If you have some kind of build process in place, like continuous integration, you could have that build fail if (at least) the auto-generation of documentation (like javadoc/phpdoc/doxygen) fails or reports problems.
(And send a mail to the whole team about it ; no-one likes being the breaking the build ^^ )
That obviously only works for javadoc and the like... But that's a start ; and I've noticed that many developpers (includin myself :-( ) don't maintain that as much as they should...
At work, I'm currently working on a project with developpers in several cities ; we have a wiki in which we post stuff... And we noticed the same kind of problem you are reporting...
One thing we did to help with that is that now, when someone creates/updates a wiki-entry, he speaks about it on the IRC channel we all are.
This way, other developpers know there's been an update, they know there is an entry about that stuff, and they often go check it out.
It is more motivating to know people will go read the documentation you've written than telling to yourself "why would I take time to write documentation when no-one ever reads it?"
Another way is to considered an outdated/wrong documentation entry as a bug, and report it and track it alongside other bugs in the application (using the same bugtracker that is used for any other bug).
It will make those problems notices -- and no-one wants to have bugs in parts of the application/documentation he is responsible of ;-)
Unfortunatly, just saying "we need an up to date" documentation is never enough...
Documentation has to be considered as one part of the project, the same way the code or the GUI is. And that means treating it like a real part of the project!