Which tool to choose
For this task you only need text, and all three major assistants do it well at zero cost. The choice depends on what you have at hand.
- Do you need to attach the competitor's quote or a contract to cite? Go to Claude. The free plan includes file upload (up to 20 files per chat and 500 MB per file) and web search. You upload the PDF, it reads the exact figures and uses them in the email without you having to copy them out.
- Want to write the email starting from what you type? ChatGPT free is immediate. Free users can search the web, analyze data, upload images or files. There's a message cap on the best model every few hours: once you exceed the limit, the chat scales down to a lighter version until the reset. For a single email the margin is wide.
- Already inside Gmail and Workspace? Gemini is the logical shortcut. The free version runs on the Flash model and handles quick drafts, summaries and everyday text questions.
If you don't know which to open, start from ChatGPT free: it's the fastest when you write from scratch.
How to do it
From browser or app the path doesn't change: open the tool, paste the prompt, check, send from your inbox.
- Gather the three pieces of data that make the difference: current price, the figure you want to reach (your counteroffer) and the lever (a competing offer, the volume you bring, the years as a customer, a rigid budget).
- Open the AI and paste the prompt below, replacing the values in quotes with yours.
- Read the draft. Check that the figures are the ones you gave and not invented numbers.
- Adjust the tone: if you know the recipient well, soften it; if it's a formal supplier, leave it lean.
- Copy the text into your email, add a subject and signature, send.
The operational syntax:
Write a professional email in Italian to ask for a discount.
Context:
- I've been a customer of "company/supplier name" for "X years/months"
- Current price proposed: "e.g. €1,200 per year"
- The figure I want to obtain: "e.g. €950 per year"
- My lever: "e.g. I received a competing quote at €900, but I'd prefer to stay with you"
- My recipient: "role, e.g. sales account manager"
Requirements:
- Courteous but assertive tone, never pleading
- Anchor the request to a concrete reason, not a whim
- Leave the other party a dignified way out (e.g. propose an alternative plan)
- Maximum 150 words
- Subject included
- Close with a clear request and a date by which I expect a reply
Check: a good draft opens by acknowledging the relationship, states the desired figure with a why, and closes with a direct question. If the email begs or apologizes too much, it needs redoing: add to the prompt "make the tone more confident, no apologies".
A concrete example
Marco renews the subscription to the practice's management software. The supplier proposes €1,440 per year, +20% on the previous year. Marco has found a competitor at €1,100, but switching software would cost him days of migration, so he'd prefer to stay.
He pastes into the prompt: customer for 4 years, price €1,440, target €1,150, lever the competing quote at €1,100 plus loyalty. The AI produces an email with the subject "Subscription renewal – price alignment proposal", which thanks them for the 4 years of collaboration, cites the received quote without aggression, asks to revise the fee to €1,150 and proposes as an alternative to keep the old price. It closes asking for a reply by Friday.
Marco shortens a couple of sentences and sends. The supplier makes a counteroffer at €1,200. Savings: €240 a year, with ten minutes of work.
When it does NOT work (and how to fix it)
If the AI invents the numbers
It can happen that the draft contains figures or percentages you never provided. Don't trust a number you didn't write yourself in the prompt. Reread every euro and every date before sending; if you uploaded a file (quote, contract), add to the prompt "use only the figures present in the attached document, don't add any others".
If the tone is too submissive or too aggressive
The free drafts tend to overdo the courtesy. Reply in the same chat with "more direct, drop the apologies and conditionals" or "soften it, it sounds too harsh". Iterating in the same conversation costs one message and hits the mark.
If you run out of free messages mid-task
On ChatGPT free, once the cap is used up, the chat scales down to the lighter version until the reset: for an email it holds up without problems. Alternatively, move the conversation to Claude or Gemini, which have separate limit windows. You have three free tanks, not one.
If the email must go directly from your inbox
Chat tools write the text but don't send: you copy and paste into your client. If you use Gmail with integrated Gemini you can generate the draft inside the compose window, but the text needs to be reread before sending in any case.
A tip from someone who actually uses it
Don't ask "write me an email for a discount" and little else: you'll get a generic letter that the supplier recognizes at a glance as copy-paste. The value lies in the lever. A request anchored to a verifiable fact (a real quote, an order volume, a multi-year renewal) moves the negotiation; a vague request ends up filed away. Give the AI the precise lever and the reply you get changes in weight.
And always anchor higher than where you want to land: if you aim for 1,150, ask for 1,100, because the counteroffer will land in the middle.
Frequently asked questions
Do I have to pay for ChatGPT Plus to write a discount email?
No. A single email falls within the free limits of any assistant. The free plan covers quick questions, drafts and isolated tasks well. You pay only if you write dozens of emails a day and bump into the usage caps.
Will the recipient realize I wrote it with AI?
Only if you leave it as-is. Raw drafts have recognizable tics: openings that are too formal, long sentences, excess courtesy. Change two or three sentences with your own words, shorten, add a personal detail (a recent project, a past conversation) and it becomes indistinguishable.
Can I have the AI read the competitor's quote to use it in the email?
Yes. Even on the free plan Claude allows file upload. You upload the PDF, the AI extracts the figures and inserts them into the email with no transcription errors. Check the numbers before sending anyway.
Isn't it dishonest to use AI to negotiate instead of doing it "myself"?
The AI doesn't negotiate in your place: it writes a draft that you decide, correct and sign. The strategy — how much to ask, which lever to use, when to give in — remains entirely yours. The tool removes the blank-page block and gives you a calibrated tone, like a colleague who proofreads your email before sending. Whoever gets the discount isn't the one who writes best: it's the one who brings the right lever. You choose that, the AI just puts it in good form.