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Emails you wish you hadn't sent

28th Aug 2009
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Ever had that sinking feeling when you realise a email clanger has just thudded its way into cyber space?

Everyone's sent emails that they've lived to regret, but we're not going to give you another list of email etiquette dos and don'ts.

There's a common five-stage reaction that happens 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.

Embarrassing emails take many forms, but here are a few of the most common:

  • 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.

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 5-second delay in outgoing emails, the new feature allows users to quickly catch messages with errors before it arrives at the recipient’s inbox, preventing some potentially embarrassing situations.

Despite this, it's clear that the only surefire defence against email blunders is cool-headedness and attention to detail.

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'!


Replies (5)

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By Anonymous
28th Aug 2009 10:00

Costly Mistake

I was advising a client last year on transferring his property business into a partnership and had discussions with the bank to novate the mortages over to the partnership name along with the properties and they confirmed in writing that this could be done without additional fees.

Subsequently the bank advised (by e-mail) that they had reviewed the old loan agreements and the terms did not allow the loan to be novated. The only alternative would be to redeem the old loans and issue new agreements (at a cost of some £9,000).

Unfortunately the e-mail included forwarded conversations with other members of the bank and included an admission that the loans could not be novated as the bank had lost the original paperwork.

The bank concerned is now the subject of litigation!




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By jwwatson
28th Aug 2009 14:02

Put a delay into an Outlook rule
One way of giving yourself a second chance to catch bungles like these is to set up a simple rule in Outlook (or Outlook Express) – via the Tools/Rules&Alerts menu – to delay sending messages for 1 (or more) minute(s). This gives you an opportunity to fish the offending item back out of the Outbox folder before it gets moved to the Sent Items folder.

I find a one minute delay acceptable for this purpose, but anything longer and it would probably start to be inefficient.

Hope this helps.

John W

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John Stokdyk, AccountingWEB head of insight
By John Stokdyk
28th Aug 2009 14:32

The time-delay technique revealed

Good afternoon Sir Les,

As JohnWW points out the automated delay trick can save you from many of these situations (several of which I have experienced). Simon Hurst explained how to do it earlier this year in his Top efficiency tips for Microsoft Office (it's tip number 4):

go to the Tools drop-down menu and select Rules and Alerts. From there, create a new rule using the following rule descriptions: ‘Check messages after sending’, leaving the next set of conditions blank (triggering a warning box that can be ignored), selecting "Defer deliver by a number of minutes" from the next list of conditions, and selecting the number of minutes to delay the message. Give the rule a name, press Apply, and it’s in place ready to offer a safety net.
John Stokdyk, Technology editor



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Rebecca Benneyworth profile image
By Rebecca Benneyworth
01st Sep 2009 20:39

One from a client

One of my clients is in management training at quite a high level - board level at plc - providing one to one training. One delegate provided very poor work for a set session, and my client forwarded this to their senior manager with a brutal analysis of the delegate's abilities and professionalism. Except that she clicked "reply" and not "forward"...

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By cathygrimmer
07th Sep 2009 12:19


Many years ago, I sent a joke about management skills (something to do with monkeys, if I remember rightly) to a few colleagues - unfortunately one of those colleagues had the same first name as the managing partner and the automatic system picked up his email address instead and I didn't notice (but I learnt to check after that!).

I'd only been in the job a few weeks and never met the managing partner (who was based in another office). Fortunately he was a nice man with a good sense of humour. He phoned me up to thank me for the joke, which he thought was very funny!

But it's funnier when it happens to someone else, of course. In a large firm I once worked for, a trainee accountant managed to send an email with a large attachment full of jokes to everyone in the firm instead of just a few friends - and screwed up the email system for a while!


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