CEOs often delay removing an underperforming senior leader because they haven’t planned how the business will run after that person leaves, not because they avoid difficult conversations. A senior departure moves decisions, customer relationships and team direction onto someone else, and the CEO usually expects to carry most of it. Designing the first 90 days after the exit, before the conversation happens, tends to turn that undefined risk into responsibilities that can be assigned and reviewed. The 90-day bridge does this in three stages: stabilise essential work in days one to thirty, transfer knowledge and ownership in days thirty-one to sixty, and rebuild the role or structure in days sixty-one to ninety.
The need-to-know:
The gap you fear is probably already open. When a struggling executive stays, their role tends to be quietly redistributed to the CEO and colleagues, so the business is already paying in executive time and slower decisions.
Ask what you would do if they resigned tomorrow. The question tests your organisation’s resilience without debating the exit, and shows where the business depends too heavily on one person.
Distribute continuity rather than handing it to one person. Name an owner for each essential decision, relationship and commitment, and take work off anyone absorbing extra responsibility so the pressure doesn’t simply move elsewhere.
Let’s go a little further
Many CEOs carry a name for months. It surfaces in performance reviews, delayed decisions and customer problems that land back on the CEO’s desk. The conclusion has often been reached through a fair process. Yet the person stays.
The usual explanation is reluctance to have a difficult conversation. That is rarely the whole story. More often, the hesitation sits in what the CEO pictures happening the day after: the decisions, customers and team direction that will need a new owner, and the likelihood that much of it lands back on them.
There are two connected responsibilities here. The first is reaching a fair, evidence-based decision about the person. The second is designing the business to function without them. The second tends to receive far less attention, and that uncertainty is often what keeps the first decision open.
A common misconception is that leaving the arrangement unchanged preserves stability. In practice, part of the role has usually been redistributed already. The CEO attends meetings that once didn’t need them. A colleague helps settle decisions. The leadership team learns that accountability can be adjusted informally, and that lesson can spread well beyond one role.
Planning for continuity doesn’t mean presuming the outcome of an employment process. Fairness, proper advice and the right process still matter. But the business needs a continuity plan whatever the eventual decision.
The 90-day bridge gives that plan a structure.
Days one to thirty: stabilise. List the decisions that cannot wait, the relationships that cannot be left unattended and the commitments that must still be delivered. Put a current name beside each one, with the authority and support to hold it, and check what comes off that person’s existing workload.
Days thirty-one to sixty: transfer. Document critical knowledge, clarify decision rights and turn temporary coverage into deliberate ownership. Drop work that no longer needs doing, and ask what the role should achieve over the next eighteen to twenty-four months rather than copying the old job description.
Days sixty-one to ninety: rebuild. Decide whether the answer is a replacement, a supported promotion or a redesign of executive roles, and assess whether decisions, customers and the people providing cover are being well served.
The plan is built before the exit and carried out after it. Once the business can see how it will function, much of the uncertainty becomes manageable, and the CEO is better placed to communicate calmly, respect the individual and give the board confidence.
A practical start takes thirty minutes this week. Choose the role you are most concerned about, assume it becomes vacant tomorrow, and write down what must be protected, transferred and rebuilt. Put names beside the essential responsibilities before returning to the question of the individual.
If the person you have been carrying for more than three months resigned tomorrow, would your business know what to do the day after?
Question for you
When you picture the day after a senior leader leaves, which responsibility can you not yet see an owner for, and would it help to talk that through with Phil by email?
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