Similar to https://en.wikipedia.org/wiki/Wikipedia:How_to_run_an_edit-a-thon or http://www.meetup.com/sfhtml5/events/232261764/ but just for our leadership team and maybe only a couple hours, not a whole day. Could be virtual and/or in person.
The goal would be to proofread any existing docs, hash out details of half-finished ideas, and plant the seeds for any new ideas.
Doing this in a social setting would make this somewhat boring/tedious task of documentation more fun :) Plus it's hard to make time to do this sort of thing regularly so a short burst of work could be a good way to spark some motivation here.