Around with Randall

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 ultimately create more meaningful gifts.

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 recognize today's donors; it's to make decisions that will still make sense 30, 40, or 50 years from now.

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 making an impact on the things they deeply care about.

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.