Coverage of the baby boomer succession wave has focused largely on small business owners approaching retirement without a transition plan. Roughly 12 million businesses representing nearly $10 trillion in assets are expected to change hands over the next decade.¹
A parallel crisis at the top of major organizations has received far less attention, with consequences proportionally larger and far less often discussed.
A recent analysis found more than one-third of S&P 500 firms sampled had a CEO and CFO simultaneously sitting in the retirement window with no clear succession plan disclosed. That is not a small business problem. It is a governance failure at scale.
The Same Paralysis, Higher Stakes
Regardless of context, succession planning failures mirror the same pattern. They are treated as a future priority until circumstances make them an immediate one. Boards and owners alike approve the logic of proactive planning in the abstract and defer execution in practice. The urgency never quite arrives until the departure does.
For ownership transitions, that deferral often results in closure rather than transfer, with wealth not passing forward and opportunities not created. For leadership transitions at the executive level, it results in a process managed under pressure rather than by design, with searches compressed and options narrowed before they begin.
When the CEO and CFO are simultaneously approaching a transition horizon, the board has an obligation to understand the specific plan. One that is funded, actively managed and tied to a timeline that reflects reality. Too often, the succession conversation stops at acknowledgment.
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The Window Is Narrower Than Organizations Realize
The gap between acknowledging succession risk and acting on it is where most organizations lose time they cannot recover. Building a succession plan is a multi-year process of understanding what a role will require, assessing whether capability exists internally and engaging external perspective early enough to act. Organizations waiting until six months before a planned departure have already narrowed their options considerably.
Organizations that manage this well share one characteristic: they treat succession as a standing agenda item rather than a response to circumstance. They know which seats are approaching a transition horizon, maintain an honest assessment of internal readiness and engage external perspective before urgency forces the question.
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SOURCE
(1) JPMorganChase, Powering 10 Million Small Businesses, September 2026.
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