Boss scolds 29-year-old employee for being too direct in emails: 'The emails were literally things like: “Hi, can you send the updated file when you get a chance?”'

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Emmy Pratt • Writer and Editor
Mar 9, 2026 11:00 AM EDT

The workplace has gotten so casual that normal communication is perceived as a slight against your incredibly sensitive coworkers. 

Have you ever been told it's better to err on the side of sounding too professional in workplace communication? I've been told that, especially when you're in your first couple of months working at a new company. As you settle into your role, you can observe how others communicate and adjust accordingly. If everyone else uses unprofessional language in the office without getting reprimanded, you can probably get away with doing that too! But not everybody wants to push the boundaries of professionalism, and that's okay! There's nothing wrong with wanting to play it safe when there's always the possibility that you could get in trouble for going too far with a coworker. On the flip side, you could also get punished for not "playing ball," by connecting with your coworkers on a more human level.

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  • A boss talking to his employee about his direct tone in emails
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

  • If you've ever been referred to as a “wet blanket” in the office, you know that it can negatively impact your career. If you never say yes to getting drinks with your coworkers after work, you might just get passed up for your next promotion, even if your work is better than everyone else's. You would think that if you worked a remote position, office politics wouldn't affect you, but it still can! The employee in this story has worked in his remote position for the past year, and his boss recently scolded him for not being “nice enough” in his emails. What a joke!

  • My boss scheduled a meeting to discuss my “tone” in emails

    I've been working remotely for about a year now and overall the job is pretty relaxed.
    via u/TheUnofficialBOI
  • Everyone communicates mostly through Slack and email, so it's not like we interact face to face much.
    via u/TheUnofficialBOI
  • Last week my boss put a meeting on my calendar called "communication improvement discussion." Which already sounded a little ominous.
    via u/TheUnofficialBOI
  • The meeting was at like 9:30 in the morning, so I figured it was probably about some project update or something I missed.
    via u/TheUnofficialBOI
  • But when the meeting started he pulled up a few emails I had sent recently and said some people felt my tone was coming across "a little blunt." The emails he showed were literally things like: "Hi, can you send the updated file when you get a chance?" and "Just checking if there's an update on this." That was it.
    via u/TheUnofficialBOI
  • At first I honestly thought he was joking. Those seem like completely normal work emails to me.
    via u/TheUnofficialBOI
  • Man wearing headphones working on laptop
    via Vitaly Gariev

    Image is representative only and does not depict the actual subjects of the story.

  • I wasn't being sarcastic or annoyed or anything, I was just asking for updates. Apparently a couple people interpreted them as passive aggressive.
    via u/TheUnofficialBOI
  • Two women wearing beanies sit on a couch complaining about their coworkers blunt emails
    via Giulia Squillace (Unsplash+)

    Image is representative only and does not depict the actual subjects of the story.

  • Either his coworkers are just overly sensitive, or they've never been in an environment where a colleague has communicated with them directly and professionally. Those are the only possible explanations for this misunderstanding.

  • Which confused me because I genuinely had no idea they sounded that way. Then he suggested I try adding more exclamation points or emojis so the tone feels friendlier.
    via u/TheUnofficialBOI
  • So now I'm sitting there writing emails like "Hi!! Just checking in on this when you have a moment "which honestly feels kind of ridiculous.
    via u/TheUnofficialBOI

  • A coworker sending a message with too many emojis would come off to me as more passive-aggressive than the messages he was sending. If you're so happy, why do you need emojis to communicate that? And if they already perceive him as passive-aggressive, I don't think adding emojis will help his case.

  • I get that tone is harder to read through text when everyone's remote, but now I'm weirdly self-conscious about every message I send.
    via u/TheUnofficialBOI
  • Like I'll type something normal and then sit there thinking "does this sound r_de somehow?" Remote work is strange sometimes.
    via u/TheUnofficialBOI
  • Maybe I'm overthinking it but I didn't realize punctuation was such a big deal. EDIT: Me (M29)
    via u/TheUnofficialBOI
  • JasonMallen Add "lol" to the end of every email. Works on texts
    via u/JasonMallen
  • TheUnofficialBOI Original Poster's Reply like, seriously!
    via u/TheUnofficialBOI
  • toastedmarsh7 Mild infuriation reached. At least you were told exactly what he wants you to change instead of you having to guess.
    via u/toastedmarsh7
  • Krasskas I would send all my emails like normal but end each with a paragraph of smiling emojis "Hi just checking for any updates on this? • • ..
    via u/KrassKas
  • TheUnofficialBOI Original Poster's Reply you're using the same emoji 69 times! that bothers me! I'm arranging a meeting for the same.
    via u/TheUnofficialBOI
  • ThereInAFortnight Do you work with children? If so, that sounds like good advice.
    via u/ThereInAFortnight
  • TheUnofficialBOI Original Poster's Reply Just adults who need exclamation points for emotional support!!! (wink emoji)
    via u/TheUnofficialBOI
  • ScowlyBrowSpinster You were just being succinct and, dare I say, professional. Are the complainers slackers in some regard? Does your follow up inquiry 'pressure' them? Ask for specific phrases he wants you to use to be compliant. "Hi, hope you're having a great day! Please update me regarding the Penske file when you have a chance! Cheers!" or whatever. Make him define the language he wants to see so the complainers will be soothed. Telling you to use emojis is unprofessional, imo.
    via u/ScowlyBrowSpinster
  • TheUnofficialBOI Original Poster's Reply thought the same when they told me to use emojis.
    via u/TheUnofficialBOI
  • Eversnuffley Hey, uh, can you watch your tone there? Without a capital T on that sentence I feel like you are being passive aggressive. 31
    via u/Eversnuffley
  • TheUnofficialBOI Original Poster's Reply I'm SORRY about that. pardon me. thank you!!
    via u/TheUnofficialBOI
  • mindspringyahoo Imo, the easiest thing is to set your signature with some overly ebullient sign off like 'Thanks!', 'It's been a joy!!', 'It's been my pleasure!!! (or similar). This can help soften things in case the message above is too 'straight to the point'...
    via u/mindspringyahoo
  • whrthwldthngsg Guaranteed this dude gets an email with subject "Professional communication improvement discussion" where the boss tells him using too many smiley faces isn't processional and recommends toning it down. 3 months.
    via u/whrthwldthngsg

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boss meetings remote work employee scolding email communication tone exclamation emojis
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