The difficult email

Everyone has one. The email you've started three times and closed without sending. Chasing an unpaid invoice. Saying no to a favour. Telling a parent their child's behaviour needs to change. Explaining to a customer that the delay is, in fact, their fault.

These messages are hard because the words matter. Too soft and nothing changes. Too sharp and you damage a relationship you need.

An AI assistant (a chat tool such as ChatGPT, Gemini, Copilot or Claude) can't take the awkwardness away, but it's very good at one part of the job: giving you a calm, well-structured first draft to react to. It's much easier to edit a draft than to face a blank screen.

The formula: situation, goal, tone, limits

The difference between a generic, robotic reply and a genuinely useful draft is almost always what you tell the AI before it starts. Give it four things.

1. Situation. What's happened, in a few plain sentences, and who the email is to.
2. Goal. What you want to happen after they read it.
3. Tone. How you want to come across. Firm but friendly? Apologetic but clear?
4. Limits. What it must not do: make promises, sound cold, blame anyone, run past a certain length.

The message to copy

Here's the formula as a message (often called a "prompt") you can paste straight in, changing the parts in square brackets:

Please help me write a short email.

Situation: [A client hasn't paid an invoice for £450 that was due three weeks ago. I've sent one friendly reminder. They're a good client and I'd like to keep working with them.]

Goal: [I want them to pay by Friday, or tell me when they will.]

Tone: [Firm, polite and warm. Clear that this needs sorting, without sounding annoyed.]

Limits: [Under 120 words. No threats. Don't apologise for asking. British English.]

Please give me two versions: one slightly softer and one slightly firmer.

Keep your details out of it

You don't need to give the AI real names or private details to get a good draft. In fact, it's better not to.

Make it sound like you

A first draft from an AI tends to be a little too polished, a little too eager, and fond of phrases nobody really says ("I hope this email finds you well"). This is where you come in. Try replies like:

Make it shorter and more direct.

That sounds too formal. I know this person well.

Remove the first sentence and any phrases that sound like a template.

Here's an email I've written before that sounds like me. Match this style. [paste an old email, with names and personal details removed]

Then read it through as the person receiving it. Would it make sense to them? Would it feel fair? Would you be happy if they forwarded it to someone else?

A few more situations it helps with

The same four-part formula works for:

• declining a meeting, invitation or extra piece of work
• replying to a complaint without being defensive
• asking your manager for something (time off, a pay review, more support)
• a follow-up after someone has gone quiet
• a tricky message in the class or club WhatsApp group

Where to stop

The human bit

The AI can find the words. Only you know the relationship, the history and what's really at stake. Always read it before you send it, change anything that doesn't sound like you, and remember: the best difficult emails are usually shorter than you think.