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Matt Henkes



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Emails you wish you hadn’t sent


Most people will know the sinking sensation one feels as an email blunder zips its way across cyber-space, your embarrassment moving irretrievably towards its destination at light speed.

We’re not going to give you another list of email etiquette dos and don’ts – we want to hear about interesting and entertaining email mistakes you’ve witnessed, and how the aftermath was dealt with.

Here is a common five-stage reaction experienced following a serious email blunder.

  1. Disbelief: "Oh no, surely I haven’t done that…"
  2. Denial: "Check sent box 50 times."
  3. Twitch: "I have done that, bugger."
  4. Panic: "PANIC!"
  5. Damage limitation: "Please ignore my previous message, I was on drugs."

It’s a problem that some tech companies have tried to address. Google’s free email service, Gmail, added an unsend message function in March. Taking advantage of the five second delay in outgoing emails, the new feature allows users to quickly catch messages with errors before they arrive in the recipient’s inbox, preventing some potentially embarrassing situations.

But the only surefire defence against email blunders is cool-headedness and attention to detail. Here is a classification of some of the many types of embarrassing email you might have sent.

  • The angry reply: The recipient is unhappy with you and they’ve made that perfectly clear. You feel you’re being unjustly blamed for something or that this person is being unnecessarily curt. Time to give this bozo a textual pummelling so severe he won’t sit down for a week; prepare to unleash the hounds. SEND – Read your reply again five minutes later, refer to the five stages.
  • The idiot response: Some recent lobotomy patient has misunderstood what you’ve asked five times, pushing your blood pressure across the 500psi danger-line and wasting your precious time. Looks like it’s time to let this moron know what you think of their cognitive reasoning. Set it out in short sentences, CAPITAL LETTERS and language that would patronise a turnip. SEND:Read your reply again five minutes later, refer to the five stages.
  • The classic ‘Reply All’: Dave has invited you to his get together; good old Dave. Unfortunately you notice on the recipient list that Dan and all his friends are also invited. You reply to Dave that you’ll be happy to attend his party, but it’s a shame that Dan and co are coming, as they are a bunch of utter douche-bags. SEND: Oops, reply all; refer to the five stages.
  • Forwarded conversations: A customer makes a legitimate email complaint, but there’s no need for them to be so rude. You have a quick email discussion with a colleague to formulate a reply, but part of this conversation includes a comment from one of you alluding to the customer’s dubious parentage. A seemingly satisfactory response is decided upon. SEND: Read your reply again five minutes later, refer to the five stages.

This is only a small selection of the many, many email blunders that it’s possible to commit. Let us know, by posting a comment below, if you think we’ve missed a key one. Or have you witnessed an embarrassing email blunder that you’re willing to share for the benefit of our sadistic enjoyment? Don’t forget to check it before you click ‘submit’.

2 Responses

  1. Beware: Autocomplete may not be your friend
    It’s very convenient how most email programs anticipate the address you’re writing in the TO: field so you don’t have to type the whole address since it automatically fills in. I found it very handy when emailing my boyfriend because all I had to type was M-A-R and hit tab because it brought up his address every time. I had grown so accustomed to this feature, that I totally forgot that I had a new client… a marketing director. A M-A-R-keting director, I should say, with an email address of

    Since my boyfriend and I would try to cheer each other up during the day with short emails, most of which would be rather shocking to a client, I don’t even have to tell you what happened next. I noticed the TO: address as I was clicking SEND, but it was too late. The best solution was to call the client right away before he checked his email. Heck, he’ll probably get a laugh out of it. Nope, no laughs… very negative experience. I hope the same thing happens to him some day so he knows what it’s like!

  2. HR is fly…
    I have watched and wondered (thankfully!) at others who have involved me in this. Once, the marketing director of a previous company I worked with, used to tease me that I was in a woman’s job working in HR, as a man. I used to accept the abuse, as it was light hearted in nature, and I used to return semi-insults about marketing persons’ inability to complete a worthwhile task.

    One day I sent what might be described as a “fluffy” email to the whole company, I forget the subject matter but it showed our company’s caring side. Within seconds I had a reply in my inbox declaring that “HR is for birds!” Unfortunately so did 250 other people in our organisation. I have never seen the marketing director move so quickly in running to my boss’ office (my boss was a lady) and apologising. Very funny in retrospect, however could have been a lot worse.

    I don’t think I can share the others without betraying confidences (the difficulty of responding to this thread).

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Matt Henkes


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