Navigating nonprofit leadership transitions is seldom smooth sailing, but sometimes the challenges are even greater than expected. (Illustration by iStock/NatuskaDPI)
I read the first draft of the first essay in this series while riding the New York City subway in early March 2020. Eventually titled “The Five Stages of Founder Transitions,” it shared Celine Coggins’ insightful, honest, and vulnerable perspective on stepping down from her position as CEO of Teach Plus. And as I read her words, “The last month before the transition team announced my successor was arguably the hardest,” I choked up. And the insight that followed in her essay hit home: It’s challenging to lead a team that knows you are on the outs. Earlier that day, I’d led an internal meeting at Generation Citizen, the civics education nonprofit I co-founded but was preparing to leave in June. Knowing the board would be announcing my successor within the next month, some team members pushed back against decisions I was making. At that point in the transition, they saw me as the steward of an established vision, not the person who would lead them into the future. They craved clarity on the direction the organization would take under the new leader and certainty about the roles they would play.
I should have expected this internal pushback. After all, when I decided in 2019 that Generation Citizen was ripe for new leadership, I reached out both to founders who’d transitioned—like Celine—and to leaders who’d succeeded founders to glean as much advice as possible. Everyone was willing to talk about their transition experiences—the good, bad, and ugly—and share lessons they’d learned. Their advice laid the foundation for this essay series and informed my own exit plan. By August 2019, the board and I had mapped out when to tell the news to funders, partners, our internal team, and the general public. We’d formed a search committee to find my replacement and contracted a reputable search firm. We’d planned a mid-April 2020 gala to mark 10 years as an organization and my departure, and to announce the next CEO. The plan seemed fool-proof.
But it can take time to internalize lessons. In addition to Celine’s wisdom, I probably also should have taken to heart a piece of advice later outlined in Jacob Mnookin’s “When Co-Founder Transitions Collide” essay and Laura Weidman Powers’s “Getting Past the Glorification of the Founder”: Be prepared for the unexpected. Just a week after the meeting described above, the COVID-19 pandemic forced us all to begin sheltering in place. It totally disrupted the work of our organization and entire nonprofit sector—and my transition.
Putting a Transition on Hold
It’s easy to forget how quickly everything changed in March 2020. In a moment, our offices were closed indefinitely, and lockdowns went into effect across the country. The economy seemed to crater. Schools went virtual overnight. Our board of directors and I knew that managing a transition on top of everything else was too much, and the board quickly and graciously accepted my offer to stay on longer. We agreed to pause the search, if just for a few months.
Even in the midst of uncertainty about the world around us and the leadership transition, our team worked endlessly to put our content and training materials online and remain relevant. We launched a virtual training program for educators and moved all of our end-of-semester events online. I’m proud of how our team met the moment. Operationally, recognizing the deep and differing toll of the economic shutdown on all our employees, we aimed to provide team members, especially those struggling with childcare and sick family members, with more support. We also offered unlimited paid time off. Unfortunately, necessary budget cuts required that we lay off a number of employees, so we attempted to offer significant transition time and support for them. Meanwhile, like all of American society, we grappled with how to respond to growing awareness of racial inequities on numerous levels, both in relation to our teachers and students, and as a white-led, civic-focused organization. It was a lot to manage.
Despite the uncertainties, we made a lot of progress as an organization. We passed a new strategic plan that placed racial equity at the very foundation of everything we do, made all of our programming virtual, and launched an ambitious new policy agenda to help drive new, nation-wide investment in civics education.
Leadership Lessons in Review
Six months later, I’m still at the helm of Generation Citizen. Since 2009, we’ve trained thousands of US educators to teach our civics education curriculum, and almost 100,000 students have completed the course work. We’ve helped pass landmark civics education legislation in Massachusetts, and we’ve led efforts to ensure that equity is a fundamental component of civics education via a listening tour and steering committee funded by the Hewlett Foundation. But while I’m proud of our success, I’m as ready for something new as I was at the beginning of the year. I still feel the organization would benefit from having a leader whose lived experience is more similar to our students—predominantly students of color whose government continues to perpetuate practices like unjust policing and housing discrimination, and devalue their voices and experiences. It’s still time for me to leave. We’re finally ready to announce my successor, and so that last, hardest month has come again.
