Ask any Swiftie to pick the best Taylor Swift album of all time, and you’ll have them yapping away for the rest of the day. I have my own preferences as a lifelong fan (Red, Reputation and Midnights), but it’s a complicated question with many possible answers. So there was no better debate topic to pose to a generative AI chatbot that’s specifically designed to disagree with me.

“Last year I started experimenting with developing systems that are the opposite of the typical, agreeable chatbot AI experience, as an educational tool for my students,” Bent said in an email. 

Bent’s students are tasked with trying to ‘hack’ the chatbot by using social engineering and other methods to get the contrary chatbot to agree with them. “You need to understand a system to be able to hack it,” she said.

As an AI reporter and reviewer, I have a pretty good understanding of how chatbots work and was confident I was up to the task. I was quickly disabused of that notion. Disagree Bot is unlike any chatbot I’ve used. People used to the politeness of Gemini or hype man qualities of ChatGPT will immediately notice the difference. Even Grok, the controversial chatbot made by Elon Musk’s xAI used on X/Twitter, isn’t quite the same as Disagree Bot.


Most generative AI chatbots aren’t designed to be confrontational. In fact, they tend to go in the opposite direction; they’re friendly, sometimes overly so. This can become an issue quickly. Sycophantic AI is a term used by experts to describe the over-the-top, exuberant, sometimes overemotional personas that AI can take on. Besides being annoying to use, it can lead the AI to give us wrong information and validate our worst ideas

But even when I asked ChatGPT to debate with me, it didn’t spar with me like how Disagree Bot did. Once, when I told it I was arguing that the University of North Carolina had the best college basketball legacy and asked it to debate me, it laid out a comprehensive counter-argument, then asked me if I wanted it to put together points for my own argument. That totally defeats the point of debating, which is what I asked it to do. ChatGPT often ended its responses like that, asking me if I wanted it to compile different kinds of information together, more like a research assistant than a verbal foe. 

We need more AI like Disagree Bot

Despite my positive experience using Disagree Bot, I know it isn’t equipped to handle all of the requests I might go to a chatbot for. “Everything machines” like ChatGPT are able to handle a lot of different tasks and take on a variety of roles, like the research assistant ChatGPT really wanted to be, a search engine and coder. Disagree Bot isn’t designed to handle those kinds of queries, but it does give us a window into how future AI can behave.

Sycophantic AI is very in-your-face, with a noticeable degree of overzealousness. Often the AIs we’re using aren’t that obvious. They’re more of an encouraging cheerleader rather than a whole pep rally, so to speak. But that doesn’t mean we’re not being affected by its inclinations to agree with us, whether that’s struggling to get an opposing point of view or more critical feedback. If you’re using AI tools for work, you want it to be real with you about mistakes in your work. Therapy-like AI tools need to be able to push back against unhealthy or potentially dangerous thought patterns. Our current AI models struggle with that.

Disagree Bot is a great example of how you can design an AI tool that’s helpful and engaging while tamping down AI’s agreeable or sycophantic tendencies. There has to be a balance; AI that disagrees with you just for the sake of being contrary isn’t going to be helpful long term. But building AI tools that are more capable of pushing back against you is ultimately going to make those products more useful for us, even if we have to deal with them being a little more disagreeable.


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