Which tool to choose
There's no single best tool, but there is the right one for how you work. Three profiles cover almost all cases.
If you write emails occasionally and want zero costs and zero installations: use an external chatbot with copy-paste. ChatGPT is fast and structured: for a standard business email it delivers something usable on the first try. Its limit is the tone: without precise instructions it tends toward the generic, with formulas like "We're thrilled to announce" that recur often. You avoid them if you say so in the prompt.
If you care about the tone of voice and write delicate emails (unhappy clients, negotiations, sensitive communications): choose Claude. When the text needs writing quality — elaborate emails, reports, proposals — it tends to avoid clichés better than the competitors. Useful when you want a result that doesn't sound like everyone else's.
If you want AI inside your inbox, without copy-paste: it depends on your provider.
- On Gmail the feature is called "Help me write". With eligible Google Workspace or Google AI plans you write drafts with Gemini in Italian too; for personal Google Accounts the feature is for now available only in the United States.
- On Outlook, "Draft with Copilot" is reserved for the business world: it requires an eligible Microsoft 365 Business, Enterprise, US Government, or Education subscription. It's not available in email composition on Personal or Family licenses.
Operational conclusion: if you're a private individual or a small sole trader in Italy, the most reliable and free path is the external chatbot. The integrated features are convenient, but they require the right subscription.
How to do it
The method is the same for all tools: only where you paste the prompt changes.
- Open the tool. From browser or app the path doesn't change: go to chatgpt.com or claude.ai, or open the assistant's chat.
- Paste the filled-in prompt (the syntax is below). The more specific you are about recipient, goal, and tone, the better the draft.
- Read the first version and request changes in natural speech: "make it shorter", "remove the enthusiastic tones", "add a June 20 deadline".
- Check the sensitive data by hand: names, amounts, dates, links. The AI can invent them.
- Copy the final text into your email and send.
The operational syntax for any chatbot:
Write a professional email in Italian.
Recipient: purchasing manager of a client company, I don't know them personally
Goal: chase the payment of an invoice overdue by 15 days
Tone: courteous but firm, no aggressiveness
Points to include:
- invoice number 2026/142, amount 3,200 euros, due May 28
- offer availability to look into any problems
- ask for confirmation of the payment date
Length: maximum 120 words
Constraints: no enthusiastic formulas, no "Dear Sirs", open with a simple greeting. Sign with "Marco Bianchi, Accounting".
If you're on Gmail with an eligible plan, the work happens inside the inbox. Open a new message, turn on the "Help me write" feature, and describe what you need: the AI takes into account the context and previous messages. You'll find the same levers from the prompt as shortcuts too — making the text more formal, expanding or shortening it. If the feature doesn't respond, first of all check that Gmail's smart features are turned on in the settings.
On business Outlook the principle is identical: open a new message, turn on Copilot from the message bar, and write a prompt that describes content and recipient. From the draft you can correct tone and length, regenerate the text, or confirm it, and then touch it up by hand before sending. The command names change from version to version: look for the Copilot icon in the compose window, that's where it all starts.
Feedback: if the draft sounds robotic or full of superlatives, the culprit isn't the tool but the too-vague prompt. Add the constraint "no enthusiastic formulas" and indicate a maximum length: it changes everything.
Concrete example
Real situation: Marco handles the administration of a small agency. A client hasn't paid an invoice overdue by two weeks and Marco has to write to him without cracking the relationship. He doesn't know where to start and fears coming across as aggressive.
Action: he pastes the chaser prompt into ChatGPT (the one above). He gets a draft of about a hundred words, with a neutral opening, reference to the invoice, an offer to clarify any disputes, and an explicit request for the payment date.
Marco finds two things to fix: the AI wrote "invoice 2026/142 for 3,000 euros" (wrong figure, it was 3,200) and added "we're certain of your usual punctuality", which is out of place in a chaser. He asks: "Correct the amount to 3,200 euros and remove the last sentence". He gets the clean version.
Result: email sent in three minutes instead of twenty, measured tone, correct data. The client replies the same day with the transfer date. Marco's real work was checking the figure, not the writing.
When it does NOT work (and how to fix it)
If the AI invents numbers, names, or details
The models generate plausible, unverified text, and should not be used as medical, legal, financial, or professional advice: they may suggest inaccurate information. The way out: never ask the AI to "remember" amounts or dates. Provide them yourself in the prompt and always reread invoice, IBAN, names, and figures before pressing send.
If "Help me write" doesn't appear in Gmail
Often it's a matter of language or settings. Check that the device language is among the supported ones and that Gmail's smart features are turned on. If the button stays gray and won't select, reload the browser or close and reopen the app, and try again: it happens that the service is momentarily unavailable.
If the draft sounds fake or full of superlatives
It's the most common flaw of AI output. Immediate fix: add to the prompt a line of constraints like "no enthusiastic adjectives, short sentences, dry professional tone". Alternatively switch to Claude, which tends to produce less standardized texts.
If Outlook doesn't show you Copilot
Almost always it's a licensing issue, not a fault: Personal and Family licenses don't include Copilot in email composition. The way out: use a free external chatbot (ChatGPT, Claude) and paste the finished text into Outlook. You get the same result without changing subscription.
A tip from someone who really uses it
Save a "skeleton" prompt of yours in a phone note, with recipient-goal-tone-points-constraints already set up like in the model above. Each time you only change the specific content. You save time compared to those who rewrite a prompt from scratch every time, and you get emails consistent in tone. The line on stylistic constraints is the difference between an email that seems written by a machine and one that seems written by you on a good day.
Frequently asked questions
Can the AI read my confidential business emails?
It depends on the tool. The integrated features of Gmail and Outlook work inside your account according to the provider's policies. With external chatbots you're pasting the text onto a third-party service: for emails with sensitive data (contracts, clients' personal data, financial information) avoid pasting the entire content and describe the situation generically.
Can I use the free version or do I have to pay?
For writing emails, the free version of ChatGPT or Claude is more than enough. They work as external assistants: you give context and tone, copy-paste, and get maximum flexibility. The subscriptions are needed if you want integration inside the inbox or you handle very high volumes.
In Gmail does "Help me write" work in Italian?
Yes, but with a precise condition. With eligible Google Workspace or Google AI plans you write drafts in Italian; for personal Google accounts the feature is for now available only in the United States. If you have a free personal Gmail in Italy, the external chatbot is the way to go.
Are Gmail's free AI features already available in Italy?
Not right away. Google has made some Gemini features in Gmail free, like "Help me write" and suggested replies, but they start in the United States and in English, to reach other regions and languages in the following months. If in Italy you don't see them active yet, it's not a mistake on your part: the rollout proceeds in stages.
Doesn't writing emails with AI make all communications the same and impersonal?
It's the most reasonable fear, and it has a basis. Without precise instructions the AI falls into stock phrases. But the impersonality comes from the lazy prompt, not from the tool: if you state your tone, give the concrete details of the case, and impose stylistic constraints, you get a text that starts from you and sounds like you. The AI writes the first draft; the voice remains your choice.