What do leaders need to make difficult decisions?

Farra Trompeter: Welcome to the Smart Communications Podcast. This is Farra Trompeter, co-director and worker-owner at Big Duck. In today’s episode, we’re going to ask the question: What do leaders need to make difficult decisions? I’m sure many of us have had to ask ourselves that question many times in the past few years, and I’m delighted to be joined by Dr. Traci Lester. Dr. Lester uses she/her pronouns and is a nonprofit leader whose career has been devoted to supporting and uplifting diverse voices and communities across the country. She is the final president of The Opportunity Agenda, a pioneer in using values-based communications, cultural engagement, and strategic collaborations to advance social justice that dissolved in late 2025. She’s held other executive roles, including executive director of The Center for Fiction, National Dance Institute, and Reach Out and Read of Greater New York. She has an MBA from Rutgers University, an MPA from San Francisco State University, and a Doctorate in Education from New York University. Traci is also on the board of one of our clients, Nonprofit New York, and is a fellow adjunct professor at CUNY Baruch College. Traci, welcome to the show.

Dr. Traci Lester: Hi, thanks so much for having me.

Farra Trompeter: So Traci, you have held leadership positions at five different organizations in the arts, education, and philanthropy and have a really exciting background. And given your deep experience, what’s one thing you’ve learned early in your career that informs how you lead or manage an organization regardless of what sub-sector it’s in? I just want to start with that.

Dr. Traci Lester: Yeah, that’s a great question, and thanks so much for having me. I had a professor when I was getting my MBA at Rutgers University, a little plug, and we walked into the class, and we asked her for the syllabus, and she said, “I don’t have a syllabus.” And we were like, “Wait, what do you mean? We need the syllabus?” And she said, “The first thing you’re going to learn from this class is to embrace change and embrace ambiguity.” And I feel like that’s been a guiding principle all along: that nothing is straightforward in this work that we do, and that you have to be open to change and be flexible.

Farra Trompeter: I love it. And, you know, we can talk later if I can get rid of my syllabus for teaching; I’m intrigued, but I’m not sure I’m ready to do that! But that’s a great lesson and great idea. Now, let’s talk about your current role, which is the final president of The Opportunity Agenda, or TOA, which was actually one of the first organizations I personally got to work with at Big Duck almost 20 years ago. And I was, of course, surprised when I first heard the news that TOA was closing. At Big Duck, we’re big fans of all the incredible resources The Opportunity Agenda has produced over the years, guiding communications and framing. And folks should know that those resources are now transferred to Reframe and Define American.

Farra Trompeter: But I want to go to the sort of decision of dissolution. So closing an organization is, I would say, perhaps the most difficult decision a leader has to make. And you wrote about that process recently in Nonprofit Quarterly, or NPQ, in an article titled How dissolving your nonprofit can strengthen the sector. Before we get into the sector-wide implications, I’d love for you to just share a bit about the process itself. As the challenges of the political climate and funder responses intensified in 2025, you led a process of engaging the staff and board and decided to sunset the organization. And I’m just curious if you could talk a little bit about what framework you used to wind down in a way that would align legal compliance, financial stewardship, and supporting staffing transition.

Dr. Traci Lester: Yeah, thank you for that. It’s a great question. The decision to dissolve didn’t come easily, and it involved sort of a collaborative decision-making model. I had arrived at the organization. The organization was 20 years old, and I was brought in to figure out, assess a way forward. But first I had to understand sort of what was presently in place. And I was new to the org, so I didn’t know everything, and I really needed to speak with everyone and kind of lean into what I was hearing and receiving by way of information. And coming out of a doctoral program recently, I had a lot of theory on my mind. So, you know, some of it was applicable, some of it wasn’t.

