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Leadership change is a recurrent challenge facing American organizations, yet many leaders remain focused on finding replacements instead of preparing for transitions. With more than half of small and medium-sized business owners in the U.S. now over the age of 55, and nonprofit leaders facing mounting pressure to sustain missions through periods of uncertainty, succession planning has moved from a behind-the-scenes HR function to a board-level leadership priority.
Amid the shifting demographics of the workforce, organizations across the world are increasingly confronting the challenge of transferring institutional knowledge. For mission-driven organizations, that might mean higher stakes. A poorly managed transition can affect donor confidence, organizational culture, staff retention and, most importantly, the continuity of the mission itself.
Will Heath, founder of Sherpa, believes many organizations have misunderstood the purpose of succession planning. After nearly two decades studying leadership transitions across nonprofits and mission-driven organizations, he argues that succession doesn’t end with identifying the next person to occupy a role, but involves preparing an organization to navigate change successfully.
“Succession is personal before it becomes tactical. Too many governance structures only speak to the tactical conversations. They do not create space for the emotions that come up,” he says.
Heath’s focus on succession began in 2007 with a conversation with a longtime pastor and mentor named Steve. At the time, Heath was working in banking and had asked a question: what would leadership look like after the current leader stepped away? The discussion, he notes, revealed a gap he would continue exploring for years. Heath observed that organizations had extensive resources for developing leaders, but far fewer conversations existed around helping leaders leave well.
Through his work supporting nonprofit organizations, Heath began viewing succession through a risk analysis and management lens. He argues that organizations investing significant resources into communities and programs need to consider whether leadership transitions could threaten that investment.
Heath says, “I approached it by asking questions like: how do we care for leaders, how do we help older leaders understand what it looks like to leave well, and how do we ensure continuity through a transition?”
A major challenge is that organizations often confuse executive search with succession planning. While recruitment plays an important role, Heath argues that the search process happens too late to solve the deeper issues surrounding transition readiness.
“The search process does not prepare the organization, it only reveals how the organization prepared itself,” he says. Many succession models rely on the image of a relay race, where one leader passes the baton directly to another. Heath believes the metaphor has shaped organizational thinking in ways that limit preparation because it places too much emphasis on the final handoff.
A leadership transition, he argues, requires organizations to examine their culture, governance, communication practices and future direction before a search ever begins. Without that foundation, organizations risk hiring accomplished leaders who may be successful elsewhere but are not equipped for the realities of the organization they are entering.
Heath also points to the challenge of timing. Organizations often assume that having several years before a leader’s departure means there is plenty of preparation time. He argues that transition readiness depends less on calendar years and more on the frequency of meaningful conversations.
“A board might say, ‘We have five years before this happens,’” Heath says. “But if they only meet quarterly, that is 20 conversations, and those conversations are competing with everything else governance requires. Calendar time is not the same as conversation time.”
His response is a framework of six conversations spanning emergency readiness, care for the departing leader, organizational preparation, transition strategy management, leader identification and communication, which he insists boards must hold before retirement arrives. He resists prescribing a single playbook, preferring instead to help boards think wisely and see clearly enough to lead well and determine their own pace and priorities.
With the approaching “silver tsunami,” Heath does not expect the pressure to ease. The workforce keeps aging, and departures keep coming faster than most institutions can absorb them. Within that landscape, he believes organizations will need to rethink succession as an ongoing responsibility. The organizations that prepare intentionally will be better positioned to not only attract candidates but to protect their missions, cultures and communities through change. Those who wait for the vacancy, he says, might find themselves managing a crisis they had years to prevent.
He adds, “Great leaders are not remembered only for how long they stayed, but for how well the organization thrived after they left.”
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