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/upfront:assess

/upfront:assess is a focused conversation about a specific concern. Not feature definition — problem-solving. The AI brings domain knowledge you don’t have, maps the landscape, teaches you the risks, and helps you choose between tradeoffs.

  • “X seems like a security risk, how should we handle it?”
  • “What are the options for caching here?”
  • “Is our auth approach solid or are we missing something?”
  • “How should we handle rate limiting?”
  • Any time you have a specific concern and want to think it through before acting

This skill auto-triggers on phrases like “how should we handle”, “is this a problem”, “what are the options for”, “seems risky.”

  1. Understand — restates your concern, asks one clarifying question if needed
  2. Map the landscape — real risks ranked by likelihood, common approaches, counterintuitive traps
  3. Explore tradeoffs — explicit option/benefit/cost/failure for each viable approach
  4. Land on next actions — what to do, what to watch for, what to revisit

This is a teaching conversation. The AI brings knowledge — it doesn’t just ask you questions. You came to it because you don’t know the landscape. It maps it for you, then lets you decide.

If the outcome is a code change, brainstorm routes you to the right skill: /upfront:quick, /upfront:patch, or /upfront:feature depending on size.