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Smiley Faces and Senior Managers

A senior manager whom I will call Kate wrote to me asking for advice about the use of smiley faces in email.

Kate's question had an unusual twist involving her boss: he wanted her to use smiley faces, but she was resisting.

Kate told me she views smiley faces as silly and unprofessional, but her boss wants her to use them in internal emails to "better express" her emotions.

It is difficult for me to imagine how a smiley face could help Kate express herself any better than words can, especially at the senior manager level. In fact, the only reason I can think of for Kate to use smiley faces would be to come across as more approachable if, in her role as a senior manager, she runs the risk of intimidating others.

I don't know that Kate has the issue of coming across as aloof or unapproachable. She was friendly yet professional in her message to me. But perhaps her boss is trying to help her appear more down to earth to employees. 

Plenty of people have written to complain to me about the unprofessional, smiley face-pocked messages they receive daily. Especially offensive are the blindly habitual smiley faces that decorate sentences all through a message, even the signoff. So I cannot side with Kate's boss, not without knowing more. I suggest that she use words to "better express" her emotions, phrases such as "happy to," "thank you so much," and "look forward to working with you."

Do the senior managers who write to you use smiley faces? Do the emoticons change your feelings about the messages or the managers? 

For a range of views on smiley faces expressed in excellent comments, read "Smiley Face Suggestion" and "Celebrating Emoticons–No, Not Me on this site.

Syntax Training

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By Lynn Gaertner-Johnston

Lynn Gaertner-Johnston has helped thousands of employees and managers improve their business writing skills and confidence through her company, Syntax Training. In her corporate training career of more than 20 years, she has worked with executives, engineers, scientists, sales staff, and many other professionals, helping them get their messages across with clarity and tact.

A gifted teacher, Lynn has led writing classes at more than 100 companies and organizations such as MasterCard, Microsoft, Boeing, Nintendo, REI, AARP, Ledcor, and Kaiser Permanente. Near her home in Seattle, Washington, she has taught managerial communications in the MBA programs of the University of Washington and UW Bothell. She has created a communications course, Business Writing That Builds Relationships, and provides the curriculum at no cost to college instructors.

A recognized expert in business writing etiquette, Lynn has been quoted in "The Wall Street Journal," "The Atlantic," "Vanity Fair," and other media.

Lynn sharpened her business writing skills at the University of Notre Dame, where she earned a master's degree in communication, and at Bradley University, with a bachelor's degree in English.

18 comments on “Smiley Faces and Senior Managers”

  • This reminds of a friend I have who has a lot of trouble expressing himself with words. To overcome this difficulty he uses pictures and music videos.

    I imagine that smileys serve the same purpose in this case, except the manager does not want to admit his inability to use words to express his emotions.

  • Isn’t the boss potentially opening up a can of worms? What if occasionally Kate wants to express other emotions?

    The list of emoticons on Wikipedia includes representations for “creeped out”, “drooling” and “distressed, frustrated, sick of crap, mainly frustrated”.

    The last of these pretty much sums up how I’d feel if my boss asked me to use emoticons.

  • I don’t have a problem with emoticons and use them in my personal e-mails all the time. I don’t use them in most professional e-mails. An exception is with e-mails sent to co-workers with whom I have a certain level of comfort. Even then, I use them sparingly, maybe when I’m making a clever play on words in an otherwise serious e-mail. (To do that, I would definitely need a certain level of comfort with the recipient!)

    I find it odd that the boss asked the writer to use emoticons. The corporate culture where she works must be very laid back, or else her boss is under 35. (Maybe both.)

  • =:-o

    I agree, smileys are for personal or casual emails only. Even then they can be overused.

    Is anyone else sick of seeing LOL everywhere?

  • I agree that smileys are not professional expression in Email writing.
    I only use smileys(like ^_^) in Email/MSN with good buddies.

  • Thanks for commenting, everyone.

    Hi, Yoav. What is different about this situation is that the manager does NOT want to use smiley faces, but her boss wants her to. Interesting, no?

    Hi, Clare. I can’t imagine a senior manager ever wanting to express being creeped out or drooling. Thanks for those odd images–and for your clever close.

    Nina, I appreciate your guess about the company culture and the boss’s age. Good point.

    Val, “LOL” HAS become meaningless. However, I enjoy the same idea expressed in words such as “Thanks for my first good laugh of the day,” “You brought me a big smile,” or even “I am laughing out loud.” Although that last comment is the same as “LOL,” the words make it seem more real to me than the quick, constant “LOL.”

    Larry, although I don’t use emoticons, I like your ^_^. Thanks for stopping by.


  • Great topic here. I believe that using smiley faces within formal communications is unprofessional and definitely lessens the managers ability to be taken seriously later down the road. Thank you for affirming my belief. Furthermore, it really changes the tone of emails in general. Write what you mean, and mean what you write!

  • Perhaps it is telling that Kate thinks smiley faces to be silly or unprofessional; her e-mail style is probably direct, very business like, not unfriendly, but perhaps a bit impersonal.

    Imagine getting an e-mail from a manager that had a very serious demeanor and it was “Great job.”
    How does this feel in comparison to:
    Great Job!
    Great job πŸ™‚
    or even a sarcastic, great job πŸ™

    For someone that has been e-mailing for nearly 15 years, emoticons have become a form of punctuation. I use them to not only clarify communication, but because I like to smile.

