Around with Randall

Right now, too many nonprofits are frozen in place—boards and CEOs so paralyzed by funding cuts and political chaos that they've stopped thinking strategically altogether. When organizations stall, donors lose confidence, talented development staff grow frustrated, and transformational gifts slip through the cracks. In this episode, we unpack four practical ways fundraising professionals can respectfully ‘manage up'—from reframing strategy as a leadership duty to enlisting donor voices and phasing in focused roadmaps. You'll hear real-world examples of how anonymous donor feedback and targeted feasibility studies have reignited momentum and unlocked six- and seven-figure gifts. Tune in to discover how to break the paralysis and turn chaos into catalytic, strategic philanthropy.

Most first-time donors are testing the waters—curious if your nonprofit delivers on its promise and if a deeper connection is worth their investment. That's why speed isn't just a courtesy in stewardship; it's a strategy. In this episode, I explore how re-qualifying new donors within the first 90 days can mean the difference between a one-time gift and a lifetime of giving. The data is clear: fast, thoughtful follow-up—especially from the right people—dramatically boosts your donor retention and major gift potential.

Today marks a milestone—250 episodes of Around with Randall! This journey has been one of service, storytelling, and sincere gratitude for those unseen moments of influence we have on each other. What started as a simple goal to make a difference in just one life has blossomed into a community of listeners across the globe. I never imagined the reach or the impact, but I am deeply humbled and more inspired than ever to keep showing up, sharing insights, and building this classroom of compassion and purpose. Here's to the next 250!

Some of our most transformational donors are the ones you'll never see on a wall or at a gala. They drive up in Hondas, not Bentleys—and they give in silence, often more generously than the loudest names on the marquee. But here's the catch: treating anonymity like invisibility is a critical failure. These quiet philanthropists still crave impact, connection, and trust—they just want it without the spotlight. Ignore them, and you don't just lose a gift; you risk losing a legacy.

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 and the mission of your nonprofit. Join us for a thoughtful discussion on refining donor relationships and maximizing philanthropic impact.

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 isn't just about dollars—it's about building the long-term foundation for transformational philanthropy.

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 of interaction you last had. It's time to stop waiting and start prompting. If your portfolio includes “zombie” proposals, this conversation offers the tactics to revive them.

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 master the art of asking at the perfect time, this episode is a must-listen.

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 recognition aligns with values and long-term strategy. A thoughtful, transparent practice grounded in ethics is essential for sustainable fundraising and donor trust.

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 building a culture of trust and genuine relationship-building.

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. If your board is stuck in neutral, this might be the starting point you didn't realize you needed.

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 work, and what nonprofit leaders can take away to strengthen their own fundraising efforts.

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 long-term risks for the organization. What makes this shift happen? What are the consequences? And—most importantly—how do you restore strong nonprofit governance? Find out more here.

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 relationships to development teams. The broader nonprofit sector can apply this approach by leveraging board members, executives, or faculty as trusted connectors. In a shifting philanthropic landscape, where fewer donors are giving but at higher amounts, mastering these relationships is vital for long-term fundraising success.

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 build relationships with financial advisors and community foundations. By embracing DAFs and integrating them into fundraising strategies, organizations can strengthen donor relationships and unlock new philanthropic potential. The key is adapting to this shifting landscape rather than resisting it.

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 software—while emphasizing the importance of data analytics and cybersecurity knowledge. By continuously improving, nonprofit professionals can increase their value to their organizations and adapt to an ever-changing landscape.

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 who is most likely to engage. This transformation presents opportunities for deeper donor relationships, it also raises challenges in adoption, ethics, and the role of gift officers. As AI continues to refine donor strategies, organizations that embrace the change will be better positioned to thrive in the next era of philanthropy.

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 evaluating potential hires based on their emotional impact, highlighting the value of creating a supportive, uplifting environment for personal and organizational success.

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 model, enabling long-term sustainability and greater impact in their communities.

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-driven donor screening to leveraging volunteers for thank-you calls. The key takeaway? Thoughtful stewardship isn't just about efficiency—it's about strategically building relationships that elevate giving over time.

