Ep 243: What 2025 Taught Us About Real Leadership with Darlene Nipper

Summary

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Podcast Summary: Nonprofits Are Messy, Ep 243

Title: What 2025 Taught Us About Real Leadership with Darlene Nipper
Date: December 20, 2025
Host: Joan Garry
Guest: Darlene Nipper (CEO, Rockwood Leadership Institute)

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Overview

This candid conversation between Joan Garry and Darlene Nipper explores the seismic shifts in nonprofit leadership witnessed throughout 2025. In a year defined by urgent crises, complex challenges, and high stakes for democracy and community safety, Joan and Darlene reflect on what “real leadership” has looked like, how ordinary people have stepped into new leadership roles, and why investing in leadership development is crucial for the sector’s future.

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Key Discussion Points & Insights

1. Redefining Leadership in 2025

• Leadership Goes Beyond the Titled Few:
  • Both guests challenge the traditional notion that leadership is restricted to those in official positions.
  • Darlene emphasizes, “No, actually it is all of us. People are leading in their families, their church and synagogue communities, their community centers… people are showing up where a need has arisen.” (07:56)
• The Myth of the “Nonprofit Industrial Complex”:
  • Joan addresses criticism that nonprofit work isn’t “real work,” citing examples like running a domestic violence shelter or a food pantry as vital and essential labor (00:40).

2. The Rockwood Approach: Leading from the Inside Out

• Darlene explains Rockwood’s philosophy that effective leadership stems from understanding one’s own experiences and emotions and their ripple effects on others.
• "We need a set of skills...that allows us to be skillful in how we show up and collaborate...to get these common goals and visions for the world achieved." (04:09)

3. Leadership in Crisis & Community Resilience

• Emergent Grassroots Leadership:
  • Darlene shares firsthand accounts from Los Angeles during community safety crises (e.g., the Eaton fire, ICE raids).
  • Example: Community members form lookout corners and communication trees, demonstrating rapid, self-organized response when institutions fall short.
  • “Why am I waiting for the government?...I am going to call a couple of people and we're going to hang out on multiple corners where we think we'll have a good vantage point...just report to each other.” (08:49)
• Mutual Aid Evolution:
  • The shift towards mutual aid and spontaneous community organizing—distributing not just food but also information and creating barriers to protect vulnerable people (14:56).

4. Hope Amidst Hardship: Inspiration from 2025

• Community Mobilization Around Threats & Celebrations:
  • Joan and Darlene share stories of their communities rallying to protect one another during ICE activity, particularly at public events like Halloween or Dia de los Muertos (11:53).
• Younger, More Diverse Leaders:
  • Example: Asbury, NJ electing its first Hispanic woman to the Board of Ed, symbolizing new, inclusive leadership (20:44).
• Civic Engagement Surges:
  • Increased election turnout, protests, and collective action are seen as indicators of renewed hope and investment in democracy (18:36).

5. Transforming Organizational & Philanthropic Structures

• From Professionalization Back to Accessible Leadership:
  • Darlene observes a shift from a strictly professionalized nonprofit sector to one with more “easy on-ramps”—low-barrier ways for people to get involved and lead (25:43).
• Leadership Development vs. Professional Development:
  • Both debunk the idea that leadership training is about molding people to fit “white” or traditional professional norms; instead, it’s about broadening access to power, advocacy, and self-determination (27:18).
• Supporting Leaders Beyond Structures:
  • Practical leadership can occur outside formal titles—“It doesn't need to be an ED of an organization...it could be something else in your community that's really just moving the community forward.” (29:53)

6. Challenges & Role of Philanthropy

• Call for Philanthropic Boldness:
  • Both speakers call on philanthropists and foundations to “pivot from what we've always done,” not just supporting immediate needs but also building infrastructure and leadership capacity for the long haul (30:40, 32:35).
• “If you have X million, billion dollars sitting in an endowment somewhere, what are you waiting for?... It is time for foundations to think about...what are you waiting for to give that money out, given everything that's going on?” (33:56)
• The Need to Fund Leadership, Not Just Programs:
  • Joan: “I wish you were the one with the money because you would invest in leaders who are actually going to try to take this work forward and get it over the finish line.” (35:46)
• Let it Hurt a Little:
  • Memorable line from Darlene on grantmaking: “When someone...asks someone to give, it should hurt a little... that's the way it needs to feel for philanthropy.” (46:01)

7. Practical Advice for Leaders and Funders

• For Leaders:
  • “Go deep and hard on what you know...really, this is a time to be almost laser focused.” (41:49)
  • Emphasize both intuition and strategy, stay adaptable and open to pivots—whether that means merging, partnering, or getting smaller before growing again (43:09).
• For Philanthropy:
  • “There’s a role for philanthropy that’s so powerful and so important. It’s called giving money.” (45:13)
  • Fund bravely and substantially, especially in times of crisis—“We need those folks to be brave too.” (47:04)

