Doh! The Most Disastrous E-Mail MistakesWant some light entertainment? Check out our readers' true tales of e-mail faux pas, and find out how to prevent them from happening to you.
What's in an e-mail? Potential disaster, that's what. With the click of a mouse, you can accidentally broadcast that torrid note to 200 coworkers, forward a catty message about your boss to your boss, or send several thousand customer credit card numbers to, um, the journalist writing this story.
There are probably 8 million similar stories in the Naked Internet. PC World invited readers to share their most embarrassing moments (or somebody else's). Gathered here are ten tales of e-mail gone awry that will make you think twice before clicking Send. In fact, after reading these cringeworthy confessions, you may want to toss your PC and go back to carrier pigeons. Or clay tablets.
The following stories show just how mortifying (and funny) errant e-mail can be. For obvious reasons, the names of the individuals involved have been omitted. But believe me, I'm not making these up.
Death of a Salesman
"A very successful salesman at our networking company had a large e-mail address book filled with his best customers, including some very important and conservative government contacts. With a single click, he accidentally sent a file chock-full of his favorite pornographic cartoons and jokes to everyone on his special customer list. His subject line: 'Special deals for my best customers!' Needless to say, he's cutting deals for another company these days."
Slip Into Something Comfortable
"An editor at my magazine was discussing with an office pal via e-mail what to wear for her big romantic date with the new boyfriend. Unfortunately, she inadvertently copied everyone in the office about her dilemma. She got fashion advice ('Wear the silk teddy with the explosive bolts!') for weeks afterward."
Big Brother Is Reading
"Two jobs are better than one--if you can work on the second job while at the first. That's what my former boss, an event planner for a nonprofit, did to pad her already fat salary. She blithely organized a seminar for job number two using the e-mail system at job number one. To cover her absences from job number one, she invented a serious illness for her saintly mother, who just happened to be at death's door the day the seminar took place. Our heroine, however, never made it to her mom's bedside--her boss checked the e-mail server and read a few random messages. Our plucky heroine is now pulling down unemployment."
Secrets From the Spreadsheet
"A helpful HR person at my company sent an employee phone extension list to everyone at our company. But the spreadsheet had hidden columns that were easily unhidden to reveal everyone's pay, bonuses, and stock options--including senior management's. Luckily, she had a new job lined up."
The Deadly Reply All Button (Part One)
"The insurance company I work for maintains an internal mailing list devoted to one of our customers. One day, one of our sales reps sent an e-mail to everyone in my group asking about a policy we were selling. I replied that we could easily convince the customer to buy it--even though the customer didn't need it. Unfortunately, I clicked Reply All. Hiding in that massive list was the customer's e-mail address. We didn't make the sale."
The Deadly Reply All Button (Part Two)
"A woman was in torment over a busted romance. She wrote a lengthy, detailed message to a girlfriend, adding that her ex-boyfriend preferred men to women. But instead of hitting Reply to a previous message from her girlfriend, she hit Reply All. Her screed was sent to dozens of people she didn't even know (including me), plus the aforementioned ex and his new boyfriend. As if that weren't bad enough, she did this two more times in quick succession! I finally wrote to her and told her about her addressing problem."
Third Time's a Charm
"I received an e-mail from an assistant at a competing consulting firm, CC'd to the firm's entire e-mail address book. What a piece of luck. Now I know who all of their employees, associates, and many of their clients are. Attached was a proposal to one of their clients, so even better: Now I know how much they charge. Several hours later, I received another e-mail from the assistant, again CC'd to everyone, with a revised proposal. The next day, I received a third e-mail from the assistant: 'Please ignore the previous e-mails.'"
"A troublesome employee in my department sent me an e-mail saying he wouldn't make it in to work because of a sudden death in the family. He said that he would be flying out to the East Coast for a few days. He'd been less than honest with me in the past, so he attached an airline itinerary as proof. Except the itinerary showed his destination to be Hawaii! When he came back, I innocently asked, 'How was Hawaii?' 'Wonderful,' came the reply, followed by 'Oh $#@%@$%!' He very quickly found a new job and left the company."
P.S. Your Cat Is Dead
"I've been using e-mail since the days of MCI Mail. I've suffered through flaky service, flame wars, e-mail rants from customers, and yes, stupid e-mails I never should have sent. But I never expected e-mail to pierce my heart.
"I met her at a company picnic, we traded stories about our repressed childhoods, and we soon became a couple. On a Sunday six months later, I proposed and she accepted. On a Thursday four days later, she broke up with me--via e-mail. She sat four cubicles down the hall from me.
"I now insist that women reject me in person. It saves Internet bandwidth."
Do you want to avoid becoming one of the embarrassing stories in the Naked Internet? Check out "Seven Rules for Gaffe-Free E-Mails."
Seven Rules for Gaffe-Free E-Mails
E-mail is like a digital postcard--anyone can read it. Of course, that doesn't mean you have to send that postcard to everyone on the planet. But with instant communication can come instant e-gaffes. One wrong click can drop your career or your reputation into the dumpster. Follow these rules to save yourself from embarrassment.
Rule 1: Always check the To field before you click Send.
Rule 2: Always check the To field before you click Send.
Rule 3: Always check the To field before you click Send.
Rule 4: Remember the carpenter's rule, "Measure twice, cut once," and think twice before sending once. In other words, put that message aside and let your temper (or lust) cool before you send it.
Rule 5: Use draft folders with caution. No matter what e-mail program you use, it can be easy to send an e-mail in progress by accident. Save that hot-and-heavy note on a floppy--and lock it in a vault.
Rule 6: Old news can become bad news. Find your inner Yoda (or inner editor) and pause before you write something that could come back to haunt you later. In short, avoid future embarrassment by not writing anything even remotely off color or off the cuff. When in doubt, hit the Cancel key instead of Send--and remove anything potentially mortifying. Remember, too, that deleting sent e-mails on your system is only half the story; they could be sitting out there on some server, just waiting for a subpoena. (Remember the ancient e-mails exhumed for Microsoft's antitrust trial?)
Rule 7: Don't make jokes or comments via e-mail that you wouldn't make in person. "E-mail can be a minefield of unintended insults," says Judy Heim, communications maven and longtime PC World writer. "I've stopped wisecracking in e-mail. It's too easy for comments to be misconstrued."