Dr. Traci Lester: But one thing that really stuck with me was this notion of sort of organizational culture and the espoused beliefs that exist that guide people internally. And so I’d stepped into an institution that had a very deep sense of organizational culture and sort of the way we do things. And because I consider myself a cross-sector specialist (I’ve run organizations in different kinds of environments and focusing on different populations), I was bringing sort of a different lens to it. I was bringing an arts and cultural lens, a human services lens, an education lens. And all of those sort of sectors address their work in different ways. And so I was inviting staff to think differently about sort of the way they were doing the work and the way they were sharing information, so I could get at the root of what needed to be addressed.

Dr. Traci Lester: And so I always say that when you have a board of directors, they should never find out anything by surprise. And so in the case of the board, I was also pulling them in. Like, I needed them to sort of hear about my findings and be sort of active participants in the process of learning about what was ahead of us. And so, by pulling the staff in and pulling the board in through regular sort of convenings and gatherings, we were able to sort of collectively come up with kind of like, “What are we going to do to get us forward?” And while there were many options that emerged, one of the ones on the table, probably a couple of months into my tenure, was: should we dissolve? So it wasn’t the primary option. And I’m not even sure that it was something I would’ve considered when I first arrived, but it began to emerge sort of as a possibility. And I think as leaders, you know, we’re trained to solve problems. We’re trained to execute. We’re trained to move things forward. We’re trained to, you know, get through the forest, at the end, the light at the tunnel, all the metaphors. And so that’s what I was trying to do, but I was also feeling like it’s possible that this might not be the way for this organization to go. But I didn’t know that in the beginning. And it really sort of emerged through this collaborative process of speaking with staff and speaking with the board and speaking with partners, past and present employees, current and past donors, everybody in the ecosystem who knew The Opportunity Agenda, had worked with them and, you know, believed in the mission.

Farra Trompeter: Yeah. And you do outline a little more about the process too in the Nonprofit Quarterly article. We’ll link to that in our show notes at bigduck.com/insights. One of the things in that article that I loved (it’s a great article), I loved in the beginning, you said, “In some cases, the most responsible and perhaps most radical act of leadership is to pause, assess, and consider unconventional alternatives such as dissolving with intention, integrity and transparency. This allows the field to absorb, carry forward, and evolve the work rather than forcing an organization to persist in a weakened state.” So ending an organization, as we said, is an incredibly difficult decision. And for some, it can be seen as a failure, but I appreciate how in that quote and in the article, you’re recasting this decision as a sign of strength. And for those who may be facing similar challenges, how can they create an environment where a solution like what you did for The Opportunity Agenda can even be named and considered, right? Can even be put on the table? A lot of times people are afraid to suggest something as bold as that, but I’m curious if you have any advice in that way.

Dr. Traci Lester: Yeah. I mean, fear is really an important point. You know, there are repercussions if you make the wrong decisions. I feel like radical honesty involves sort of speaking truth regardless of the repercussions. And that, you know, that takes time to get to that. And so because I had been doing this work for so long, I felt quite comfortable sort of being able to say like, “This is what I’m seeing. And I don’t have to sort of prove to you, or I do have to prove to you, but I can tell you with certainty that like these things are actually happening and here’s some things that I think you should consider.” You know, sometimes you’re heard, and sometimes you’re not. I could say that, and someone else could say that and might have a different sort of reaction.

Dr. Traci Lester: And I think because I was stepping into both an organization that was really existing in a tumultuous time in this country, you know, the political environment shifting, the funding landscape was shifting. I was also dealing with sort of internal challenges. There was board and staff fatigue. I mean, the organization had been through leadership changes. They were dealing with the brunt of these sort of external changes while trying to fight the good fight and get the messaging out around key social justice issues. But managing a crisis meant that everybody had to listen. And I feel that that’s really kind of where my strength came in. I was able to sort of tease out what I saw as the key issue areas, elevate them in a way that both the staff and the board could hear me, and then figure out how we sort of collectively could move forward. Because it wasn’t just my challenge, it was everyone’s challenge. And if we’re not sort of all in it together, I don’t know what the point of doing the work is. So we need to believe in it. We need to move forward together. And in that we will find sort of solutions.