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Notable Quotes & Memorable Moments

• On Leadership's Everyday Face:

  • “No, actually, it is all of us.” — Darlene Nipper (07:56)

• On Community Power:

  • “So stuff like that I think is just profoundly important and really, really helpful to leading.” — Darlene Nipper, referencing grassroots mutual aid during emergencies (10:50)

• On Philanthropic Risk:

  • “If you've been waiting for the rainy day...like, it's a tsunami out there, like, it's the moment.” — Joan Garry (46:27)

• On Hope:

  • “Just the practice of, like, sharing a long view with each other, I think, is an incredibly hopeful, helpful situation.” — Darlene Nipper (17:17)

• On Supporting Leaders:

  • “I imagine you want my brain on what do leaders really need...I think that’s where I should have my brain.” — Darlene Nipper (38:11)

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Timestamps for Key Segments

• Redefining Leadership: 00:00–08:49
• Rockwood Leadership Institute Approach: 04:09–06:15
• Community Mutual Aid in Crisis: 07:56–11:53
• Mobilization Against ICE Raids; Halloween/Dia de los Muertos Story: 11:53–14:56
• Hope and New Leaders: 17:17–21:35
• Democracy & Political Engagement: 22:19–23:32
• Role of Philanthropy: 30:35–39:41
• Advice for Leaders and Funders: 41:35–47:10

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Tone & Takeaways

The tone is frank yet supportive, with both guests acknowledging the immense pressures facing nonprofit leaders in 2025 but also underscoring the surprisingly vast stores of hope and resilience they’ve witnessed. Real leadership, they agree, is everywhere—often outside the spotlight or unaffected by official titles and structures. Success requires resourcefulness, relationship, community, and above all, brave investment not just by leaders, but by those with the means to empower them.

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For those who haven’t heard the episode, this summary captures the essence: 2025 demanded new kinds of deeply personal, community-rooted leadership. The challenges have never been greater, but so too are the opportunities for real, transformative change—if the sector, and its funders, have the courage to act.

Transcript

[A]

So when Joan and I tell people that we're in the business of leadership development, there can be some scoffing. It's not like they suggest we should get out of this line of work. People are just increasingly skeptical, I think, about leaders and that there are authentic leaders out there, especially given some of the things we've seen this year from people in leadership positions. But from our vantage point, we see leaders every single day as clients coaching clients in our nonprofit leadership lab at keynote speaking gigs, organizations doing remarkable work, and leaders who are out there doing the hardest work of all, even despite the challenges. So we really wish people could meet the people that we meet and the folks that we coach instead of reading all the crap on social media like people saying, boo, down with the nonprofit industrial complex. Get real jobs, do some real work. And I think both of us, Darlene, you and I could say, could name a lot of instances where people are doing that real work. Running a domestic violence shelter, that's real work. Feeding people, that's real work. Don't tell me those are not real jobs. Nonprofit leaders sign up to do hard things all the time. And this year, it feels like the things are more and they are harder than they've ever been. And so today, I'm really excited to be joined by Darlene Knipper, one of our favorite guests who is a kindred spirit in the world of nonprofit leadership development. And our question to Darlene is really a simple one. What did leadership look like in 2025? We're almost at the end of it right now when every day seemed to bring some new, fresh hell. It's time to talk about lessons in leadership in a year when leaders were tested like never before.

[B]

Absolutely. Oh, Glenda, thank you so much. Thank you, thank you. I'm so grateful to be invited back. You know, it's always a good thing when you get invited back. So thank you for.

[A]

You are welcome. You are welcome. And I. It's always a pleasure to talk to someone who's a colleague in the space and kind of seeing things in a different way and different people. We're going to put your bio in the show notes for folks who want to hear all about the impressive. You have quite an impressive bio, Darlene. You have. You have done quite a few things and you are now running the Rockwood Leadership Institute. And so maybe it just helps to give folks a sense of. Of what that is for folks who might not know. What is it that you're doing right now?

[B]

Sure. Thank you so much. And you know that impressive Bio is really just a function of time. I'll leave it at that.

[A]

That's very humble. I don't believe you. Check out the bio, listeners.

[B]

You stay around long enough, you get to do a bunch of things. Foreign.

[A]

Welcome to Nonprofits Are Messy with Joan, Gary and experts. This podcast is your go to space for insights, advice and inspiration, designed to help nonprofit leaders overcome challenges and drive impact. Whether you're navigating small beginnings or leading a larger organization, we're here to support you every step of the way. Together with Joan and a diverse group of expert guests, we tackle the big questions nonprofit leaders face and offer actionable advice to fuel your leadership journey. A special thank you to donorperfect for sponsoring this episode and supporting nonprofits that we love. Now let's jump in.

