Test Executive Readiness Before the Role Is Vacant

Strong performance is not proof of readiness

As boards and executive teams finalize 2027 plans, leadership development needs a harder question: what evidence shows that someone can do the next job?

A divisional leader may consistently deliver results while relying on the CEO to resolve conflicts over capital, customers or shared resources. That record proves something valuable. It does not yet demonstrate readiness to carry enterprise responsibility.

Michael Watkins describes the transition from functional leadership to enterprise leadership as a series of shifts, including moving from specialist to generalist and from analyst to integrator.^[1] These are changes in the work, not simply increases in its volume.

Yet development plans often add coaching, courses and exposure without changing what the leader must actually resolve. The person becomes more visible. The evidence of readiness remains thin.

For each critical role, define the work that becomes materially different at the next level. Then identify where a potential successor can practice that work before a vacancy makes the lesson expensive.

Give leaders real work with clear limits

Development assignments should involve genuine business tension. Leading a meeting or presenting an approved strategy is not enough. The leader needs a problem with competing interests, incomplete information and consequences that cannot all be avoided.

For example, ask a business-unit leader to develop and carry out a plan to recover margin on a product line that serves several divisions. Sales wants pricing flexibility. Operations wants fewer exceptions. Finance wants a credible return. No function can solve the problem alone.

Set the assignment up explicitly:

• Business outcome: Define the result, its deadline and the constraints that cannot be breached.
• Decision rights: State what the leader can decide, what requires approval and who resolves a deadlock.
• Executive sponsor: Name the person who will provide access, challenge assumptions and intervene when risk exceeds agreed limits.
• Learning objective: Identify the unfamiliar responsibility, such as negotiating an enterprise trade-off or changing course after contrary evidence.

Remove enough existing work to make the assignment feasible. Otherwise, the exercise primarily tests endurance and access to informal support.

Keep the risk proportionate. A development assignment is not permission to gamble with a material customer relationship or bypass controls. It is a controlled opportunity to carry responsibility that the current role does not provide.

Examine judgment, not the polish of the presentation

The final result matters. But it cannot explain readiness on its own. A strong market can conceal weak judgment. An inherited constraint can obscure sound leadership.

Review the decisions made along the way. What alternatives did the leader consider? Which assumptions were tested? When did they surface an emerging problem? What did they change after hearing a credible objection?

Use concrete records: the original proposal, major revisions, agreed decisions and business outcomes. Ask participating executives where the leader clarified a difficult choice and where the sponsor had to step in. Make the review process transparent from the outset.

This also tests the organization. Research discussed in Harvard Business Review argues that leadership training can fail when organizational conditions prevent people from applying what they learn.^[2] If every meaningful trade-off still goes back to the CEO, the assignment has not provided the intended experience.

Separate the development conversation from the appointment decision. A candid discussion of mistakes should produce a better next assignment, not an automatic rejection. Equally, completing an assignment should not create an entitlement to promotion. Accountable executives and boards must judge readiness against the actual requirements of the role.

Put the work into the 2027 plan

Leadership development should appear in operating plans as work, capacity and oversight—not just a training budget.

For each critical role, specify the missing experience, the assignment that will address it, the sponsor and the review date. Agree on what evidence would support broader responsibility and what would require more practice.

Harvard Business Review's analysis of leadership development identifies the difficulty of transferring learning into workplace behavior as a central problem.^[3] Building development around live business responsibilities addresses that problem directly, provided feedback and reflection remain part of the work.

This week, select one critical role and inspect the evidence behind its succession plan. If the case rests mainly on reputation, tenure or current-role results, commission a better development assignment. Do not wait for the vacancy to discover what has never been tested.