How to write a difficult email

I’m instinctively pretty bad at this, but luckily the whole point of writing coaching is to help people overcome their less useful instincts and understand that good writing is all about the editing! (And I’m breaking the first of my own rules already.)

As recent psychometric testing has clarified for me (thanks, sis!) I’m a fairly direct person, but I also get incredibly stressed at the thought of conflict. That means I can end up tying myself in knots trying to respond well to an email I disagree with. My definition of a difficult email might be very different to yours, but I think we all have them – the one that sits in our drafts (or in our own heads at 3am) waiting be finished and pointing an accusing finger at us. So here’s my guidance for writing that tricky response.

1. Be direct. You need to find the sweet spot between apology and irritation. The worst tricky email of all is simultaneously cringing and angry, thus making everyone who reads it stressed too. The trick to achieve this is to be direct. Say exactly what is on your mind clearly and straightforwardly. Edit it to avoid indirect and circuitous writing and just get it down in as few words as possible.

2. Break the bad news first. Like a doctor with the worst news, say it first and say it clearly. I still remember when we’d been told that our father had just days to live (typically of Dad, two days previously to that he’d been going about life as usual – he was not a man to be pigeonholed into predictability.) Anyway, we all travelled to the hospital  and waited for hours to be allowed to see him. Eventually the doctor came out and said she’d put a tube in so he ‘wouldn’t be able to eat for a few days’. I, and I guess the rest of my family, immediately thought, ‘brilliant, he’ll be eating eventually!’ She was actually giving her standard explanation of a tube, while avoiding the far worse news that eating wasn’t really going to be an issue here ever again. Anyway, hopefully your tricky email doesn’t involve telling someone their dad has a couple of hours to live, so look on the positive side – the bad thing you want to say is comparatively fine! Say it at the start of the email, don’t work your way towards it, and say it in a short, plain sentence.

3. Explain. There’s no reason my client necesssarily understands that making some quick amends to text about a subject I’m not personally an expert on within a few days of writing it (when the research document is still fresh in my mind) is different to dealing with comments on it two months later, when I’d have to go through that hundred page document all over again. Don’t assume your addressee knows why something’s a problem. (We’re all too tied up with our own plans for dinner, shopping thoughts and broodings about our unwritten novel to be acutely aware of other people’s stress points.) So explain in cheerful, straightforward terms.

4. End with a bit of good news, if there is any. If there isn’t, finish with something positive like you’ve loved working on the project or you’re looking forward to the next stage.

5. Lying is fine.

6. Once you’ve written it, edit out all the feeble apologies and qualifiers. Out goes ‘just’, ‘a bit’, ‘sorry’, ‘I should have’, or anything like that. Sweep those out and you’ll still sound friendly, you just won’t sound confusing and neurotic.

7. Edit out any exasperation. You’ll still sound assertive, you just won’t sound like you’re on the verge of smashing all your plates against the garden wall.

8. Check once more and press send – don’t overthink it. Congratulate yourself on dealing with it and make a cup of tea.



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