After 20 years of successful leadership by charismatic founder Christa Gannon, Fresh Lifelines for Youth (FLY) underwent a leadership transition in the midst of the COVID-19 pandemic, economic downturn, and social turbulence on a national scale. FLY’s transition took hard work but, by all accounts, went nearly without a hitch. In Part Three of our series on FLY, we get a “board’s-eye-view” of how FLY’s leadership, Gannon (FLY's outgoing CEO) and Ali Knight (FLY's new CEO), and FLY’s board, represented by Board Chair Mark Donnelly and Board Vice Chair June Wang, made choices that created a smooth transition. (See Part One and Part Two of the series.)

Their suggestions focused on the benefits to be gained from 1) adopting a leadership development mindset, 2) engaging the board early on in the process, 3) creating a task force to lead the process, and 4) considering ways to keep the founder engaged without undermining the new leader.

Adopt a leadership development mindset

Long before Gannon’s decision to step down from the CEO role, FLY and its board had a commitment to leadership development that made it easier for them to determine a transition strategy. “Many organizations view succession planning as an externally focused activity,” says Donnelly. “At FLY, we use leadership development to prepare future leaders, effectively creating a strong and deep bench that includes leaders like Ali.” (Knight and the FLY team participated in Bridgespan’s Investing in Future Leaders program.)

In choosing whether to hire from within FLY or consider external candidates, Donnelly says FLY weighed the prospect of getting a “fresh” perspective from outside the organization versus the “deep experience and cultural fit” of Knight. “The board looked hard at the choices,” Donnelly says. “Should we look for somebody who wasn't steeped in FLY’s organizational thinking? Maybe somebody who already had been through a founder transition before, or perhaps somebody who had broader experience in the justice system?” At the end of the day, they were convinced they had the right person for the job in Knight, who had successfully led two strategic plans during his five-year tenure at FLY and had given the board a chance to witness his leadership style while he held the acting CEO title during Gannon’s sabbatical in 2019.

“And then we were concerned that doing an external search would signal our lack of faith in Ali,” adds Wang. “We might have lost two leaders, and we already knew first-hand how much value Ali brought to the organization.”

Engage the board early on

Boards generally don’t love surprises, especially those involving the stepping down of their agency’s charismatic founder. After all, Gannon had personally recruited many of FLY’s board members who had experienced how she inspired people about FLY’s mission. Gannon and Knight, who had discussed the idea of Knight succeeding Gannon, mitigated board shock by looping them in early through a series of one-on-one meetings—effectively inviting the board to “join the conversation” the two had been having about their and FLY’s future. The happy result was more time and space for the board to embrace the continuity and change Knight sought to bring to FLY.

“It’s the board’s responsibility to do due diligence on what kind of search we would do,” observes Wang. “We all really liked and respected Ali, but we still wanted to engage the full board before deciding not to look externally.” The board had a series of discussions, culminating in an official vote at a board meeting in September 2019 to appoint Knight as CEO and for Gannon to take on a newly approved founder role beginning July 1, 2020. Once this CEO-succession decision was made, the lengthy advance notice permitted new Board Chair Donnelly to become better acquainted with CEO-elect Knight.

Six months before Knight took the reins, Donnelly (who had just assumed the role of board chair) asked Gannon whether he could begin meeting with Knight one on one to establish a working relationship. She agreed and the two began meeting regularly, which turned out to be an important step that wouldn’t have been available had the board looked externally. Recalls Donnelly, “Ali had some bold ideas that I needed to be able to process to see where Ali was coming from. It wasn’t just that he wanted to expand FLY geographically; he also wanted to move FLY deeper into areas such as policing and the whole justice system.”

By the time the transition was completed, both Donnelly and Knight had achieved a strongly shared comfort level with FLY’s strategic direction.

