By Nadira A. Hira
July 31, 2007

As much as I’d hoped to avoid it, I’d be remiss if I didn’t direct our attention to this weekend’s New York Times article, “(-: Just Between You and Me ;-)”, about emoticons in the workplace. “There are many ways to console someone when a multimillion-dollar business deal falls through,” the story opens. “Firing off a ‘tough break’ e-mail message punctuated by a frown-face emoticon is not one of them.”

Agreed. But just as the vast majority of parents aren’t calling their children’s bosses to negotiate salaries, I’d venture to say that most of us aren’t using sad faces to ease the pain of deal disasters like these — at least not with our clients or business partners.

But should a friend or colleague go through a rough patch, it’s certainly not beneath me to send a smiley e-mail — e.g. “Nothing a gimlet couldn’t fix ;o).” And those of you who’ve read The Gig once or twice have probably noticed that I don’t hesitate to wink at you either. But that makes sense; most snarky people use visual cues like smiling to keep from actually offending people, and given the chance to translate that into e-mail and IM, why wouldn’t you? Especially considering the damage just one misinterpreted sentence in an e-mail can do, in the office and elsewhere, a point the Times story makes, too.

Like everything, there’s a time and place. And there’s a certain e-mail trust that must be established before anyone starts throwing smileys around. But if your boss signs off with a winky face — as mine, Fortune Managing Editor Andy Serwer, sometimes does — it’d be silly for you to respond with, “Dear Mr. Serwer,” and, “Sincerely yours,” don’t you think?

But smileys, like so many other signs of the Gen Y casualness apocalypse, do get under some people’s skin. Some of you might remember that the cover for our Gen Y story read “‘Manage’ Us? Puh-leeze…” with the subhead, “Today’s twentysomethings have their own rules. You just don’t understand them :-)” Truth be told, that particular smiley was my fault. Andy showed me the cover and said he liked the subhead, but that some people thought it might be too harsh. And I, musing like your standard ineloquent Gen Yer, said, “Well, what we’re really trying to say is, ‘You just don’t understand them, smiley face,’ you know?” Visionary that he is, Andy jumped up and shouted, “Yes!” I, as usual, was lost, and Fortune “history” was made.

But don’t ask me how many letters we got predicting the downfall of American business and the death of culture itself because Fortune had a smiley face on its cover. We’ve had dogs, Dilbert, even post-prison Martha Stewart on our cover and it’s basically all good, but put a smiley in there and all hell breaks loose. Well, I’m not sorry; it’s a new world, people, and it has smileys in it! (And there, folks, is a great example of an entire paragraph that, sans smiley, might be more likely to get me fired than communicate the good-natured ribbing I intended. Good thing I’m not afraid of emoticons ;o). You?

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