Coach the CEO to Make Succession Possible

Put the incumbent inside the succession plan

As boards review 2027 priorities, succession deserves more than an updated list of names. It needs a practical test: can another executive carry significant responsibility without the CEO quietly taking it back?

The obstacle is not always a weak leadership bench. Sometimes it is an incumbent whose habits prevent that bench from developing. The CEO answers questions directed to other executives. Reopens settled decisions. Maintains exclusive relationships with critical customers. Steps into difficult discussions before the accountable leader can resolve them.

Each intervention may look helpful. Together, they can make the CEO indispensable and everyone else appear less capable.

This is a legitimate executive coaching agenda. Not preparing the CEO emotionally for an eventual departure in the abstract. Changing the behaviors that keep authority, knowledge and relationships concentrated today.

The classic management problem described in “Management Time: Who’s Got the Monkey?” is responsibility migrating upward through everyday interactions.^[1] In succession, that pattern has a larger consequence: the board cannot distinguish an executive who needs development from one who has never been allowed to operate independently.

Transfer responsibility before judging readiness

A succession assignment should involve work that matters. A cross-business investment. A major customer relationship. An operating review. A difficult trade-off between current performance and future capacity.

It should not be a ceremonial presentation while the CEO continues to make every substantive choice backstage.

Before the assignment begins, the CEO and executive should agree on four things:

• The outcome: What business result must the executive deliver?
• The authority: Which decisions belong to that executive, and which remain reserved?
• The boundaries: What financial, legal or reputational conditions require escalation?
• The review: When will progress be discussed, and what evidence will matter?

The coach’s work starts with the incumbent’s side of this agreement. Where is the CEO likely to intervene? Which relationships will be hardest to share? What difference in style might the CEO mistake for poor judgment?

A different approach is not automatically an unacceptable approach. If the successor must reproduce the incumbent’s methods to retain authority, the assignment tests imitation rather than leadership.

Boards and management should also distinguish development from selection. A stretch assignment provides evidence. It does not guarantee appointment. Human judgment, explicit role requirements and the board’s governance responsibilities remain central.

Coach the moments when the CEO takes work back

The most useful coaching material is often a specific interaction, not a broad discussion of leadership identity.

An executive brings two options to the CEO. The CEO immediately chooses one. The executive leaves with an answer but no opportunity to exercise judgment.

A more useful response is: “What do you recommend? What are you trading off? Is this within the authority we agreed?” If it is, the CEO can leave the decision where it belongs.

This does not mean withholding expertise. It means making advice distinguishable from a decision. “Here is a risk I want you to consider” leaves room for ownership. “Here is what I would do” can become an instruction, regardless of intent.

The coach should also examine what happens after an imperfect result. Does the CEO review the reasoning and adjust the boundaries? Or reclaim the entire responsibility?

Research discussed in “Why Organizations Don’t Learn” identifies fear of failure and an excessive focus on success among barriers to learning.^[2] A development assignment that permits no recoverable mistakes offers little room to learn.

Equally, the executive must be able to surface uncertainty early. Psychological safety concerns the ability to take interpersonal risks, including asking questions and acknowledging mistakes.^[3] It does not remove performance expectations. For succession work, both matter: candid discussion and clear accountability.

Give the board evidence of reduced dependence

Coaching remains confidential. Succession progress should not be invisible.

The board does not need private session notes. It needs agreed evidence that responsibility is moving and performance is holding. Useful observations include who leads consequential discussions, who owns key relationships and whether decisions remain intact when the CEO is absent.

For this quarter, select one material responsibility to transfer. Document the boundaries. Schedule reviews. Ask the CEO to track occasions when they intervene, including why the intervention was necessary. This is a record of the incumbent’s own behavior, not employee monitoring.

At the review, examine both sides. Did the executive deliver sound work? Did the CEO honor the transfer? If not, was the boundary wrong, the support insufficient or the incumbent unwilling to let go?

Executive coaching should make those questions discussable before a departure forces them. A credible succession plan requires capable successors. It also requires a CEO who gives them room to become capable.