Create a transition task force

“In the for-profit sector, the companies I worked for never created leadership transition task forces. We just hired a leader, restructured, and moved on. It was often painful,” says Donnelly. “So, all I have to say is whenever you do a transition—whether it’s to replace a founder or long-standing CEO or somebody who just up and left—always, always create a CEO transition task force!” Donnelly says the creation of such a team proved critical to FLY’s transition, both in terms of workload for board members and for aligning internal and external stakeholders behind Knight.

Comprising board members as well as FLY staff, the task force created a work plan outlining key elements of the transition process—crafting the CEO and new “founder” job descriptions, communicating to key stakeholders, making any organizational changes, and celebrating both outgoing and incoming CEOs (see sidebar below, "Building a Transition Work Plan"). The communication plan was particularly important—given Gannon’s relationship with funders, partners, and staff, so it was critical that the leadership team get on top of communications to head off the inevitable leaks about the transition. The plan had Gannon and the board members focusing on key external stakeholders—Gannon alone had 200 key contacts. Knight and Gannon were entrusted with cascading the news internally from directors to managers to front-line staff and building excitement for change while listening for and allaying the fears that change inevitably brings to staff, who are too often left to wonder where they will fit in the new order of things.

“Our goal was to maximize support for Ali, while causing as little surprise and alarm as possible,” says Donnelly. “The task force largely achieved this by determining the risks and opportunities that might surface at every step of the way—from private and public announcements to internal communications. It was a daunting task that was made possible through the coordinated efforts of the task force and key staff members.”

Consider ways to keep your founder engaged

If your founder truly wants to ride off into the sunset, there’s nothing you can do to stop them. And the last thing a new CEO or executive director wants is a founder looking over their shoulder. However, Bridgespan research has shown that founders who choose to stay on board for a limited and bounded period of time can have a beneficial impact on a transition’s success.

“In Christa, FLY had a founder who excelled at inspiring people to the agency’s cause—of turning people in probation departments into advocates for children instead of their jailers, for example,” Donnelly says. “She’d been a systems change agent from the get-go. The fact that she wanted to stay on in what we eventually called a ‘founder’ role was very important. We believed we could leverage this type of role in a way that would advance FLY’s strategy.”

The “founder” job description, along with an updated CEO job description, were written together by the task force, Knight, and Gannon, and designed to enable Knight to step quickly into his role as leader, while allowing Gannon to continue to offer highest-level value to some of FLY’s special projects and fundraising efforts. The founder role was scoped to be a one-year position to start. “The fact that both Ali and Christa thought the founder role was a good idea gave the board confidence that it would work,” says Wang. “They came to us with some ideas of how their roles would differ, but the transition task force worked up actual job descriptions.” The CEO position was easier to describe because FLY leveraged what was well known about the work Gannon had been doing for nearly 20 years. Gannon’s drafted ideas for what her new position might entail included special projects work, such as the Lifeline Institute, a key pillar of FLY’s Imagine 2030 strategic plan, and ambassadorial duties with key funders and policy people who FLY views as crucial partners. Gannon’s eventual job description also included a list of items where she would not engage, to create a clear delineation between this role, her former role, and Knight’s role as CEO. It also included “grey areas”—places of potential overlap that she and Knight would need to navigate in real time.

One duty she no longer has is attending board meetings. “That’s part of the letting go piece, right?” says Donnelly.

Deepen your bench as an organizational practice

It says everything about FLY that the board’s final charge to Knight before he formally took the reins was to have him draw up his own succession plan. “We told Ali that the transition wasn’t completed until he had his own plan in place,” Donnelly says. Donnelly describes himself as “a strong believer in internal succession,” not because he thinks the goal of organizations should be to continue doing things as they’ve always done them, but because “so much of what happens in an organization is informal.” Properly developed, trained, and experienced inside candidates will already know how things get done in the organization, giving them more bandwidth to plan ahead and think strategically. “It’s like flying a plane,” says Donnelly, who is himself a pilot. “Wouldn’t you want your pilot to know how to operate the airplane systems before he gets in the cockpit? Wouldn’t this enable him to focus better on where he’s going and how to accomplish the mission effectively and safely?”

At an airline called FLY, the answer seems to be yes.