Email Mistakes at Work: How to Survive Them

Last Updated Dec 22, 2010 11:59 AM EST

The Scenario: "That guy was promoted to VP? That guy? The only reason he brings in revenue is because he never got married (gee, wonder why) and can stay out boozing with clients 'til half-past Jimmy Kimmel. He gets by on Tic-Tacs, Visine, and the hard work of others. Mapquest lists him as a detour on the road to success." Well said. If only you had just forwarded those observations to your buddy instead of accidentally hitting "reply all," and sending your thoughts to everyone in your work group -- including your boss.

Who knew that, in the information age, "send" would become a four-letter word? The inadvertent delivery of nasty emails to the wrong boxes (such as this list of "office hotties" at PriceWaterhouseCoopers that's making the rounds now) can be mortifying at best, job-destroying at worst.

In 2008, Stephen J. Dubner, coauthor of the bestseller Freakonomics, blogged quite openly about an email exchange he'd had with researchers he wished to interview. The exchange went bad and he wrote to his coauthor, Steven Levitt, about the "bunch of liars" he'd been dealing with. Well, he accidentally sent it to one of the liars himself.

Several years ago, CNN reported the story of Jamie Diamond, an employee at a public relations firm, who emailed his boss about how to deal with a client. His boss wrote back about the clients' incompetence and how they hindered the team's ability to get anything done. But, oops -- the clients received the email as well. They yanked their $5 million account immediately.

Accidental emails have become a sometimes amusing, sometimes nuclear subset of electronic communications. How often to people do it? In a 2008 AOL survey, 32 percent of respondents admitted to accidentally forwarding an email to the wrong person. And in a recent survey of advertising and marketing professionals, a whopping 78 percent copped to the same mistake (individual responses described multiple instances of folks losing their jobs over scathing mistake emails). Email blunders occur so often that there are whole message boards devoted to them.

"This happens more than we want to think about because it's so easy to do," says Alison Doyle, a job search expert for and author of Internet Your Way to a New Job. "There still seems to be a false anonymity or safety factor with email. Plus, when Outlook starts auto-filling the 'to' field, it's easy to get the wrong person or group in there."

So what should you do if a white-hot set of your choicest words lands in the wrong inboxes? Here's your action plan:

1. Forget About Retrieving It

You can't "unsend" an email. "That's a farce," says David Gitkos, vice president of forensic services for Global Digital Forensics. "It'll put a red line through it on the receiver's screen, but once someone receives it, it's there, they have it." Then he chuckles. "Unless you go to their computer and delete it." Which is an idea but a little George Costanza-like in its desperation. In rare cases -- say a high-level employee accidentally sends out highly sensitive company secrets -- an IT administrator could theoretically go into individual company mailboxes remotely and delete the email. But unless you sign the annual report, that's probably not an option.

If your company uses Gmail, you do have access to a new feature that allows you to cancel sent email, but you'll have to set up the option ahead of time -- and realize your mistake quickly. Log in and click on either the green "Labs" beaker or "settings." In "Labs," scroll down to "Undo Send" and enable it. Then whenever you send a message, you'll be given an option to "Cancel" at the top of the message before it's sent. It's really just a 30-second send delay, but if you need to bail on an email in that crucial half-minute, you can.

2. Ignore It

What? Really? Yes, says Doyle -- at first. Don't go running to the mistaken receivers and draw attention to something they may not have even seen. "In the average company, people get a huge volume of email," says Doyle. "It just may get lost in people's in-boxes." Meanwhile, for those who have seen it, depending on the tone and language you used, their reaction may not be as severe as you think. So wait for the reaction. If it causes an even moderate uproar, you'll know soon enough. And that's when you

3. Apologize -- but Only to Your Boss

Again, this is all about pacing yourself and not panicking. If you immediately send out a gushing apology email to the same big group, all you're doing is emphasizing a blunder that a good portion of them may not have considered a big deal. "The more you focus on it, the more attention you draw to it," says Doyle. So talk to your boss, be contrite, and again wait to see what happens. If the negative responses come in and it's clear you need to do more -- and boy, will you know! -- then you can

4. Do the Full Letterman

Dave's on-air apology to viewers after his extramarital indiscretion was a model combination of self-deprecation and class. And yours will be, too, if you go face-to-face with the people you've offended. Don't tempt fate by trying to do it via "reply all."

Depending on the brand of email you initially sent -- for example, criticizing the company or its management -- you could be facing discipline or dismissal. If that's the case, it might benefit you to mix your apology with business, says Doyle. Your mea culpa should include your version of the following delivered in a serious, professional manner: "Look, you can't hear tone of voice in an email. I clearly hit the send button too soon and it was a lousy way to say what I said. But I think it's a legitimate problem and I'd like the opportunity to clarify and expand on what I was talking about." Depending on how much you've pissed people off, and particularly if the offending email is personal, this may not fly. But you have nothing to lose and if you show that you're an adult about how you're handling a juvenile act, you just may be heard.

Meanwhile: Make Sure This Never Happens

Of course, crisis management wouldn't be necessary had there been no crisis. Part of the problem, says Gitkos, is that people have no understanding of what work email is, how it's designed, and why. First off, it's supposed to be about allowing the business to function better so it can make more money. A crazy concept, to be sure, but when you boil it down to that one truth, you see how all the personal emails flying around begin to sap company resources -- and why companies monitor employee email use. "The company owns that email," warns Doyle. "And they do audit."

There's more. As a computer forensics expert, a big part of Gitkos' job is retrieving what could eventually become evidence in litigation. Companies deliberately design their information infrastructure to make sure the business is protected at all levels. Most corporate email goes through the company's server before it arrives at its destination. Which means that even if the sender and recipient delete it from their machines, a copy will exist on the server for as long as the individual company policy dictates. They also archive older emails. "Every one of your emails will probably be around for a very long time," he says.

The smart play: Minimize or eliminate personal use of work email. "You don't have to retract it if you don't say it in the first place," says Doyle. Setting up a personal Gmail account isn't that hard. And when you do send something? Assume the entire company will read it.

"I've been doing this for 26 years," says Gitkos. "Take some good advice: If you don't want someone to see something, don't put it in an email. Because someone always sees it."

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