Managing a nonprofit leadership transition, especially one involving the replacement of a long-standing founder, offers challenges even in the best of times. But when times are turbulent and marked by great uncertainty and disruption, as they have been for much of 2020, the transition faces greater obstacles. The nonprofit sector is likely to see many such leadership transitions as baby boomers retire, accelerated in part by the COVID-19 pandemic and economic downturn, as well as a recognition for the need of greater racial diversity in nonprofit leadership.

One such organization is the Bay Area-based Fresh Lifelines for Youth (FLY). Founded in 2000 by Christa Gannon, FLY provides legal education, leadership training, and mentoring programs to motivate and equip young people to change the course of their lives, and works to dismantle the pipeline to prison for all youth. In June of 2020, Gannon, FLY’s president and CEO, was succeeded by Ali Knight, the organization’s former chief operating officer.

“Do I really want to do this?”

FLY’s leadership change began when Gannon returned from a four-month sabbatical in April of 2019 and discovered that her management team, led by Knight, had managed quite well during her absence. So well, in fact, that she gave serious thought to the possibility either of retirement or a new role outside of day-to-day leadership. Her obvious choice for a successor was Knight, whom she’d hired five years earlier. To test her feelings, Gannon set up a long meeting for the two to have a heart-to-heart.

Transition was not open and shut. “I had to ask myself, ‘Do I really want to do this?’” recalls Knight. “There were pros and cons, including the birth of my second child. I want to be a present father.” Three hours later, however, Gannon understood that she was ready to focus on her passion of fundraising, and Knight knew that he was ready to lead.

Knight credits his and Gannon’s honest working relationship with ensuring that the transition would focus on “how best to advance FLY’s mission and seize the opportunities to do more on behalf of young people.” This, and the fact that the organization was on a strong and exciting trajectory, having just completed a bold and ambitious strategic plan that the team was calling “Imagine 2030,” gave both Gannon and Knight confidence that the transition would be positive.

Given their mutual trust and respect, Gannon and Knight established their rules of engagement for managing the transition. “How do we do this in a way where you feel good, I feel good, and other folks who will be deeply impacted by this feel good as well?” they asked. “Other folks” included the board, staff who worked with Gannon for much of the 20 years since FLY’s founding, and others who joined FLY in part because of the magnetic pull of Gannon’s leadership style. “We wanted to communicate to our team and community that we were committed to them,” Knight says.

Gannon approached the board in late 2019, which unanimously approved Knight’s succession to CEO, and then turned to planning for the leadership transition, which was set to officially happen in mid-2020.

Setting down rules of engagement

Gannon and Knight convened a transition task force that included members of the board and a small group of executives on staff to come up with a plan to manage the months leading up to the official transition in mid-2020, and through the first six months of Knight’s CEO tenure: everything from vacation strategy to job descriptions for the CEO and the founder to what the new organization would look like as a result of the change in leadership. “There’s an old adage that goes, ‘If you want to go fast, go alone. If you want to go far, go together,’” Knight says. Knight wanted buy-in all around, and says the committee provided the instrument he needed to build both buy-in and shared vision for where he wanted to take the organization, both at the board and staff levels.

“That task force was a great tool, and I highly recommend any organization that's doing internal transition to take a similar approach,” says Knight, who added that while he’s happy with the outcome, it took “a lot of emotional energy” to manage the team through a period of ambiguity.

Transition communications started at the end of 2019 to funders, staff, and other stakeholders, and the plan was set in motion.

Transition plan, meet COVID-19...

In the first months of 2020, as the task force put the finishing touches on their plan, the world turned upside down. COVID-19 and shelter-in-place disrupted most, if not all, of FLY’s services; an acute economic downturn introduced uncertainty about future funding sources, public and private; and the killing of George Floyd by Minneapolis police officers set off a wave of protests across the country, bringing into even sharper relief what FLY had always been focused on—the need for racial justice on a broad scale.

Knight recalls, “There was a moment where Christa and I stopped and asked: ‘Does this affect the timing of our transition? Does it call into question the transition itself?’” Then they realized that each unfolding crisis also presented an opportunity.

For example, leading FLY through COVID-19 would disrupt operations and furnish both Knight and Gannon with the opportunity to step fully into their new roles at a time when their unique leadership skills would be needed in particularly meaningful ways. Staff, board members, and stakeholders—who all were already galvanized around Knight’s leadership—were further inspired by his public and internal responses to Floyd’s death and the aftermath of protests and activism, which gave the FLY community hope and optimism for the future. The economic crisis then gave Gannon space to use her talents as a fundraiser and FLY evangelist.

Notwithstanding the confidence Gannon, the board, and Knight himself had in his suitability for the job, the transition was not without its vulnerabilities. First and foremost, says Knight, history has shown that during economic downturns, funders often want to invest in populations with fewer needs or at lower risk in order to see more immediate returns; whereas FLY youth often need more intensive support for longer periods of time, and often show promise later in life.

“As public resources are reallocated and reprioritized, we're at grave risk of not having our resources being prioritized in the new order of things,” Knight observes. “But on the flip side,” he says, “racial justice, immigration justice, and economic justice are on the forefront of everybody's mind right now, and FLY's model is perfectly primed to serve as a catalyst for a new tomorrow.”

A new era dawns

On June 30, her last day as CEO, FLY’s board and Gannon put the icing on the transitional cake by throwing a virtual CEO transition ceremony for all staff, donors, volunteers, system partners, and youth, to hear her parting words as well as Knight’s words about his vision for the organization. By the end of business on that Tuesday, a new era began at FLY.

In part two of our series on FLY’s leadership transition, we will connect Knight’s personal history and growth as a leader to FLY’s organizational pivot in 2020. We’ll chart the key changes Knight and his team envision for FLY against a backdrop of dynamic flux and uncertainty, with emphasis on the organization’s deeper engagement with issues of justice reform.

Dave Moore is a freelance writer and editor who frequently writes about purpose-driven people and organizations. He lives in Lee, New Hampshire.