    Although unpopular as determined by the above comments, I use smilies in e-mails to my clients and they often reciprocate as well. Exclamation points (one per e-mail maximum and never in sequence) are also used.

    Sometimes projects become difficult due to circumstances out of either of our control and a smile is something that tells them, “I’m not taking your criticism/your team’s lack of project management skill/canceled request badly. And they do the same when they make the 20th “final” copy change knowing that they need to soften the blow so to speak.

    Even though requests and work are done to better the company/corporation that I am assisting, I communicate with a living, breathing person and like to build a relationship that transcends the worksphere.

    Does a smile in an e-mail work towards bettering my business or communication, I don’t know. But working hundreds or thousands of miles away from clients takes away some of the personal interaction that e-mail and phone calls can only slightly seek to replace. When a client repeats business or refers others, I know my attitude has something to do with it.

    Acronyms such as LOL are something I don’t use. I’ve heard at least one person thought LOL meant Lots of Love…

    My other caution is to put a space between the eyes and mouth of an emoticon. : ) instead of :). The reason? Microsoft Outlook puts a smiley in automatically when your type colon parenthesis, and this shows up as a J when a recipient viewing in plain-text mode.

  • Hi, Christian and Kevin. It was fun to read your comments back to back.

    Christian, I generally agree with you. Yet I love Kevin’s energy for communicating well with human beings around the world. What do you think of his ideas (just below your comment)?

    Kevin, of your choices, I use “Great job!” We need something–punctuation, words, or a smiley face–to be sure the comment comes across as sincere. I would add at least a brief comment about why the job is great.

    Thank you for your helpful examples of when smiley faces work, Kevin. I also appreciate your comment on LOL and your advice about spacing with : ). I looked over the many emails you have sent to me when working on projects with me. I see that you never used a smiley face but expressed lots of enthusiasm with well-placed exclamation points. You know your audience.


  • Perhaps we’re overlooking the receiver here? We are following this blog because we’re interested in writing well, expressing ourselves well. That’s fine, but how do we guarantee that the person at the other end of the email is similarly enthusiastic about language? We can’t. And you don’t have to look far to find examples of writing that fail miserably to communicate emotional context and leave a receiver to figure out a meaning completely in the dark.

    There’s also a pretty compelling case to see email as an inherently less formal mode of communication. Would ANYONE, for instance, use a smiley in a formal letter on the firm’s letterhead? I’m not brave enough to say it would never be done, but surely it would be very rare.

    I can certainly understand that Kate may prefer not to use smilies, but I think they help me to provide an emotional context for textual comments in an easily-understandable shorthand β€” when I feel it’s needed and when I don’t have the luxury of a couple of hours to find the *right* word. πŸ™‚

    Would I use a smiley with my boss? Hell, no! I’m with Clare on that one.

  • Smiley faces and other emoticons are crutches of some passive-aggressive people at my office. One coworker I exchange e-mails with all the time uses smileys in a vague way – they could be friendly, they could be snarky. I tend to think he’s being snarky, but he can claim he’s not. Please. To quote a previous poster, “Say what you mean and mean what you say.”

  • I just came across this post, and while I realize it’s a couple weeks old, I did want to pipe in and add my thoughts. I, too, like Kevin have been online for many years. And I use smileys quite a bit. Usually it’s a ;o) (a wink) to let my reader know I’m kidding – which I do a lot and I want to be sure I’m not taken seriously.

    I think one of the issues here is senior management. I would never use my smileys with high level execs, simply because I understand them to have a more professional attitude/demeanor than the lighthearted Internet marketing clients I typically work with.

    I’ve found that my smileys help me take an impersonal client relationship to a more friendly level and find that it makes my clients become more real with me after a bit.

    As with anything, there is a time and a place. If you’re dealing with executive managers, smileys probably aren’t the best thing. But if you know the people you’re corresponding with at all, they can be helpful. They ARE a form of communication, after. And they speak, even without words. ;o)

  • Hi everyone. I’m Amalia, I;m from Malaysia. =D

    Interesting. I do admit, I’m one of those emoticon users, but only with certain people and to convey a certain kind of expression I want to emphasis. Like letting them (my Boss and colleagues) know I am open to commentaries and criticism when I feel they might be reluctant to in case of hurting my feelings (I work as a Copywriter, btw). These commentaries are important to me, so I need them to know I am happy to receive them.

    I find them to be friendly, and best communicate warmness and openness. Although I don’t believe it is appropriate for everyone, and especially not for clients and top managements. I have, however, received text messages from a very friendly vendors who uses these friendly emoticons quite a lot. But she uses them in such a way that makes me warm up to her more easily, making our communication and business deals easier as well.

  • Thanks for commenting, Amalia. If I wanted to get commentary, I would say, “I am very open to your suggestions and criticism.” That way, I would feel sure my readers would know what I meant. I would worry that a smiley face would not communicate clearly.

    Let’s both do what works for us.

    I am glad you stopped by.


  • i would have to agree with the NOT using them in emails where possible. I think of it is un-professional and it can be seen taken the wrong way. wth out htem there can be no wrong context!

    intersting hearing that people want to use them though, as i here the opposite.

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