Nonprofits Are Messy: Lessons in Leadership | Fundraising | Board Development | Communications

Darian Rodriguez Heyman, a nonprofit author and consultant, and Cheryl Contee, a technology entrepreneur, share insights from their new practical guide, AI for Nonprofits. They discuss the pressing need for tactical AI guidance post-ChatGPT and how nonprofits can embrace AI while keeping human-centered approaches in mind. Key topics include ethical AI adoption, using AI as a super-assistant in fundraising, and the importance of mission-first leadership. They also emphasize building trust and capacity for responsible technology use within organizations.

Too many Development Directors feel like failures if they don't hit their revenue numbers — even when circumstances are beyond their control. In this episode, I explore why this mindset is harmful and what nonprofits can do to redefine success.

Mitch Stein, Head of Strategy at Chariot and a thought leader in donor-advised fund payments, joins Glennda Testone to clarify the complexities surrounding Donor-Advised Funds (DAFs). He shares his inspiring journey from investment banking to nonprofit fundraising, revealing the connection between finance and philanthropy. They discuss common myths about DAFs, emphasizing their accessibility to diverse donors and the potential for growth through legislative changes. Insights on personalizing donor experiences and strategies for nonprofits to maximize DAF contributions are also highlighted.

Succession planning gets treated like a worst-case scenario when it should be a regular part of nonprofit leadership. In this episode, Glennda and I get candid about our own transitions—and what we wish we’d known sooner.

In this insightful conversation, Alex Love, an executive coach and founder of Alex Love Consulting, joins Glennda Testone to discuss leading amid chaos. They explore how nonprofit leaders can remain grounded and uphold their mission through continuous upheaval. Alex shares strategies for fostering inclusivity and support in organizations, emphasizing the importance of open dialogue and active listening. They also address the emotional impact of current events on teams and the need for authentic commitment to diversity, equity, and inclusion.

Nonprofit leaders face turbulent waters, but resilience is key to navigating challenges. Self-care practices, like solitary walks and connecting with nature, are vital for renewal. Health screenings highlight the importance of early detection in sustaining leadership. Strategic planning emerges as a tool for overcoming obstacles and engaging communities. The discussion emphasizes flexibility, authenticity, and gratitude, reminding listeners that they are not alone in their journeys.

Omar Lopez, Principal at DRG Talent and Deputy Mayor of Ossining, is a talent search expert dedicated to helping nonprofits succeed. He discusses the challenges of attracting and retaining talent in the nonprofit sector, emphasizing the need for clear communication and engaging job descriptions. Omar elaborates on connecting purpose with opportunity and shares insights on appealing to Gen Z candidates. He advocates for intentional hiring strategies that align with organizational missions, highlighting the importance of reducing turnover to foster a healthy workplace.

Amy Eisenstein, CEO and co-founder of Capital Campaign Pro, brings her expertise in fundraising to the forefront. She debunks misconceptions about capital campaigns, emphasizing that success doesn't rely on wealthy board members. The conversation covers the importance of feasibility studies, the joys of matching donors with impactful causes, and the significance of strategic storytelling. Eisenstein also highlights practical strategies for nonprofits, urging organizations to embrace boldness and harness technology for fundraising growth.

Many nonprofit leaders feel like they’re just one mistake away from being “found out.” Even experienced executives, including myself, wrestle with that nagging voice of doubt, especially in moments of high visibility or pressure. But instead of letting imposter syndrome win, here are 6 tangible strategies.

Nonprofits are under attack in 2025—from hostile federal policies, harmful public misconceptions, and risk-averse boards. Glennda Testone and I urge nonprofit leaders to push back, speak up, and lead with boldness and creativity. Despite the challenges, we spotlight moments of hope and courage from organizations stepping up to protect communities and sustain impact.