Lately I have taken to using the smiley face in my emails at work. Sparingly, of course. I’m not an idiot.
It started a couple of months ago when sending an email to a colleague. I was in a bright and convivial frame of mind, so I finished off the last sentence with a smiley face.
“John – I finally spoke to Kathleen about the fitchstrap initiative, and I agree that it would serve as a solid baseline for accountability. Aren’t you glad we uncovered this can of worms before it got too far out of hand?
You see, I had become so accustom to the occasional use of that little guy in personal emails, text messages and blog commenting, that it seemed only fitting to also use it at work. Otherwise, I was not being truly authentic, which, as you know, is the hallmark of a good leader.
See how disarming that is?
I can assure you that I am not the only manager serving up this particular blend of happy-text while at work. My daughter, who is interning this summer at an advertising agency, reported a smiley face appearing at the conclusion of a supervisor’s email message to her the second week on the job. This totally eased her sense of intimidation:
“C – When you finish the Brock project, you can get started on the website materials. You’ll find the file in the cabinet next to Marie’s desk. 
That little smiley face somehow made that supervisor suddenly appear wholesome and supportive, even though she was still just barking out orders the same as before. But now, with the deft tap of two additional keystrokes, my poor distraught daughter felt welcomed as part of the team, perhaps even finding a hint of recognition among the older staff.
Emails can be problematic with their lack of emotional context, especially in a work setting. Unlike exclamation points, or italics or those abrupt periods, the smiley face has the potential to serve a grander purpose in business correspondence, far surpassing the limitations of your commonplace grammar and punctuation. Oh, the possibilities!
But, dear social media savvy reader, you must be cautious, because that seemingly innocent smiley face can easily trip up your reputation if used improperly. Here are some important guidelines:
1. Do not overuse. Like multiple exclamation points, the smiley face can come off as if you were a nine year old girl gossiping about the latest Justin Bieber and Selena Gomez sightings, rather than the confident professional that you are. You must use sparingly!!! Or else!!!!
2. Be selective with whom you are using it. Listen, just because I am giving you permission to use the smiley face, don’t be a dope about it. For instance, never include it on mass emails, or with your superiors. Limit its use to emails to peers with whom you have a friendly, personal relationship. Otherwise, it is inappropriate. Which is to say, it just looks creepy.
3. Use only in a cheerful context. The smiley face is quite versatile in that it can be used as sort of a wink, or a pat on the back, or simply as a cheerful expression to lighten the mood. The important thing is that it be preceded by equally uplifting content, or else it will come off as awkward. But you knew that already.
As you can see, using the smiley guy in business situations comes with an extremely high risk of making you look stupid, or creepy, or immature – especially when used in the wrong context or with anyone other than your good friends of equal ranking.
Otherwise, let ‘er rip.
