Around with Randall

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 acc...

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...

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. Da...

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 rela...

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 mom...

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...

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 disqualificat...

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, i...

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 unco...

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 communic...

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 rela...

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 fract...

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 en...

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...

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 ho...

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 i...

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 suppo...

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...

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 connect...

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...

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, Randal...

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 w...

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,...

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—...