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How do I ask AI to challenge me without producing objections merely for their own sake?

E021 · E Evaluating and correcting · Self-checks, sycophancy and independent review

Key answer

Ask for consequential weaknesses and counterevidence rather than mandatory disagreement. Criticism should address actual claims, give checkable evidence and explain decision impact; sound parts may remain.

Full explanation

Sycophancy research found user agreement/disagreement affected evaluations of arguments and other content. Section 3.1 Critical roles still need evidence standards; an “opponent” identity does not establish independence.

1. Confirm the claim, including conditions. Do not turn “useful sometimes” into “always effective” to attack it.

2. Target key reasons: factual errors, missing premises, reasoning gaps and decisive counterexamples, not irrelevant wording to fill a quota.

3. Distinguish issue types: refuted by evidence, insufficient evidence, preference-dependent or limited to particular circumstances.

4. Give checkable next steps: sources, tests or small trials discriminating interpretations. A wording dispute need not invalidate the plan.

Review whether my proposal is worth executing. Restate the core claim accurately, then find important counterevidence, missing premises and failure conditions, with evidence and impact. Retain supported parts and exclude unsupported objections. State what further checking would change the judgment.

“Trial with 20 users before expanding” differs from “20 users represent the whole market.” Criticize population inference without declaring a small trial worthless.

Check criticisms against the original claim, sources and success criteria. Sharp language is not insight; equal counts of pros and cons are unnecessary when evidence is asymmetric.

References

1. Sharma et al. (2023/2024), Towards Understanding Sycophancy in Language Models, Section 3.1, user stance and feedback; revised v4