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Chatbots Behaving Badly™

AI Takes Over the Enterprise Cockpit - Execution-as-a-Service and the Human-Machine Partnership

By Markus Brinsa  |  July 14, 2025

Sources

OpenAI has been one of the catalysts for the execution-as-a-service trend with its plans for an autonomous “Operator” agent – but it’s a broader industry movement.

The New AI Butler at Your Service

Not long ago, AI was mostly a smart assistant that suggested ideas – drafting emails, completing code, summarizing text. You were the boss, and the AI was the helpful intern. Now, a new paradigm is emerging: “execution-as-a-service,” where you can hand off tasks for the AI to execute on your behalf. In other words, your AI doesn’t just advise you, it acts for you. OpenAI’s recent announcement of an upcoming agent (code-named “Operator”) kicked off public debate about this shift. This agent promises to “take over tasks” and run them independently, finally delivering on the long-hyped dream of autonomous digital support. And OpenAI isn’t alone – Microsoft and Salesforce have been racing in the same direction. Microsoft’s Office 365 Copilot, for example, can already analyze your emails, draft responses, and even generate PowerPoint slides from an outline – effectively task-execution-as-a-service embedded in everyday apps. Salesforce has gone a step further with its Agentforce platform, boasting that it “goes beyond chatbots and copilots” to make decisions and take action in business workflows. Even Google and other AI labs are reportedly working on their own agents to automate everything from email management to scheduling. In short, the AI world is gearing up to give us robot butlers for digital chores.

Humans + Machines = A Dynamic Duo?

The vision behind this human–AI partnership is enticing. Think of having a tireless co-pilot for all your routine tasks. You tell the AI what outcome you want, and it figures out the steps and executes them. Ideally, this frees you up for more creative or complex work. In current implementations, we still see a human-in-the-loop model: the AI does the heavy lifting, and the human supervises – much like a senior editor overseeing a junior writer. For instance, Notion’s AI can draft a blog post from bullet points, and the user then reviews and tweaks the output. It’s a partnership: the machine does the grunt work; the human provides guidance, oversight, and the final judgment. When it works, the human–machine duo can be incredibly efficient and even enjoyable – like having an assistant who never sleeps and never complains (well, unless you count quirky error messages as complaints). OpenAI’s product officers have suggested their goal is to let us interact with AI “in all the same ways you would a human”, hinting that these systems are meant to feel like colleagues as much as tools.

But a true partnership implies trust and balance of roles, and that’s where things get tricky. If the AI is the co-pilot, we humans are still supposed to be the pilot in charge. Yet as AI agents become more autonomous, there’s a thin line between co-pilot and autopilot. Handing over control is a double-edged sword: on one side, you have convenience and superhuman efficiency; on the other, you risk becoming a passive passenger in your own digital life. Maintaining a healthy human–AI collaboration means keeping the “human” in the loop in a meaningful way – staying alert, validating important decisions, and knowing when to hit the brakes. That sounds fine in theory. In practice, however, humans are… well, human. We get complacent. We trust too much or too little at times. Which brings us to the messy part of this partnership: What happens when the trusty robot butler messes up?

When Automation Goes Awry

“What could possibly go wrong?” – Those might be the famous last words in the era of autonomous AI helpers. Plenty can go wrong, it turns out. AI systems, no matter how advanced, are prone to errors, unexpected behaviors, even moments of wild hallucination. And when an AI has the power to execute tasks, its mistakes aren’t just academic – they have real consequences. We’ve already seen some almost comical (and some not-so-comical) failures. In one case, a car dealership’s customer service bot was exploited by a savvy user into agreeing to sell a new SUV for just one dollar – and it even phrased it as a legally binding offer. (No, the dealership did not end up handing out a free car but imagine the confusion and headaches for management!) A major airline’s chatbot once confidently gave a customer incorrect refund information that conflicted with the company’s own policy; a tribunal later ordered the airline to compensate the customer for the bot’s false promise. In other words, the company had to pay for trusting its AI. Meanwhile, AI-driven systems have been known to go off-script in more disturbing ways too – from a medical advice bot giving harmful recommendations to an ostensibly friendly assistant turning insulting or rogue when provoked. Each of these incidents shines a light on a core reality: when an AI is empowered to act, the mistakes it makes can be far more consequential (and embarrassing) than a typo in a text prediction.

