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For all the talk out there about Gen Y’s informal workplace tendencies, I’ve found one “casual” office practice that has challenged me as a Y-er time and again: emoticons. Before my re-introduction to them in business emails, formerly from my Boomer Boss and now from Anastasia (Gen X,) I was pretty vehemently against any and all usage of smiley/frowny/winking faces in online or mobile communication. To me they were associated with the AOL era of my using the Internet way back in sixth grade, a time where most people I knew had screennames that incorporated the words ‘Grl’ and/or ‘CuTie.’

But then I started working and there they were again, a blast from my AOL past in my current Outlook inbox. At first, I thought I could be passive and accept their inclusion without actually adopting the practice for myself. And this worked pretty well for a while. Sometimes I would see where a smiley face would go and replace it with an extra exclamation mark. But recently (around the time Google had a similar revelation about Gmail), I realized resistance was futile. This was partially because I started working from home and most of my communication was taking place over instant message and email, but also because as much as I may not like them, I actually do see the usefulness of a well-placed smiley face.

Look at them as a versatile form of punctuation. A smiley face after positive feedback does reinforce the feeling of praise; after a point of criticism it actually does soften the blow (If you want to see a more scientific explanation, check out this recent psychological experiment done with emoticons on energy bills.) That said, and lest anyone think I’m a full-fledged convert, I should be clear that I don’t endorse emoticons for every occasion. I wholeheartedly agree with the quote in this old Times article on the topic that says a frowning face after devastating news would be more infuriating than comforting. Just like any other “casual” behavior in the office, there’s a time and a place.

P.S. The image above comes from the New York Times’ article referenced in the post.

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