Asking ChatGPT to “write a polite email telling my client the project is late” gets you the same draft every time. Two paragraphs of pleasantries, a vague reason, the news buried in the middle, and an apology long enough to sound guilty. A Reddit user on r/ChatGPTPromptGenius takes the opposite route, and the result is shorter, clearer and easier to trust.
The Key Idea
Stop asking for politeness. Give the model four real facts and a few hard constraints instead. The tone then comes out right on its own, because the draft has something concrete to say.
The four facts are:
- The news. Say it plainly, such as “the project will be two weeks late.”
- What happened. One line with the real reason.
- What they care about most. The thing the news puts at risk for them.
- What you can offer. The part you can still deliver.
Old Way vs New Way
The old way: “Write a polite email saying the project is late.” The model has no facts, so it fills the gaps with its average customer-service voice. You get “I hope this finds you well,” “unforeseen challenges,” and an ending that is just an apology.
The new way: you hand over the facts. Here is the example from the post:
I have to tell a client their project will be two weeks late. What happened: the payment integration needed a security review we didn’t plan for. What they care about most: the launch date they already announced to their own customers. What I can offer: everything except payments working on the original date. Put the news in the first sentence. One sentence of apology at most. Don’t use “unfortunately”, “I hope this finds you well” or “rest assured”. Under 120 words. Then tell me the question they’re most likely to reply with, and work the answer into the message.
The contrast is easier to see once you know what each line blocks 🔍
- Plain news line. If you soften the news in the prompt, the draft softens it twice.
- What happened. Leave it out and ChatGPT invents a reason. It is usually “unforeseen challenges,” which reads like you are hiding something.
- What they care about. This turns the message from “here is my delay” into “here is what it means for your launch.” Without it, the draft is all about your team.
- What I can offer. Without it the email ends on an apology. With it, the email ends on a plan.
- News in the first sentence. The default order is greeting, context, news. Readers skim past the context looking for the news anyway.
- Banned phrases. Those three are the ones that make people stop trusting everything that comes after them.
- Under 120 words. Long bad-news messages read as guilt. Short ones read as someone in control.
The Line That Does the Most Work
The last instruction asks the model to predict the client’s most likely reply and answer it inside the message. That saves a whole round of back and forth. It also tends to surface the exact question you were hoping they would not ask, which is better to find out before you hit send. One commenter put the underlying problem well: without a fact about what the reader cares about, the model falls back on that generic customer-service voice.
How to Use It Yourself
- Write the four facts first. Spend two minutes on them before you open the chat. If you cannot state the real reason in one line, the email is not ready.
- Paste the skeleton. Keep the constraints as they are: news first, one apology sentence at most, banned phrases, a word cap.
- Ask for the predicted reply. Make sure the answer is worked into the draft, not left as a side note.
- Read it as the client. Does the first sentence tell you what happened? Does the last tell you what happens next?
- Swap the facts for other news. The same skeleton works for a missed deadline, a price increase, saying no to a friend, or cancelling plans ✅
The author saves the skeleton in their browser extension, AI Toolbox, with the four facts as {{variables}}. Typing // drops it in, and they only fill in what is different this time. You can get the same effect with a saved note or a text-expander snippet.
Your Move
Next time you have bad news to deliver, skip “make it polite” and write the four facts instead. Run it once on a real message you have been putting off, then save the skeleton so the next one takes a minute. Tell the crew in the comments what you used it for and what you changed 🏴☠️
Frequently Asked Questions
Q: Should I ask for a polite tone or something else?
One commenter suggests naming the tone as ‘direct, not cold’ instead of ‘polite.’ Their reasoning is that ‘polite’ is the word that pulls the pleasantries back into the draft, while ‘direct, not cold’ cuts the fluff without making the message sound curt. It only takes one test run on your next bad-news email to see if it works for you.
Q: Should the banned phrase list stay fixed or grow?
The commenter who asked this didn’t answer their own question, but the thread points toward growing it. Start with the three phrases from the post, and add one each time a draft includes a phrase you’d delete by hand. Over a few sends, the list will match your clients and your own writing habits.
Q: Why do the banned phrases matter so much?
Commenter Easy-Purple points out that phrases like ‘I hope this finds you well’ and ‘rest assured’ are the tells people spot as a template. Once a reader catches one, they start discounting everything else in the message. Cutting them forces the model to write a real sentence about your situation instead of reaching for the stock version.
The prompt I use for bad-news messages, taken apart line by line, and what each line stops ChatGPT from doing
by u/Ok_Negotiation_2587 in ChatGPTPromptGenius