When an email arrives in an undoubtably professional context that contains a smiley face, I do a double take. On one hand, it certainly creates a warm tone in a way that Kind Regards never will be able to do. On the other hand, we’re not in junior high and we don’t need to be cutesy to convey warmth. I’ve invoked the smiley on a few rare professional occasions, and I never quite know why I hit send even though I don’t feel stupid for it either. As long as it’s used in a ‘normal’ written flow, a smiley will probably be harmless because it has a positive connotation. As with pokes on Facebook from folks of a different generation or a certain type of relationship, however, it could be seen as creepy or inappropriate, albeit unknowingly so.
Verdict: As I often argue, people
are should be hired for their overall selves as much as for how well they can directly fill their professional shoes. If it’s within a person’s written repertoire to occasionally smile, let ‘em smile if they feel so moved. It’s not hurting anybody, just raising some eyebrows.