Plan on doing something you don't want to get caught doing? Have something private you'd like to discuss with someone special? Careful what you type over email!

Software programs like Catorpha are out there to sift through millions of emails to look for suspicious and damning things that people type. And incidentally, some people think that by specifically NOT typing damning things (such as "let's talk about that thing we talked about before..."), they've found a loophole. Not so. In actuality, they're typing the very triggers that raise the red flags.

At a time when numerous scandals have been uncovered, or caused by, email (Wal-Mart, HP, Starwood), it's best to know how to be safe about email. Or, better yet, don't try to start an affair with the admin assistant over email, don't try to get a front-running scheme going over email, and, also (lest you want to be a laughing stock), don't email your secretary asking her to pay your dry cleaning bill after she accidentally gets a little ketchup on your pants.

Those sorts of things can spread...

Sometimes bad e-mail happens to high-achieving people. Consider Steven Heyer, the recently departed CEO of Starwood Hotels, who stepped down last month after the company's board reportedly pressed him to explain allegations of suggestive e-mails between him and a younger female employee.

An amorous e-mail is also at the center of Wal-Mart senior vice president Julie Roehm's wrongful termination suit. Fake "tracer" e-mails meant to smoke out disloyal board members played a role in Patricia Dunn's fall at Hewlett-Packard.

(Continue reading this story on CNNMoney)

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