The Bravery of Being Wrong

Every CEO knows the moment. The strategy has been announced. The deck has been presented to leadership. The organization has been rallied. Targets have been set, compensation plans aligned, and resources committed. The plan is out.

And then reality gets in the way.

Markets shift. Execution friction appears. Customers behave differently than forecast. Sales don’t materialize as expected. A few early indicators start flashing yellow or red. At this point, CEOs face a defining test of leadership where intelligence, experience, or preparation play a role, but it’s bravery that guides the outcome.

After decades of advising leadership teams, one truth is consistent. No strategic plan is 100 percent correct out of the gate. Not annual strategies. Not major operational changes. Not reorganizations. Not new compensation models. Strategy is a hypothesis, not a certainty. The best leaders know this going in. The most effective leaders act on it.

The bravest CEOs understand that strategy does not end when the plan is approved. That is where it begins. They treat execution as a learning process. They watch closely. They listen deeply. They adjust deliberately. Sometimes the adjustments are small and tactical. Sometimes they are material and structural. What matters is not the size of the change, but the willingness to make it.

What separates strong CEOs from struggling ones is not whether the original plan was perfect. It is whether the CEO has the courage to respond honestly to what the organization is telling them.

Less effective CEOs often fall into a dangerous trap. When results do not match expectations, they cling to the plan more tightly because changing it feels risky. They worry that acknowledging flaws will make them look weak. They say things like, “I sold this plan. I cannot change it now,” “we need more time”, or “If I pivot, people will lose confidence.”

In reality, the opposite is true.

Organizations lose confidence when leaders ignore evidence. They lose respect when leadership insists on certainty in the face of contradictory data. Employees, boards, lenders, and investors can tolerate change. What they struggle to tolerate is denial.

Jeff Bezos offers a powerful example of this kind of leadership courage. In Amazon’s early years, the company expanded into too many categories and products at once. That expansion left Amazon with costly unsold inventory, the result of overly optimistic bets that did not pay off. Bezos has openly acknowledged these mistakes rather than trying to rewrite history.

More importantly, he institutionalized the lesson. Bezos has repeatedly said that experimentation and visible failures are essential to innovation. He has argued that Amazon’s scale of success is directly tied to the scale of its failed experiments, from initiatives to products that never worked. Instead of protecting the original plan, he defended the organization’s ability to learn and adapt.

Just like Bezos, the most respected CEOs do not frame adjustments as failures. They frame them as leadership in action. They say, “Here is what we believed. Here is what we are seeing. And here is how we are adapting.” That posture builds trust, signals strength, and demonstrates that the CEO is committed to outcomes, not ego.

From a CFO’s vantage point, this matters enormously. Capital allocation, incentive design, and operating leverage all depend on feedback loops. When CEOs are willing to adjust early, before underperformance compounds, the organization preserves optionality. When they wait too long, the cost of change becomes exponentially higher.

Great CEOs are not reckless pivoters. They are disciplined adapters. They create space for learning. They establish clear metrics, review them relentlessly, and act decisively when assumptions prove wrong. They understand that the willingness to course correct is not a sign of indecision. It is a sign of mastery.

In the end, the bravest thing a CEO can do is detach their identity from the plan. Strategies are tools, not reflections of self-worth. The leaders who recognize that, and who are willing to be wrong in service of getting it right, are the ones who build enduring organizations.

That is leadership.