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

It is a misnomer. There is nothing ‘micro’ about microaggression. What is the real meaning of microaggression, what should it truly be called, and how can a leader recognize and take action to tackle it? Dr. Tiffany Jana shares her insights, why she has stopped using the word ‘crazy’, and what organizations can do to create a culture of awareness.

2025 felt like a year when everything became more and harder. More crises. More fear. More civic strain. More communities under pressure. And yet – more leadership, too. In this episode, Glennda connects with Darlene Nipper, President of the Rockwood Leadership Institute, for a grounded look at what leadership truly looked like in 2025. Darlene shares what she and her team witnessed across the country: communities organizing, mutual-aid volunteers pivoting to meet urgent needs, families creating rapid-response communication networks, and leaders of small organizations adapting and strategizing for the future. This wasn’t leadership from the podium. It was leadership from the sidewalk, school hallway, boardroom, and living room. Together, Glennda and Darlene talk about what broke, what held, and what grew stronger this year:  How democracy became a shared responsibility, not just a political concept What “leading from the inside out” looks like in high-pressure environments Why the long view and the short view have to coexist What nonprofit leaders need to prioritize amid uncertainty And through it all, one truth kept surfacing: leadership is no longer reserved for the chosen few. It is happening everywhere, often in people who never expected to step into the role. Whether you lead a nonprofit, neighborhood group, faith community, or simply your own family, this episode offers clarity on what your leadership means right now, and what it needs next. TUNE IN TO LEARN: How 2025 redefined who counts as a leader: This year showed us that leadership doesn’t just come from titles or org charts – neighbors, parents, volunteers, and everyday people stepped in where systems fell short. Why democracy became a litmus test for leadership this year: In 2025, leaders weren’t just asked to run programs. They were asked to choose whether to protect democratic values or remain silent as they eroded. How easy on-ramps – rather than professional gatekeeping – brought more people into meaningful action: Grassroots movements gained momentum because people could simply show up, proving accessibility is what fuels community power. What nonprofit leaders need to prioritize amid uncertainty: From pivoting quickly to listening deeply, this episode breaks down the practices that helped organizations stay grounded and effective. How leaders are thinking ahead while addressing immediate crises: Even while navigating fires, funding losses, and political turmoil, visionary leaders shifted into long-view strategy – imagining a future they may never personally see. KEY QUOTES: “I think this notion of leadership is this far-off behavior or category of people that's not us, totally is a thing, you know, and it's like – no, actually it is all of us.” - Darlene Nipper “I do think this moment is calling a lot of people into leadership in ways that are really motivating.” - Glennda Testone “So money should not be a problem. You know? That should not even be an issue. If we believe in the work, we need to give it away is such a level that people are just not even leaders are not even thinking about where the money is going to come from.” - Darlene Nipper “Listen to your constituents, your community, your people, and come out with what you know, because your role, your place, your space is very unique to you and the work that you're doing.” - Darlene Nipper ABOUT GUEST: With over 25 years of leadership and advocacy experience, Darlene Nipper joined Rockwood as a trainer in 2012 and now serves as CEO. Darlene’s knowledge of the challenges facing leaders and the practices required for effective leadership is informed by her own background at a range of organizations. She has held key leadership roles in nonprofit and social justice organizations, as well as city government and foundations.  Darlene previously served as the executive director of the BET Foundation, and as the chief operating officer at National Alliance on Mental Illness (NAMI), during which time she founded NAMI’s Multicultural and International Policy Center. She is the former director of LGBT Affairs in the Executive Office of the Mayor of D.C., and the 2024-25 Visiting Senior Fellow for Movement Infrastructure and Explorations at the Freedom Together Foundation. A native Washingtonian, Darlene is an ordained interfaith minister, and practices mindfulness meditation, deep presence, and living joy. RESOURCES: Darlene Nipper LinkedIn Rockwood Leadership Institute Glennda Testone LinkedIn Nonprofit Leadership Lab DRG Talent Consulting Experts Joan Garry’s Guide to Nonprofit Leadership – 2nd Edition by Joan Garry FREE WORKSHOP: Let’s Build the Nonprofit Board of Your Dreams! FREE WORKSHOP: The 5 Practices of Outstanding Nonprofit Leaders Music by Jukebox the Ghost Disclosure of Material Connection: Some of the links in the post above are “affiliate links.” This means if you click on the link and purchase the item, I will receive an affiliate commission. Regardless, I only recommend products or services I use personally and believe will add value to my readers. I am disclosing this in accordance with the Federal Trade Commission’s 16 CFR, Part 255: “Guides Concerning the Use of Endorsements and Testimonials in Advertising.” Sponsored By DonorPerfect DonorPerfect provides nonprofits with powerful fundraising tools to drive success. Built on a foundation of integrity and innovation, the company prioritizes its clients over investors, cultivating a culture of collaboration, continuous improvement, and a commitment to making a difference. Check out their resource(s) below. 2026 Fundraising Calendar Design Tips for Nonprofits  A Fundraiser’s Guide to Donor-Advised Funds Sponsored By DRG Talent Consulting Experts DRG is a talent advisory group helping nonprofit organizations to identify, attract, and nurture innovative, diverse leadership. Our team of 40+ experts serves over 200 nonprofits a year of all sizes and in various sectors across the country. Learn more at drgtalent.com. Check out their resource(s) below. Interviewing with Reduced

