There are differences between how experts make decisions and how novices do. Gary Klein has studied decision-making, and his results have been somewhat counter-intuitive. (All of the quotes in this article are from his book Sources of Power)

Before we did this study, we believed that novices impulsively jumped at the first option they could think of, whereas experts carefully deliberated about the merits of different courses of action. Now it seemed that it was the experts who could generate a single course of action, while novices needed to compare different approaches.

Take the typical startup. In many cases, many people have been hired into roles to be generalists. When you only have a few people, everyone needs to do everything. At this stage, being good at your job means powering through to find an answer in every situation and usually means comparing all the choices available to you.

While this can often get the job done, in the longer term, people may be unprepared for what arises or have built solutions that lead to difficult circumstances.

An expert may have been able to act more quickly and would have had a better sense of what to do or not do. They would have understood the risks and long-term implications. Thinking long-term is not usually an option at the startup stage, nor is hiring an expert for every part of the business. And this works ok. The problems come later when the company has hit the next stage.

At the next stage, you turn from survival to scalability, and being able to under the future implication becomes critical.

The ability to see the past and the future rests on an understanding of the primary causes in a domain and the ability to apply these causes to run mental simulations. This is one way to distinguish true experts from people who pretend to be experts. The pretenders have mastered many procedures and tricks of the trade; their actions are smooth. They show many of the characteristics of expertise. However, if they are pushed outside the standard patterns, they cannot improvise. They lack a sense of the dynamics of the situation. They have trouble explaining how the current state of affairs came about and how it will play out. They also have trouble mentally simulating how a different future state from the one they predicted might evolve.

Time and time again, I have seen successful startups hit this challenge. The people that got them to that first stage of success will not be the ones that will get them to the next. The great scrappy PM that you hired right out of college who got the first product shipped is unlikely to be a great CPO. The talented engineer that built your prototype is unlikely to be a great CTO.

What is worse, the lack of experience in these more senior roles means they often can’t see what they are missing.

Experts can detect differences that novices cannot see, cannot even force themselves to see.

This leads senior executives to ignore and doubt experts because they can’t see it themselves.

[Experts] understand what types of goals make sense (so the priorities are set), which cues are important (so there is not an overload of information), what to expect next (so they can prepare themselves and notice surprises), and the typical ways of responding in a given situation.

This certainly doesn’t mean expertise should not be questioned. It should. But it does mean that experience and expertise matter, and it can be difficult to see patterns without them.