Adventures in e-mail
Getting past the oops moment: Think before you hit "send."
By Donna Rosato, MONEY Magazine staff writer

NEW YORK (MONEY Magazine) - You dash off a scathing e-mail complaining about your boss to your co-worker -- but you send it to your boss by mistake.

Don't let the boss find you first. When Yvette Martin's manager at a bank in Austin chewed her out for a mistake that was the manager's fault, Martin vented in an e-mail to a co-worker. A few minutes later, Martin stopped by to ask her friend if he thought the missive was too harsh. The co-worker's response: "What e-mail?" Just then the manager showed up fuming.

For Martin, it was too late. But the moment you find out the wrong person received the e-mail, walk directly to that person's office, apologize and explain yourself. If she's not there, wait.

Since you're busted, you might as well air your grievance. Tell your boss that you regret what you did but that there's a legitimate gripe behind it. When another manager dragged his feet on an urgent request that Bill Tookoian made for a client of his communications firm, Tookoian fired off an angry e-mail complaining to his boss -- and accidentally cc'd the offending manager. Both recipients were upset, but Tookoian took the opportunity to improve the way requests were processed across the firm.

"That e-mail opened up communication on an important topic and changed how things were done," he says. "That enhanced my reputation as a get-it-done guy." Tookoian is now a senior account executive at that same firm in San Francisco.

Just say no. Still, the best option is to not lambaste anyone in an e-mail.

An e-mail from one of your underlings lands in your inbox by mistake. It describes some of your, shall we say, negative personality traits.

Suck it up. If the criticism is fair, consider this a chance to find out what your employees are saying about you.

"It takes real courage, but have a conversation with whoever sent the message about what it says," says Shotwell, the Taleo executive.

A workaholic client whom consultant Barbara Moses worked with accidentally got an e-mail from an employee complaining about his bad habit of dumping work on people at the last minute. He met with employees individually and asked for their feedback.

"He said it was a real wake-up call for him," says Moses. "This was someone who was really disorganized, and it made him a better manager."

Issue a warning. That's all very nice, but tell the numskull who sent the e-mail to be more careful next time.

You receive a confidential e-mail -- about someone else's salary -- by mistake.

Alert the sender. Maybe he's not aware of what he did, but he might figure it out later and wonder why on earth you didn't tell him, says Darnell Lattal, a psychologist and the author of Ethics at Work.

Reassure him. Tell him you saw only enough to figure out that the e-mail wasn't meant for you. Promise to keep the information to yourself. Then tell the first five people you see.

Just kidding.

How to deal with:

Public speaking gaffes, the boss factor, interview irregularities, adventures in e-mail and eating on the jobTop of page

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