PlaybookPrompts

Pressure-test a new market entry before committing resources

Business Strategy market-entrycompetitive-strategydecision-making

Entering a new market on optimism is expensive. This prompt applies structured skepticism to your entry thesis so the fatal flaws surface before you've hired a market-specific sales rep.

Prompt
You are a strategy consultant stress-testing a market entry decision. We are considering entering {{TARGET_MARKET_DESCRIPTION}}. Our core product or service is {{CORE_PRODUCT_DESCRIPTION}}. Our hypothesis for why we can win there is {{ENTRY_HYPOTHESIS}}. Our planned entry motion is {{ENTRY_MOTION}} (e.g., direct sales, a partnership, a self-serve trial).

1. Identify the five assumptions embedded in our entry hypothesis. State each assumption explicitly—many founders leave these implicit.
2. For each assumption, rate it as (a) validated with data, (b) plausible but untested, or (c) speculative. Use my description to assign ratings, but tell me when you're speculating.
3. For the two or three most speculative assumptions, describe the cheapest, fastest test we could run in 60 days or less to gather real signal.
4. Name the two most likely ways this market entry fails within 18 months. Be specific—not 'competition' but what a specific competitor would do.
5. Write a go / no-go criteria checklist: five conditions that, if met after the initial tests, would justify committing full resources. If any condition is a hard blocker regardless of other results, flag it.

Do not be encouraging for its own sake. The goal is to find the holes.
Variables to fill in
  • {{TARGET_MARKET_DESCRIPTION}}
  • {{CORE_PRODUCT_DESCRIPTION}}
  • {{ENTRY_HYPOTHESIS}}
  • {{ENTRY_MOTION}}

How to use this prompt

  1. Copy the prompt above (Copy button on the top-right).
  2. Replace each {{VAR}} with your own value. Variables: {{TARGET_MARKET_DESCRIPTION}}{{CORE_PRODUCT_DESCRIPTION}}{{ENTRY_HYPOTHESIS}}{{ENTRY_MOTION}}.
  3. Paste it into one of the recommended tools below.
  4. Iterate: tighten constraints in the prompt if the output is generic.

Why this prompt is structured this way

The prompt is split into explicit steps because LLMs do better when the path is named, not implied. Each variable forces specificity at the input layer — vague inputs get vague outputs.

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