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 genuine, transparent, and lasting relationships with donors, a theme central to philanthropy but often overlooked in discussions about fundraising strategy.

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 through strategic process changes without compromising their core missions. As a BONUS, explore a roadmap for nonprofits, focusing on identifying sacred values, engaging stakeholders, incremental change, and consistent communication to ensure long-term growth and sustainability.

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 strategies such as engaging disconnected donors, utilizing crowdfunding, and collaborating with other organizations to rebuild and maintain operations.

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-you call?). Buckle up for a ride through the wild world of philanthropy and learn how to turn your donors into lifelong fans, minus the high-pressure sales pitch!

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 larger gifts, and increased emphasis on addressing basic needs like food and housing, nonprofits face a dynamic and competitive landscape. And a bonus: strategic insights to help organizations prepare for these shifts and thrive in the year ahead.

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. With holiday cheer, Randall shows how nonprofits can sleigh their way to success.

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.

This Thanksgiving episode we sit down at the family table to discuss the transformative power of gratitude in our lives. Randall reflects on the top reasons for gratitude, from health and supportive relationships to personal growth, freedom, and a sense of purpose. He shares heartfelt insights about the profound trust and faith others have placed in him— personally and professionally. Randall invites listeners to reflect on the people and experiences that bring meaning to their lives, encouraging gratitude not just for the destination, but for the journey and those who walk it with us.

Don't want to be the gambler with that year-end ask? We get it. You have to know when to hold 'em and know when to fold 'em in your push for year-end major gifts. Make the ask or wait for the right moment to ensure transformative impact. Great fundraising isn't about the nonprofit's calendar—it's about the donor's timing, passion, and connection. Whether it's a December 31 gift or a future commitment, “every hand's a winner” when you prioritize your donors' needs and goals.

In this week's episode, we look at the importance of leveraging referrals from board members, clinicians, and data to maximize major gift fundraising efforts. Learn how referrals significantly increase the likelihood of donor engagement and gift size, with studies highlighting how connections from trusted sources like board members and physicians improve fundraising success. Finally, we answer the question: What are the strategic approaches can you use today to select the right referral sources?

This week on Around with Randall, we share invaluable advice for younger nonprofit professionals. What is the importance of staying observant and proactive, keeping your heads down and ears open to understand the dynamics of a workplace? We'll also bring key recommendations, how to strategically take chances, and prioritize skill development over career advancement. Integrity, mentorship, and continuous learning are essential for long-term success in the nonprofit sector.

This week on Around with Randall, we share invaluable advice for younger nonprofit professionals. What is the importance of staying observant and proactive, keeping your heads down and ears open to understand the dynamics of a workplace? We'll also bring key recommendations, how to strategically take chances, and prioritize skill development over career advancement. Integrity, mentorship, and continuous learning are essential for long-term success in the nonprofit sector.

Joel Fleischman, though not widely known, profoundly shaped modern philanthropy by professionalizing the field and championing transparency and accountability. His work at Duke University and his book, A Great American Secret foresaw the growing influence of fewer major donors and the need for foundations to be held accountable for their impact. Fleischman's legacy continues to influence how we approach giving and measure the effectiveness of philanthropic efforts today.

Today on Around with Randall, Randall Hallett explores the importance of developing concise, two- to three-page case statements for nonprofits, moving beyond traditional multi-page documents typically used in large campaigns. These shorter statements foster organizational alignment by clarifying needs and facilitating conversations between departments and leadership, ultimately enhancing donor engagement. By focusing on measurable outcomes and balancing emotional stories with data, nonprofits can create impactful mini-campaigns that resonate with potential donors.

In this edition of Around with Randall, we examine the role hope plays in philanthropy and our communities. How does hope motivate action and foster resilience, especially in challenging times? Looking at historic examples, we see that hope is not merely an emotion, but a powerful catalyst for positive change, encouraging us to engage and uplift those around us in our quest to make the world a better place.

In this special edition podcast, we bring a guest synopsis of Vibrant Vulnerability: Mastering Philanthropy for Today and Tomorrow's Healthcare CEOs generated by AI.

