First, a confession, because it explains why I care about this at all.
A few years ago I wrote an email I never meant to send. A client had moved a deadline for the third time, owed me money, and was ignoring my messages, so I opened a new email and just… vented. Typed everything I actually thought. The plan: read it next morning, laugh, delete, write the polite version.
Except I’d typed it in the reply box of his actual email thread. And instead of “save draft,” tired past-me hit send. Then — don’t ask me why — I hit reply-all on my own panic message to a colleague, so the client ALSO got “ignore that last one, it wasn’t meant for you.” Which confirmed it absolutely was.
He paid late anyway. We don’t work together anymore.
So when I say I now draft important emails with an AI and read them twice before sending — that habit was born from shame, not productivity content. The speed came later, as a bonus.
The actual problem with email
You already know what to say. That’s rarely it. My old enemy was a two-line email to a landlord — two lines! — that took ten minutes because every version sounded furious or like begging. Tone is the whole game: the reader can’t see your face and will assume the worst version of your voice.
That’s the bit AI is good at. Not judgement. Not facts — God, not facts, we’ll get to that. Just your rough thoughts, arranged into sentences that sound like a calm adult wrote them.
The formula (there is one, sorry)
People moan that AI emails sound generic, and when I check their prompts, the prompt is “write a professional email about the meeting.” Well. Yes. It had nothing else to work with.
Give it five things: role + situation + key points + tone + length.
Real one I use constantly: “Help me write a polite business email. My client meeting Tuesday at 11 needs to move to Thursday morning because our office is closed for maintenance. Say sorry briefly, offer 10 or 11:30, ask them to confirm. Warm, under 120 words.”
See the difference? It can’t invent an excuse — I gave it the excuse. It can’t pad to 300 words — I capped it. Nearly every dreadful AI email I’ve been shown started with a two-line prompt and a shrug.
Five emails I actually send versions of
These are based on real emails, names changed — I’m not making the reply-all mistake twice. The scribbled “before” note is the only part you truly have to write yourself.
1. Chasing a reply without sounding desperate
I’ve sent some version of this maybe forty times. Rough note, always some flavour of: “Sent proposal last week, no reply, need answer, don’t sound pushy.”
Subject: Proposal from last Monday — any thoughts?
Hi Daniel,
So, just nudging this up your inbox. I sent the proposal last Monday and wanted to check it landed okay.
No rush on the full decision — even a “still looking at it” helps me plan my week.
Thanks,
Arsal
Forty versions taught me this: people don’t ignore follow-ups out of rudeness. Replying means deciding, and deciding is effort. Give them a smaller decision — “still looking” takes four seconds.
2. Asking for leave (short, because managers are busy too)
Rough note: “Need two days off next month, family thing, ask nicely.”
Subject: Leave — 12–13 November?
Hi Sarah,
Can I take 12 and 13 November off? Family commitment, been booked for a while.
My reports will be done before I go, and Imran’s got the urgent stuff while I’m away, so nothing should land on you.
Thanks!
Arsal
P.S. If those two days are a problem, the week after works for me too.
That’s the whole email. Managers don’t want an essay about your family; they want to know what’s happening to the work. Answer that worry inside the email and the yes turns up within the hour.
3. The late-delivery apology (and the time AI nearly cost me money)
This one’s longer — apologies can’t be rushed — and it carries the most important story in this article. Rough note: “Project two days late, supplier problem, sorry, send Friday.”
Subject: Your project — new date is Friday
Hi Mr. Khan,
Straight to it: your project is going to be two days late. Friday instead of Wednesday. Our supplier delivered late and it knocked everything back.
I know that messes with your schedule, and I’m sorry. I’ll update you Thursday either way — no silence from my side.
Regards,
Arsal
Now the story, because it matters. The first apology an AI drafted for me ended with “and we’d like to offer you 10% off your next order for the trouble.” I never said that. I offer nobody 10% off anything. The tool just decided apologies contain discounts, and politely invented one — in my name, in writing.