Dr. Traci Lester: And so that’s kind of how I approached it with them. And I said that pretty much out the gate, like, “I’m new. You don’t know me, but we’re in it together. So let’s see how we can figure this out, whatever it is.” I think in my early years as a leader, I may not have exhibited that level of confidence. And some of this comes from, you know, trying and failing and trying and succeeding. And so I feel like this was sort of the cumulative effect of having been a leader and seen many different organizational challenges and really pulling on a lot of different skill sets to present solutions that I felt like everybody could get behind. You know, dissolving isn’t the solution you necessarily want, but dissolving became the solution that we all could agree on.

Farra Trompeter: That’s helpful. And I want to talk a little bit, you know, we think a lot about in our work about change management. And of course we also think about communications. Both of those things came up a lot for you in this. And, you know, you just mentioned this was not your decision alone. Of course, there was a lot of conversations with staff, with board, with funders, with donors, with partners. And I’m just wondering if you could talk a little bit about that engagement piece and particularly what did communications look like before this all was happening, while it was happening, and of course after?

Dr. Traci Lester: So I had taken over the organization after a few leadership transitions. And so communication looked different at different times for the staff internally and for external constituents. But at a granular level, I did sort of a few different things. I began meeting with the staff one by one, literally one by one by one. And then when I got through all of them, I looped back around, and we met again, and we kept looping around. So I was meeting with the staff one by one.

Farra Trompeter: And I’m curious at the time, how big was the staff? Just to give us a sense of that.

Dr. Traci Lester: We were about 20 at the time. Yeah. The organization had been bigger. There had been some reductions before I arrived. And so when I came, there were about 20 or so.

Farra Trompeter: Okay. So individual conversations.

Dr. Traci Lester: Individual conversations. And not everybody wanted to meet. They didn’t know why I wanted to meet. They were sort of like, “What are these meetings about?” And I really was just wanting them to know that they were being heard, that there was a direct communication loop with me because I was the president. I then began meeting with the board: same way. Every board member, and it was a small board, about 10, 12 people. So I met with all of them, and then I would loop around, and I kept doing that until the end. And the board was accustomed to having quarterly board meetings. They had committee meetings in between, but that wasn’t frequent enough for what I was seeing. So we went to monthly convenings, and then we went to twice a month. And then we went to once a week, and sometimes it was even more frequently than that.

Dr. Traci Lester: And along with that, I partnered with our chief development officer and our vice president of programs. And of course there was a comms team because that’s what we did. We were a communications organization. And we crafted messaging and updates at regular stages along the way for external audiences. So, that’s donors, large philanthropic supporters, individual donors, and partner organizations. We let everybody know about the concerns, the current climate, sort of what we were seeing, some of the stressors the organization was experiencing. Then we shared our strategies for sort of securing resources and what we were thinking about doing and ways to sort of elevate that, sort of monetizing certain offerings and trainings and other things that maybe hadn’t been monetized previously. And we also communicated that we were considering other options, that we were looking at potential sort of collaborations or strategic collaborations or, you know, the term mergers and acquisitions probably floated around for a minute. Like, is there somebody else who might want to, we might want to merge with? And I think that wasn’t necessarily a new conversation for them.

Dr. Traci Lester: And ultimately we decided to wind down. And when we did, we sort of shared with our external partners that we were considering dissolving. And then when we decided to dissolve, we shared that too. So we were sort of communicating at different intervals along the way with key constituents. And that aligned with my communication internally. I mean, I was sending weekly updates to the board and the staff around sort of what was going on at different stages. So it wasn’t like we were telling everybody else outside, but nobody in-house knew. Like everybody was sort of learning it in the same way. And that was really important.

