Why smart boards still fail to challenge CEOs, (even when they know they should)

When boards don’t challenge the CEO, it’s rarely because directors lack intelligence, independence, or courage. More often, it’s because the system quietly works against challenge.

Some patterns I see again and again:

• Narrative control: The CEO shapes the information, the timing, and the framing. Debate narrows long before the boardroom discussion begins.

• Success bias: Past wins create trust. Trust hardens into deference. What once felt prudent starts to feel untouchable.

• Relational risk: Challenging the CEO can feel like risking the cohesion and influence the board depends on to function.

• Blurry tripwires: Directors sense something’s off, but struggle to define when discomfort should turn into decisive challenge.

The irony?

Board members often wait for a “big enough” moment to speak up, by which point the cost of silence is already high, sometimes catastrophic.

Strong governance isn’t about being adversarial.

It’s about normalising constructive dissent before it feels courageous.

The best boards don’t rely on bravery in the moment.

They design for challenge by setting clear expectations, seeking independent information flows, and providing explicit permission to ask the uncomfortable questions early.

Challenge isn’t a breakdown of trust.

In high-performing boards, it’s how trust actually shows up.

So the real question is: does your board make challenge safe early? Or does it act heroically but too late?