Tell me what I do not know that I do not know

Tell me what I do not know that I do not know.

That sits just behind please advise me on the trade-offs as the thing I ask most. It is worth explaining why it works, because the reason is older than the technology.

In February 2002, a year before the invasion, Donald Rumsfeld was asked what evidence there was that Iraq was handing weapons to terrorist groups. There are known knowns, he said. There are known unknowns, the things we know we do not know. And there are unknown unknowns, the ones we do not know we do not know.

People laughed at the way it sounded. It is one of the more useful things anybody has ever said about making a decision.

Very little goes badly wrong in the first two boxes. A known known you act on. A known unknown you go and find out, because you already have the shape of the question. You can search it, read it, or pay someone who has the answer.

The damage lives in the third box. You cannot look up a thing you do not know exists. You cannot search for what you never thought to ask. Every search engine ever built needs you to already know roughly what you are after, which makes all of them useless in the one place you need the most help.

That is the box this prompt is for. I give it the whole picture and ask for the gap. Here is what I am about to do. Here is what I know. Here is what I know I still have to find out. What is missing from that list?

What comes back is almost never clever. It is the plain question nobody in the room asked. Who else has to say yes before this can happen. What does this cost me in month seven. What breaks if the one person who understands it stops answering the phone.

Then it is obvious. That is the whole point. It was always going to be obvious once somebody said it out loud. Nobody said it.

Slavoj Žižek later pointed out that Rumsfeld had left out a fourth box: the unknown knowns. The things we do know, and quietly refuse to admit we know.

No prompt will reach that one. That one is yours.