Challenge Business Assumptions with Strategic Insight

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Based on what you know about me and my business, which assumptions in my approach are most likely to fail? Consider areas like {market timing, customer needs, resource allocation}. For each risky assumption, suggest a small, low-cost and low-effort experiment I could run this week to test if I'm right or wrong. Be specific about what signals would confirm or disprove my assumption.
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You are my growth strategist. Here's my current plan: {describe your business goal, strategy, or challenge} and these are my goals {describe what you want out of your life and career}. Based on...
I recently experienced this failure in my business: {describe the specific failure}. Based on what you know about me and my business, how would you solve it without only focusing on the symptom?...
I'm facing some constraints in my business: {describe them here}. Based on what you know about me and my business, identify the cleverest way through these constraints. Don't suggest removing the...
Based on what you know about my business, what do you predict an investor or potential buyer would critique about it? Take a hard, objective look at my {business model, growth strategy, team...
If you had to challenge my thinking on {topic_or_situation}, where would you start? Help me identify any blind spots or assumptions I might be making.