Why the Smartest Person in the Room Keeps Getting It Wrong

There is a particular kind of failure that only happens to competent people.

An executive with twenty years of experience looks at a recurring problem and immediately knows what is going on. They have seen it before, and they know what levers to pull. When they pull it with confidence, the room follows their lead because the diagnosis sounds right and the person delivering it has earned the benefit of the doubt from experience and a past track record of success.

Six months later, the problem is back. Not a new version of it, though it may see some slight variations. But all in all, it is the same problem.

The instinct in our life working in organizations is to assume the execution was off, or the team did not follow through, or something changed in the environment. Name the laundry list of reasons it could have not worked, and it probably will be accepted with minimal thought on the post-mortem-esque review of the problem.

But it is rare that anyone revisits the diagnosis itself. If they did, they might have found what would have worked better for those who are actually executing the idea. Or perhaps the team that did not follow through needed additional diagnosis around relational capital building to move their part across the finish line. Or perhaps even still the environmental changes could have been anticipated better with a better diagnosis process.

But because the diagnosis came from the smartest person in the room, nobody questioned it. Smart people do not get the diagnosis wrong. They get unlucky, or under-resourced, or undermined by timing. But wrong? Certainly not...

Except sometimes they are wrong.... and probably more often than smart people care to admit.

Here is a pattern that probably sounds familiar:

Someone with a high-ranking management title and deep expertise encounters a problem in their area of expertise, they reach for what has worked before. They call for more data, a better analysis and a sharper version of the framework that served them in the the last crisis or last business cycle. Thus, all of that effort is pointed in the same direction: understanding the problem more precisely so the right solution becomes clear. They drill deeper into their area(s) of expertise to better understand the problem from the lens of a microscope's lens.

But some problems do not respond to precision and narrow sight of the problem. Rather, they respond to a fundamentally different kind of optic view. I would argue you need a wide angle lens from 10,000+ feet in the sky instead of a microscope.

An expert asks analytical questions like "what is happening, and how do we fix it?" In the case of a wider and higher view, more structural questions like what is the system doing that keeps producing this outcome? Why does it make sense from inside the system that it keeps happening?"

Obviously, those are not the same questions. In fact, the nature of expertise, almost by definition, is built for the first one. Expertise makes it harder to ask the second type of questions. The more you know, the more confident your first read tends to be... and the more confident the first read, the less likely anyone is to slow down and ask whether the question itself is right.

In other words, you've dug 3-4 feet deep into a diagnosis path, when the wider view required you to be 40 yards south of where you are to dig! The structure of the diagnosis was flawed from the start. This is why structural questions are different from purely analytical ones. Structural questions ask what the system rewards, what it punishes, what feedback the people inside it are actually responding to. These questions ask whether the conditions that produce turnover are load-bearing features of how the organization operates, not bugs to be patched.

That question is uncomfortable because it often points back to decisions that senior management made deliberately and would probably prefer not to revisit. The losses those with experience face taking through such questions are more than many would care to admit, as the burden for those structures built fall on their shoulders. Thus is why inidivdual-centric leadership methodology usually does not work well for complex challenges: more people need to be a part of the process to better diagnose, intervene, experiment, and repeat.

Thus, smartest person in the room does not need better answers. Complexity almost gurantees that those answers are not going to be found from those with expertise or authority alone. Rather, the smartest people in the room to act more like Socrates: ask better (and sometimes, tougher) questions.