In May 2023, the education technology company Chegg faced a challenge that few executives expected.
Over the years, the company has built a successful business around helping students access answers, tutoring and learning support. Its leaders had deep experience educationtechnology and customer behavior. Then AI generator entered the mainstream. For months, students have turned to ChatGPT and similar tools for many of the same needs. Chegg’s stock fell sharply as executives acknowledged that AI would fundamentally change how students ask for help.
Such stories reveal an uncomfortable truth leadership.
The problem was not a lack of expertise. The problem was that the assumptions underlying this expertise changed faster than expected.
In my work studying organizational disruption, I’ve focused on what I call Rogue Waves—sudden and impactful shifts that transform industries, markets, and organizations with little notice. These violations are rarely the result of poor management. Often they happen because successful leaders operate with mental models for a world that no longer exists.
The problem is not that expertise is important. It does. The challenge is to know when expertise is helping us and when it is quietly preventing us from seeing what has changed.
When expertise becomes a blind spot
Most leaders are rewarded for expertise. Experience allows us to understand patterns, make faster decisions, and navigate complexity. confidence.
However, experience can create what psychologists call cognitive reinforcement.
Research by Eric Dane suggests that deep experience can reduce cognitive flexibility. As our knowledge grows, we become more efficient at interpreting information through the lens of what we already know. The downside is that we are less likely to question the assumptions behind our interpretations.
In a stable environment, this efficiency is superior. In fast-changing environments, it becomes a liability.
The world changes, but the mental model remains the same.
This is not stubbornness. This is a natural consequence of how experience is built, and why the very experience that has made us successful can make it harder to recognize when the rules have changed.
Why success breeds overconfidence
Cognitive reinforcement often leads to a second problem: overconfidence.
Confidence is often seen as a leadership strength. Teams want leaders who can make decisions under pressure and communicate clear direction. But success naturally builds confidence. When a decision is made repeatedly, we trust our judgment more deeply. Over time, this belief can quietly harden into an assumption that our understanding of the situation is complete.
Research by David Dunning and Justin Krueger showed that people are often much less aware of the limits of their knowledge than they believe. Recent leadership studies consistently show that overconfidence contributes to it decision making errors, especially in an uncertain and rapidly evolving environment.
Confidence itself is not an enemy. Many developments require leaders to be willing to act in the face of uncertainty. The problem is trust without calibration – when leaders don’t ask what they’re missing.
The greatest risk in times of rapid change is not uncertainty. It is definitely built on outdated assumptions.
Leadership skills are what we really need
If experience can lead to reinforcement and overconfidence, what helps leaders adapt?
Researchers are increasingly pointing to intellectual humility.
Growing body psychological research defines intellectual humility as the ability to recognize the limits of one’s knowledge while remaining genuinely open to new information and alternative perspectives. The concept is often misunderstood. Intellectual humility is not self-doubt. It is not a lack of conviction or the ability to decide. It is a willingness to admit that even our strongest judgments may need to be revised as circumstances change.
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Expertise, in other words, is a resource, not a judgment.
The most adaptive leaders I know are not the ones who respond the most. They are the ones who continue to ask questions after they become experts. They regularly challenge their own assumptions, actively seek out irrefutable evidence, and make room for those around them to disagree with them.
Why organizations are vulnerable too
It’s not just individual leaders who are vulnerable to these blind spots. There are also organizations.
This realization led me to develop what I call the Octopus Organization, a business framework designed for companies to be more distributed, smarter, and adaptable to rapid change. Unlike traditional hierarchies that focus intelligence above, octopus organizations spread it throughout the system. Information is constantly fed back into the core decision-making process from customers, front-line employees, partners and emerging markets.
When leadership teams rely solely on their own experience, old assumptions can spread throughout the organization without being challenged. As information is disseminated and assumptions are continually tested, organizations become more adaptable to disruption.
The goal is not to eliminate specialists. The goal is to build systems where experience is regularly updated by reality.
The organizations that lead most effectively through disruption are the few that have the smartest leaders. They are the ones who learn the fastest.
Experience is not enough
The central problem of leadership in our time is not the acquisition of expertise. It knows when to question it.
The pace of changes is accelerating. Technologies are developing rapidly. Customer expectations change without warning. Entire industries can be changed in months, not decades.
Cognitive reinforcement reminds us that experience can be a blind spot. Overconfidence shows how success can create false certainty. Intellectual humility offers the way forward.
The leaders who will emerge in the coming years will not be the ones who hold on to what they know. They will be the ones who remain willing to learn – because surviving the waves of fraud requires more than experience. It requires the ability to recognize when yesterday’s experience is insufficient for tomorrow’s challenges.
