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AI Writes Perfect Counter-Offer Letter, Creates Infinite Negotiation Loop

November 25, 2025
3 min read
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Picture this: Sarah, a software engineer with more Python skills than a reptile sanctuary, receives a job offer. Being a modern professional, she feeds the offer letter into ChatGPT and asks it to write "the perfect counter-offer." The AI delivers a masterpiece—eloquent, data-driven, peppered with phrases like "market-rate compensation" and "total rewards package alignment."

She hits send at 2:47 PM on a Tuesday. By 2:49 PM, she has a response. Suspiciously fast for HR.

The Robot Wars Begin

Turns out, the company's talent acquisition team also uses AI. Their shiny new "Offer Optimization Assistant" analyzes Sarah's counter-offer and fires back with a professionally worded rejection of her terms, complete with Bureau of Labor Statistics citations and a thoughtful acknowledgment of her "unique value proposition."

Sarah's AI isn't backing down. It reads the response, recalibrates, and sends another counter—this time introducing equity considerations and flexible work arrangements. The company's AI responds within minutes, proposing a compromise on equity but holding firm on base salary.

By 4:00 PM, they've exchanged 23 emails. By end of business, 47. The AIs are now discussing 401(k) matching percentages, PTO accrual rates, and whether the company's "unlimited vacation" policy is technically better than 25 fixed days.

The Human Intervention

At 9:37 AM the next day, Sarah's inbox has 89 new messages. All from the same thread. The AIs have moved on to debating the monetary value of free snacks and whether "casual Fridays" constitutes compensation.

The hiring manager finally notices when IT flags the email server for unusual activity. He calls Sarah directly. "Can you just... take the job? Please? Our AI is threatening to counteroffer with a ball pit."

The Recruiting Wisdom: Technology should support negotiation, not replace the human conversation. Also, maybe put a daily email limit on your AI tools. Just a thought.

Sarah accepted the offer. The AIs are still arguing in a forgotten email thread somewhere, probably discussing dental insurance coverage by now.

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