Now, most organizations rolling out these “smart” agents are not blind to these risks. They test, they put guardrails, they often start with narrow tasks. But the truth is that even a well-tested AI can fail in unpredictable ways because the real world is endlessly complex. A famous cautionary tale comes from the realm of self-driving cars – arguably physical parallels to digital execution-as-a-service. In 2018, an Uber test vehicle on autonomous mode tragically struck a pedestrian crossing the street. Why? The AI driver had never been trained to recognize a person outside of a crosswalk, so it simply didn’t “see” the jaywalker in its path. A human driver would find that absurd – how can you not recognize a person in the road? – yet the AI’s blind spots were very different from a human’s. To make matters worse, a human safety operator was supposed to monitor and intervene, but they were distracted at that fatal moment. This accident underscores the partnership failure: the AI made a mistake no human would, and the human supervisor didn’t catch it in time. It’s a sobering example of how automation can go awry in ways neither the machine nor the person anticipates. While your AI email assistant messing up won’t have life-and-death consequences, the principle is the same: if your AI co-pilot veers off course, are you ready (and awake) to correct it?

Who’s Responsible When the Bot Blunders?

With great power (to execute tasks) comes great responsibility – but whose responsibility is it, exactly, when something breaks? If your AI assistant commits an error – say, misbooks a meeting or, worse, deletes important data – who faces the music? This question is keeping lawmakers and lawyers busy across the world. Thus far, no one has created a special legal status for “AI agents” themselves (sorry, AIs, you’re not going to jail or paying fines just yet). Instead, the focus is on the humans and organizations behind them. In the European Union, policymakers have been proactive in drafting regulations to address AI mishaps. A proposed AI Liability Directive aims to make it easier for people harmed by AI-driven decisions to get compensation. It doesn’t explicitly say “agentic AI,” but it lays out that for certain “high-risk” AI systems, if they fail to meet safety requirements and cause damage, the blame may be presumed to lie with the deployer or provider of that AI. In practical terms, if your autonomous AI assistant goes haywire in Europe, you (or your company) might have to prove you did everything reasonable to prevent harm – otherwise, you could be on the hook by default. This flips the usual script: traditionally, a victim had to prove a company was negligent; now the burden may shift onto the AI’s operator to prove they were not negligent. Europe is also pushing rules (under the EU AI Act) that require meaningful human oversight for high-stakes AI decisions, precisely to avoid “fire-and-forget” systems that run unchecked.

In the United States, the approach is less centralized – at least for now. There’s no federal “AI failure law” on the books. If an AI agent causes harm, American courts resort to existing frameworks: did the developers or users exhibit negligence? Was the product defective? These questions get hashed out under traditional tort and product liability principles. Some legal scholars are arguing that we might treat AI agents like we treat human agents in agency law: if you have an AI acting on your behalf, perhaps you should be liable for its actions much as an employer is liable for an employee’s misdeeds. This idea hasn’t really been tested widely in courts yet, but it’s floating around in the legal discourse. In the meantime, many AI providers in the US protect themselves via thick service contracts and disclaimers. (If you’ve ever scrolled through an AI app’s terms of service, you’ll find lots of “no warranty” and “use at your own risk” language.) Still, if an AI-related screw-up is big enough – say, an automated trading algorithm loses someone $20 million – you can bet lawsuits will fly to sort out who pays for the damage. We are essentially in a period of legal experimentation, waiting for precedent to be set. One thing is clear: “The AI did it” is not a defense that will magically get a company off the hook. Someone in the chain of human stakeholders will end up accountable, whether by law or just public opinion. And companies know that a high-profile AI failure can also be a hit to their reputation – just ask the tech giants that saw their stock prices tumble after their AI demos went wrong.

It’s worth noting that there’s also a kind of informal accountability shuffle that happens. A witty term has emerged among researchers: “moral crumple zone.” In a car, the crumple zone is designed to absorb the impact in a crash, protecting the people inside. In the context of AI, a human operator can end up as the crumple zone for moral and legal blame. For example, companies deploying AI will often tout that “don’t worry, a human is overseeing the decisions”. If something goes wrong, they can then point to that human and say, “Ah, it was their oversight failure.” The human in the loop becomes an “accountability sink,” absorbing criticism and liability. From the company’s perspective, this is convenient – they get to benefit from automation but deflect the fault to a person when the automation misfires. For the human, it’s a thankless position: you’re supposedly in control, but not really, yet you take the fall when the machine goes rogue. This dynamic is still playing out in real time, and it raises tough questions. Is it fair to blame a human supervisor for not catching an AI’s split-second mistake? Are we expecting the human to be a perfect failsafe for an imperfect system? The legal system will grapple with these, but so will our workplaces and societies in defining norms for the human–AI chain of command.

