Thinking about this morning’s link about web forms, if you abstract why it’s so powerful, you get to the point of human-computer interaction: the computer should do what the user intends, not the buttons they push.
Matt Webb reminds us about the DWIM, or Do What I Mean philosophy in computing that was coined by Warren Teitelman in 1966. Webb quotes computer scientist Larry Masinter:
DWIM is an embodiment of the idea that the user is interacting with an agent who attempts to interpret the user’s request from contextual information. Since we want the user to feel that he is conversing with the system, he should not be stopped and forced to correct himself or give additional information in situations where the correction or information is obvious.
Webb goes on to say:
Squint and you can see ChatGPT as a DWIM UI: it never, never, never says “syntax error.”
Now, arguably it should come back and ask for clarifications more often, and in particular DWIM (and AI) interfaces are more successful the more they have access to the user’s context (current situation, history, environment, etc).
But it’s a starting point. The algo is: design for capturing intent and then DWIM; iterate until that works. AI unlocks that.

The destination for AI interfaces is Do What I Mean
Posted on Friday 29 Aug 2025. 840 words, 10 links. By Matt Webb.