In a previous post we saw that it’s all too easy for your email to find its way to people you hadn’t meant it for. So, what can you do when sending a sensitive message, to prevent such embarrassment (or worse)?

Here are some tactics to consider:

• You can put in the message an explicit plea for discretion, such as “For your eyes only” or “DO NOT FORWARD”. You can also put “[Private]” in the subject, though that may draw the attention of hackers and people passing by an unlocked PC in the recipient’s absence. But of course, this is only a first line of defense…
• Before hitting SEND, read through the To and CC fields carefully – make sure you’re sending to whoever you think you are. This is especially true if you’re mailing to a mixed group having people both internal and external to your company.
• Be proactive: formulate sensitive messages as if you know they’ll leak. For instance, remove the “tail” of earlier exchanges, and then allude to it indirectly: don’t say “I agree with you that it was probably George who stole Jennifer’s wallet from her office, he always seemed dishonest to me”; say instead only “I think you’re right about what happened, and I’m not surprised, knowing the person involved”. Your correspondent will know what you mean, but if she accidentally shares your message no one else will.
• Encrypt any really sensitive information in a file and attach it to your email. And don’t rely on Pig Latin; there are powerful encryption tools available out there!
• And despite all that – you should always assume that sooner or later your mail will be shared with people you hadn’t intended to see it. If you can’t accept this risk at all, don’t send the message via email – period!

Lastly: you are a recipient yourself. Protect your friends and coworkers by not disclosing their messages to others, unless you’re sure they’d approve. Do unto others…