It think it'd be his hardware or software. The ipod isnt specificly made to be compatible with a PC, make sure ur boss has all the newest software in iPod Updater and iTunes. Try turning the ipod on before plugging it in, or turning it on after its plugged and stuff like that. Also, restore the ipod and try again.
P.S. it also might be Murphies law "Anything that can go wrong, will". You boss just might be having a bad luck streak and got a couple dead ipods in a row. Good Luck!!!!!!