The Email You've Rewritten Four Times and Still Haven't Sent

Draft four of the email to the landlord says "I appreciate you're busy" twice.

Draft three called the damp a disgrace. The tab has been open since Tuesday.

Every version is either so soft it says nothing or so sharp you'd never send it.

Swap in your own if you like. Maybe it's the note telling your manager you won't take the extra project, or the resignation, with four drafts written and the tab still open.

AI can help here, but writing the email is the wrong job to give it.

An email written by a machine, sent to someone who knows you, reads like a machine wrote it. The useful job is different. Ask AI to lay out three ways the conversation could go, so you can pick the one you want to have.

Tonight, decide

A hard email is hard because you want two things that pull against each other.

You want the damp fixed and the landlord on side, or a firm no and a manager who still thinks you're reliable.

Each of your four drafts tries to fit both into one paragraph. Each one fails, because you haven't decided which wins when you can't have both.

Leave the drafts out of it. Tell the AI what's going on the way you'd tell a friend in the pub, both halves included.

I need to write to [who] about [what]. What I want to happen is [the outcome]. What I'm afraid of is [the thing you don't want]. Here's the history in a few lines. [what's happened so far] Don't write anything yet. Tell me what you think I'm really asking for, and what you think the other person is likely worried about.

Half the time the reply names what you've been circling. You want an apology more than a repair.

You don't mind the project, but you mind being asked last. Four emails become one.

Some messages shouldn't be emails at all, like ending a relationship or telling a friend something hard about how they behave. The same goes for anything where their face would change what you said next. For these, use tonight's prompt to find out what you want, then say it out loud.

An email that should have been a phone call is remembered as the email.

And maybe tonight's draft runs to four furious paragraphs, and you feel better for writing it. Then that draft has done its work in the drafts folder, so go to bed.

Tomorrow, three conversations

Now ask for drafts, and ask for three different outcomes, because three tones of the same email get you nowhere.

Write me three versions of this email, each under 150 words, and label what each one is for. One that keeps the peace and gets a small result. One that's direct and gets the full result at some cost to the relationship. One that asks a question instead of making a statement, and lets them come to it. Plain English, no corporate phrases, nothing I wouldn't say out loud. Then tell me what each version is likely to get back.

Side by side, the three show you which one you want. Often the direct one looks smaller on the screen than it did in your head.

People forget the question version, and it's often the best one. "Can I check where we are with the damp?" opens a conversation, while "The damp is unacceptable" closes one.

Pick one, or take the first half of one and the end of another.

Watch for office-speak creeping in. If you see "I wanted to reach out regarding", the reader has stopped reading. Cut anything you'd never say across a table.

Before you send

Have the AI read the draft as if it were them.

Read this as [the landlord / my manager / the head teacher], someone who's busy and slightly defensive. What's the first thing they feel? Where could they take it the wrong way? What's the one line they'll quote back at me?

Expect guesses, and expect some of them to be wrong.

The AI might decide your manager is "likely concerned about team capacity", when in fact what worries her is her own boss. Correct the AI, because you know her.

Then do the two jobs the AI can't. First, cut the whole email by a third. People reading a difficult email don't want to be reading it, so the shorter the email, the more of it lands.

Second, write the last line yourself, from scratch, without looking at the draft.

They'll remember that line more than any other. So the last line is the one that most needs to sound like you.

"Thanks for sorting this, I know you're busy." "I'd rather we talked than emailed, so I'll ring you Thursday."

If no last line is coming, you haven't decided what you want yet, so go back to last night's prompt.

A well-made email won't win an argument you're wrong about, and last night's prompt sometimes tells you so.

Send the email from your own account, after a cup of tea, nowhere near 11pm.

Tonight, give the email that's been open since Tuesday the first prompt, and leave the drafting until morning.