Which tool to choose
You don't need ten apps. Choose based on where you usually write.
Do you use Gmail for work? Go straight to the built-in feature. Help me write, suggested replies and text correction let you compose the message without leaving the inbox: you write and send in the same place, no copy-paste. Watch out though: these features require a Google Workspace account with the Gemini add-on (Business, Enterprise or Education) or a Google One AI Premium subscription. On a free personal Gmail account you might not see them.
Want something that always works, free, from any device? ChatGPT. Since April 2024 the free plan is accessible even without an account: anyone who visits the site can open a conversation and start writing, without even an email address. For a single email the free plan covers everything; the limits only emerge in long sessions or complex work on documents.
For this specific task — a short email, once in a while — free ChatGPT is the right choice: no subscriptions or corporate requirements, and it works the same on phone and computer.
How to do it
From browser or app, the path doesn't change:
- Open ChatGPT (chatgpt.com) or the app on your phone.
- Copy the prompt below in a single block.
- Replace the parts in quotes with your real data: manager's name, dates, reason, days of notice.
- Paste into the message field and send.
- Read the reply: check that the dates are exact and that the tone represents you.
The operational syntax:
Write me a formal but cordial email to request vacation from my manager.
Data:
- My name: Marco Bianchi
- Manager's name: Dr. Laura Rossi
- Type of absence: vacation
- Period requested: from July 14 to 18, 2026 (5 working days)
- Reason: family commitments (do not go into details)
- Availability: I'll leave the handover organized with colleagues before leaving
Use a professional register, get straight to the point, keep it under 120 words.
Do not add details I haven't provided.
Also propose a subject for the email.
For a few-hours leave instead of full vacation, change the period line like this:
- Type of absence: leave
- Period requested: Monday July 14, 2026, from 9:00 to 13:00
- Reason: medical appointment
Check: a good reply gives you subject + body, the dates you wrote appearing identical, and no invented information about your reason. If the AI adds details you didn't give it (a contract number, a colleague's name), delete them before sending.
A concrete example
Giulia works in a shop and needs to ask for three days for a move, but she doesn't want to seem curt or write a poem. She opens ChatGPT on her phone during the break. She pastes the prompt, puts the owner's name (Mr. Conti), the dates (May 22-24), as reason "personal matters" and adds that she's available to make up the shifts.
In a few seconds she receives a subject — "Request for leave days May 22-24" — and an email body of about ninety words: greeting, clear request with the dates, the sentence about availability to reorganize the shifts, courteous closing awaiting confirmation. Giulia changes only one word that sounds too formal to her ("I would be grateful" becomes "Thanks in advance"), copies everything into her work email and sends. Total time: less than three minutes.
When it does NOT work (and how to fix it)
If the AI invents details you didn't give
Sometimes it adds a project name, an employee number or a more specific reason than the one you wanted to reveal. Don't trust it sight unseen: always reread before sending and delete any data you didn't provide. In the prompt it helps to write explicitly "do not add details I haven't provided".
If the tone is too rigid or too informal
Don't rewrite from scratch. Reply in the same chat with a curt instruction: "Make it warmer" or "More formal, I'm writing to an executive I barely know". The AI regenerates keeping the dates and the structure, changing only the register.
If in Gmail you don't see "Help me write"
Almost always it's because you have a free personal account: as seen, the feature requires a Workspace plan with the Gemini add-on or a Google subscription. The way out: write the email in free ChatGPT and paste it into Gmail. Same result, zero cost.
If you've reached the free message limit
It rarely happens for a single email, but it does. On the free plan, after a certain number of messages on the flagship model within a few hours the session switches to a lighter model. The lighter model writes a vacation email well anyway: continue without problems, or wait for the limit to reset.
A tip from someone who actually uses it
The first version the AI gives you is almost always too long and too polished. Vacation requests that work are short: two sentences of substance cover everything. After the first generation, write "halve it and drop the useless pleasantries". You'll get an email that a manager reads in ten seconds and approves without a second thought — and that's exactly what you want. Save the prompt in your phone notes: next time you only change the dates and you're done.
Frequently asked questions
Do I have to register to use ChatGPT?
No. From the site anyone can open a conversation and start writing, without an account or email address. For an occasional email this is perfectly fine. Registering is only needed if you want to find your old chats again.
Can I do it from my phone while I'm out?
Yes. For this task the app does the same things as the computer version: you copy the prompt, paste it, and then move the text into the new Gmail email with a copy-paste.
Does the AI know the vacation rules of my contract?
No, and it doesn't need to. The AI writes the text of the request, it doesn't verify how many days you're entitled to or the notice deadlines of your collective agreement. You put that information in the prompt (the days of notice, for example) after checking it in the contract or asking the HR office.
Will my boss notice I wrote it with AI?
It's the right fear to confront. The honest answer: if you send the raw, long and impersonal text, maybe yes — all "robot" emails look alike. But a vacation request isn't an exam essay: it has to be clear and correct, not original. Cut the pleasantries, put a word of your own here and there, and it becomes indistinguishable from one written by hand. The tool saves you time on a standard text, and nobody expects poetry in a leave request.