I have sat in boardrooms where the most important question in the room went unasked, and I have watched the cost of that silence compound for years. The question is simple. Do we still believe this CEO is the right person to lead what comes next? Most chairs ask it once, early, when they hire. Then they stop. They confuse loyalty with judgment, and they let the answer they gave on day one stand in for the answer the evidence keeps revising. I have done it myself. I have given a leader the benefit of the doubt long after the doubt had earned its keep.
The Comfort That Quietly Becomes a Liability
A board hires a CEO with conviction. That conviction is supposed to be a starting position, not a permanent one. What happens instead is that the relationship grows comfortable. The chair and the chief executive build trust, share wins, develop a shorthand. That comfort is valuable right up to the moment it becomes the reason no one is willing to say the hard thing out loud.
Boeing is the case I keep returning to. After the 737 Max failures, the board kept backing Dennis Muilenburg. The chairman went on television and said the board believed the CEO had done everything right. When the board finally moved, Muilenburg walked away with roughly eighty million dollars. The signal that sent inside the company was not subtle. The board had confused defending its earlier decision with doing its current job. By the time the question got asked honestly, the answer had become very expensive.
What the Numbers Are Now Saying
The data has started to expose how late many boards act. Forty two percent of S&P 500 companies that changed chief executives in 2024 had total shareholder returns below the twenty fifth percentile. In 2017 that figure was thirty percent. Read that plainly. A growing share of CEO changes are happening only after performance has already cratered, which means the board waited until the market forced its hand rather than reaching its own conclusion first.
There is a more encouraging signal underneath the same research. The proportion of CEOs departing within thirty to thirty six months rose seventy nine percent year over year. Some boards are making definitive judgments earlier in the tenure, before the numbers turn ugly and before the narrative hardens. That is the discipline I want every chair to build. The willingness to revisit the founding question on a schedule, not only in a crisis.
The Conflict Most Chairs Avoid Until It Is Forced
Kohl’s offers the other version of this story. Their chief executive lasted five months before the board found he had directed the company into vendor transactions involving undisclosed conflicts of interest. The independent directors and the chair did act, and several of them left over the differences that surfaced. The lesson is not that they removed him. The lesson is how much can go wrong inside a relationship that looked settled, and how fast a board has to be willing to reopen a question it thought it had closed.
I have learned that the chairs who do this well treat their own prior conviction as the thing most likely to mislead them. They ask the question on a cadence. They invite the directors who are least comfortable with the CEO to speak first, because the comfortable directors will fill the silence with reassurance. They separate the person they like from the performance they are accountable for. None of this is hostile. It is the difference between governing and spectating.
What I Tell Chairs Now
When a chair asks me how to avoid the Boeing trap, I do not give them a framework. I give them a habit. Once a quarter, in executive session, with the CEO out of the room, ask the board one question and require an answer from every director. If this seat were open today, would we hire the person sitting in it. Not whether you would fire them. That bar is too high and too late. Whether you would choose them again, knowing everything you now know.
The answers will be uncomfortable the first few times. Directors are not used to saying it. But the discomfort is the point. A board that can only affirm its CEO has stopped functioning as a board. It has become a fan club with fiduciary duties. The chair’s job is to keep the founding question alive, to keep asking it when nothing is wrong, so that the muscle is there when something is.
Here is the takeaway I would give any chair reading this. Your conviction about your CEO is the one belief in the room you are least equipped to audit, because you formed it and you defend it. Build a process that audits it for you. Ask the question out loud, on a schedule, before the market or a scandal asks it for you. The chairs who do this rarely face the eighty million dollar exit. The ones who stop asking almost always do.