The Proper Use of Smiley Faces in Business Correspondence

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. :)

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About JBW

JBW is a business executive living and working in the Northeast USA.

  • Nancy

    Given your hip and happening Justin Bieber/Selena Gomez reference, you’ve clearly got your finger on the pulse of cultural relevance. I’d say you’ve earned the right to speak authoritatively on the proper use of the smiley face. Started my Monday with a smile after reading this. Hope saying so doesn’t make me look stupid, creepy, or immature.

    • shrinkingthecamel

      My girls keep me up to date with the latest teen culture, just by hanging around them. I try not to pay too much attention, but the other day I said, “can you actually show me a song by Justin Bieber?” I’ve never heard what he sounds like. He’s a pretty good singer.

  • Sheila

    I’ve been known to use them occasionally as a tone-clarifier with subordinates, when the message is “tone-free” and I want to be clear.

    Sounds like a facial product, though, when I put it that way.

    • shrinkingthecamel

      You’re right, a tone clarifier with subordinates would probably sell pretty well at Sephora.


  • Network for Managers

    BJM, these tips are like totally great!!!! :)

    • Network for Managers

      Wait, I believe proper use here should have been : 😀

      • WDYWFT

        Or :p – maybe that’s another blog post :) !!

    • shrinkingthecamel

      Thanks, Anna. I, like, totally knew this would be critical info for professional managers.

  • G. Page Singletary

    Bradley, Here’s some good material for additional thoughts on business writing.

    • shrinkingthecamel

      Thanks Page. I really have to get Seth’s blog on my blogroll! He is so consistently brilliant.

  • Loren Pinilis

    Communicating over Email or text opens a whole new world of problems. We fire them off quickly (out of necessity), and it’s hard to convey tone. It’s a recipe for miscommunication. That’s why I actually am in favor of using emoticons where reasonable. I am especially prone to use an emoticon or a “haha” or “heh” or something similar to convey tone when I sense that my true tone might be hard to pick up on.

    • shrinkingthecamel

      Heh. I like that. But definitely NOT “Tee hee”. That is really 9-year-old-girlish. Let’s ban that from professional correspondence altogether.

  • David Rupert

    I hate the smiley face at work…as well as excessive exclamation points and the word “SMILE.” Just get the point…

    • shrinkingthecamel

      Aw, c’mon David!!! SMILE!!! :) :) :)

      (do people do that to you at work?)

  • Susan DiMickele

    Too funny. All true. I have also recently experienced the smiley face creeping into my work emails. Don’t be a dope goes a long way — we all need to be reminded of that harsh fact!

    The advice to only use in a cheerful context is duly noted. I find myself using the smiley face for sarcasm — which probably says something about my workplace (or me).

    • shrinkingthecamel

      Oh, yes, sarcasm! That’s a great use of the smiley face, and so much more appropriate at work than cheerfulness. :)

  • Megan Willome

    This was a fun post! I prefer the smiley face to multiple exclamation marks any day.

  • Tammy

    Nice post Bradley. I tend to be a person of efficient words which I’ve discovered can appear terse at times. Softening with a smile works wonders.

  • nance

    isn’t justin beiber the love child of engelbert humperdinck? 😮

  • Alicia

    That’s great advice! A university administrator I was corresponding with over e-mail had used the smiley face in one of her e-mails and it actually made me feel better because if she hadn’t used it her tone would have sounded very strict and short rather than friendly and relaxed. Which is very important when your talking to potential costumers/ students! It was professional but appropriate. Also. What do you think about using universal acronyms such as “lol” in e-mails?