A topic comes up that nobody in the room actually works in. Someone offers a framing. It's clean, the analogy is familiar, and within ninety seconds, the group has agreed on what the problem is, what it should cost, and why it isn't already fixed. The practitioner in the room, if there is one, says nothing.
The easy read is Dunning-Kruger, and it's not wrong, but it misses what's going on. These people aren't dumb. They got to those rooms by being good at pattern-matching from a high level, and that works fine when the new situation really does look like the old ones. The same instinct that makes executive judgment fast makes it brittle in the cases where slowing down would matter most.
Compression Is the Job — and the Problem
Executive work runs on compressed stuff. The deck, the one-pager, the steerco update, the hallway summary. Compression is the job. A CEO who wanted the full unedited version of every decision would be useless inside a week. But compression is lossy, and the parts that get lost aren't random. What gets dropped is whatever doesn't fit the model already in the room, because that's the part that doesn't land when you present it. The person building the deck learns which slides survive and which get skipped, and adjusts. Over time, the work product of executives selects against the information that would correct executive mistakes.
The Signal That Never Arrives
The second-order problem is the one that does the real damage. The people closest to the work usually know when the simple version has drifted from reality. They usually decline to say so. Telling a board that something is more complicated than they think reads as making excuses, or empire-building, or not being a team player. So the practitioner nods, takes the frame, and eats the gap privately. The board never gets the signal that would correct them. Their confidence in the simple model gets deeper because, from where they sit, it keeps getting confirmed.
Looking Valuable vs. Being Valuable
Underneath all of this is something simpler, and it's worth saying plainly. The pressure to add value — or at least to look like you're adding it — is what drives most of the bad behavior in these rooms. Nobody wants to be the executive who sat through a forty-minute discussion and said nothing. So they say something. And the fastest way to say something is to offer a conclusion, because conclusions sound decisive and questions sound unsure. The room rewards saying a dumb thing that sounds smart over saying nothing at all.
This is backwards. The actual value of a board or an executive has never been their conclusions. When one of my people brings me a problem, I expect them to bring a solution with it. That's their job. My job is to ask the questions that pressure-test the solution in real time, using whatever breadth of experience I have that they don't. The information flows up, and the scrutiny flows down. The executive who tries to supply the information, too, is doing both jobs badly — and usually doesn't know it.
"What Do You Think?"
One of the moments that shaped how I think about this happened years ago, in a room I was sitting in during merger discussions. The CEO of the company being acquired got hit with a hard scenario. I don't even remember what it was anymore. What I remember is what he did. He turned to someone on his team and asked, with no edge in his voice, "What do you think?" It wasn't a trap. It wasn't a test. He genuinely wanted to know, because that person knew something he didn't, and the room needed the answer more than it needed him to look like he had it. That moment has stuck with me ever since, and it's framed one of my core behaviors as a leader (at least I hope it has).
The fix is mostly about self-awareness, and it's not glamorous. An executive — or any manager — who can sit without having an answer and use that to ask a better question is worth more in a room than three who can't. The urge to fill the silence with a conclusion is the urge to look valuable instead of being valuable. Humility here isn't a soft virtue; it's a working tool. It's what lets you get to the right answer through the people who actually have it, instead of stepping on them with the wrong one because the room expects you to say something.
Postscript. The merger referenced earlier didn't happen. The CEO on the other side of the table was everything the first guy wasn't — bravado, arrogance, noise. At the eleventh hour, the other leadership team pulled the plug. Not over price or terms. They pulled it because they couldn't stomach working for a blowhard. I watched a deal die because one man couldn't stop talking long enough to let anyone else be right.
