Usually, they just contact the player who's number is retired and unretire it for a short amount of time... if he's still alive, of course.
Happend with Jerry Rice for instance. He asked Steve Largent to use nr. 80 for one season and got permission to do just that. It happened more often, but I can't think of any more examples right now. The players themselfs don't seem to take retired numbers as heavy as some fans do.