Turn AI Into Your Strategic Advisor

Make AI argue both sides, find blind spots, and give a clear recommendation for any decision

Copy & Paste this prompt

I need to make a decision about [DECISION].

Context: [YOUR SITUATION - budget, timeline, goals, constraints]

Act as a strategic advisor. Analyze this by:

1. List 3 strongest arguments FOR
2. List 3 strongest arguments AGAINST
3. Identify 2 blind spots I might be missing
4. Rate the decision 1-10 for:
   - Risk level
   - Potential upside
   - Reversibility
5. Give your final recommendation with
   a clear "If X, do Y. If Z, do W" framework

Be brutally honest. Challenge my assumptions.

Use as Template

#strategy#analysis#decision-framework#critical-thinking

Works with

chatgptclaudegemini

💡 Pro Tips

•Works for career moves, investments, business decisions, big purchases
•Include as much context as possible about your specific situation
•Follow up by asking AI to challenge its own recommendation

🧠 Why This Works

By assigning the AI a specific expert role and requiring multi-perspective analysis, this prompt activates deeper reasoning patterns. The structure of argue-both-sides plus blind-spot identification prevents the AI from defaulting to generic advice and forces nuanced strategic output.

📅 When to Use This Prompt

Use before any important strategic decision—whether to pivot your startup, enter a new market, hire a key executive, or restructure your team. Best when you need a thinking partner who won't just agree with you but will challenge your assumptions with structured analysis.

🎯 What You'll Get

You'll get a structured strategic brief covering the strongest case for each option, hidden risks and second-order consequences, and a clear recommendation with rationale. Expect the quality of output you'd get from a strategy consulting engagement.

🔗 Related Prompts

Decision MakingPremium

Build a Risk Assessment Matrix for Any Decision

Identify, score, and prioritize risks with mitigation strategies before committing to any project or plan

decision-makingstrategybuild

★4.7

intermediate

Decision MakingPremium

Calculate the True Opportunity Cost of Any Decision

Understand what you're really giving up — not just what you're choosing, but the best alternative you're rejecting

decision-makingstrategycalculate

★4.7

intermediate

Business & Strategy

One-Page Strategy — Your Entire Business Plan on a Single Page

Condense your business strategy into one powerful page that aligns your whole team.

strategyplanningone-page

★0.0

beginner

Business & StrategyPremium

The Root Cause Analyzer

From chaos to clarity — find the real "why."

root-cause-analysisproblem-solvingtroubleshooting

★4.7

intermediate

Decision MakingPremium

Map Stakeholders by Influence and Interest

Identify every stakeholder, understand their motivations, and build a targeted engagement strategy for any initiative

decision-makingstrategystakeholders

★4.7

intermediate