684. The Courage to Disappoint: Trust-Based Leadership for Nonprofits - Glennda Testone
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What does it really take to lead with courage in the nonprofit sector—especially when growth, complexity, and crisis collide?
In this powerful conversation, Jon and Becky sit down with Glennda Testone, CEO of the Nonprofit Leadership Lab and co-host of Nonprofits Are Messy, to explore what it means to lead with integrity, accountability, and heart. With more than 14 years as Executive Director of New York City’s LGBT Community Center—where she tripled the budget, led a $9M capital campaign, and guided the organization through transformational change—Glennda brings lived experience and hard-earned wisdom to the mic.
Together, they unpack:
How trust is built through transparency, vulnerability, and doing what you say you’ll do
Why accountability isn’t about fear management—but about strengthening mission and relationships
The mindset shift from “trying not to disappoint anyone” to deciding who you’re willing to disappoint
Practical tools for prioritizing when everything feels urgent
The power of community—and why going it alone is a leadership trap
If you’re navigating growth, wrestling with hard decisions, or feeling the weight of leadership, this episode is a reminder: you don’t have to do this alone. Trust is the work. Community is everything. And sometimes the most meaningful wins come from getting it right according to the right people.
“Those have been some of the most meaningful moments in my nonprofit career…getting it right according to the right people.”
Episode Transcript
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Episode Highlights:
Glennda’s origin story and path to nonprofit leadership (2:41)
Leading through growth, complexity, and making mistakes (6:27)
Building trust and centering justice and connection (10:59)
Reframing accountability to build trust (16:58)
How to prioritize when everything feels urgent (21:23)
Learning to say no and let go of people-pleasing (25:47)
A powerful moment of philanthropy in Glennda's career (28:15)
Playing the long game in fundraising relationships (32:31)
One Good Thing: Don’t go it alone in leadership (34:43)
Powerful Quotes
"Those have been some of the most meaningful moments in my nonprofit career…getting it right according to the right people, not always the people in power, sometimes, often the people with the least power." -Glennda
"I consider myself a learner. I don't have all the answers. I don't know everything, and I believe in working with other people deeply and consistently." -Glennda
"You have to earn people's trust. They do not and will not just give it to you." -Glennda
"My values are connection and justice. When I am making a decision, I hold those up and ask, does this further these two things, or does it actually go against them?" -Glennda
"Being a leader right now is not about trying not to disappoint anyone. It's about deciding who you are okay with disappointing." -Glennda
"There are so many broken promises in this country. I can control myself, and I can do things differently, and I can keep going even when I mess up." -Glennda
"If you only focus on the urgent, you're never going to do the important things." -Glennda
"Don't try and go it alone. It's not gonna work. It's much harder, and it's much less fun." -Glennda
"The most fun that I have had in nonprofit is linking arms with other people to try and do a really hard thing that was really important." -Glennda
Connect with Glennda
LinkedIn / Nonprofit Leadership Lab
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Connect with Becky
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