AI Made This Worse
Five minutes became twenty
Written by AI Tools AcademyLast checked on 27 September 2026
Helpful first: Choosing the right tool
This is a fictional example. Fernway Group is a made-up UK company, and everyone in it is invented.
Nothing went badly wrong in this story. No one was misled and nothing false was sent. The cost was time, which is the thing AI was supposed to save, and it's a pattern worth recognising because it is easy to miss when you are in the middle of it.
Before
Grace Lynch is Fernway's Finance Assistant. Part of her week is chasing overdue invoices. For a first reminder, Fernway has a short, approved template: a polite line saying the invoice is now overdue, the invoice number, the amount, the due date, the payment details and a contact name. Grace fills in four fields and sends it. On a normal day that takes about five minutes, most of which is looking up the invoice in the finance system.
This reminder was for a customer who had always paid on time until now, and whose office manager Grace had spoken to on the phone. The template felt a bit stiff for them, so Grace decided to ask AI for something friendlier.
The AI approach
Grace knew not to paste customer names, invoice numbers or bank details into an AI tool, so she wrote around them:
Write a friendly first reminder to a long-standing business customer whose invoice is 14 days overdue. They normally pay on time. Keep it polite and short, and don't make it sound like a demand. Use [CUSTOMER], [INVOICE NUMBER], [AMOUNT] and [DUE DATE] as placeholders.
Why this works: There's nothing wrong with the prompt itself. The problem is the work around it, which this prompt can't show.
What went wrong
The draft was fine. Getting to "fine" was the problem. Grace noted the time afterwards because it felt longer than it should have:
| Step | Minutes |
|---|---|
| Decide what to leave out and write the prompt around it | 4 |
| Read the first draft: too warm, sounded like marketing | 2 |
| Ask for a plainer version, then a shorter one | 4 |
| Remove a line offering "flexible payment options" Fernway doesn't offer | 1 |
| Put the real customer name, invoice number, amount and date back in | 3 |
| Check every figure against the finance system | 3 |
| Compare with the template to make sure nothing required was missing | 3 |
| Total | 20 |
Three things turned a five-minute job into a twenty-minute one:
- The template already existed. Someone at Fernway had done the thinking once. Grace was paying to redo it, and the AI didn't know what the template had been designed to include, such as the payment details and a named contact.
- The information that mattered couldn't go in. Everything specific about this reminder (who, which invoice, how much, when) was exactly what Grace was right to keep out. So she did the redacting on the way in and the reinserting on the way out, and every reinserted figure then needed checking. Your organisation's policy and approved tools still take priority here: if Fernway's approved tool had been cleared for this kind of data, some of that work would disappear, but the checking would not.
- The AI added something untrue. An offer of flexible payment options sounds kind and is exactly what a friendly reminder might say. Fernway doesn't offer it, and sending it would have created an expectation Grace couldn't meet.
What Grace actually needed was one sentence of warmth.
A better approach
If Grace sends friendlier reminders often, there is a better use of AI: improve the template once and reuse it. She could ask AI (with no customer data at all) to suggest two softer versions of the template's opening line, pick one, get it approved, and save it. The AI cost is paid once, and every future reminder takes five minutes again.
A quick way to decide before you open the tool is to ask three questions:
- Is there already a template, a previous example or a standard wording? If yes, start there.
- Is the sensitive information the whole point of the task? If you would have to strip out everything specific, the AI is only helping with the part you could do yourself.
- Would checking the output take as long as writing it? For anything under a paragraph, it often does.
Two or more yes answers usually means doing it by hand is faster. AI earns its time on longer, messier or unfamiliar work: a reply you don't know how to start, a long thread to untangle, a new template to design.