E-mail may be hazardous to your career

Careless e-mailing has brought down some high-flyers. Fortune shares tips on how to keep safe.

By David Shipley and Will Schwalbe, Fortune

(Fortune Magazine) -- Sometimes bad e-mail happens to high-achieving people. Consider Steven Heyer, the recently departed CEO of Starwood Hotels (Charts, Fortune 500), 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 (Charts, Fortune 500) 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 (Charts, Fortune 500).

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Starwood Hotels CEO Steve Heyer stepped down amidst allegations of suggestive e-mails.

And e-mail doesn't ensnare just the top brass. Richard Phillips, an IT specialist at the London law firm of Baker & McKenzie, reportedly sent his secretary an e-mail demanding she pay the £4 dry-cleaning bill he incurred after she spilled ketchup on his pants. The secretary chose to forward the e-mail to colleagues, and Phillips soon became tabloid fodder as "Ketchup Trousers."

For most of us, common sense and good values keep such problems at bay. But there are plenty of gray areas when it comes to e-mail, and even sensible executives - the ones who stayed awake in the HR training sessions - can be tripped up by an unintended nuance or other inadvertent slip. Fortunately, following a few surprisingly basic rules can help.

The first step is knowing what investigators look for. The latest software doesn't just hunt for obviously hot words and phrases like "insider trading" or "Let's break the law tomorrow at 3:47." Cataphora, a company that helps lawyers mine data in cases where millions of e-mails need to be analyzed, uses software that searches for more subtle tendencies: language that seems intentionally vague ("that thing we talked about") and word combinations that indicate worry ("can't sleep," "confused and bewildered," "regret"). A smoking gun from an investigation involving corporate fraud in the software industry: "Can we talk about that thing we talked about the other day when we spoke about that other thing? When I was visiting you? It's quite urgent."

It is not just the words themselves that companies are examining but any shift in e-mail habits. One investigation was launched when an accountant who normally e-mailed between the hours of nine and five started corresponding in the middle of the night. "Since you can never tell when you might find your company and yourself in the midst of litigation," says Cataphora CEO Elizabeth Charnock, "you want to do everything you can to keep your e-mail from being subject to the type of scrutiny we can bring to bear."

Even the seemingly innocent subject line can cause grief - particularly if you don't change it every time you move on to a new topic. Let's say you put Company X in your subject line in January. And let's say, like many of us, you keep that subject line in place, even though you aren't e-mailing about Company X anymore. Then let's say that Company X gets in big legal trouble in April. All your Company X e-mails - even those that have nothing to do with Company X - could be scrutinized.

In one white-collar criminal case, the people under investigation wrote about work and their fondness for bondage in the same correspondence thread. Bondage had little to do with the matter at hand, of course, but because it was mentioned in the suspicious e-mails, it became far more public than the senders might have intended.

The further business gets from an industrial workplace, the more workers underestimate the dangers of technology, particularly e-mail. Imagine if there were a piece of machinery, one that made it easy for an employee not just to hurt himself but also to bring down an entire organization. Corporations would restrict its use to a few impeccably trained operators. That's not possible, of course, when it comes to e-mail. Its ease lulls us into being unaware of its danger - until we end up with ketchup on our trousers and egg on our faces.

David Shipley and Will Schwalbe are the authors of Send, a new guide to e-mail.  Top of page