A former licensed insurance agent of 27 years gave Grok a wish list for his parents' Medicare Advantage cover and asked for its recommendation. It picked the same plan he would have chosen himself.
I'm helping my parents choose [TYPE OF INSURANCE PLAN] in [AREA]. Their must-haves are: [WISH LIST, E.G. KEEP CURRENT DOCTORS, LOW MONTHLY COST, TRAVEL COVER]. Here are the plans we're considering: [PASTE PLAN NAMES OR SUMMARIES]. Compare them against the wish list in a table, recommend one with your reasons, and list anything we should confirm directly with the insurer before signing up.
Replace the [PLACEHOLDERS] with your own details before you send it.
How to try it
- Write down your parents’ must-haves before you start (doctors, costs, cover).
- Give Grok the wish list and the plans you’re considering, and ask for a comparison table.
- Confirm the details with the insurer or an adviser before you decide.
More money use cases
Spot a wrong charge on a medical bill with ChatGPT
A friend of the poster uploaded her hospital bill to ChatGPT, which picked out an incorrect charge and drafted a dispute letter. The hospital removed the $4,200 charge and marked the account as paid in full.
Here is an itemised bill I've received: [PASTE THE LINE ITEMS, WITH PERSONAL DETAILS REMOVED]. Please 1) explain each line in plain English, 2) flag anything that looks duplicated, unusually priced or inconsistent with [WHAT I WAS ACTUALLY TREATED FOR], and 3) draft a polite letter asking the billing department to review the items you've flagged and send a corrected bill.
Log your spending by just telling Claude what you bought
A student who'd never stuck with budgeting apps had Claude build a full budget spreadsheet, then set up a Claude Project with the template and instructions. Now they type things like 'bought matcha, spent this on the commute' from their phone and Claude categorises each item, asks when unsure, and returns the updated sheet.
You're helping me track my spending in the attached spreadsheet. Each time I tell you what I've spent or earned, add a row to the Transactions sheet with the date, amount and the right category from [YOUR CATEGORIES]. If you're not sure of a category, ask me first. Today is [DATE]: [WHAT YOU SPENT].
Track down and cancel forgotten subscriptions with ChatGPT
Listing the ways ChatGPT saved him money, one user said it cancelled a forgotten streaming subscription and a golf app subscription, and told him which card to use to earn the most miles.
Here are my bank and card transactions for the last 3 months: [PASTE, WITH ACCOUNT NUMBERS REMOVED]. Find every recurring payment, name the service if you can, show the monthly and yearly cost, and flag ones I may have forgotten. Then give me step-by-step cancellation instructions for the ones I tell you to cancel: [LIST].
Reference: X @JodyOnTheCouch