In May 2023, education technology company Chegg faced a challenge few executives anticipated.
Over the years, the company has built a successful business helping students with feedback, tutoring and learning support. Its leaders had deep experience educationtechnology and customer behavior. Then generative AI entered the mainstream. Within months, students started turning to ChatGPT and similar tools for the same needs. Chegg’s stock has plummeted as executives acknowledge that artificial intelligence is fundamentally changing the way students seek help.
Stories like these reveal an unpleasant truth leadership.
The problem was not lack of experience. The problem is that expertise-based assumptions have changed faster than anyone expected.
In my work studying organizational disruption, I focus on what I call Rogue Waves—sudden, high-impact shifts that reshape industries, markets, and organizations with little warning. Such disruptions are rarely the result of poor leadership. Often they arise because successful leaders operate with mental models built for a world that no longer exists.
The issue is not whether specialization is important or not. This will do. The challenge is to know when experience is helping us and when it is silently hindering us from seeing change.
When expertise becomes a blind spot
Most leaders are rewarded for experience. Experience allows us to recognize patterns, make faster decisions, and manage complexity trust.
However, over time, 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 what we already know. On the downside, we are less likely to question the assumptions behind our interpretations.
In a stable environment, this efficiency is an advantage. In a rapidly changing environment, 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 created, and why the very experience that helped us succeed can make it difficult to recognize that the rules have changed.
Why success breeds overconfidence
Cognitive reinforcement often leads to a second challenge: overconfidence.
Confidence is commonly seen as a leadership strength. Teams want leaders who can make decisions under pressure and communicate clear direction. But success naturally breeds confidence. When a decision works over and over again, we become more confident in our opinion. Over time, this belief can quietly harden into the assumption that our understanding of the situation is complete.
Research by David Dunning and Justin Kruger showed that people are often less aware of the limits of their knowledge than they believe. Recent leadership research consistently finds that overconfidence contributes decision making errors, especially in an uncertain and rapidly evolving environment.
Trust itself is not the enemy. Much success requires leaders to be willing to act decisively in the face of uncertainty. The problem is trust without calibration—when leaders stop asking what’s missing.
The greatest danger in times of rapid change is not uncertainty. This is, of course, based on outdated assumptions.
The leadership skills we need
If experience becomes reinforcement and confidence becomes overconfidence, what will help leaders adapt?
More and more researchers point to intellectual humility.
the growing body of 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’s not insecurity or indecisiveness. We are willing to admit that even our strongest conclusions must be revised when circumstances change.
Essential Readings in Leadership
Expertise, in other words, is a resource, not a judgment.
The most flexible leaders I know are not the most responsive. Even after they become experts, they continue to ask questions. They regularly challenge their own assumptions, actively seek out counter-arguments, and make room for those around them to disagree.
Why organizations are also vulnerable
Individual leaders are not susceptible to these blind spots. So are organizations.
This realization led me to develop a business system, which I call the Octopus Organization, to make companies more distributed, smarter, and able to adapt to rapid change. Unlike traditional hierarchies that concentrate intelligence at the top, octopus organizations distribute it throughout the system. Data is constantly fed back into the key decision-making process from customers, front-line employees, partners and emerging markets.
When leadership teams rely only on their own experience, outdated assumptions can inevitably spread throughout the organization. Organizations are more adaptable to disruptions when information is shared and assumptions are constantly tested.
The goal is not to destroy the experience. The goal is to create systems where experience is constantly updated by reality.
The organizations that manage disruption most effectively rarely have the smartest leaders. They are the fastest learners.
Expertise is not enough
The leadership challenge of our time is not one of experience. It knows when to question.
The pace of change continues to accelerate. Technologies are developing rapidly. Customer expectations change without warning. An entire industry can be transformed in months, not decades.
Cognitive reinforcement reminds us that experience can become a blind spot. Overconfidence shows how success can be a false confidence. Intellectual humility leads the way.
The leaders who thrive in the coming years will not be those who cling to what they know. They’ll be the ones willing to learn – because surviving rogue waves takes more than experience. It requires the ability to recognize that yesterday’s experience is insufficient for tomorrow’s challenges.
