'My boss trusts a broken AI bot more than the people actually doing the work': Boss blames employees when their AI productivity tool fails to update properly—why trying to fix workflows that aren't broken might not be such a good idea

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Brad Dickson • Managing Editor
Nov 10, 2025 10:00 PM EST

A manager who replaced their own judgment with blind trust in an AI productivity tool was upset with employees for not updating them when the AI program made an error.

As we offload more and more simple mental tasks to AI, you have to wonder: What really is the actual point? AI has quickly gone from a novelty to a crutch, and the longer it exists, the more you see the signs of the sameness of everything. It has quickly turned all of our work into a homogenized blandness, a beige wall of productivity where the color is actually provided by a thinly spread layer of—you know what, let's just end the analogy there.

And the signs of AI are everywhere, and even where something hasn't been AI-generated, we're increasingly skeptical that it might have been. Those who are aware that ChatGPT has a tendency to favor the use of the "em dash" are at least suspicious that my writing may have been AI-generated based on that alone. It wasn't—but who is going to believe that when they've "seen the signs."

I have, however, had to begrudgingly retire my most beloved punctuation mark, whose use and overuse in the snazzy and engaging internet copy, written by copywriters like myself, dominated the internet for the better part of the last 15 years. This copy, which was widely and readily accessible across the internet, was material that LLMs (Large Language Models) like ChatGPT were subsequently trained on.  Hence, its frequent use of the snappy punctuation mark.

But while I lament the loss of the em dash, your mildly illiterate coworker, who could hardly write an email before ChatGPT, is now turning in suspiciously passable reports. However, with random emphasis, bolding, and a tone that doesn't quite suit the work. But they're increasingly blind to and careless about the glaring mistakes in every bit of slop they generate.

People without any skills, or at least without skills in the area they're using AI for, are the ones who think AI is giving them an edge. Those who use it to complete a task they don't fully understand also don't understand the problems with what they've generated. And that there are already 100,000 other instances of that same work in existence. However, it emboldens the careless and disarms the careful who find themselves victims of managers and workplaces that care less about accuracy and quality, and more about whether something has been completed. 

All the LLM is doing is enhancing the effect of Dunning-Kruger that has dominated society since the rise of social media. Those who are overreliant on AI prompts simply don't know enough to know that they don't know anything, and that the result they're getting from their AI prompt is absolute garbage to anyone who can see past the thin veil. 

They think they're dining at a Michelin-star restaurant when they are, in fact, eating directly out of the trash. 

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  • And, going back to where we started, it's the blandness, the sameness of everything AI touches that is the real crime. Go ahead and see what I mean for yourself. Go to chatGPT. Ask it to give you a band name or the name of a song. Be as specific with your prompt as you like and really hone in on the vibe you're going for.

    Now go to Spotify. Search for those song and band names you have selected, the ones it gave you that you thought were really good and unique. You will find hundreds of bands with that name and songs with that title, all featuring AI-generated music that is equally offensively bland. 

    So, when you're running a business off the answers you're receiving from an LLM, are you really getting an edge? Is introducing an AI productivity tool to a workflow that isn't broken really going to fix anything?

    Certainly not in this case, where this boss's insistence that employees endure spammed reminders and broken automated check-ins resulted in a workflow that was altogether worse than the one that hadn't been broken in the first place.

  • An employee updates their company's communication platform while simultaneously working on their phone
    via Austin Distel austindistel

    The image is representative only and does not depict the actual subjects of the story.

  • "My boss trusts a broken AI bot more than the people actually doing the work"

    Our team uses this "productivity" tool called Stand which is supposed to handle daily check-ins automatically through Slack. In reality, it's a glitchy nightmare. It keeps spamming reminders for tasks. that are already done, flags the wrong people, and randomly decides someone hasn't updated when they actually have.
    via Wander_tea
  • Last week, it told my boss I hadn't. completed a task I finished a week ago. Today, he called me out in front of the entire team for "not updating my status." I tried explaining that Stand messes up constantly and everyone knows it does. His response? "We just need to adapt to it."
    via Wander_tea
  • So yeah. Instead of fixing a broken system, we're expected to adjust ourselves to whatever an automated bot spits out. Where is the accountability here? There's no room for human error and just blind faith in whatever software says.
    via Wander_tea
  • Feels like we're not being managed by people anymore, just algorithms pretending to know better.
    via Wander_tea
  • ACrossing Troll Haha dumb management. Nothing you can do. Thy have to learn by failure that ai isn't the holy Grail
    via Wander_tea
  • OP Wander_tea I am waiting for the day when it blows up in their face.
    via Wander_tea
  • Lorelessone get it in writing that you should comply with Stand's reminders and instructions then do so, as maliciously as possible. If it says drop what your doing and focus on the work completed a week ago do so, log your hours accurately and report "As instructed I am adapting to suit this system, although I'm unsure what it wants me to do."
    via Wander_tea
  • OP Wander_tea Lmao yeah, that's actually not a bad idea. The problem is it keeps spamming the same reminder over and over, even after I've already marked it done. So if I "comply" every time, I'll just be redoing the same thing endlessly
    via Wander_tea
  • dhgatethrowawaay Document everything. Send emails (BCC to your personal account) asking your boss how to adapt to the system that isn't working? Specifically - how do I deal with this boss? Cover your ass!
    via Wander_tea
  • OP Wander_tea Yeah, 100%. I've started doing that already. Every time I get any weird Stand alert or mixed instruction, I politely email asking for "clarification." If that man want me to adapt, he can start by giving written directions on how.
    via Wander_tea
  • altM1st Professional managerial class needs to go.
    via Wander_tea
  • OP Wander_tea Fr, they've built entire careers around "managing" people who actually do the work
    via Wander_tea
  • SamuelVimes Trained How can you adapt to a system that is provably wrong? Hey boss "stand" says payment hasn\'t gone through.. why is that? or "reviews are still not completed as per 'stand" - do I need to check with HR if there is a legit reason for delay? You know - make that things fails a boss problem and it should go away.
    via Wander_tea
  • OP Wander_tea Like seriously, what part of "the system is broken" is so hard to grasp? We're not the ones who need adapting, it's the damn tool that needs fixing.
    via Wander_tea
  • mittyhands "Now Stand, in the place where you work..."
    via Wander_tea
  • OP Wander_tea Stand's basically our new cult. anthem at this point.
    via Wander_tea
  • drdeadringer Your boss trusts clippy more than the admin on duty at the front desk. I'd rhetorically say, imagine somebody trusting clippy over a real person, but you don't have to imagine. You're working for them. I'm sorry.
    via Wander_tea
  • OP Wander_tea it's wild. Like we actually have people who know what's going on, but sure, let's take orders from the ghost of Clippy instead
    via Wander_tea
  • Only_Tip9560 Al can't stop your boss being a dumbass.
    via Wander_tea
  • OP Wander_tea exactly, Al can't patch a dumb boss bug.
    via Wander_tea
  • RestaurantTurbulent7 You don't have manager, you have reta* xD I think he makes it easy to be removed and someone to step up - if it's worth/someone is willing
    via Wander_tea
  • OP Wander_tea Lmao exactly, he's basically speed-running his own replacement at this point.
    via Wander_tea
  • MaleficentShame1546 Computer says No, even though computer talks shit 70% of the time, computer talking to other computer at 70% shit means 60% of instructions are wrong, and three computers ...
    via Wander_tea
  • OP Wander_tea ...end up forming a whole committee of nonsense. Next thing you know, they're arguing with each other while we sit here waiting for a green light that'll never come.
    via Wander_tea

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