Gaffes, Faux Pas and Awkward Moments: Tips for Successful Emailing in the Workplace
On September 7, 2012 | 0 Comments

By Lauren Fleming

Published in CEO Refresher.


No longer beholden to the Pony Express or pneumatic tubes, today’s communiqués are zipped off like magic at the click of a button, reaching their destinations in seconds. Email makes interactions fast and clean and, above all, easy. No longer must we worry about finding a stamp and then trotting down to the post office to mail a one-page letter of medium importance. As well, actually picking up your phone for a quick answer to a quick question is becoming more and more archaic.  Email of course lets you send something at 2 o’clock in the morning when you suddenly remember it and even send off as many as you want, eschewing your clunky printer and its expensive ink cartridges for more of the important things.

But with this new medium also comes a whole new set of rules—and a whole new set of problems. How do you send effective e-mails, for example, and how do you recover from e-mistakes? Everyone has committed an embarrassing email gaffe at some point, but often we’re not sure what to do about it.

A prime example of this is an incident that occurred recently in my office. After waiting several weeks for a response, someone we shall call “Herbert” finally heard back from an editor. No, she had not read his article, and she attributed her email delay to a recent (and sudden) death in her office. Forwarding the explanation to a colleague, Herbert quipped “She’s had the article since last month!” But when Herbert’s thoughtful colleague, Keith, decided to send his condolences to the editor, he hit reply on the email chain too quickly—sending his considerate comments along with the snarking Herbert witticism underneath.

In these sorts of situations, there are a few ways it can go. The recipient of an unfortunate forward can realize that the comments weren’t meant for them and ignore them, but alternately they can assume they were indeed meant for them and respond. Or they can decide that the comments were private but respond anyway. Once an unfortunate email is sent off however, how it is going to be received cannot be predicted.

In this situation, the editor did respond. After expressing thanks to Keith for the condolences, she added, “…Please communicate to Herbert that I receive dozens of submissions weekly, and simply cannot review them all as quickly as I — and no doubt, he — might like.” Ouch!

Situations such as these can be particularly awkward because you have irritated someone whom, in order to fulfill your goal, you need to stay in the good graces of. But fortunately, in all probability, an email faux pas even this embarrassing will not ruin your life. It is unlikely that your truly nasty thoughts will be broadcast to the public—we all know better at this point than to type them up. But mis-sending and carelessly forwarding more than once or twice is sure to get you a reputation.

Consistently clumsy emailers are people to slowly remove from the loop and to guard your sensitive information from. Lack of attention to detail is something that many consider a fatal character flaw, and, just as scuffed shoes at a job interview supposedly act as some sort of all-knowing indicator, you never know what will be someone’s litmus test.

When a situation does crop up, sometimes it’s difficult to know how to react. If you had offended someone face-to-face, you would certainly apologize although with email it is somewhat different. That’s because sometimes the best way to make a situation go away is to ignore it.

For example, recently I was corresponding with an editor whom I had contacted about publishing an article about “exit planning” in her business journal.  Also the editor of a newsletter for funeral homes, she suggested instead that the article I was pitching to her would be more suitable for her funeral director readers.  This suggestion, though welcome, surprised me at first, and struck me as rather humorous. Funeral director readers? The picture in my mind made me chuckle.

When she emailed me with this show of interest, I quickly forwarded her email to my boss and typed a short message: “The funeral lady has set a deadline.” I sent it off but then, about two minutes later, was hit with a sudden rush of panic! When I went to check my “sent mail,” I saw that I had not forwarded the email to my boss as intended, but had clicked “reply.”

Our dear funeral lady editor did not respond to this, leaving everyone in my office wondering. Was she so irritated by the potentially disparaging nickname I had given her that she would never respond to me again?  Or did she realize that the email was not meant for her at all and simply deleted it?

In this situation, we discussed what to do—should I apologize? Should I make excuses?—but then chose to ignore the entire thing. Then, by accident, I found a reason to email her the end of the same day, needing to ask her a follow-up question. In this exchange, she responded promptly, no mention of my faux pas, so the “crisis” was over. Thus, a second benign and totally unrelated e-mail can often erase any memory of an error or gaffe in your collective memories. You both may very well know what had happened but upon sending that follow-up e-mail, one’s choice to ignore the first is made very clear.

In terms of general guidelines to avoid or ameliorate such situations of your own, here are a few tips, whether to rescue awkward e-situations or stave them off altogether.

1. Don’t type in the email address first. Instead, type your email out, look it over once or twice, then, as a final act, add in the address. This will prevent half-finished, or heat-of-the-moment emails from being accidentally sent off.

2. Follow the same rules in crafting your emails as you would a letter you plan to print. That means including “Dear so and so,” as well as “Sincerely.” Don’t get cute with your capitalization either unless you want everyone to think you’re a “tween.” Always, always, always spell-check.

3. Don’t include your witty nicknames or grumpy remarks in e-mails at all! If you must, walk across the hall and tell your likeminded coworker that your peanut brain boss has just stupidly rejected your proposal. But don’t insert it into an email that might eventually find its way back to Peanut Brain Boss himself.

4. Slow Down! There are no awards for shooting off an email in two minutes as opposed to five. Take an extra minute to proofread too. Just giving something an extra once-over has caught many an error and provoked many an audible sigh of relief.

A few simple changes to your emailing routine thus can make a huge difference. You never know when spell-check, for example, is going to accidentally change your client’s unusual last name to an obscene idiom. Or when you forget to check who has been CC’d in the message you so “wittily” replied to. Double-checking a few things can save you a lot of headaches and a ton of grief.


Lauren Fleming is a Publishing Specialist at emerson consulting group, inc.  Her articles have been published in CEO RefresherBusiness Review USA, and The Concord Journal. To contact Lauren, click here

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