I write a difficult email with AI when I know what I mean and I don’t want it to come out wrong.
I’m 67. I spent decades in restaurants. The hard conversations used to happen face to face. You could hear your own voice. You could stop if the other person went quiet. An email does not give you that. It sits there. They can read it twice. They can send it to someone else.
So I care more about the words now.
This is not a list of ten uses. I already wrote about everyday uses in How I Use AI Every Day as a 67-Year-Old. This is one job: the note you have been putting off because you don’t want to start a fight.
A contractor who didn’t show. A neighbor. A well-meaning adult child who is taking over. You know the facts. You don’t want the first draft that comes out of your thumbs.
This works for a text too, not just an email.
If you’re brand new, start with What is AI? and How to Start Using AI Without Feeling Overwhelmed. Then come back here for the hard email.
How I write a difficult email with AI
I open Grok or ChatGPT. Those are the two I actually use.
I do not dump a rant and hope for the best. I give the facts. Then I ask for a draft I can edit.
If typing is the part that makes you cranky, talk the rough draft instead. I wrote about that in You Don’t Have to Type: How I Talk to AI Instead. Speak the facts. Then read the text before you do anything with it.
Here is the order I use:
- Fill in the prompt below. Keep it to the facts.
- Read the draft as if you are the other person.
- If it sounds sharp, ask for a calmer version. I included that follow-up.
- Copy it out of the chat. Change anything that does not sound like you.
- You hit send. The AI does not.
The prompt I copy
Paste this. Fill in the brackets. Leave out anything you would not put on a postcard.
I need to write a difficult email. Help me say this clearly without starting a fight.
Who I am writing to: [neighbor / contractor / adult child / other] What happened, in facts only: [what was promised, what actually happened, dates if you have them] What I want to happen next: [a new date, the work finished, a quieter evening, a conversation] How I want to sound: [firm, polite, short] Do not apologize for things that are not my fault. Do not pile on extra complaints. Do not make threats. Do not add jokes. Give me one draft I can edit. Keep it to [6] sentences or fewer.
That’s the whole prompt. You can say it out loud if you’d rather talk than type.
If the draft still sounds like a scolding
Sometimes the first draft is too sharp. That is normal. You were mad when you started. Paste this next:
Make this shorter and less sharp. Keep the facts. Take out anything that sounds like I am scolding them. Keep my request. Do not add a smiley tone I would not use.
Read that second draft the same way. If one sentence still pokes, delete that sentence. You are allowed to.
What not to paste into the chat
Do not paste account numbers. Do not paste a Social Security number. Do not paste medical details. Do not paste a login, a password, or a full contract.
If you would not write it on a postcard and hand it to a stranger, do not put it in the chat. You can say “the invoice from last Tuesday” without typing the invoice number. You can say “the work on the back fence” without attaching the whole estimate.
The AI is helping with tone. It does not need your private paperwork to do that job.
What this will not do
This is the part I want to say out loud.
AI drafts. I read. I edit. I hit send.
It does not send the email for you. It does not make the other person reasonable. It does not win the argument. A calm note can still get a bad reply. That is not a failure of the prompt. That is people.
It is a tool. Not a person sitting at the table with you. Not a companion. Just a way to get the first heat out of the words before a real human has to read them.
Try it tonight
Pick one note you have been avoiding. Not five. One.
Open Grok or ChatGPT. Paste the prompt. Fill in the brackets. Read the draft twice. Make it sound like you. Then send it yourself, or wait until morning if you still feel hot. Waiting is allowed.
If you try it, tell me in the comments how it went. I read every one. I’m still learning this with you.
— Andrew
