Employee starts prompting his boss as if she were an AI chatbot to get the responses he desires and it works: 'I try different prompts in my chat to see which wording of a question will give the affirming answer I want. I then bring up my decision to her'

Author image for Olivia Arocena
Olivia Arocena • Writer and Editor
Jul 12, 2026 1:45 PM EDT

Maybe we're the chatbots after all

I admit it: I have a complex relationship with ChatGPT, and by complex, I mean I use it to think through pretty much most of my decisions. I'm a writer, so I'm used to developing ideas through text in a couple of languages. I also write short stories, and every day I write in my diary; still, today, I asked ChatGPT for help with writing a WhatsApp message. In my defense, it was a tough message to write emotionally, but still. In the end, when she (yes, she) gave me her version, I was like : yes, this is correct, it is well-structured and assertive, but I want to be human. The text message didn't by no means capture the depth of what I was feeling, and while it communicated a very clean, honest, and impartial take, I needed it to be short-sighted, personal, and raw. Perfect feelings are not feelings. In the end, I ditched the version the chatbot gave me, and I stuck to mine. Maybe one day we'll all realize that we need more honesty and more biased opinions to create a fruitful diversity of experiences and life. Anyway, I digress; what happened to this employee is likely to start happening way more often, and I think he found a clever way to resolve it. It doesn't resolve the issue deeply, but it creates gaps through which the light can hopefully begin to come in.

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  • 01
    man watching MacBook
    via Xu Haiwei

    The man crafting the perfect prompt

    Subject is a model

  • 02

    I prompt my boss just like AI

    My boss has given her brain away to chatgpt. She constantly needs reassurance from it I guess. for decisions. It was
    via RandoSFX
  • 03
    getting annoying to have to constantly defend my work and ideas against what her chat result would say.
    via RandoSFX
  • 04
    Now if I make a change to something (that I know is the right decision), I try different prompts in my chat to see which wording
    via RandoSFX
  • 05
    of a question will give the affirming answer I want. I then bring up my decision to her and when she has doubt, I ask her the same
    via RandoSFX
  • 06
    "question" and on cue, she types it into chat, it validates what I want, and I go on my merry way.
    via RandoSFX
  • 07
    silver human robot
    via Xu Haiwei

    How the employee sees his boss

    Image is representative

  • In the near future, we will have to do something about how we’re using the chatbots; it has definitely gotten out of hand, and every one of us has a chatbot in our ears telling us everything we do is right, and everything everybody else does is wrong. I don’t know if I’m being too optimistic, but I do think that we are going to get tired of this and figure out new ways of writing, thinking about ideas, and searching the internet.

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workplace-stories toxic-workplace work workplace toxic-work-environment
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