Don't: Email anything you know violates companies policies and include the line "this probably massively violates the HR equal opportunities policy." Holly Leam-Taylor knew the email was a fire-able offense but in "good fun" she sent an email to female co-workers asking them all to rate the "fittest boys" in the office. Within hours it had been leaked to the world and Leam-Taylor quickly resigned.
Do: Assume every email you send to co-workers could potentially end up in the inbox of your boss, HR and half the world. These days, it can.
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