If you’re asking when to start succession planning, you’re already late
The mid-market businesses with the smoothest leadership transitions started planning for them years before anyone announced a departure.
Succession planning gets treated as a project to run when a senior leader signals they’re leaving. By then, the options have already narrowed to whoever happens to be ready, whether or not they’re the right fit for where the business is going.
Organisations that handle transitions well build the bench continuously — identifying the two or three people per critical role who could step up, and investing in the gaps between where they are and where the role needs them to be, years ahead of any vacancy.
It is a structural discipline, not a reaction. Treated as the latter, it always arrives too late to give the board real options.