Around with Randall

What is the concept of "choice architecture" in nonprofit fundraising? How can organizations better present options to donor and strike a balance between too much and too little information? Learn how to avoid common mistakes like the "Menu of Doom," false equivalency, and overselling, and discover practical strategies for curating meaningful giving opportunities that connect with donors' passions...

With fewer households making charitable gifts, annual giving is under pressure and needs a more strategic approach. Randall argues for evaluating annual giving through three-five year data trends rather than single-year snapshots. If nonprofits focus on trends, they can better allocate resources, elevate donors into major gifts or planned giving, and create lasting cultural shifts. Annual giving i...

Are you staring at stalled proposals and wondering what to do next? This episode dives into the root causes of donor dormancy—like misaligned timing, a disconnect in perceived value, or inconsistent follow-up—and offers a framework to triage and reengage major gift prospects. Learn how to categorize your dormant proposals, prioritize them by impact, and take practical next steps based on the kind...

1.Timing is everything — especially when it comes to making a major gift ask. In this episode, Randall explores the psychology behind donor readiness, uncovering the emotional and strategic signals that reveal the right moment to solicit transformational gifts. Learn the four critical feelings every donor must experience and the key questions to evaluate before making your move. If you want to mas...

In this episode, we check into the often-overlooked ethical complexities of donor recognition. Randall explores how poorly managed recognition can lead to mission drift, disproportionate acknowledgments, access inequities, problematic associations, and excessive donor involvement. With high-level donors becoming more sophisticated and competitive, nonprofits must be clear and intentional about how...

Building strong donor relationships goes beyond just securing gifts—it's about creating a meaningful feedback loop that fosters deeper, lasting connections. By listening to donors' perspectives, nonprofits can identify pain points, refine processes, and show that their voices matter. Randall also explores how this approach leads to better retention, upgraded gifts, and risk mitigation, all while b...

What does it really mean for a board to be strategic—and why does it matter? In this episode, Randall breaks down how defining strategy is the key to unlocking true board ownership and aligning long-term impact with community needs. It’s not about documents or retreats—it’s about thinking ahead, asking better questions, and creating a shared vision that reshapes roles, meetings, and expectations....

What can we learn from some of the world’s most influential philanthropists? In this episode of Around with Randall, we explore the giving philosophy of Steve and Connie Ballmer—how their approach to philanthropy started at the kitchen table and evolved into a multi-billion-dollar effort to drive economic mobility. Discover how data, trust-based giving, and a deep commitment to impact shape their...

Who really owns a nonprofit? Unlike for-profit businesses with clear ownership, nonprofits are technically owned by no one—but that doesn't mean responsibility is absent. In reality, the community is the true owner, and the board of directors serves as its steward. But what happens when boards become passive? CEOs can gain too much control, leading to governance failures, weakened oversight, and l...

Physicians play a critical role in philanthropy, particularly in health care, as trusted referral agents for grateful patient giving. This episode explores why physician engagement is essential and how their involvement leads to significantly larger gifts. While doctors shouldn't be asking for donations directly, they can recognize moments of gratitude, engage meaningfully, and transition relation...

Donor-advised funds (DAFs) are growing rapidly, presenting both challenges and opportunities for nonprofits. While they offer donors tax advantages, investment growth, and simplified giving, they also create barriers between nonprofits and the donors themselves. To effectively engage with DAF donors, nonprofits must proactively promote DAF giving options, retrain gift officers to discuss them, and...

This episode of Around with Randall explores the concept of upskilling, inspired by Amazon’s billion-dollar investment in workforce development. Randall discusses how acquiring new skills enhances career growth, job security, and personal satisfaction, particularly in the evolving nonprofit sector. He highlights practical ways to upskill—such as online courses, mentorship, and learning new softwar...

Wealth screening has long been a staple of donor identification, but the future lies beyond wealth—it's about connection and inclination. Let’s explore the evolution of screening, from manual processes to internet-driven data aggregation, and now the rise of artificial intelligence. AI is shifting the focus from static wealth indicators to behavioral patterns, predicting not just who can give but...

In this week’s episode of Around with Randall, we discuss the impact of positive and negative influences in our personal and professional lives, especially in the nonprofit sector. What is the science of emotional contagion, how others' emotions affect our well-being and productivity, and the importance of surrounding ourselves with positive individuals? We end with some practical advice for evalu...

In this week’s episode, we focus on the importance of endowing positions, particularly outside higher education, to create financial stability and attract top talent to nonprofits. Look at universities that have successfully endowed faculty chairs. How much could those endowments help nonprofits manage rising costs and ensure critical roles are funded? The goal is to help nonprofits adopt this mod...

Balancing personalization and automation in donor stewardship is a challenge every nonprofit faces. In this episode, Randall dives into the critical question of how to effectively engage donors at all levels—ensuring major donors feel valued while nurturing smaller donors with potential. He explores practical tactics for segmenting, automating, and personalizing stewardship efforts, from data-driv...

In the world of philanthropy, trust is the backbone of any successful donor relationship. A recent lawsuit against the Red Cross, over their handling of restricted donations for Haiti, highlights how crucial this element is. Donors feel their contributions weren't used as promised, and that breach of trust could lead to a class action lawsuit. This situation underscores the importance of building...

This episode of Around with Randall explores the balance between preserving core institutional values and embracing necessary change in the nonprofit sector. While institutions serve as the foundation of trust, mission, and community impact, stagnation leads to decline. Drawing from historical figures like Martin Luther King Jr. and Franklin Roosevelt, illustrates how institutions can evolve throu...

In times of disaster, nonprofits face unique challenges, especially when they’re directly serving within the disaster zone. Today, we highlight the importance of preparedness, including having a clear plan for data access and communication, and the need to prioritize core functions like payroll and outreach. Effective disaster response involves not just immediate action, but also long-term strateg...

In this episode, we’ll unpack why building donor relationships is a bit like buying a car—except instead of haggling over prices, you’re building trust and listening to what your donors actually want. We talk about the art of prospecting (it’s not just for salespeople, promise), handling objections (like “I don’t know if I want to give this year”), and stewardship (because who doesn’t love a thank...

It’s that special time of year on Around with Randall, when Randall sets his predictions for 2025! This year highlights three key areas: the economy, giving trends, and the nonprofit industry's trajectory. He also discusses the potential impact of tax policy changes, the growing prominence of planned giving, and the challenges posed by a "K-shaped" economic recovery. With fewer donors contributing...

In this festive episode of Around with Randall, we imagine the perfect holiday nonprofit team. Santa stars as the visionary CEO (because who else could handle that job?), Rudolph beams his way through major gift asks, and the Grinch—shocker!—steals bad ideas as the perfect change manager. Frosty keeps his cool under pressure at events, while Mrs. Claus proves she’s the real COO running the show. W...

In this episode, we highlight the power of advisory groups in enhancing nonprofit outcomes and fostering community connections. These groups bring expertise, credibility, and fresh ideas while offering volunteers meaningful engagement. Success requires clear roles, listening to advice, and recognizing contributions. Done right, advisory groups can elevate both mission impact and community support.