[C]

Foreign.

[B]

Is a leadership development, a transformational leadership development organization institute. We focus on all kinds of leaders with a real emphasis on, you know, as leaders who are working towards social justice, social change, you know, social good, those kinds of things. And our work is developed out of this one approach that is has to do with leading from the inside out. And what that is really all about is understanding that the terrain that's happening within our constellation of our bodies and our own communities, families inside of us, what's impacting us will inevitably impact whomever we've been invited to lead with. Right. And so we need to put attention there and we need a set of skills that allows us to be a set of practices that allows us to be skillful in how we show up and collaborate and be in partnership with others to get these common goals and visions for the world achieved. Right?

[A]

Absolutely. Absolutely.

[B]

That's us. And we have week long programs. We've got shorter things now. We do things online, we do things in person. Our approach has typically been focused on like really bringing leaders out of their normal context and into conversation and cohorts, often with other leaders who are grappling with very similar challenges. And then we can help them to both practice the kinds of behaviors that will support their leadership and deeper collaboration. And also sometimes, obviously, we're introducing new practices to people around that. Anyway, in a nutshell, that's what we do. We do it with thousands of folks, as you already know. And folks can go to rockwoodleadership.org and find out more about all of our programs and there are many out there for folks to choose from.

[A]

Awesome. I know some of the best leaders I know are Rockwood graduates of some sort. So I can, I can testify that it really works. And I think Listeners are probably very familiar with the Nonprofit Leadership Lab, which is the leadership development program that we run, focused primarily on leaders of small to mid sized nonprofits. So these are the folks who are, some of them are just starting out or maybe they've done this before, but they're trying a new thing and they want some support. And as it goes in our country, the little folks usually get overlooked and they don't get the support, they don't get the resources that they need. And so we're trying to fix that.

[C]

Are you a staff or board member of a small to mid sized nonprofit? Now, you might feel alone, but trust me, you are not. I built the nonprofit Leadership Lab for the millions who are just like you. You'll find time saving resources when your pants are on fire, opportunities to uplevel your skills, and a warm, nurturing private community of what we call superheroes. Thousands of board and staff leaders call the lab home and we'd love for you to join us. Learn more at nonprofitleadershiplab.com/podcast.

[A]

But all of that to say, I mean, I guess the thing I'm most curious about, Darlene, is, is just what are you, when you reflect on, on 2025 so far, what have you been seeing? What have you been seeing that has given you hope? What have you been seeing that surprised you? Answers to any of those questions?

[B]

Sure, sure. I mean, I honestly think there's so much hope out there. What, what I've been seeing is leaders who, and, and people, frankly, you know, 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. You know, people are leading in their families, they're leading their church and synagogue communities, they're leading in their mosque, they're leading in their community centers and you know, third places all over. So it's. I, I think we need to focus in this year has helped me to do this, focus more on how people are leading in all kinds of places because they're showing up where a need has arisen.

[A]

Yes.

[B]

And you know, that I was, I'm living in the, you know, in Los Angeles and was impacted directly by the Eaton fire and that, you know, I'm like embedded in that community and what I'm seeing even just right at home is people showing up when the need presents itself and finding really impressive and like tremendously simple but incredibly impactful ways to address their needs. When say government or certain other entities might not Be doing what they think they need. You know, it's like, yeah, why am I waiting for the government to come and set up a lookout corner to protect people who are being, you know, kidnapped off the streets by. Right. Like, no, I'm not going to wait for the government to do that. I am going to, and I see this every day. I'm going to call a couple of people and we're going to hang out on multiple corners where we think we'll have a good vantage point if somebody's coming to do something and just report to each other, like old school telephone tree reporting. Hey, there's suspicious folks in our community. Just want you all to know that. And that's happening in a way that's really become robust and has provided a lot of safety because here in Los Angeles there have been unfortunately some really dangerous situations that have happened, including people running, not knowing what's going on because they didn't even know whether that it was even ice. And so like running out into dangerous traffic and kids being in lockdown in their schools because people jumped out of cars with black on and guns, you know, and so then the school just automatically has to go to shutdown. I'm not saying whether they may have needed it anyway, but the point is they have to go to shutdown because, you know, these folks are jumping out and they don't know what's going on. And so these kinds of things where leaders are like, you know what, we can set up a lookout corner and we can communicate with each other to be aware that folks are in our community. They have started funds to feed families, provided food to families because nobody, everyone's afraid to come out. And so they're not able to work or whether they're, whether they, these are working people. I'm not talking about criminals or anything like that. So people are afraid to come out and the community is surrounding them with lots of support and love, like whatever they need so that they can actually stay underground in safety until they figure out a way to re engage in work, life and community. So, so stuff like that I think is just profoundly important and really, really helpful to leading.

