I had a boss like this and I simply handled it this way.  I told him part of my job was to keep him organized.  In order to do that he would have to help.  I set up files and folders for him to put daily stuff in, gave him cubbies to tuck things (since he just *had* to have things filed vertically) and warned him that anytime he wasn't in his office I would be putting things away.  Then anytime I saw him start to put something in a pile, or on a chair (for example, a report I new he had wanted or something he had signed and wanted back) I would tsk-tsk him and ask him (with humor) "Is that where that's supposed to be?".  It took time, but he started using the filing system I had created for him and found he liked knowing where things were and being able to see his furniture and floor.  And anytime he was out for an hour or so, I would go into his office and start filing things for him, removing piles from everywhere as I went.  I wouldn't get it all done at once, but it started to make a difference.



It sounds like your bossie would best be handled with some humor and good-natured threats.  Good luck getting him to change his spots!  From someone who's been there, I know how much work this will be for you.  Good Luck!