Asked "what do you think?", models often respond with encouragement. To get useful critique, ask for it explicitly.
Ask for Problems, Not Opinions
"Identify the five biggest weaknesses in this proposal, ranked by impact, with a specific fix for each."
Specify the Criteria
Clarity, persuasiveness, accuracy, completeness, audience fit — tell the model what to judge against.
Assign a Critical Perspective
"Review this as a sceptical investor", "as a regulator", "as a customer who's never heard of us".
Discourage Flattery
"Don't praise the strengths; focus on what needs to change." Or ask for strengths and weaknesses in separate, balanced lists.
Ask for Specifics
"Quote the sentence and explain the problem" beats general comments.
Compare Against Standards
Provide a rubric, style guide or example of excellent work and ask where your draft falls short.
Challenge the Critique
Models can be wrong or overly harsh. Push back: "Why do you think that paragraph is unclear?" and judge the reasoning.
Iterate
Revise, then ask for a fresh critique of the new version against the same criteria.