If you’ve been following the headlines, you’ve probably noticed a wave of layoffs sweeping through major companies from Amazon to Microsoft. Many of those cuts have targeted middle management, as organizations flatten their hierarchies in the name of efficiency. Microsoft even said its latest layoffs were meant to “reduce organizational layers” and streamline decision-making.

While some companies point to AI as the driving force behind these restructures, the data tells a more complicated story — one that suggests AI isn’t always to blame.

Still, the news got me thinking: could AI actually do one of these jobs? Could a chatbot convincingly apply for a mid-level management role and maybe even get a virtual foot in the door?

To find out, I ran an experiment. I took a real job listing for

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