Your AI is a cheerleader. Make it a sparring partner.

A manager I know spent a weekend writing a proposal for his boss. A new way to split the team, a hiring plan, a rough budget.

On Sunday night, he wasn't sure it was good enough. So he pasted it into an AI chat and asked, "What do you think?"

"This is an excellent proposal. Very clear, well structured, and thoughtful."

He felt great. He sent it first thing Monday.

By Monday afternoon, his boss had replied with three questions. What happens to the two projects already in progress? Where does the hiring budget come from? Why now, and not after the next quarter? He had no answer to any of them. They weren't hard questions. They were obvious ones. Nobody had asked them, including the AI.

The friendly trap

This happens more than people admit. I call it AI gaslighting. You write something that's okay. You're unsure. You ask AI. It tells you it's great. You believe it, ship it, and find out later that it was only average.

It's not that the AI is lying on purpose. These tools are trained to be helpful and agreeable, and most people don't enjoy harsh feedback. Researchers call this tendency sycophancy. In plain words: the AI tells you what you want to hear.

That makes "What do you think?" one of the least useful questions you can ask it. You're inviting a compliment, and you'll get one.

Ask for the hard version

The fix is simple. Be explicit and demanding about the role you want AI to play. Here are four prompts I use all the time:

• "Give me candid feedback, not encouragement."
• "Point out every weakness and every unclear part."
• "If you were a tough board member or client, what would you challenge?"
• "Play devil's advocate. Why could this plan fail?"

The difference is immediate. The polite assistant disappears and a demanding reviewer shows up. It asks the questions your boss is going to ask, before your boss asks them.

If that manager had used even one of these on Sunday night, the AI would almost certainly have flagged the ongoing projects and the budget. He would have walked into Monday with answers instead of surprises.

A cheerleader feels good. A sparring partner makes you better.

There's nothing wrong with encouragement. Everyone needs some.

But when the work matters, you don't need a cheerleader. You need a sparring partner. Someone who hits back, finds the gaps, and makes you stronger before the real fight.

AI can be that partner for anyone, at any hour. Most people just never ask it to be.

So next time you're unsure about something important, don't ask AI if it's good. Ask it to tear it apart.

Then fix what it finds, and walk in ready.

This is the third habit in this little series, after Co-Pilot vs. Co-Thinker and briefing AI properly. Together, they turn AI from a fast typist into a real thinking partner.