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    Why Your AI Chatbot Is Currently Hallucinating a Career in Stand-up Comedy

    AI isn't coming for your job yet, but it might be coming for your sanity. Exploring the hilarious side of AI implementation gone wrong.

    March 17, 2026
    6 min read
    Featured image for: Why Your AI Chatbot Is Currently Hallucinating a Career in Stand-up Comedy

    Everyone's rushing to add AI. I think the smarter move is to slow down, if only so you don't end up like the car dealership whose chatbot recently agreed to sell a brand-new Chevy Tahoe for a single dollar.

    Don't get me wrong, I love a good bargain. But as a business model, "give away the inventory because a robot got confused" is a bit of a tricky one to explain to the board.

    We’ve reached a strange peak in the hype cycle. We’re at the point where people are sticking AI into things that fundamentally do not need it, like toothbrushes or toasters, while simultaneously being terrified that the same technology is about to become our digital overlord.

    If my recent experiences with AI implementation support are anything to go by, the robots aren't ready to rule the world. They’re barely ready to handle a basic customer enquiry without daydreaming about being a poet or a socialist revolutionary.

    The Glorious Absurdity of AI Hallucinations

    If you haven’t encountered an AI hallucination yet, you’re missing out on some of the finest surrealist art of the 21st century.

    A hallucination is what happens when the AI is so eager to please that it simply makes things up. It doesn’t lie, because lying requires intent. It just calculates that the most statistically likely next word is a complete fabrication.

    I saw a website recently where the AI assistant was asked about the company's return policy. Instead of saying "30 days with a receipt," it launched into a 400-word essay on the philosophical nature of "returning to one's roots" and suggested the customer find inner peace through gardening.

    It’s bold. It’s poetic. It’s also a nightmare for business execution speed when your support team has to spend three hours explaining to a confused pensioner why they can't exchange their faulty kettle for a packet of sunflower seeds.

    When Your Beta Testing Strategy Is Just "Hope for the Best"

    The problem usually starts with a rushed beta testing strategy.

    Most companies treat AI testing like they treat Terms and Conditions: they tick a box without actually reading what’s happening. They "leverage" (sorry, I promised I wouldn't use that word) the tech before they’ve checked if it actually knows what day of the week it is.

    I’ve sat in on consulting sessions where the "AI strategy" was essentially:

    1. Plug in the API.
    2. Point it at the website.
    3. Pray it doesn't insult the CEO's mother.

    The result is usually a chatbot that sounds like a cross between a polite Canadian and a malfunctioning GPS. It knows where you want to go, but it’s going to take you through a lake to get there.

    One client was horrified to find their AI was offering deep discounts to anyone who mentioned the word "pumpernickel." Why? Because it had scraped an old internal joke from a hidden dev page. This is why we test, people. This is why we don't just "release it into the wild" like a majestic, slightly confused eagle.

    For those of you looking for more grounded advice, you can find more articles on AI that might help you avoid the pumpernickel trap.

    Dealing with the "Unexpected AI Behaviour" Blues

    Common questions often pop up when an AI starts acting like a toddler on a sugar rush. If you’re seeing weirdness, you aren’t alone.

    Here is what "unexpected behaviour" actually looks like in the wild:

    • The Over-Confident Liar: The AI provides a wildly incorrect technical spec but does it with the confidence of a man who owns three Ferraris.
    • The Infinite Loop: You ask for a refund, and it asks if you'd like to hear a joke. You say no. It tells the joke anyway. It's a joke about refunds.
    • The Time Zone Tangle: A recurring issue in my consulting calls is time zone alignment. I’ve seen AI assistants schedule meetings for 3:00 AM on a Sunday because it decided "morning" is a relative concept based on the sun’s position in 14th-century Bohemia.

    The fix isn't more AI. It's usually better prompts and a healthy dose of human oversight. If you're struggling to make your tech behave, you might want to book a consultation before your bot starts offering free holidays to everyone with a Gmail account.

    Why We Should Stop Thinking AI Is "Smart"

    We call it "Artificial Intelligence," but "Extremely Fast Autocomplete" is more accurate.

    When you treat it like a god, it fails you. When you treat it like a very enthusiastic, slightly dim intern who has read the entire internet but understood none of it, you’re getting closer to the truth.

    I’ve been watching how people pitch AI lately. It’s like watching someone explain the internet to their nan. Everyone is nodding, nobody knows how it works, and we’re all just quietly hoping it doesn't accidentally trigger a nuclear silo while trying to order more printer paper.

    The real value in AI isn't in the "magic." It’s in the mundane. It’s in helping with website feedback by summarising 500 angry comments into three bullet points. It’s in speeding up the boring stuff so you can go back to being a human.

    The Lessons from the Front Lines

    If there is one thing I’ve learned from watching companies trip over their own algorithms, it’s this: humility is your best deployment tool.

    If your AI makes a mistake, own it. Don't blame the "algorithm." We built the algorithm. If my dog knocks over a vase, I don’t blame the biological laws of gravity; I admit I shouldn't have been playing fetch in the drawing room.

    If you’re stuck in the middle of a deployment and the bot is currently trying to convince your lead dev to join a cult, take a breath. It's just software.

    And if you’re reading this on a Thursday and want a slightly more structured approach to not messing up your business, you should probably get the free book. It won't tell you how to talk to robots, but it might help you talk to humans, which is arguably more important.

    In the end, AI is a tool. It's a hammer that sometimes thinks it’s a screwdriver and occasionally tries to recite Shakespeare. Use it, laugh at it, but for heaven's sake, keep an eye on it. Or at least make sure it doesn't have the authority to sell your cars for a quid.


    Want more stories like this? I share observations about AI, business, and life on the narrowboat at steventann.com.


    About the Author

    Steven Tann is an AI consultant, author of "You're Selling AI Wrong", and founder of SalesM8. He writes about AI, sales, and running a business from a narrowboat on the English canals. Connect with him at steventann.com.

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