When the CEO Wants His Hotmail

But despite the convenience of working online, wouldn't it be nice to have the luxury of an old-fashioned secretary to clean up your firm's inboxes? Someone would maintain the traditional files, store all messages arranged by client, subject and date. When something is needed, whether because a question arose about what a contract requires, a request is received to produce documents in e-discovery, or a copy of the latest or final draft of a contract is needed, it would be a simple matter of asking the secretary to assemble messages from that neatly sorted file. (Sophisticated document-management systems purport to create this result, but they are as good only as the documents that make it into the system. For reasons discussed in this article, many documents and e-mail messages might never make it there.) When all business correspondence took place on paper, in a 9-to-5 work world, that system made perfect sense.

Unfortunately, that world (and its secretaries) hasn't existed for many years. Not only do most of us not have a secretary tidying up our e-mail inbox each evening, but we also have many alternative inboxes for our business correspondence. For work, a busy executive may have an office e-mail account, a Blackberry for around-the-clock access and an online mail account (such as through Gmail, Hotmail or Yahoo!) for convenience when traveling. He or she probably also has a personal account for non-business e-mail, like jokes, that must be kept out of the firm's accounts. Going through 'the file' has become an exercise not only in finding the appropriate messages and attachments, but in simply identifying all places and accounts where 'the file' might exist. Indeed, multiple accounts often are created by employees to bypass the hassles of security measures and record-retention policies diligently created by IT departments who often diligently enforce these polices and whose employees read and apply the information in publications like this one. (My IT staff would call those hassles 'necessary inconveniences' to comply with the rules that lawyers perpetrate.) If the most convenient e-mail device ' typically the Blackberry ' is supplied by the employee herself, or by a third party, then the IT department might not know about all the accounts on which it is used, much less be able to monitor them, or apply the firm's retention or other policies.