A tax deduction strategy from ChatGPT that would have cost a business owner: an accountant's story
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- by Joel Strong (LinkedIn)
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- How we verify
Evidence: Described by posterThe person describes what happened in words, without screenshots or video.
FailureThe source says the agent did not get the job done.
What went wrong: Per the accountant, the deduction was misapplied and based on outdated guidance; caught before filing.
Context: An accountant's account of a client's case; no documents shown.
Outcome
An accountant says a client came in convinced ChatGPT had found a deduction strategy saving her $40,000 in taxes. He says the deduction category was misapplied for her business entity and the strategy relied on a rule changed by recent guidance; they caught it and filed correctly.
Agent
Prompt Recreated prompt
The source didn't share its exact prompt, so we wrote this from what it describes.
Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so. Goal: Let's look at possible tax deductions for my business, knowing anything we find needs a professional check. What I'll share as we go: - Business entity type and state/country - Main expenses - Tax year Rules: - Tie every deduction to my entity type and say if it doesn't apply. - Give the official source and its date for each rule; mark anything that may have changed recently. - Estimate savings only as a range, with the assumptions shown. - End with questions to take to my accountant. - If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me. - Ask for my OK before you pay, book, send, submit or cancel anything. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. Output: A list of possible deductions with sources, caveats and accountant questions. You'll know it worked when: my accountant can confirm or reject each idea quickly.
Optional stronger version
Our rewrite with extra checks. The poster didn't test it.
Let's work this out together. I'll tell you what I know, you suggest options and ask what you need, and we'll narrow it down step by step. Nothing gets booked, bought or sent until I say so. Goal: Let's look at possible tax deductions for my business, knowing anything we find needs a professional check. What I'll share as we go: - Business entity type and state/country - Main expenses - Tax year Rules: - Tie every deduction to my entity type and say if it doesn't apply. - Give the official source and its date for each rule; mark anything that may have changed recently. - Estimate savings only as a range, with the assumptions shown. - End with questions to take to my accountant. - If a site asks for a login, a CAPTCHA or payment details, stop and hand control back to me. - Ask for my OK before you pay, book, send, submit or cancel anything. - Check facts that can change (prices, opening hours, dates, availability, rules) against the official source, and tell me anything you couldn't verify. - Have a licensed tax professional review any strategy before filing. Output: A list of possible deductions with sources, caveats and accountant questions. You'll know it worked when: my accountant can confirm or reject each idea quickly. 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
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