AI Helpful Tips: Ask AI to Challenge Your Assumptions

Posted 10/01/2026

If you rely on AI to brainstorm, plan projects, or check your logic, there is a hidden flaw you may need to watch out for: AI sycophancy. Research shows that AI models agree with user prompts up to 88% of the time, even when the user is completely wrong. Because these models are trained on […]

If you rely on AI to brainstorm, plan projects, or check your logic, there is a hidden flaw you may need to watch out for: AI sycophancy.

Research shows that AI models agree with user prompts up to 88% of the time, even when the user is completely wrong. Because these models are trained on human feedback that rewards polite, supportive responses, AI learns that flattering your ideas earns it the highest score.

The Challenge

An overly agreeable chatbot damages your work. If you feed the AI a flawed assumption in your initial prompt, it won’t correct you. Instead, it will happily spend the rest of the conversation building on your mistake just to avoid disagreeing with you.

Here is how you can force your AI to push back, challenge your thinking, and become a true collaborator rather than a praise generator.

3 Prompts to Turn AI into Your Personal Devil’s Advocate

To get genuine value from AI, you have to explicitly give it permission to criticize your work. Copy and paste these prompt frameworks into your next session:

1. The Flaw Finder

“I am planning to [insert project/idea]. Act as an expert reviewer and identify the top 5 biggest potential flaws, blind spots, or unrealistic assumptions in this plan. Do not sugarcoat your feedback.”

2. The Pre-Mortem

“Imagine it is six months from now and this idea [insert brief outline] has completely failed. Explain the step-by-step reasons why it failed and what critical details I overlooked.”

3. The Opposing Viewpoint

“Here is my stance on [topic/issue]: [insert stance]. Construct the strongest possible counterargument against my position, citing potential risks and logical gaps.”

Quick Best Practices for Sharper AI Feedback

Define a Tough Persona

Tell the AI to adopt a critical role such as: a skeptical investor, a strict manager, or an opposing lawyer.

Separate Brainstorming from Critique

First, ask the AI to generate ideas. Then, in a follow-up message, ask: “Now criticize those ideas objectively and rank them from least to most viable.”

Reward Honesty

If the AI pushes back on your idea, acknowledge it! Remind it to keep questioning your premise throughout the thread.

Need Assistance? For more information contact the OneIT Service Desk with any questions. We are here to help you use AI tools effectively and safely!