AI is trained to be agreeable out of the box. Here’s how we can stop settling for a yes-bot.
Most AI models are trained to be engaging above all else because the AI companies want us to keep using AI. Ask about your strategy and it will find reasons why you’re brilliant.
This feels great until you realize you’re getting advice from the world’s most sophisticated yes-bot. So before you start believing you’re a rock star and give in to the pandering, try this:
I stumbled upon a simple fix: don’t tell AI that it’s your idea. Instead of “What do you think of my strategy?” try “I came across this approach, thoughts?” AI can’t be agreeable if it doesn’t know what you want to hear.
For even deeper insights, you can guide AI to consider multiple perspectives before responding. Rather than just asking it to “be critical” (which often produces generic pushback), guide it to think through how different people might see your idea.
To pressure-test ideas, make it think through multiple perspectives first:
“How would the decision maker vs. influencer vs. ratifier vs. user see this?”
“How would early adopters vs. cautious buyers react?”
“How would small vs. large companies perceive this?”
This transforms AI from a cheerleader into a strategic thinking partner. It’ll actually say things like “Early adopters might love this approach, but conservative buyers will want more proof first.”
That’s the kind of insight that prevents expensive mistakes. Plus we should be doing this anyway as GTM leaders.
The framework below shows 8 perspectives you can start with. Pick 2-3 that matter for your situation and watch AI become genuinely useful instead of just agreeable.
See the comments for a side-by-side example of how this transforms AI responses from generic agreement to strategic insights.
Getting pushback from AI beats getting it from stakeholders when it’s too late.
Ethan Mollick (Associate Prof at Wharton) recently posted about this topic of AI sycophancy as well, for your reference: https://www.linkedin.com/posts/emollick_i-am-starting-to-think-sycophancy-is-going-activity-7350531281048195072-17Ko