I caught it because I read the draft. Had that gone out, it’s a promise. This is why I bang on about never letting the tool add a fact — a date, a price, a “we’ll cover the cost” — that you didn’t hand it. It can be as generous as it likes with its own money.
4. Saying no to a meeting
Four lines. Sometimes fewer. Rough note: “Can’t do Thursday meeting, deadline, say no nicely.”
Subject: Re: Thursday review
Hi Ayesha,
Thanks for this — I can’t make Thursday, I’ve got a deadline that afternoon I genuinely can’t move.
I’ll send my updates over by email beforehand. And if anything needs me, Friday morning I’m free.
Sorry again,
Arsal
People agonise over this one for longer than the meeting would take. It’s a no, an alternative, done. Nobody replies offended — everyone secretly loves a cancelled meeting.
5. The cold email to a client I wanted
This one I nearly didn’t send — rewrote it four times, walked away, came back. Rough note: “Introduce myself, freelance design, want work, ask for a call.”
Subject: Quick intro — design help, if you ever need it
Hello Fatima,
I’m Arsal, I do freelance design work here in Lahore. I saw your new product launch last week — the packaging is lovely, properly clean.
I help small brands with social media designs and product visuals, usually turned around in three or four days. Happy to send samples if useful.
And if you don’t need anyone right now, no worries — just saying hello while I was being brave.
Would a short call next week suit you?
Kind regards,
Arsal
She replied in two days: “send samples.” Work came a month later. The line that did it, she told me, was the packaging one — proof I wasn’t blasting the same message to fifty businesses. I was blasting it to about six.
The tools, as I actually use them
I mostly open ChatGPT. Habit, partly, but it follows tone instructions — “warmer, shorter, less formal” — better than anything else I’ve tried, and email is basically tone instructions.
Claude writes the nicest first drafts, the least robotic of the lot, and I still forget it exists for weeks. A me problem, not a Claude problem.
Gemini only gets used because it lives inside Gmail, and laziness is a powerful feature.
Grammarly annoys me — coloured underlines everywhere, half of them wrong for how I actually talk. But it catches the subject-line typo, the one place a typo makes you look truly careless, so it stays. A proofreader, not a writer. Bring your own draft.
Copilot I’ve barely touched; it belongs to the Outlook world. One writer, maybe one checker — that’s the whole stack.
One more safety thing, from watching a colleague nearly do it: don’t paste the sensitive stuff in. He had a client price sheet — names, numbers, the lot — ready to paste into a chatbot to “summarise this.” On a public tool. Strip it first. The tool needs the shape of your problem, never the crown jewels.
Why some AI emails still smell
The fingerprint is the untouched draft. “I hope this email finds you well” up top, padded middle, closing line repeating the opening one. People feel it before they can name it.
My test takes ten seconds: read it out loud. If I’d never say that sentence to this person’s face, it doesn’t go in. Then I cut — there’s always one sentence that’s only there because AI thinks emails should be longer. There it goes.
Questions people actually ask me
Can AI write the whole thing, subject line and all?
It can, and mostly does for me. I still read every word before it leaves, because of the 10% discount incident. That story is my answer to this question forever.
Will people realise?
If you send the raw draft, quite possibly. Cut it, add one real detail, delete the phrases you’d never say — and it sounds like you on a good day. Which, in a sense, it is.
Is it safe to put work emails into these things?
Shape yes, secrets no. Draft the wording all day. Passwords, client figures, anything confidential: strip it or don’t paste it. Boring rule. Keeps you employed.
Last thing
None of this will make you a brilliant writer. It removes the worst ten minutes — the blank box, the tone wrestling.
Start with a boring follow-up — not the sensitive one, not the angry one (we know how that goes). A few weeks of drafting, reading, cutting, sending, and you stop typing emails from a standing start. And stop sending the ones you’d be apologising for at midnight.