AI Made This Worse
The email that got longer
Written by AI Tools AcademyLast checked on 27 September 2026
Helpful first: Prompting that works
This is a fictional example. Fernway Group is a made-up UK company, and everyone in it is invented.
Most of the time, asking an AI tool to tidy up an email is a sensible use of it. This is a case where the tidy-up made the email worse, and the reason is worth understanding, because it happens far more often than outright errors do.
Before
Sam Price is an Account Manager at Fernway, covering customers in the South. One of them, a small architecture practice, is waiting for a replacement multifunction printer. The warehouse has just told Sam the delivery will slip by two days, from Tuesday to Thursday, and the engineer will arrive in the morning.
Sam wrote this in about a minute:
Hi Nadia,
Quick update: your replacement printer will now arrive on Thursday 15 October
(not Tuesday), with the engineer on site between 9am and 11am. Sorry for the
change. Let me know if Thursday doesn't work and I'll rearrange.
Sam
It is short, it leads with the news, and it offers a way out. Sam was worried it sounded a bit abrupt for a customer who had already waited a while, so Sam pasted it into the company's approved AI tool before sending.
The AI approach
Sam's instruction was the one most of us would type:
Make this email more professional and customer-friendly. [Sam's three-line email]
Why this works: This is the version that caused the problem: it asks for improvement without saying what 'better' means.
What went wrong
The AI did what it was asked. The trouble is what "more professional and customer-friendly" means to a tool that has learned from millions of business emails: more greeting, more apology, more reassurance, more sign-off.
Subject: Update Regarding Your Replacement Printer Delivery
Dear Nadia,
I hope this email finds you well.
I wanted to reach out to provide you with an update regarding the delivery of your replacement multifunction printer. At Fernway, we are committed to providing an excellent service, and we understand how important reliable equipment is to the smooth running of your practice.
Unfortunately, due to circumstances beyond our control, there has been a slight change to the original delivery schedule. Please accept our sincere apologies for any inconvenience this may cause.
Your replacement printer is now scheduled to arrive on Thursday 15 October, and our engineer will be on site between 9am and 11am to complete the installation.
Should Thursday not be convenient, please do not hesitate to get in touch and I will be more than happy to arrange an alternative date that better suits your schedule.
Thank you for your patience and understanding.
Kind regards,
Sam Price
Nothing in it is false, which is why it is easy to send. But look at what changed:
- The date moved from line one to paragraph four. Nadia has to read nearly 90 words before she finds out when the printer arrives. On a phone, that is below the first screen.
- The word "Tuesday" disappeared. Sam's version said what changed. The new one never mentions the old date, so Nadia has to remember it to understand the update.
- It added a claim Sam didn't make. "Circumstances beyond our control" is a guess. Sam doesn't know why the warehouse slipped, and if Nadia asks, Sam now has to explain or retract it.
- It sounds like a template. Nadia has had several emails from Sam. This one reads as if someone else wrote it, which is a small loss of trust for no gain.
The email got roughly four times longer and harder to act on. The AI didn't make a mistake in the usual sense. It followed a vague instruction in the direction its training pulls: towards more.
A better approach
There are two good options here, and the first is simply to send the original. Sam's worry about sounding abrupt was really a worry about the opening two words. Changing "Quick update:" to "A quick update on your printer:" would have settled it without any tool.
If you do want AI to help with tone, tell it what to keep, what to cut and how long the result can be. "Improve" and "make it more professional" are open invitations to add.
Weak
Make this email more professional and customer-friendly.
Better
This is a short update to a customer whose delivery has slipped by two days. Keep the new date and time in the first sentence and keep the mention of the original day. Make it sound warm but not formal, under 60 words, and don't add any reasons, promises or phrases I haven't written. Show me only what you changed and why.
Why it works: It names the audience, protects the one fact that matters, sets a length limit, bans invented reasons, and asks for the changes to be shown so you can accept or reject each one.
Asking to see only what changed is the most useful habit here. A full rewrite is hard to check, because you have to compare two versions line by line. A short list of changes ("softened the opening", "added 'I'm sorry for the wait'") takes seconds to accept or ignore.
A quick test before you send any AI-edited email: read only the first two lines. If the reader would know what you need them to know, or do, from those two lines alone, the email is doing its job. If not, move the key fact up, whoever wrote it.