at one of the biggest hidden problems in fundraising: confusing wealth with philanthropic interest. Let’s explore how better qualification questions, smaller portfolios, and clearer disqualification standards can improve donor relationships and fundraising outcomes. Effective fundraising is not about collecting more names, it’s about identifying alignment and moving the right relationships forward.

Most nonprofits talk about stewardship, but few can actually show you a structured plan for how it happens. In this episode, we explore the idea of a donor stewardship matrix. A simple but powerful framework that brings clarity, accountability, and consistency to donor relationships. Stewardship is no longer just about thank-you letters; it’s about creating intentional systems that deepen trust, improve retention, and ensure donors feel connected to the impact they make possible. A practical reminder that meaningful philanthropy often depends less on grand gestures and more on disciplined follow-through.

A tragedy in the Apollo program revealed a powerful truth: the greatest failures aren’t always technical; they’re failures of imagination. In this milestone 300th episode, Randall challenges nonprofit leaders to rethink how they see risk, innovation, and the future itself. Drawing lessons from NASA and the space race, he outlines five practical ways to break free from limiting assumptions and uncover new possibilities. Because in a rapidly changing world, the organizations that thrive won’t just react, they’ll imagine what others never considered.

Nonprofits don’t have an overhead problem, they have a narrative problem. When organizations obsess over keeping costs low, they often starve the very investments that drive growth, impact, and long-term sustainability. The truth is simple: low cost does not equal high impact. The organizations that truly move the needle are the ones willing to reframe overhead as strategic investment and communicate that clearly to donors, boards, and stakeholders.

Succession planning isn’t just a CEO issue. It’s a frontline necessity in a nonprofit sector where turnover is constant and stability is fragile. When organizations fail to plan, they risk revenue disruption, donor attrition, and cultural erosion that can take years to rebuild. The strongest nonprofits don’t react to transitions. They prepare for them by developing internal talent, protecting relationships, and creating clear operational frameworks. Done right, succession planning isn’t about replacing people. It’s about strengthening the entire organization before change ever happens.

Fractional employees are quickly becoming a practical solution for nonprofits facing talent shortages and budget constraints, but they’re not a simple fix. This episode explores how fractional roles can unlock high-level expertise without full-time costs, while also exposing the hidden risks to continuity, culture, and donor relationships. The key insight: success isn’t about whether you use fractional talent, but how intentionally you design and manage it.

Nonprofits often hesitate to engage in public policy, fearing they might cross into prohibited territory. But the real risk may be staying silent. Missing opportunities to shape the very systems that define their impact. This episode reframes advocacy as a strategic, mission-aligned responsibility, showing how organizations can influence policy through education, data, and relationships without engaging in direct lobbying. When done thoughtfully, policy engagement becomes not a distraction, but a powerful extension of a nonprofit’s mission.

Every fundraiser eventually hits a drought. Calls go unanswered, meetings stall, and momentum disappears. In those moments, the instinct is to hesitate, to overthink, or to pull back entirely. But the most successful fundraisers operate like great shooters: they keep showing up, trusting that consistent effort, not short-term results, drives long-term success. This episode explores the psychology behind those slumps and offers practical ways to stay confident, consistent, and moving forward when nothing seems to be working.

Emotional intelligence isn’t a “soft skill” in nonprofit work. It’s the foundation of everything that works. In a field built entirely on relationships, the ability to read the room, manage your own reactions, and understand others often determines success more than strategy or data. The challenge is that most organizations talk about it, but few build it intentionally. This episode breaks down how developing emotional intelligence (personally and organizationally) can quietly transform performance, culture, and long-term impact.

Talent alone doesn’t determine success – culture does. The same individual can struggle in one environment and thrive in another, not because their ability changed, but because the system around them did. Over time, what’s tolerated becomes the norm, and those patterns quietly shape performance, trust, and retention. The real question isn’t whether culture matters, it’s whether you’re shaping it intentionally or letting it shape you.

Most fundraisers know the Donor Bill of Rights – but what about the Fundraiser’s Bill of Rights? It’s about the organization behind them. Leadership engagement, board functionality, strategic clarity, data systems, realistic expectations, and culture all shape whether philanthropy can thrive. The real question isn’t simply “Can this fundraiser raise money?” but “Is this organization built to support fundraising success?” When those pieces align, philanthropy becomes a shared responsibility — and the mission moves forward.

