World's Worst E-Mail Gaffes, Read 'em and Reap Some Lessons

Nov. 16, 2009— -- There's a new contender for the worst e-mail gaffe of all time. Actually two.

John and Lisa, a pair of very married (not to each other) and very adulterous employees at Cornell University mistakenly sent a long and graphic e-mail string to a general e-mail list at the Johnson School at Cornell.

As a result, last week John and Lisa's co-workers opened their inboxes and were greeted with an eye-opening blast of salacious text, very little of which can be printed here except perhaps this: "I had visions of strutting into your office in nothing but a trenchcoat?" You get the idea.

If John and Lisa, whose last names have mercifully been withheld, can take comfort in anything, it's that they are not alone.

The list of people who have humiliated and embarrassed themselves via e-mail is a long one, said Chas Newkey-Burden, author of "Great E-Mail Disasters," as he ticked off some examples. "There are so many stories of people who have just made complete idiots of themselves. In one way or another, everybody has done something stupid via e-mail."

Check Before You 'Send'

In 2000, the Pentagon mistakenly included a school girl's e-mail address to a group list. Claire McDonald, and her parents, were surprised to see sensitive defense briefings showing up in her inbox.

After a trip to China, an aide to then-chancellor Gordon Brown sent out an e-mail that included advice on pulling the corners of your eyes back to "look Chinese." The racist e-mail was sent to dozens of journalists by mistake.

On Sept 11, 2001 a public relations executive e-mailed some colleagues after the Twin Towers fell with the following message: "This would be a good day to bury bad news."

Even Bill Gates, founder of Microsoft, got tripped up by e-mail. On the stand to testify in an anti-trust suit, Gates claimed he couldn't recall a number of important points related to his testimony. A check of his e-mail revealed that Gates' was actually far more involved in decisions about Microsoft than his testimony implied.

And who could forget poor old Joseph Dobbie who became known as the "Rambling Romeo."

According to Newkey-Burden, the Joe Dobbie story all started innocently enough. Dobbie briefly met a woman, Kate Winsall, at a party. Winsall passed him a piece of cake.

Two days later, Dobbie sat down to compose an 800-word over-the-top e-mail that read in part: "This is the part where I throw caution to the wind, the part where I listen to my heart and remember that I should live my life as an exultation and revel in the opportunity to try; the part where I refuse to apologize for who I am; the part where I trust that the lady I met on Saturday night is, as I suspect, able to see sincerity where others would see cliché.

"I am fortunate enough to have been able to collect a number of special memories. They are memories of moments that made any struggle leading up to them worthwhile -- your smile is the freshest of my special memories." And so on.

That 2006 e-mail was forwarded by Winsall to her sister and quickly went viral. Dobbie became such a household name that street vendors started selling Joe Dobbie t-shirts. Dobbie himself had to disconnect his phone.

Boston attorney, Dianna Abdala, knows all about e-mail gaffes. In 2006, Abdala, fresh out of law school, applied for a job with Boston attorney William Korman. Abdala agreed to take the job and then backed out when the terms of the contract changed.

That's when things got ugly with Abdala writing, "The pay you are offering would neither fulfill me nor support the lifestyle I am living." And Korman writing back, "Do you really want to start pissing off more experienced lawyers at this early stage of your career?" And, Abdala responded "bla, bla, bla." At which point Korman hit the forward button.

Now, three years later, after receiving e-mails from as far away as Australia and China, Abdala admits she is "more careful about how I word e-mails and the content of them." She is still angry that Korman forwarded her e-mails and called it unprofessional. But she insists it "wasn't the career suicide that everyone believed it was. I got all that publicity without paying a dollar." Abdala is now a criminal attorney in private practice.

It's unlikely John and Lisa feel the same way at this point.

Cornell University would not comment on the e-mail exchange between the two employees except to say that the "matter is a personnel issue and we do not comment on personnel issues."

Cornell's e-mail policy reads as follows: "Cornell IT policy permits limited uses of the university's e-mail system for personal communications. But the policy also makes it clear that in granting that access, the university expects users to adhere to the same high standards for behavior that govern all other aspects of working, teaching, and studying at Cornell."

So, how do you avoid your own e-mail faux pas?

Newkey-Burden has some thoughts. "Don't e-mail when you're drunk. Disable the reply all option from your e-mail program. And if you're e-mailing person x to say that person y is an idiot, double check the e-mail address."

This year, in an attempt to save people from themselves e-mail-wise, Google announced a way to reduce "Gmail embarrassment." The feature includes a five-second cancel window to send e-mail. Add to that their Mail Goggles app, a sort of sobriety check that requires the sender to answer math questions before hitting send late on a weekend.

Adulterous Cornell Pair Exposed in E-Mail Gaffe

The Emily Post Institute, named for the famous etiquette expert, has added a "communications package" to its business seminars which include a discussion of e-mail fiascos and how to recover from them. "The biggest thing that comes to mind with e-mail," said Anna Post, "is to always remember those e-mails are not yours. Ask yourself if this information should even be in an e-mail. You can't control the people who forward or print up your e-mail."

Newkey-Burden agreed. "Don't e-mail anything you wouldn't say in court or in front of your grandmother."

One can only imagine what grandma would have to say about John and Lisa.

The Emily Post Institute, named for the famous etiquette expert, has added a "communications package" to its business seminars which include a discussion of e-mail fiascos and how to recover from them. "The biggest thing that comes to mind with e-mail," said Anna Post, "is to always remember those e-mails are not yours. Ask yourself if this information should even be in an e-mail. You can't control the people who forward or print up your e-mail."

Newkey-Burden agreed. "Don't e-mail anything you wouldn't say in court or in front of your grandmother."

One can only imagine what grandma would have to say about John and Lisa.