What the Assistant Can See

Go back to the brilliant stranger. For each reply, everything they can use has to be on their desk at once: your message, any files you have added, notes the app has saved, the conversation so far, and room for the reply they are about to write. That desk is the context window, and its size is measured in tokens.

Two things follow. What isn’t on the desk doesn’t exist for this reply, however much you have told the app before. And the app puts things on the desk you never see: its own instructions about how to behave, and sometimes saved notes or search results.

In modern assistants the desk is large, often big enough for long documents. But as you are about to see, a bigger desk is not the same as a better-read one.