In a world of overflowing inboxes and nonstop notifications, nonprofits risk becoming part of the noise. Tackle donor fatigue head-on. Most organizations don’t have a generosity problem. They have an attention and trust problem. With six practical tactics, Randall outlines how to audit communications, segment by motivation (not wealth), rebalance ask-to-impact ratios, create quiet periods, clarify priorities, and even let donors choose their preferences. The solution isn’t more creativity or more volume – it’s more discipline. Do less, do it better, and build relationships that last.

Faith-based giving and secular nonprofits aren’t opposites. They share a powerful common thread: values. Today, we explore how nonprofits can learn from faith-driven philanthropy without becoming religious organizations. The key is aligning with a donor’s core motivations (identity, legacy, duty, compassion) and designing language, stories, and discovery questions that tap into that deeper connection. When you move beyond transactions and speak to values, you unlock loyalty, retention, and transformational giving. Done well, this approach strengthens relationships today and opens the door to long-term legacy support tomorrow.

Peer-to-peer fundraising isn’t a magic fix for struggling nonprofits. It’s a strategy that requires discipline, clarity, and real support. In this episode, Randall breaks down what peer-to-peer fundraising is, where organizations overestimate its impact, and why it often underperforms. From building the right case to stewarding volunteers like donors, he outlines seven tactical steps that separate sustainable pipeline growth from volunteer fatigue. Done poorly, it creates frustration and distrust. Done well, it expands reach, deepens relationships, and strengthens long-term donor development.

Interim leadership is no longer the exception in nonprofits, it’s becoming the norm. As executive tenures shrink and pressure mounts, organizations increasingly rely on interim CEOs, CDOs, and senior leaders to stabilize, reset, or prepare for what’s next. But interims don’t just affect the C-suite; they reshape staff behavior, donor confidence, and organizational momentum. In this episode, Randall breaks down the three true roles of interim leaders (caretaker, stabilizer, and change agent) and explains what success actually looks like for both the interim and the team navigating the uncertainty. Whether you are the interim or reporting to one, t...

When donors experience loss, the instinct to “do something” can quietly turn into pressure—yet the most meaningful work in these moments has nothing to do with closing a gift. Gratitude after loss is not transactional; it is deeply emotional, relational, and rooted in honoring experience, memory, and connection. Whether in healthcare, education, or social service, people give because of how they were treated, not simply what happened. The best gift officers know when to speak, when to listen, and when silence itself is the greatest form of respect. If we lead with compassion instead of urgency, relationships grow—and philanth...

The title “Chief Philanthropy Officer” doesn’t fully capture the real job, because much of the role is political, relational, and deeply strategic. CPO's navigate power dynamics, align competing priorities, translate donor realities, and build trust across the organization. Success isn’t about control or title; it’s about influence, diplomacy, and internal partnerships. When CPO's educate simply, make invisible work visible, invite leaders into the process, and stay calm under pressure, alignment follows. The result is stronger internal cohesion and better outcomes for donors.

Adversity isn’t a pause for nonprofits - it’s a pivot point. As we head into 2026, organizations facing leadership turnover, donor fatigue, staffing gaps, and revenue volatility must decide whether to act, watch, or wonder what happened. This episode reframes adversity as a moment for honest assessment, disciplined focus, and intentional adjustment. Progress doesn’t come from busyness or optimism—it comes from clarity, choices, and the willingness to engage discomfort. The organizations that emerge stronger will be the ones that choose action.

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 behaviors. Change the incentives, and you change the outcomes.

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 deeply held values with long-term impact. The real opportunity isn’t about asking for money, it’s about helping donors make confident decisions in uncertain times. For nonprofits willing to lead with curiosity and care, this moment may define the next decade o...

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 gifts, and accelerated planned giving will reshape how generosity flows, while AI moves from novelty to necessity in forecasting and stewardship. In 2026, one thing is clear: waiting is no longer a strategy. The nonprofits that win in 2026 will b...

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 failing—but it is becoming more concentrated, more strategic, and less forgiving of organizations without a plan.

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 relationships. Done poorly (or too early) it adds cost, confusion, and duplication without impact.

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-aligned flexibility turn endowments into a powerhouse for stability, innovation, and generational impact. When we build wisely, we protect our mission, our donors, and the future we serve.

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, personalizing communication, and becoming trusted conveners of multi-generational giving conversations. When done well, you don’t just secure a gift, you become part of a family’s story for decades.

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 gratitude intentionally, not seasonally. When we shift from “what’s happening to me” to “how do I respond,” our relationships deepen, work sharpens, and our well-being expands. If you give yourself a few quiet moments this week to reflect, you m...

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, thoughtful hosting, and timely follow-up, salons become a fast track to trust, insight, and transformational philanthropy.