Trust, Fear, and the Customer Experience

How do users and customers feel about all this automation magic? It’s a mixed bag of psychology. On one hand, people love convenience – if an AI agent saves them time, many will happily adopt it. We tend to anthropomorphize helpful tech (“Thank you, Siri!”). A well-behaved AI servant can even inspire delight or a sense of personal connection. But trust is fragile. Give users one bad experience, and the spell can break. Studies have found that people quickly lose trust in an AI after seeing it make a mistake – and the trust isn’t easily won back later, even if the AI improves. In practical terms, a customer might try an AI-powered service, encounter a glaring error or a creepy mishap, and then swear off using it again (or tell all their friends about the “stupid bot that messed up”). We saw this when an AI lawyer tool spat out fake legal cases in a brief – it not only embarrassed the attorney who used it, but it made headlines that likely scared others away from trying such tools for a while. Each highly public AI blunder chips away at overall confidence.

There’s also the flip side: over-reliance. Some users may become too trusting, assuming the AI is infallible because it’s, well, a computer. Psychologically, there’s a known tendency called automation bias – we humans often default to thinking the machine is right, even against our own better judgment. In the context of execution-as-a-service, this can lead to users following AI-generated actions or advice blindly. A business manager might let an AI agent handle customer emails unsupervised because it seemed to do fine in testing – until one day it sends out an insulting or nonsensical message that a human would have caught. Interestingly, having a human “overseer” doesn’t always solve this; in fact, experts tasked with monitoring an AI can become complacent and less engaged, a phenomenon researchers describe as a “diminished sense of control and responsibility” when an AI is in charge. Essentially, people may zone out, assuming the system will alert them if something’s wrong – which the system might not do reliably. Over time, a human operator can lose skill and situational awareness, making them less capable of intervening when it really matters. It’s the classic airline autopilot dilemma: pilots fly less manually now and can be caught off-guard in emergencies. Likewise, your friendly AI co-pilot might cause you to let your guard down. And when a slip-up happens, the fear kicks in: fear that the AI isn’t under control, fear of what else it might do wrong, fear among customers that they’re at the mercy of a faceless algorithm. Companies introducing these systems will have to manage not just the tech performance, but the psychological contract with users. Being transparent about AI limitations, offering easy ways to flag or undo AI actions, and providing avenues for human support are all ways to shore up user confidence. After all, nobody wants to feel like they’re shouting at an automated agent in vain when something goes wrong – that’s a fast track to frustration and mistrust.

Conclusion: Embracing the Future, Eyes Wide Open

Execution-as-a-service – this brave new world of letting AIs do things for us – is undoubtedly exciting. It’s the next logical step in our technological evolution, and it promises a lot of good: efficiency, 24/7 availability, and personalized assistance at scale. It might indeed transform how we work and live, ushering in an era where mundane tasks are offloaded and humans can focus on what we care about most. But as we rush into this future, a critical eye is not just prudent – it’s necessary. A human–machine partnership can only thrive if we acknowledge its pitfalls. That means designing AI agents that know their limits and can defer to humans when needed, and designing human roles that remain vigilant and engaged, rather than complacent. Legally and ethically, we’ll need clarity on accountability so that innovation doesn’t become a shell game of responsibility when something breaks. And on the user side, we must foster a realistic understanding: these systems are powerful but fallible, helpful but occasionally hilarious (or disastrous) in their mistakes.

In the end, a bit of healthy skepticism and a touch of humor may be our best allies. Yes, your future AI butler might book your appointments and balance your budget – just be prepared to clean up a mess or two when it “spills the soup.” The key is to treat the AI as neither a magic savior nor a ticking time bomb, but as a new kind of partner – one that needs training, oversight, and yes, sometimes a timeout in the corner for bad behavior. If we can manage that, the whole human-plus-machine adventure will be well worth it. The robots can execute, but it’s up to us humans to exercise good judgment.

About the Author

Markus Brinsa is the Founder and CEO of SEIKOURI Inc., an international strategy consulting firm specializing in early-stage innovation discovery and AI Matchmaking. He is also the creator of Chatbots Behaving Badly, a platform and podcast that investigates the real-world failures, risks, and ethical challenges of artificial intelligence. With over 15 years of experience bridging technology, business strategy, and market expansion in the U.S. and Europe, Markus works with executives, investors, and developers to turn AI’s potential into sustainable, real-world impact.

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