[A]

I want to come back to have so many thoughts about everything you said. And I am living in a community. I lived in Brooklyn for 15 years and that felt like home and community in a particular way. And now I live in Asbury Park, New Jersey and it feels like community and home in a very different way, but a very important way. But I wanted to come back to what you said in the beginning about the way we define leaders, and we kind of anoint or elect or what have you people, and we call them leaders, and they are the leaders, and we are the followers. And I just have always kind of hated that and never really believed in it. We had a saying when I used to run the LGBT center in New York with the youth program, and we used to say we were helping young people become leaders in their own lives. Like, that's where it starts. And it kind of reminded me a little bit of your leading from the inside out. It was about, like, getting to know who you are and being able to have some. Some agency over your life and the lives. The lives of the people you care about. So I just want to underscore that point, because I think the formal structures in our country, in the US Are meant to elevate certain people as leaders and not others. And this moment that we're in, when communities feel under attack is really. I have seen it also in Asbury, where, you know, it was Halloween, and I happen to live on the street where all the kids come for candy because there are a couple of houses that really, like, do it up, you know, people in costume and the whole house and the whole thing. And one of my friends said, you know, I. We think ICE is here, and. And they're looking for people. And the mobilization of regular folks. Yeah, like, just friends and neighbors. That happened so quickly. And then we were immediately on the text chain. I love that you mentioned the phone trees. I went. I got a women's studies degree in the 90s, so I remember those phone trees and the, you know, the circles and all the things. But we were all like, OK. And tomorrow @ the boardwalk, the town is celebrating Dia de los Muertos. And we were like, we should be there to look out, because this might be. Again, this is an amazing celebratory thing where families are going to come and ICE could be there, and so we're going to be there. And I have seen that more this year than maybe ever.

[B]

Before. Absolutely. I mean, this year has called for it. Right. We've had different circumstances, and I think, you know, that's the other thing. I've seen people make enormous pivots. You know, there people were doing something else. And I see this with the mutual aid folks on the ground in, you know, places like Altadena. And there have been so many. My prayers to everyone. So, so, so many different climate disasters and catastrophes that have happened since even just this year, just since January. But in all of these places where you have a service entity or, say a mutual aid entity, and they just pivot because they see the need. They're like, oh, I was given out these sandwiches. But since we're here on this corner to give out these sandwiches, we can also make a barrier between ourselves and anything that would. Would harm our community members. Or we can also give out information about meetings that are coming up where people can learn about how to build power. To your point, in the community, it doesn't have to be some formalized organization, entity, or system. It's like we can get clear about what we're aligned about that we want to fight for, you know, as a community. And so just sharing the information for those things has become, like, really important. And I see mutual aid groups, like, turning into, like, really viable, you know, vehicles for communicating and. And doing. It's almost like popular education on the run or on foot or somehow in action or something. It's an interesting thing. It's like, kind of people need to understand that there's a lot of things going on, and here we are. So we need to become the people who help to educate everyone, because we're at that nexus of community and just real people walking around our neighborhood. So I find that very, very, very, very hopeful and just. It's just incredibly healing to have people just, like, step up in community in that way. Those are important ones. And, I mean, I think. I think organizations are making changes and shifts, and I like to see that too. You know, I see people, you know, spending more time thinking further out, which is one of the things that I get to be privy to because of my role in Rockwood. It's like I'm watching leaders asking questions about seven generations out, you know, imagining an in to some of the challenges that we have around immigration and other areas, imagining taking themselves very far out so that they can actually come up with a very different strategy for right now. And just the practice of, like, sharing a long view with each other, I think is an incredibly hopeful, helpful, you know, situation. And then you've got folks like Kaya Chatterjee in DC With Free DC and they're just doing all of this mobilizing. And then the folks who are organizing the no Kings parades, all of this mobilizing that I think is really rich and people are ready. And of course, then the elections just happen. And New York, I mean, for crying out loud, people, like, talk about burnout. I mean, that alone. Even if. Even if things don't go your way in an election, the fact that you have that level of.

[A]

Turnout.

[B]

Yes. Is incredibly.

[A]

Hopeful.

[B]

Yes. It means people care. And they. They. They can be engaged if we're hitting the right, you know, points, if they. They see potential in our leadership. So I'm excited. I'm. I'm excited about possible moving.

[A]

Forward. I. I am with you. I. Now, I kind of try and keep it secret, but it's not so secret. But now that I live in New Jersey, you know, I voted in the governor's election, and I was so.

[B]

Thrilled I got in New Jersey, Forgive me for not.

