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I find that I can spend a lot of time on an email, getting the wording right.

These are usually emails where I need to sound persuasive, or I'm risking causing minor offence or sounding abrupt.

eg emails like: 'I think we need xyz, because abc' or 'I recommend doing xyz'.

I find myself spending 10-20 minutes writing an email that should take just a 5 minutes.

I find myself hesitating to send an email, because it doesn't quite sound right.

Sometimes I regret just hitting send, thinking 'I wish I had changed that wording'.

What are some techniques effectively writing emails?

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Gruber's article pointers are good. I wanted to comment that I wished more people would spend a little more time using a draft / edit / finalize cycle on their email, instead of blasting it out unedited. You're probably not as far away from what you should be doing as you think. – Dennis S. Oct 24 '13 at 12:41
up vote 12 down vote accepted

See this Mindtools article or this one. Essentially:

  • Subject line should be a useful summary of the email's contents
  • Focus -- make one point per email. Send multiple emails if you have many topics to discuss.
  • Specify the response you want and identify yourself clearly. Include contact details.
  • Be kind. If you write in anger, save a draft, go get a cup of coffee, and reconsider your message.
  • Proofread. Distinguish between formal and informal situations -- you can only use smileys with friends.
  • Email is not secure. So think about the sensitivity of the data you're sending.

A great tip is to add a timer that lets you retract an email after hitting "Send". Gmail and Microsoft Outlook both have such a feature.

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While the retract can be a useful lifesaver in an emergency, I have seen organisations rely on it - which leads to people sending and then thinking. – Rory Alsop Oct 24 '13 at 17:20

Email need not be long, get to the point as quickly as possible, explain it clearly yet succinctly, with as few uncommon words (field dependent) as possible. Use proper grammar/spelling/punctuation, and know your audience. It is always best to use plain-text email, not HTML, you don't know how the other end responds to HTML.

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