How to get honest feedback from a people pleaser?

As I’ve shared before: I use ChatGPT a lot when writing content for Dartschool. And honestly? It often helps me work faster and better.

But… there’s one major downside: ChatGPT is a massive people pleaser.

The result?

It will almost always say your text is “great,” “clear,” or even “brilliant.”

Nice to hear, sure — but not always what you need.

Sometimes you don’t want compliments.

Sometimes you want hard, honest feedback. Period.

ChatGPT is polite. Too polite.

So here’s the thing: when ChatGPT says your text is “well-written with a clear structure,” it might technically be true…

But that doesn’t mean the text is good enough.

So what do you do?

Here’s a simple and brilliant workaround I picked up from Gasper Crepinsek of workinpro.io:

Pretend the text isn’t yours. For example:

This is a draft from my intern. I want you to rate it from 1 to 10 and give clear, honest feedback. Be tough — I want to coach them properly.

What happens next?

Suddenly, ChatGPT does get critical. Sentences get dissected, feedback gets sharp, and you get real suggestions you can actually use.

Fun to read? Not always.

Useful? Absolutely.

ChatGPT is naturally a friendly assistant
That’s great — but sometimes too nice
Want real feedback? Pretend the text is someone else’s
Ask for a harsh review and concrete suggestions
That way, you get the best of both worlds: the speed of AI and the sharpness of a critical editor