, September 20, 2026

Your Boss Is Workshopping How to Screw You With ChatGPT


AI tools can help find the right tone and language for difficult workplace conversations about performance and pay, and managers are already using them.

  •   1 min read
Your Boss Is Workshopping How to Screw You With ChatGPT

Managers are feeding your performance into AI chatbots to figure out how to tell you that you're not getting a raise without making you cry in the break room.

The headline says these tools help find the right tone and language. The right tone. As if the problem with telling someone they're underperforming was always just a matter of word choice and not the fact that you're about to financially kneecap them during record inflation.

Picture your manager typing: "How do I tell Jenkins his work is subpar but frame it as a growth opportunity?" The AI spits back some corporate therapy-speak about "developmental feedback" and "alignment with organizational objectives." Your manager copies it verbatim into an email. Jenkins thinks his boss suddenly got articulate. Jenkins is wrong. His boss got a subscription.

This is not about helping managers communicate better. This is about outsourcing the emotional labor of ruining someone's day to a language model that was trained on every HR manual ever written and somehow still has more empathy than the person using it.

The best part? The AI doesn't know you. Doesn't know if you've been staying late or covering for incompetent coworkers or whether your metrics tanked because the system you're measured on is designed by people who've never done your job. It just knows your manager asked for a tactful way to deliver bad news and it's going to deliver that tact like a f*cking room-service breakfast.

Somewhere right now a middle manager is asking ChatGPT how to justify a two percent raise to someone who increased revenue by forty percent. The AI will find the words. It always does. And your manager will read them off a screen while maintaining eye contact like they thought of it themselves.

You're not getting fired by a robot. You're getting fired by a coward who had a robot write the script.

Photo by on Unsplash

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