I also find that hypothetical "interns" are great for this. Something about "this person without a degree, who probably hasn't been working for very long, who doesn't know your organization or who to ask, and is probably very scared of looking or sounding stupid."
It doesn't necessarily imply or require stupidity, but in my experience on both sides of it (writing docs now, and having been that intern), they actually make pretty great litmus tests for documentation and how accessible organizational knowledge is.
It doesn't necessarily imply or require stupidity, but in my experience on both sides of it (writing docs now, and having been that intern), they actually make pretty great litmus tests for documentation and how accessible organizational knowledge is.