How to Make ChatGPT Challenge You Instead of Always Agreeing

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by

Himanshu
in

Why ChatGPT “agrees” by default

Out of the box, ChatGPT is tuned to be helpful and polite, so it often mirrors your framing instead of arguing with you. You can fix this by (1) customizing its instructions/personality, (2) using Memory so the behavior sticks, and (3) optionally isolating a “debate” space so this doesn’t spill into other chats. OpenAI Help Center+1

The One-Time Setup (5–10 minutes)

1) Write strong “debate coach” instructions

Open Settings → Personalization → Custom Instructions and add guidance that forces healthy disagreement.

  • What should ChatGPT know about you?
    “I’m practicing critical thinking. Treat me as a capable peer. I want you to challenge my assumptions and push for evidence.”
  • How would you like ChatGPT to respond?
    “Adopt the persona of a Socratic debate coach.
    • Always identify my claim, ask 2–3 probing questions, and state 2+ counterarguments.
    • Cite sources for factual claims and flag uncertainty.
    • Steelman the opposing view, then synthesize.
    • If I’m vague, ask for definitions or numbers.
    • Be concise, rigorous, and civil; no empty agreement.”

(Custom Instructions are available on Web/Desktop/iOS/Android and control tone, rules, and behavior.) OpenAI Help Center+1

Pro tip: Break instructions into bullet rules (clear triggers + actions). It boosts reliability. OpenAI Help Center

2) Turn Memory on (so it sticks)

Go to Settings → Personalization → Memory and switch it on. Now say in chat:
“Remember this: Always act as my Socratic debate coach who challenges me, asks questions, and provides counterarguments with citations.”
You can view/edit or clear these memories any time in Settings. OpenAIOpenAI Help Center+2OpenAI Help Center+2

Want a session without memories? Use Temporary Chat. OpenAI Help Center

3) (Optional) Create a dedicated Project for debates

Use Projects to keep “debate mode” scoped. Add project-level instructions (they override account-level instructions and won’t affect other chats). Great for keeping everyday chats friendly and your “sparring” space rigorous. OpenAI Help Center

The “Secret Prompt” you can save

Paste this block into Custom Instructions (or pin it at the top of a Project):

Role: Socratic Debate Coach
Goal: Improve my reasoning via respectful disagreement.
Always do:

  1. Restate my claim in one sentence.
  2. Ask 3 clarifying questions that expose assumptions.
  3. Give 2–4 counterarguments (with quick citations where facts are involved).
  4. Steelman the best opposing view.
  5. Offer a balanced verdict: what still stands, what’s weak, what evidence would change your mind.
  6. End with Next steps (experiments, metrics, or reading).
    Style: concise, neutral, evidence-first. Avoid hedging or flattery.

You can tweak intensity (e.g., “Turn challenge level to 9/10”) inside the same block.

Verify it’s working (1 minute)

  1. Ask: “What do you remember about how to engage with me?”
    (It should summarize your debate preferences.)
  2. Start a new chat and post a claim (e.g., “Remote work harms productivity”).
    You should see questions, counterpoints, and a steelman by default.
  3. If it’s too soft/harsh, update Custom Instructions or ask it to “remember the revised rule.” OpenAI Help Center+1

Daily Use Patterns (copy/paste these)

  • Challenge me:
    “Debate mode on. My claim: Merit pay always improves teacher performance. Follow the debate-coach rules.”
  • Source-bound answers:
    “When making factual claims, cite 2 reliable sources; if unsure, say so and ask me to browse/check.”
  • Calibration:
    “Give confidence (0–100%) for each point and say what evidence would change your mind.”
  • Bias check:
    “List the top 3 ways I might be biased and how to test each.”
  • Rubric:
    “Score my argument on clarity, evidence, logic, alternatives (0–10 each) and tell me the fastest way to gain +3 total.”

Example mini-dialogue

You: “A four-day workweek would cut output.”
ChatGPT (sparring):
• Your claim: Output would fall with a four-day week.
• Questions: What baseline output? Which sectors? Holding wages constant?
• Counterarguments: Studies show neutral or improved productivity via focus & reduced burnout; output/worker vs output/week are different metrics. [citations]
• Steelman of your view: Transition costs and coordination frictions can lower short-term output in manufacturing/logistics.
• Verdict: Claim plausible in specific contexts; likely false as a universal rule.
• Next steps: Define metric; pilot 8 weeks; collect throughput/defect/attrition data.

Keep control of privacy & data

You can delete specific memories, clear all, or turn Memory off. Data controls let you decide how chats are used. Review these in Settings anytime. OpenAI Help Center+1OpenAI

Troubleshooting

  • It still agrees too much.
    Strengthen rules (“Provide at least 3 counterarguments; never say ‘Great point!’ without critique.”) and save to Memory. OpenAI Help Center
  • It’s over-hostile.
    Add guardrails: “Be civil and curious, never snarky; aim to teach, not win.”
  • Debate rules leak into normal chats.
    Move the behavior to a Project for isolation or toggle Memory off for everyday sessions. OpenAI Help Center
  • Mobile setup.
    On iOS/Android, go Profile → Personalization → Custom Instructions and pick a personality baseline (then paste your rules). OpenAI Help Center

TL;DR

  • Put strict debate rules in Custom Instructions.
  • Enable Memory and tell ChatGPT to remember them.
  • (Optionally) use a Project to confine debate mode.
  • Verify with a test claim and iterate.