[A]

Mentioning. It's okay. And Virginia, I mean, it's just. It was such. I didn't even. My body was almost like, is this real? I haven't felt this in so long. Did we win? Are we winning this night? I'm just not used to it, but it felt so good. And it made me think that a theory that I have. It's not just me, is true, which is like, with the way things have shifted, we are. What's so often visible is sort of the dominant. The winners, you know, and their storyline and what they're doing. And that's where the thousands and millions of people turn out for the no Kings protest. And it gets maybe a line in the media, but it's like, we were there, and we know how many people were there. And this last election, this midterm election, really, it's not midterms yet. This last election really made me feel like, oh, there are a lot of people out there who feel like I do, who are looking at the choices, and they are actually saying, hell, no, I don't want this. I want this. And we saw that in New York and New Jersey and Virginia, and I do think that's incredibly hopeful. And what I love about some of that stuff, like the no Kings protests is it's not always professional organizers organizing that. You know, this is like people who. I mean, in my town, it happened like a town away from us. And I saw so many older folks there, like, holding signs and just, you know, sitting in a chair or standing up and being heard. And it was just so. It was so hopeful and so good to see. So I do think this moment is calling a lot of people into leadership in ways that are really motivating. We had, for the first time ever in Asbury, the youngest elected to the Board of Ed. Brittany Ramos, who was a graduate of Asbury Schools and has a kid in the school and lives here and is just so. First Hispanic woman on the board. Like, just so, so inspiring to. To see what she's Doing that. She's putting herself out there and. And really saying, you know what? I'm gonna go for this and try and do something.

[B]

Better. Well, I think that's a sign of a turn in leadership, too, that we have people moving into these roles that essentially, maybe even. Even a few years ago, were not very appealing to people or the. The energy of the current moment just hadn't reached the height that it has now. And so with this energy and desire to really. It's not even like to personally win. I think these are these new leaders that are coming to government roles, in particular, the mayors, the governors, etc. Really looking to. They seem to be looking to ensure that we have.

[A]

Democracy.

[B]

Yes. Not even. You know what I mean? Like, and I think, you know, preserving democracy is a. Is a. It's a noble cause. You know, it's like, it's a place where I think many of us, no matter how divergent our political views are, could agree that we would love to have our arguments in the context of a functioning Democracy, you know.

[A]

1,000%. It should go without saying, like, it shouldn't even be a thing. But the fact that it's been a thing this year where it's like, are you supporting democracy or are you working against it? Like, there's no middle ground right now. I would argue you are either doing things to participate in and preserve democracy or you are doing the opposite. And I'm. I'm. I'm, like, a little shocked that we have to do this, but I'm also glad and hopeful to see so many people show up and do it and say, oh, okay, this is on the.

[B]

Line.

[A]

Now. I wish those people had showed up a year earlier, but, you know, here we.

[B]

Are. Here we are. Then maybe we wouldn't be here. But that's another.

[A]

Podcast. That's another podcast. It is. It is. And I, you know, we're looking. We're looking forward. I've been impressed by some leaders I've worked with this year who, despite all the challenges like funding cuts and issues that clearly, like, are not cool to care about or to fund right now. And those leaders really going out and being creative and resourceful and actually growing their organizations. I saw this with Drew Dyson and the center for Modern Aging in Princeton, New Jersey. They are. They're growing. Alisa Crespo, who runs the Stonewall Community foundation in New York. LGBT issues, not popular in the. In the ruling class right now. And those folks are just the resilience of, like, oh, no, I don't care. What you throw at us. We will, we will be here. We will be here for the people, we will be here for the seniors, we will be here for the queer and trans folks. We're not going anywhere. Is always so hopeful to.

[B]

Me. Yeah, no, it's, it's really true. And I think people can see in all of this like multiple ways of leading and multiple ways of showing up and being engaged and active. It's not any one way. And I think maybe part of what we're seeing in 2025 too is just break down maybe to. I don't mean it in a negative way. I just mean like just a shift or a deep change in the way this work or engagement, if you will, is, is done. So we had gone from very heavily like volunteer spirit, spiritual, community based, you know, from civil rights and women's, you know, movement, like a very community based circle, you know, like lots of those kinds of things and maybe into a very era of.

[A]

Professionalization.

[B]

Yeah. Of a lot of the roles and, and I think that was actually useful and important. You know, it's where many of the non profits come in. But I think we are. It's important because it gives you solid infrastructure so you don't, you don't disappear or dissolve in a, in a year when you need to build back up so you're not like dissolving completely and building back up. So that was helpful. But I think what we lost in that, that, that is helpful now and that's back and it gives me hope is just easy on ramps for people who are not.

[A]

Professionals.