Dr. Traci Lester: You run the risk, I think, as a communications professional of sometimes overcommunicating. But I felt like in this moment, people needed to understand sort of there was a crisis underway. And if they wanted to be helpful, we needed to hear from them. And in a few instances, that’s how we came to partner with the organizations that we ultimately spun off our projects and programs to because people reached out and said, “We’re interested. We might be able to help you.” So if you don’t tell people you need help, they may not know to help you. And particularly when you’re a CEO, president, ED, senior leader, you know, you’re going to do everything to present that great face that things are fine. But sometimes you maybe need to be a little vulnerable and let them know. But still, you know, show that you’re in control. So we let people know.

Farra Trompeter: Yeah, That’s great advice. And, you know, I want to kind of connect this moment: You do a lot of thinking about leadership and given the challenges that so many are facing in this current political environment and all the shifts we’re seeing in giving from some donors and funders, I know that there are a lot of executive directors out there thinking about leaving their organization, potentially not being an executive director ever again. Rising leaders are second-guessing if they should even apply for an executive director or president role. And I’m just curious, like, why should someone still be an executive director? And what do leaders need to actually thrive and succeed, especially as the challenges in the nonprofit sector have just seemed to increase, year over year, and especially the past few years?

Dr. Traci Lester: Yeah. I think the challenges have been there. It’s just a different day. And so the challenges are different, but I don’t think the challenges are new. This sector was set up in a way to be resource constrained by design. So we’re always looking for money. And when the year is over, the new year starts, and you’ve got to raise more money and, you know, figure out how to get your programs, keep them going, get them off the ground. So I don’t think it’s a new story. And I think helping people matters. And I think that we’re needed now more than ever. And so I would encourage people to sort of, you know, this term “Lean in” is kind of overused, but I can’t think of another one. So let’s just say lean into the possibilities of helping people and thinking of new ways to do that. The government can’t do it all. And we have to do it. Like, I think it’s sort of, I don’t even know if it’s “moral imperative”, I’m not even sure I like that term, but like, you know, I feel like it’s what we need to do to help each other in our society. It’s why the sector exists. It exists to innovate, to problem solve. It’s solution-oriented. And so I think as emerging leaders come on, new ways of thinking how to use AI, you know, good, bad, or otherwise, to support your endeavors. You want to try new strategies to solve societal problems because they’re there.

Farra Trompeter: Yeah. All right. Love it. If you’re out there and you’re curious to learn more about the process that Dr. Lester took The Opportunity Agenda through, I’d encourage you to read the article at Nonprofit Quarterly. Again, we will link to that in our show notes at bigduck.com/insights. You can also visit the legacy website, opportunityagenda.org and there’s a lot of great information there, including links to Reframe and Define American, where the existing programs and resources from The Opportunity Agenda now exist. You can also connect with Traci at her website, tracilester.com. That’s T-R-A-C-I-L-E-S-T-E-R.com. Traci, before we go, we actually didn’t get to talk about, a little more about leaders, about what they need to make difficult decisions. I know this has kind of been the thread embedded, but let me ask you that question directly again. What do leaders need to make difficult decisions? Any other advice that comes to mind?

Dr. Traci Lester: Yeah. I think leaders need supportive environments. I also think they need to take care of themselves. Like, wellness is key. You know, they say put your oxygen mask on first. I think that’s true. If you’re not thriving and doing well, you can’t really inspire others to follow you or to work with you. And so there’s that. And then I would say find people in your life who uplift you and support you and are willing to listen to the tough decisions you have to make. And like I’m a runner and I, you know, I run the New York City Marathon, and I’ve worked through a lot of strategic issues. And so like, run with people who will listen to your stories. And I think lastly, like go easy on yourself. Like leading is hard work. We take on this work, but it’s hard work. And also it’s like okay to say “No” and to let go. Sometimes you got to let it go.

Farra Trompeter: Yeah. Well, thank you. Those are all great advice, great things to think about. And I hope folks out there do take care of themselves and consider this and many other topics we’ve talked about. So thank you, Traci, and everyone out there, have a great day.