Around with Randall

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.