[B]

Yes. You know, and it's another thing I think orgs are really getting better at. Just part of why no kings having so many people is because somehow the on ramps are easy. There's no, you know, there's, there's not the kind of barriers. You don't have to work there, you don't have whatever it's like show up thing. There's some organizing of things that are happening that's happening in a much more. I don't know if it's organic or not, but certainly in a way that invites in participation at a very intensive level. And I don't want to give all of that credit to. Oh, things are so horrible. I just don't believe that it's all about that. I do think things are tough, but I also think that people are like, things are tough and oh, here's a way that I can plug in. It's right there, you know, and that's a big. I think we've broken down some of the barriers that maybe some of the professionalism had built up to invite people.

[A]

In. I, I feel like you're saying all the things that I, I would have thought to say. Like you're just saying so many things that are resonating deeply with me. And I, I think that's part of where leadership development gets deprioritized because I think people, people conflate it with professional development and they think like, oh, you're just teaching, you know, folks of color to act like white folks or you're just teaching people with lived experience to navigate the professional setting. And there has been some of that in the nonprofit sector. There has been a professionalizing, but that's not the kind of leadership development I'm talking about or you're talking about. Like, it is, it is different than that. And I do love, that's what I love about the, the inspiring examples from this year. It's like these are folks with real, with good ideas. I'm thinking about, Madame, for example, you know, like really good life changing ideas and experiences that they want to bring to bear in this realm. It's not about who can be the most professional that I think you're right. It's changed in a way that I feel really hopeful about because I feel like everybody should have access to leadership and justice and equity and you know, these, these things that we care deeply about and maybe the place where it's like a little bit because things are so bad, it's like, and if you're not going to get that from the government, you have to have it in yourself. You have to build it in your own community and the people you love and the people that love you. And there are a number of the groups that are being targeted. Now. This is not the first time. This has been going on for a very long time. So here we go again. And you're not going to help us, so we're going to do it.

[B]

Ourselves. Yeah. And it's not just like you have to do it for yourself. It's like you have to build that power and strength in your community, in your sector. So part of the work that I think we both do and care deeply about is helping more and more people to see ways to develop and expand their capacity to lead in.

[A]

Whatever.

[B]

Yes. Entity structure, you know, that exists. It doesn't need to be an ed of an organization, though that is one example, but certainly not the only one. So it could be something else in your community that's really just moving the community forward. And that is powerful leadership. And our task, I think, is a daunting one, which is how do we support those people to move into greater and greater levels of leadership or to feel for themselves and know from their context and experience that they are leading well, that they're, like, literally doing what really guide their.

[A]

Community.

[B]

Yeah. That's needed for their community to evolve and grow.

[A]

That's. That is an amazing question. How do we do that? How do we support. How do you see. I mean, let's just look at the formal structures. Do you see philanthropy supporting those efforts more over the course of this last year? Same. Less. I.

[B]

Don'T. I mean, I think there's so many shifts in philanthropy on the side of the table that I'm working on predominantly, that it's hard to know for sure where the overarching thing is landing. I see a lot of philanthropic organizations and entities really standing up, like, really making very clear statements about what is acceptable, what is unacceptable. The need for us to focus on democracy and not backing down from supporting that. Lots of that definitely happening. But I also see a bit of the, like, we don't know exactly what we're doing just yet. We need to think more, consider more. So there's some of that. And then there are also folks that I'm seeing who. Who are doing what I think is a typical thing that happens. And look, it's your money. You do whatever you want. Who am I? I don't have any money. That's the problem. But, you know, we're going after the next shiny thing that's like, it's. It's great. And I think infrastructure, which is more in the realm of what we do, has to be considered. And as these nonprofit entities struggle more, and maybe there are more mergers or whatever happens that the structures start to change. I don't think there's less responsibility for philanthropy to. Or opportunity for philanthropy to support the. What comes out of this shift, you.

[A]

Know?

[B]

Yeah. And if we don't get those resources to folks, even if they don't end up being the ones, the entity, like, they. Even. Even. Even if their forum is. Is like, illegible in terms of what used to be versus what they will be in a couple years, I think it's time for philanthropy to invest. I think the only way we're going to get to these new forms that will really hold us structurally is to support the leadership of people now so that they can create the pathways for what's to.

[A]

Come. Yeah. I am so with you. I recently went to A philanthropy conference. And, and there were funders there, there were community groups there, there were different. There were intermediaries there, which is a term that I feel like I'm hearing more and more and people talking about the structure and, but people very clearly people in philanthropy, in the community group saying, like, it is time for us to question the assumptions we have always held. And I'm thinking about like the 5% rule. You know, it is time for foundations to think about, like, if you have X million billion dollars sitting in an endowment somewhere, what are you waiting.

[B]

For?