In addition to the “prepare for the unexpected” lesson, three other bits of advice from my initial discussions with founders and new leaders (also covered in this series) stand out as particularly useful to transitioning during uncertain times:
1. Put the Organization First (and the Ego to the Side)
Like any founder, I have many faults. I can be impetuous, impatient, and unfocused, for a start. But I was unprepared for the frustration the team felt on learning I would continue leading Generation Citizen longer than expected. Unlike our funders and partners, who seemed relieved by the news, the team wanted the new leader we’d promised, pandemic be damned. It became clear that I had a limited ability to inspire and that my words no longer carried the same value.
At first, I took this personally, but I soon realized their reaction made sense. From the moment I announced my transition plan, people began looking to the future and wondering who would guide the organization into its next iteration. Still, the changed dynamic took a while to get used to. As Celine’s essay noted, the late Ruth Bader Ginsburg once said that the key to a successful, long-term marriage is to “be a little deaf.” It helped to be a little deaf to the noise around me and to remember that I was putting the organization first by staying longer. As unpopular as it might have made me, being the person to cut staff, and make challenging financial and programmatic decisions (like ending our traditional model of partnering college volunteers with educators), had some advantages. It meant the new leader would step into a more sustainable organization and be spared from having to make major choices quickly right when they started. My delayed departure also gave the board and staff time to get used to the new normal of remote work, both internally and with our programmatic partners, without the added change of a new CEO.
2. Prioritize Finances
In the midst of an incredibly uncertain economic environment, shrinking school budgets, and reduced individual giving, we felt we needed to be as financially conservative as possible, particularly since Generation Citizen’s financial health wasn’t strong at the onset of the pandemic. (Today, I see our flimsy financial reserves at the time of the shelter-in-place orders as one of my biggest leadership failings.) The combination of these circumstances ended up necessitating a reduction in workforce and a new budget that was 30 percent lower than the previous year.
While painful, this accomplished two important things noted in the previous point. It ensured that the new leader could focus on the big picture, not just keeping the lights on, and it contributed to the near- and long-term sustainability of the organization. Several essays in this series, including Anne Marie Burgoyne’s “A Funder’s Learnings on Nonprofit Founder Transitions,” highlight the importance of ensuring that transitions take place during times of operational and financial strength. Generation Citizen is a stronger financial position than it was in months ago, but Anne Marie’s advice nevertheless rings true: “It’s … helpful if the organization is in a place of strength when the founder leaves—financially, operationally, and in terms of impact.”
3. Empower Other Team Members, and the Successor
Laura’s essay, mentioned previously, suggests that the best way to combat the inevitable glorification of founders during a transition is to empower other leaders, leading to “the perception of [the] organization as “leader-full.” By recommending them to virtual conference panels and bringing them into conversations with long-term funders, I tried to elevate and empower team members I knew would be around for the long-term. Our new senior director of programming and impact, our senior director of policy and advocacy, and numerous local site executive directors were committed to sticking with the organization, and the team needed to hear from them more than they needed to hear from me.
As I prepare to finally hand the reigns over to a woman of color, I also am keenly aware of the intense and unfair burdens new leaders of color bear. Michelle Rhone Collins’ articulates some of these in her essay “Navigating Race and New Leadership in a Time of Upheaval.” I’ve therefore tried to reinforce the foundations of the organization—by closing as many fundraising gifts as possible, clarifying our current programmatic direction in this new virtual reality, and ensuring that our team is strong and ready to move forward—so that she has room to create and start building her own vision. As Anne Eidelman notes in her essay, “When Moving a Nonprofit Forward Means Altering the Founder’s Course,” new leaders need to be more than “culture carriers focused on survival.” Rather, they need to chart a new, bold case for impact. I think we have laid the foundation for Generation Citizen’s new leader to come in and create more impact than ever before.
My transition hasn’t been the smashing success I once hoped for. We had to let people go. The process took too long. Morale is too low. But I feel strongly that the organization is headed in the right direction, largely due to work that happened in the months after I originally intended to leave. I learned in the lead up to this series that successful founders ensure the organization they launched can thrive long after their tenure. Despite the delays and hiccups, I’m confident Generation Citizen will continue to lift up young people as we continue to transform our democracy.
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Read more stories by Scott Warren.