Around with Randall

Moving into nonprofit leadership requires more than excelling at fundraising. It demands fluency in how the entire organization works. Chief development and philanthropy officers must understand finance, strategy, governance, technology, reputation, and the external forces shaping their mission. The central challenge is not becoming an expert in everything, but learning enough to ask better questi...

When should a nonprofit say no to a gift? Financial pressure, donor relationships, reputational risk, and long-term obligations can complicate what first appears to be an easy yes. Thoughtful gift acceptance is not an obstacle to philanthropy; it is a safeguard for the organization, donor, and mission. A disciplined process can turn a difficult decision into an act of responsible leadership.

Major donor conversations are strongest when fundraisers stop treating program experts as an afterthought and start building the relationship together. Shared planning, a unified case for support, clear roles, rehearsal, training, and accountability can turn technical expertise into donor trust. It confronts what can go wrong when teams make promises they cannot keep. The result is a practical loo...

Donor communication is not a one-size-fits-all. Each generation brings distinct expectations about trust, impact, access, and ease. Let’s explore how nonprofits can use generational tendencies as a starting point and still pay attention to individual preferences and relationships. The real challenge is to stop communicating in the way that is easiest and begin meeting supporters where they are. Th...

Philanthropy is typically measured by the size of a foundation or the scale of a public gift, but some of its deepest impact happens quietly. Through education, disaster relief, scholarships, and personal opportunity, Dolly Parton’s example reveals how generosity can change the course of individual lives without waiting for an institution to intervene.

Accountability is often mistaken for control, but its real power comes from alignment, clarity, and mutual commitment. This episode explores why realistic goals, regular conversations, and early intervention help teams move from mere activity to meaningful accomplishment. It also reframes accountability as a form of development to strengthen individuals, build trust, and improve organizational per...

Qualification isn't just about finding out what a donor is interested in, it's about discovering what they want to change, improve, or accomplish through philanthropy. In this episode, Randall breaks down the difference between general interest and genuine philanthropic intent and offers six practical ways to uncover it. The goal isn't simply to move prospects through a pipeline; it's to understan...

How much should you actually ask a donor for? Don’t be the fundraiser that lets capacity scores, intuition, or organizational need determine the answer. Take a more disciplined approach: quantify the risk by looking at donor readiness, purpose alignment, amount confidence, relationship strength, and timing. The goal isn't to slow down, it's to reduce uncertainty of asks, increase confidence, and u...

Naming opportunities can be one of the most valuable and most easily mishandled tools in philanthropy. But, before putting a donor's name on a building, you need a process that protects the donor relationship and the organization's future. This episode explores six practical ways to build that process, from valuation and naming tiers to morality clauses and flexibility. The goal isn't only to reco...

Gift officers can easily become isolated in the very work that requires the most strategic thinking. Moves management meetings often become reporting sessions instead of collaborative problem-solving opportunities. However, leaning into vulnerability, smaller portfolios, and a simple “bounce-off” approach can change that. The goal isn’t better metrics; its helping donors discover the next step to...

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 acce...

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...

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...

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 lea...

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 pract...

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...