PROMPT PACK — Chapter 12

I’m considering [describe decision or opportunity]. Play devil’s advocate: What could go wrong? What am I likely overestimating or underestimating? What questions should I answer before moving forward? What would cause this to fail? Be thorough—I want to catch blind spots, not just be reassured.

Help me analyze this decision: [describe]. Create a pros and cons list. For each item, rate its importance (high/medium/low) and briefly explain why. Consider: financial impact, time/effort required, risks, opportunity costs, and effects on customers/employees. End with a summary: what are the key factors that should drive this decision?

Help me compare these options: [describe Option A] versus [describe Option B]. My priorities are: [list what matters most to you]. For each option, analyze: advantages, disadvantages, risks, costs, and how well it fits my priorities. Don’t just tell me which is better—help me understand the tradeoffs so I can decide.

Here is [type of information: customer feedback, project data, survey responses, etc.] from my [type of business]: [paste information]. Analyze this and tell me: What patterns do you see? What themes emerge? What’s surprising or significant? What might this mean for how I run my business?

I’m [considering a change / planning for the future / worried about a possibility]. Help me think through scenarios. Give me three: (1) Optimistic—things go better than expected, (2) Realistic—things continue roughly as they are, (3) Pessimistic—we face significant challenges. For each scenario, describe what it looks like, what triggers it, and what I should do if it happens. What should I do now to be prepared for any of these?

Here’s my plan: [describe]. What assumptions am I making that might not be true? List the key assumptions this plan depends on. For each assumption, tell me: How confident should I be in this assumption? How would I know if it’s wrong? What happens to my plan if this assumption fails?