Writing a difficult email or letter with AI's help
A complaint, a condolence, a 'no' to a friend — the letters that sit unwritten for weeks. Here's how to use AI to get a good draft in five minutes, without it sounding like a robot.
Everyone has one: the email that’s been sitting half-written for three weeks. The complaint to the airline. The note to a friend after a bereavement. The polite “no” to a request you don’t want to fulfil. You know what you mean, you just can’t find the way in.
This is the single most useful thing AI does for ordinary people. Not because it writes better than you — it doesn’t — but because it gets you past the blank page. Here’s how to use it well.
The basic method: tell it the situation, not the words
Don’t ask “write me an email.” Tell it what happened and what you want. Like this:
“My flight was cancelled last Tuesday and the airline hasn’t refunded me after two weeks. I’ve already emailed once and got an automatic reply. I want a firm but polite email asking for the refund within seven days, and mentioning that I know my rights under the flight compensation rules (EU/UK regulation 261). Keep it short.”
That takes thirty seconds to type, and what comes back will be 80% of the way there. The more you tell it about the situation — what happened, how you feel, what you want to happen — the less it sounds generic.
Then: make it sound like you
The first draft will be competent and slightly stiff. That’s normal. Now you edit — and you can do it by talking to it rather than rewriting:
- “That’s too formal. I’ve known her forty years.”
- “Take out the second paragraph, I don’t want to explain why.”
- “Make the ending warmer.”
- “Shorter. Half the length.”
- “I’d never say ‘I trust this finds you well.’ Start differently.”
Each instruction gives you a new version in seconds. Three or four rounds and it’s yours. This back-and-forth is the whole skill; there’s nothing else to learn.
Four difficult letters, and how to ask for each
The complaint. Give it the facts in order, with dates. Tell it the outcome you want (refund, apology, replacement). Ask for “firm, polite, and no longer than it needs to be.” Ask it to put the request in the first two lines — people who handle complaints skim.
The condolence. This is the one people find hardest, and the one to be most careful with. Tell it who died, your relationship to the person you’re writing to, and one specific memory or quality of the person who died. Ask for “short, warm, no clichés.” Then read it aloud. If a sentence is something you wouldn’t say at the funeral, cut it. The AI’s draft is scaffolding; the memory is yours.
Saying no. “My neighbour has asked me to look after her dog for two weeks and I don’t want to. We’re friendly and I want to stay friendly. Help me say no kindly without a long excuse.” The AI is good at this because it doesn’t feel awkward. You’ll probably soften its version — that’s fine.
The awkward family message. “My brother and I haven’t spoken since an argument at Christmas. I want to reach out without re-opening the argument or apologising for something I don’t think was my fault.” Tell it the emotional aim — reconnecting, not winning — and it will find a tone. Then adjust until it’s honest.
What to leave out
Everything in the list of things never to type still applies. For letters, the main one is other people’s private details. You can write to your brother without giving the AI his surname, and you can complain about a doctor’s receptionist without naming her. Describe; don’t identify.
Three habits that make every letter better
1. Read it aloud before sending. Anything that trips your tongue isn’t your voice. Change it.
2. Add one sentence only you could write. A specific detail, a private joke, a memory. It’s what turns a draft into a letter from you.
3. Wait ten minutes on anything angry. The AI will draft your fury beautifully. That’s not always a service. Save it, have a cup of tea, re-read.
A short example, start to finish
You type: “Help me write a short note to my friend Anne. Her husband died last week. We’ve been friends since school. He was a funny, generous man who always did the washing up at parties. Warm, not formal.”
It drafts something. You reply: “Good, but take out ‘thoughts and prayers,’ I’d never say that. And mention I’ll ring on Sunday.”
Second draft. You reply: “Perfect. Make the first line shorter.”
Three minutes. You’ve written the note you’d been avoiding for a week — and every word in it is true.
