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http://steamcommunity.com/sharedfiles/filedetails/?id=1305770507
just replay it and leave it running . . don't do anything (be employee of the month)
Then replay it and you should be able to get that diamond :)
this worked for me at least.
I've had the same glitch for the same challenge but 2nd play though with the challenge, it worked and looking at the other comments, this is glitch very common. Happy I'm not the only one.