Nonprofits aren’t “less than” – they’re labs for modern leadership. I’ll share 8 nonprofit lessons corporate leaders need now.

Your budget isn’t just rows on a spreadsheet–it tells a story. I’ll explain how a goals-first budgeting process reduces friction, fuels creativity, and helps everyone in your organization pull in the same direction.

We say we “know” our neighbors, but do we really talk to them? Army vet and civic entrepreneur Garrett Cathcart joins Joan to share a hopeful, doable model for bringing people together across differences. If you’ve been craving belonging (and a practical path forward), this episode will give you tools and hope.

Erica Fortescue joins Glennda to debunk the myth that ADHD is a flaw at work. With simple, brain-based tools and strategies nonprofit leaders can turn friction into flow and build high-functioning, neuroinclusive teams.

People-powered fundraising isn't rocket-science, but it does take intention, bandwidth, and smart systems. Listen in as Vivian Chang shares how your grassroots, small-donor dollars can stabilize your revenue, build ambassadors for your organization, and align your funding with your mission.

AI can feel overwhelming until you make it practical. Darian Rodriguez Heyman and Cheryle Contee join me to discuss their new tactical field guide, AI for Nonprofits. Discover how your organization can adopt AI responsibly and free your staff to do more human work.

Donor-Advised Funds (DAFs) are booming—but most nonprofit leaders still find them confusing or inaccessible. In this episode, Mitch Stein from Chariot joins Glennda Testone to bust common myths, explain how DAFs work, and share how both donors and nonprofits can make the most of them.

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.

Whiplash. That’s how it feels to lead a nonprofit right now. Executive coach, Alex Love and Glennda Testone explore how leaders can stay grounded, care for their teams, and hold onto their mission through constant change.

In a time when many nonprofits fear losing that very status, we are celebrating wins as a reminder that progress and possibility still exist. Glennda Testone and I share the stories and sparks that are refueling our own leadership and hopefully, yours too.

What if a capital campaign could be your nonprofit’s ticket to long-term growth? Fundraising expert Amy Eisenstein joins the podcast to bust common myths and share practical insights from decades of experience. From feasibility studies to board engagement, she lays out what it really takes to run a successful campaign—no wealthy board members required.

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.

What if challenging times are invitations to redefine what matters most? Michael Hyatt shares what helped him redefine success, and find a fulfilling way to live and lead.

The nonprofit sector is under attack. But, there’s hope. In this episode, Glennda Testone and I talk with Amol Sinha about the unique harms facing nonprofits and how we can all take action to protect our missions.

Disability is not a niche issue—it’s a reality for 60 million Americans. Yet, systemic bias and stereotypes continue to exclude people with disabilities from conversations about inclusion. In this episode, Nancy Smith of Activating Change shares practical steps nonprofits can take to build truly accessible and equitable spaces.

Three fearless nonprofit leaders share what drives them, how they navigate burnout, and the vision that keeps them going. Tomik Dash, Laura Carmichael, and Adrienne McCue are breaking barriers and sharing their stories that prove that small but mighty nonprofits are changing lives every day.

From the Atlanta spa shootings to ongoing challenges, Deepa Iyer highlights the critical need for infrastructure, relationship-building, and centering the voices of affected communities in times of crisis.