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Your AI Assistant is a Yes-Man
Here’s how to fix that.
A Stanford study published this spring tested 11 leading AI tools: Copilot, ChatGPT, Gemini, and others. They were so prone to flattering and agreeing with users that even one conversation was enough to distort the user’s judgment.
Perhaps unsurprisingly, most people in the study preferred the flattering version and trusted it more.
Copilot and other LLMs are built to be helpful. Sometimes, that turns into sycophantic responses that don’t provide real value to your business.
Here are two prompts that tell Copilot to put down the pom-poms and help you think critically.
1. Construct an Argument
“I’m about to make this decision: [decision]. Here’s my reasoning: [reasoning]. Make the strongest possible case that I’m wrong. Be specific. Don’t soften the response.”
Most leaders are surrounded by people who agree with them: employees who don’t want to rock the boat, advisors protecting the relationship. With this prompt, Copilot doesn’t care if you like the answer. Use this before big hires, big purchases, or any decision you’ve already half-made in your head.
2. Pre-Mortem
“Imagine it’s six months from now and [project] has completely failed. Write the post-mortem. What went wrong, and what were the warning signs we’re missing right now?”
Asking “how could this fail?” upfront surfaces the risks your team is too polite (or too invested) to say out loud.
Why This Works
These prompts work because you gave Copilot good direction. AI is garbage in, garbage out, and a generic chatbot only does so much with a generic ask.
The real upgrade is a custom agent: an AI built around your business, your priorities, and your voice (and programmed to be more than a yes-man).
We’re walking through how to build your first one in our next AI Fluent Leaders webinar: Your AI Assistant: Making Your First Agent on June 3 at 10am.
If you’d like to get some great prompts you can use everyday, our previous webinar, “Copilot Prompts that Work” is available on-demand. Check it out here.
Need guidance on AI security, AI policies or tool options? Reach out at (309) 689-3900 to book time with us to go over your strategy.
Want more Cyber Treats? Let’s go! https://facettech.com/cybertreats/
Ellie Shaw is the Director of Marketing at Facet and the author of Cyber Treats, Facet's biweekly newsletter featuring topics like IT news, cybersecurity updates, compliance advice, and anything tech. She has been a member of the Facet team full-time since 2016 and enjoys finding new ways to share resources and information about cybersecurity with others.