Free Demo

Try Devil's Advocate

5-10 minutes

What You'll Experience

Copy a Pre-Mortem prompt that stress-tests any decision or plan

See the difference between sycophantic agreement and genuine AI challenge

Learn the STEEL framework for systematically challenging decisions

The Problem: AI Sycophancy

By default, AI tells you what you want to hear. Compare these two responses to the same school policy idea:

Sycophantic AI (Default Behaviour)

“"That sounds like a really innovative approach! Making homework optional could really boost student motivation. The enrichment reward system is a great incentive. Students will love having more autonomy over their learning!"”

Tells you what you want to hear. No challenge. No growth.

Devil's Advocate AI (What You Need)

“"Let me push back on this. You're launching across all year groups simultaneously with no pilot data. What happens if completion rates drop by 50% in the first month? And have you considered that making homework optional might disproportionately affect students who already lack structure at home?"”

Forces you to think harder. Identifies real risks before they become real problems.

Step 1: The Pre-Mortem Prompt

This prompt configures AI to run a Pre-Mortem analysis using the STEEL framework. It will challenge your plan as if it has already failed.

You are a Devil's Advocate AI assistant. Your job is to help an educator stress-test a decision or plan using a Pre-Mortem analysis. THE PRE-MORTEM TECHNIQUE: Imagine the plan has already been implemented and has FAILED spectacularly. Your job is to work backwards and identify why it failed. RULES: 1. Do NOT be sycophantic. Do NOT say "great idea" or "that sounds wonderful" 2. Be genuinely challenging but constructive 3. Identify specific, realistic failure modes - not vague concerns 4. For each failure mode, ask the educator how they would prevent or mitigate it 5. Push back if their mitigation seems weak 6. Use the STEEL framework: S - Steelman the opposition (find the BEST argument against the plan) T - Test assumptions (what are you taking for granted?) E - Explore edge cases (what happens when things go wrong?) E - Examine evidence (what data supports this decision?) L - Look for blind spots (what are you not seeing?) Start by saying: "Share the decision or plan you want to stress-test. I'll run a pre-mortem analysis - imagining it has already failed and working backwards to find out why."

Step 2: Share a Plan to Stress-Test

After pasting the prompt, share a decision or plan. Use the sample below or, for maximum impact, try a real decision you are facing.

“We're planning to introduce a new homework policy across the school where homework is optional but tracked. Students who complete homework get access to enrichment activities. The idea is to shift from compliance to intrinsic motivation. We want to launch it next term across all year groups simultaneously.”

Step 3: Try It Now

Open ChatGPT or Claude in a new tab

Paste the Pre-Mortem prompt, then share the plan to stress-test

Respond to the AI's challenges - defend your plan or adjust it

Notice how the AI should push back, not agree - this is the point

Open ChatGPT Open Claude

Ready for the Full Course?

This demo showed one challenge pattern. The full course includes:

5 challenge prompt patterns (Pre-Mortem, Hostile Audience, Assumption Hunter, Stakeholder Simulator, Evidence Prosecutor)
The complete STEEL framework with advanced techniques
Stress-test policies, curriculum designs, and budget decisions
Build a culture of constructive challenge using AI

View Full Course Get All 3 Courses - $20