ELI5

The person talks, and talks. He vehemently draws on a whiteboard, where he connects boxes with arrows. He calls things one way, he stops to reflect on his naming choices, then he erases the first choice, and puts another name. You can still read both because he hasn’t erased the first one enough. As time goes by, you stare at the board with a creeping unsettling feeling. Until your subconscious makes it a full realization: you have no flying clue what this person is trying to say. It’s been 45 minutes already and the more he goes, the less you understand. Things you thought you understood at the beginning are now back in the “not understood” basket. The basket is rapidly getting full.
You think: it’s not the language. Nor the tone. He stutters a bit, yes, but it’s not in his words. It is not the syntax. It’s in the semantics. This person is—apparently—trying to convey a meaning which you cannot decode because it remains hidden. All in all, it’s been almost an hour. You decide it’s time to nod your way out of that room, only to leave in a greater confusion compared to when you went in.

For a company to be really, really doomed, it must be in the hands of people who cannot explain what they’re saying in a clear way. Or, to be in the hands of people who cannot think in a clear way. The convoluted drawing you saw in that meeting is just a convoluted mind in motion. All by-products (slides, emails, plans, processes) will be as confusing as the random synapsis which produced the ideas. If you cannot understand this person, who happens to run the show, probably investors won’t either, or customers, or new talent.

The higher people climb in hierarchies, the more indirect the criticism gets. Therefore, someone in power with an incapacity to convey intelligible ideas will probably be unaware of it, because what they need the most in order to improve—someone telling them “what the dickens are you talking about?” in their faces—will never happen because subordinates will nod in approval for self-preservation, just like you did.

The sad destiny of a convoluted thinker with power: to only get worse because the same power that gives them the freedom to define the overall strategy is blocking them from knowing if the strategy makes any sense, or not.