madsushi posted:

I've worked with this before, what we did was include a code (like #X3010Q) in white at the bottom of the email (in the signature) that indicated it was sent from the assistant. The CEO has a rule that auto-filters anything with that word into a special "you don't have to read this" folder and auto-CC'd the assistant so she could read them. Nobody saw it because it blended in with the background. The assistant had a selection of signatures they could use, to either make sure replies were hidden, or make sure they were seen, or flagged as important when they came back, etc. So basically codes + Outlook rules.

There was a whitebox in the basement running Outlook all day to ensure that the rules were always processing (this was in the old days). We also did the same thing with the CEO's BlackBerry, using custom signatures so that he could send messages from his BlackBerry and the messages would still end up in his "Sent" folder.