[A]

Right? What are you waiting for to get that, give that money out, given everything that's going on? So it, what I heard a lot of that made me hopeful was a, was a dual, like, we got to have a long view and we have to have a short view view. Like, what do we need immediately now? Yeah, rapid response funding from philanthropy. If that usually means three months, that's too long for some people. That is not rapid. So it's like the immediate needs, but then it's also the people saying, we have got to be talking about seven generations down the road. We have got to be thinking long term, how do we frame and, and organize around this issue differently so we're not in the same spot 10 years from now, 100 years from now. Like, what is our long term view? And I do think this is just my bully pulpit, but I, I do think that people underestimate and under. Invest in leadership. Oh, it's not worth it. In the leaders that are actually going to. Like you joked, but I said, I. It's not a joke to me. Like you're like, I'm not the one with the money. I wish you were the one with the money because you would invest in leaders who are actually going to try to take this work forward and get it over the finish line. And I feel like there's so much infrastructure and money in political leadership and not nearly, not even a fraction of it in movement leadership, in organization leadership, in like all these other avenues. It's not just about who's elected. And I wish we would put the resources and you know, just give the, give the due that is deserved to the people willing to stick their necks out there and try and fight for and build something different. And so I wish you had all the money because I think you would give the money to those people. I know I.

[B]

Would. Yeah, no, for sure. Same. I was going to say the same thing. I wish you had.

[C]

It. Today's episode is sponsored by DRG Talent. I go Way back with drg, this team is passionate about strengthening the nonprofit sector. Their work goes well beyond a holistic executive search process with strat plans, comp analyses, culture surveys, leadership 360s, and the list goes on. I refer clients to DRG regularly and I'm excited to be able to say this with a microphone in front of me. These folks are good and they care. Reach out to them, drg talent.com and tell them, Joan Gary said, you.

[B]

You know, the structure and system that we're in, in and of itself is challenging. Right. You know, and so I think, you know, maybe some of the ways that we dealt with and been in relationship to philanthropy will shift as well. I don't know. But I appreciate the idea of we need to pivot from what we've always done. And it's not just us leaders, it's not just us organizers, it's not just us leadership development folks, it's philanthropy too. And that all of us need to think different, more directly about what is our role and how can we powerfully use whatever tools we have. And for the philanthropic leaders, it is that they have the access to the purse and they can shift also dynamics between, you know, nonprofit leaders and themselves. I said to someone not long ago, I know you don't want to invest the amount of money you're investing in me and my work here at Rockwood and know deep down that I'm spending all of the rest of my time on roller skates trying to beg other people to give me the rest of the money so that I can, so that my teams can do some work. I imagine, I imagine you want my brain on what do leaders really need? Yeah, that's what I.

[A]

Imagine.

[B]

Yeah. I think that's where I should have my brain. You know, I, I.

[A]

Agree. If I get a vote, that's where I want your brain.

[B]

So. Exactly. And that's what we want. For every leader that they have the support that they need and they don't have to spin their wheels in these areas that are not in some ways hyper focused on the, the goals and the visions that we have for our future, that's where they need to spend their energy. So money should be not a.

[A]

Problem.

[B]

Yeah. You know, that should be like not even 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. They have enough money to act over the next five, especially like the next, even the next two years, frankly, yeah, like the next two years when things are heated in this authoritarian advancing is like, really happening. Can't we just dive in and dump some resources into people? I think the mergers, the shutdowns, the breakdowns, the organizations that are not whatever, I think everything will surface in that. In that I wouldn't worry as a person with money if I had it, about who's going to surface, because whoever rises to the top will be telling us a new story about what really works to move us to the next place in our.

[C]

Democracy. Greetings, Joan. Gary here, as a nonprofit leader, you deserve tools and support that help you to thrive. That's why I feel it is important to introduce you to today's sponsor, DonorPerfect. Their All in one fundraising platform simplifies donor management, communications and reporting so you can focus on what you do best, changing lives. Plus, their expert team is always there to cheer you on. You want a partner who truly gets you. Visit donorperfect.com Joan to learn.

[A]

More. Gosh, this could be. I feel the urge to go, to turn left and go to a whole other podcast, which is what needs to change about philanthropy. But that is not actually, and I don't mean to say I agree with you. I have seen some institutions and foundations and philanthropists really step up and just double down on the things that, that we need and we believe in. So I don't mean to. To paint with a, you know, with one brush, but I think, I guess what I'm. What I'm curious about to kind of, kind of wrap this up is like, if you, you are in the seat, and I am also in the seat where I see a lot of leaders trying to navigate and do the best they can in this challenging situation. And I guess I'm, I'm wondering. And we also are fortunate to work with philanthropies who want to help those leaders. So I'm, I guess I'm wondering. I'm. I'm asked. I'm doing an Ask Darlene section. So, like, what, what advice would you give to leaders who are trying to navigate right now? And what advice would you give to the people with money, to people that have an investment to make in terms of what's going on right.

