It is easy when living in the technical world for so long to come to a technical answer to a social problem. For instance, when faced with a scenario when someone writes an e-mail that is addressed internally the pokes fun at a customer should the e-mail be deleted from the server or not? What are the risks of the e-mail inadvertently being forwarded to the customer? What are the risks of e-mails mysteriously disappearing from inboxes? These are things to consider and you will notice that neither of the risks have anything to do with technical solutions. Admittedly, my first reaction to the scenario was deletion. This is correct right, avoid damage to the customer relationship, and it should be relatively simple for the sysadmin to accomplish. Besides, the inboxes of employees are not their personal property it belongs to the company. At the guidance of my PHB, who by the way I have 9 days of wise experience on, I realize my first mistake was the jumping to the technical solution, deletion, then having the authoritarian view that puts people in a workplace at odds with each other. Not a good way to build teams of people built on trust and respect. Also it is not a good way to lead. First I should have assumed the message is already "in the wild" and it is not coming back. Then speak directly to the person that sent that e-mail and recommend they send out an apology for getting carried away. Understanding when a problem is social versus technical is a crucial skill of a technology leader. Even more so than in any other field because we are so immersed in the technical.