July 23, 2026 — 3:27pm
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The warning signs are easy to spot. Long emails with bullet points, overly formal language, wordy answers to simple questions or extensive reports and attachments.
A few years ago, any of these might have been signs of a diligent boss who worked hard or someone who thought deeply, but today they all point in a different direction. Any one of these is a sign that you’ve got a manager who’s addicted to AI, or a ‘ChatGPT Boss’.
If you find yourself working for a ‘ChatGPT Boss’, you should politely request clearer or shorter communications, and explain the reasons why.AP
Work, by its very nature, is a human-orientated process. A key aspect is interacting with other people to get an outcome, and once you start outsourcing too much of your job to technology, it has some unintended consequences.
Take one of the most common rituals in every workplace, performance reviews. The process usually involves a manager reviewing the recent work of a direct report, and evaluating it against set criteria. Have they performed well? What are the areas that they could they improve?
There’s now a growing trend for some managers to delegate the hard thinking and tricky judgement required for this to AI, asking it to draft reports and communication based on the data fed into it.
There are Reddit threads full of examples of workers complaining that their boss just cut and pasted their performance review directly from AI, giving them generic, incorrect or contradictory feedback.
‘ChatGPT Bosses’ might think the emails they’re firing off make them look good, but the people who receive them have a different view.
Some even include cases where a ‘ChatGPT Boss’ forgot to delete the AI prompts at the end of their responses that asked: “Would you like me to make this feedback more professional, more direct, or adjust the tone?”
As most workers would know, these are important moments where two humans can sit down and give honest appraisal, genuine appreciation and discuss areas of improvement. If your boss is delegating this thinking to AI, then we have a big problem.
A study published last year of 1,100 professionals by the University of Florida found that managers who use medium to high levels of AI assistance to help write their communications are putting their own trustworthiness at risk.
‘ChatGPT Bosses’ might think the emails they’re firing off at a suspiciously efficient pace make them look good, but the people who receive them have a different view. The research, published in the International Journal of Business Communication, identified a ‘perception gap’ where content that felt heavily AI-written made the receiver question the integrity, care and competency of their person sending it.
Of course, there’s a big difference between lightly using AI for low levels of assistance, like fixing up spelling or crafting an occasional sentence, to asking AI to write entire sensitive communications and reports from scratch.
The researchers found that when communications were written predominantly by AI, only around half of the workers viewed the author as sincere, with only two thirds thinking it was professional.
In other words, using too much AI to communicate is a shortcut to people questioning the leadership abilities you’ve spent your career trying to build.
Findings like this should be an alarm bell for every worker who’s been tempted by the siren calls of AI to outsource everything to it. There can be exceptional uses that save hours of time every day - like data analysis or behind-the-scenes calculations – but we need guardrails on human communication.
If you find yourself working for a ‘ChatGPT Boss’, you should politely request clearer or shorter communications, and explain the reasons why. Tell them enough times you’d like a real answer from them personally, instead of long-winded responses, and they should start to get the message.
And if any of this sounds too familiar for the way that you’re working, consider this a gentle wake-up call. The real power of AI is what you do and don’t use it for. Our workplaces are already complicated enough, so close down the AI prompt, step away from the computer and start up a simple conversation with the person in front of you. You never know where it might lead.
Tim Duggan is author of Work *Backwards: The revolutionary method to work smarter and live better*. He writes a regular newsletter at timduggan.substack.com.
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Tim Duggan is the author of Work Backwards, Cult Status and Killer Thinking. He co-founded Junkee Media and writes a monthly newsletter called OUTLET.