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Fill the family's weekly online grocery carts from a shared list with a ChatGPT Work assistant

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by Whitney Stefko Dover, reported by Ben Shimkus (Business Insider)
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How we verify

Evidence: Article or interviewA newsletter, journalist or interview account of what happened.

Outcome

Whitney Stefko Dover, a Ford director, built a family chief of staff called Gigi in ChatGPT Work after months with a Claude version. Every Friday it reads the grocery list shared with the family's nanny and fills the online shopping carts. Stefko Dover still reviews and pays for each order because it needs supervision: one grocery suggestion included 12 boxes of bow-tie pasta, and it once suggested sending flowers to a friend's wife after mistaking the friend's wife for a relative.

AI tool

ChatGPT Work

Prompt Recreated prompt

The source didn't share its exact prompt, so we wrote this from what it describes.

What the prompt labels mean

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Each week, turn our shared grocery list into a filled online cart that I check and pay for.

Fill in before running:
- Where the shared list lives: [LINK OR APP]
- Which store(s) to use: [STORES]
- Brands and sizes we usually buy: [PREFERENCES]

Rules:
- Add only what's on the list, in sensible household quantities; ask if a quantity looks unusual.
- Use our usual brands and sizes; if one isn't available, pick the closest match and flag the swap.
- Don't check out or pay; leave the cart for me to review.
- Send me a short summary of what's in each cart and anything you couldn't find.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.

Output: Filled carts ready for review and a one-paragraph summary.

You'll know it worked when: I can review and check out in a few minutes with nothing missing or doubled.

Try this in:

This prompt has blanks to fill in, like [LINK OR APP]. We'll copy it instead of filling it in, so you can edit it before you send.

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Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Run this task now, exactly as written below. Everything you need is here, so start straight away and only stop if something required is missing or a rule below tells you to.

Goal: Each week, turn our shared grocery list into a filled online cart that I check and pay for.

Fill in before running:
- Where the shared list lives: [LINK OR APP]
- Which store(s) to use: [STORES]
- Brands and sizes we usually buy: [PREFERENCES]

Rules:
- Add only what's on the list, in sensible household quantities; ask if a quantity looks unusual.
- Use our usual brands and sizes; if one isn't available, pick the closest match and flag the swap.
- Don't check out or pay; leave the cart for me to review.
- Send me a short summary of what's in each cart and anything you couldn't find.
- If a site asks me to sign in, pause and let me do it myself (including any CAPTCHA or two-step code); never guess or store passwords.
- Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify.
- Before you finish, flag any line where the quantity is more than double what we usually buy.

Output: Filled carts ready for review and a one-paragraph summary.

You'll know it worked when: I can review and check out in a few minutes with nothing missing or doubled.

Before you finish: re-read my goal and constraints, check your answer against each one, and list anything you assumed or couldn't confirm.

Source

https://www.businessinsider.com/ford-exec-claude-chatgpt-family-chief-staff-2026-9

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