[B]

Now? Yeah, I mean, I think for leaders, I think there is a practice of going deep, both intuitively and strategically. Like, you know your people, you know your communities, you know your.

[A]

Work.

[B]

Yeah. So go deep and hard on what you know, you know, like, don't. Like, really, this is a time to be, like, almost laser focused. On, like, I know this. I'm. I'm saying, 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.

[A]

Doing.

[B]

Yeah. So you have to sort of get clear about the things that you know the most. And. And then what's really helpful is to, in any way that you can not just use that for your own evolution of your work, but to share it with your colleagues and the people around you as much as possible. So that's what I would say for leaders. Go with what you know. It's probably going to take a huge pivot to make something work right now, because nothing is working the way it did last year. So it's going to mean pivots to get clear about strategy, get clear about your intuition about what you know will work, even if you don't have it in your coffers, even if you don't have it right around you. That means, what do I need to change and shift and how do I need to show up 10 toes in on, like, trying to get us to this next iteration of our beloved.

[A]

Democracy?

[B]

Yes. You know, like, 10 toes. It might be merging. It might be deeply partnering with somebody.

[A]

Else. We have to, you know, these. These moments of. Of challenge really, I think, push us to think differently. And I. That, to me is always the. The silver lining is like, you can't just sit back and kind of do what you've always done or assume what you always assumed. You have to fight for things, and you have to change. And I, you know, this moment for me has made me realize, like, we. I don't think that there's an end point. I think this is going to be a constant and, you know, just grappling to try and build the world that we want to build. And so for the leaders who do have a vision of a better world, of a. Of a place where your community that you're representing is. Is better off. Oh, yeah, probably along with everybody else, frankly, because if you center the most marginalized, that's what happens. Don't let go of that. It may change. It may take on a different form. It may be a merger. It may. You know, it may have to get real small right now so you can grow three years from now and just be huge and do what you really need to do. But I would try and stay open and creative, and my advice for philanthropy would be, please give money. Please give all the money that you are able to give the people need it. The leaders. And I'm not just Talking about the EDs and CEOs, the leaders in our country right now who are trying to protect democracy and each other. They need.

[B]

It. Yeah. Yeah, I would agree with that. On the philanthropy side, it's like, there's a role for philanthropy that's so powerful and so important. It's called giving money.

[A]

Yes. That's the.

[B]

Role. That's how it's defined, and it's really powerful and important. And I think, you know, nobody else can do it. And so, I mean, it's. How great is it to be in a situation where, you know, you're among people who are, in some ways, the only ones who can do what you're doing? And the key is to do it and to do it at a level that is for, you know, when someone. We were doing organizing back in the LGBTQ world, we. You know, you'd ask someone to give. It should hurt a little. Yeah, it should hurt a little. You know, remember, we get all of those, and we'd be like. I mean, we were completely poor. Right. So it's like people are asking us for 20 bucks or 5.

[A]

Bucks.

[B]

Yeah. Like, anything we can give. And that reminder from an organizer, like, it should hurt a little. I'm like, okay, take my $20. You.

[A]

Know. Yeah.

[B]

Fine. Fine. Take it. Like, that's the way it needs to feel for.

[A]

Philanthropy.

[B]

Yeah. Like, fine. I agree this is a lot, and I'm nervous, and I'm taking. But I'm going to take this.

[A]

Risk.

[B]

Yeah. To. To give 2, 3, 4 times the amount that.

[A]

Time. Time to take some risks. I mean, I heard someone at the conference say, if you've been waiting for the rainy day when your money. Like, it's a tsunami out there, like, it's the moment. So I agree with you. I think, you know, leaders are always encouraged to be brave. That's our assumption. I think people who are, you know, have that awesome responsibility of controlling the purse strings or the wallet and having the money. We need those folks to. To be brave.

[B]

Too.

[A]

Yeah. So maybe that's a good note to end.

[B]

On.

[A]

Yeah. But I. I so appreciate you, Darlene, and the work that you do is. Is so inspiring, and I. It's an honor to have you on the pod. Always come back anytime you have an open invitation. That's not true for a lot of people. That special for you. So. But hope you're well and thank you for your time and your.

[B]

Insights. Thanks for having me. And really thank you, too, for the work that you're doing in the world. You know, these smaller groups do in some ways get marginalized, and we need them more than ever in this time. So thank you. And thank you for having me again. Of course, of.

[A]

Course. Thank you for spending time with us today. We hope this conversation provides valuable insights as you navigate the messy but meaningful world of nonprofits. A Special thanks to DonorPerfect for sponsoring this episode and for their dedication to empowering nonprofits like yours to do more good. For more resources to support your work, visit joengarry.com podcast. We think you'll find a lot of helpful things there. Most importantly, thank you for all you do to make the world a better place, one small or large step at a time. Talk to you all next.