New employees, whether hiring or being one yourself, can be hard. In this episode, we delve into onboarding new employees, particularly within philanthropic organizations. What are the challenges? What does a thoughtful onboarding process (that extends beyond the basics like benefits, bathroom locations and parking information) look like?A well-executed onboarding leads to stronger team integration, reduced confusion, and faster productivity—key factors in retaining top talent.Plus, bonus insights! – How to create a welcoming environment that aligns with an employee's professional goals, helping them feel valued from day one.

In this episode of Around with Randall, we explore a recent study on the best ways to ask for donations. We'll chop up how the study reveals that donors respond most to requests framed around specific outcomes, such as the number of people their gift will help. At the end of the day, nonprofits need to rethink their fundraising strategies to maximize donor engagement and support.

In this episode of Around with Randall, Randall explores the importance of embracing innovation in nonprofits and drawing parallels to Ignaz Semmelweis's groundbreaking but initially rejected handwashing practice. Emphasizing that overcoming barriers to change—such as discomfort, fear, and resource constraints—is essential for organizational growth. Fostering internal talent, reinterpreting rejections as ‘not yet,' and accepting small failures as part of the innovation process, allows nonprofits to better navigate the evolving landscape and enhance their impact.

This week Randall explores the shift from transactional to transformational gifts in philanthropy and the importance of building deeper, long-term donor relationships. He examines focusing on a donor's lifetime value, involving volunteer boards for engagement efforts, and learning from unsuccessful asks. And a reminder to appreciate the journey of giving, celebrating small victories and the meaningful impact philanthropy has on individuals and communities.

In this week's episode of Around with Randall, our host reflects on an experience at a Giving Institute conference, and a discussion about corporate philanthropy. Randall leans in on the importance of understanding the history and evolution of corporate giving. Especially noting the shift from individual-driven philanthropy to employee engagement and community impact. We are also reminded that philanthropy is not just about money, but about making a meaningful difference.

Evaluations can be challenging. They're judgmental in nature and often ineffective. This week Randall emphasizes the importance of understanding organizational culture and using evaluations as a professional development tool rather than a mere judgment. We also talk about why leaders should avoid surprises and ensure evaluations are consistent with ongoing feedback, while employees should see evaluations as an opportunity for growth. The goal is to make the evaluation process less stressful and more constructive for everyone involved.

Stories create connections by sharing personal experiences and vulnerabilities, helping others see their own paths through self-discovery. They are more memorable and engaging than mere lessons, as they evoke emotions and foster empathy. Effective storytelling should include personal failures, be relevant, concise, and provide a clear summary to ensure impact. Ultimately, storytelling builds trust and rapport, which are crucial for meaningful relationships in both personal and professional settings.

Today we dig into a controversial topic - special events in nonprofit fundraising. The inefficiency and resource drain these events cause, taking away focus from building individual relationships. Perhaps partnering internally and externally to reduce staff involvement in events and using data to advocate for more effective fundraising strategies is the key. Where is the appropriate balance between strategic, relationship-based fundraising and event-centric efforts?

In this edition of Around with Randall, we focus on collaboration. From the moon landing to scientific discoveries, all rely on a collective effort rather than individual achievement. We will also address the benefits and challenges of collaboration, stressing the importance of clear roles, effective communication, and trust to overcome obstacles and achieve shared goals.

This week, we put nonprofit CEOs on a slide, power up the philanthropic microscope and examine the alarming trends of burnout and high turnover rates among our nonprofit leaders. We also talk about the importance of effective board engagement, community interaction, and strategic planning in bolstering CEO tenure and organizational stability.

In this episode of "Around with Randall," we discuss the challenges nonprofits face in maintaining donor relationships during the summer when donors are often away. We look at the importance of staying engaged through virtual events, personalized communications, and leveraging data to justify travel expenses for face-to-face interactions, with the ultimate goal of maintaining and deepening donor connections.

Congratulations! You made it to July. Now, let's look at how to maximize our efforts in the next six months, whether you follow a calendar or fiscal year. The key? Plan and focus on building strong relationships with your top prospects. Prioritize your efforts, set detailed plans, and establish good daily habits. Additionally, maintaining a balanced personal life is crucial for professional success. Let's prepare to make the next six months productive and impactful.