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Ask the right security questions about a new service

  • For Software developers
  • You practice Giving the right context
  • Time about 5 minutes

About this exercise

You're reviewing a design doc for a new webhook service. Write exactly 4 numbered questions for the author, each naming a specific component from the doc and asking about a trust boundary the doc leaves open. Skip anything the doc already answers. Plain text, under 110 words.

Common mistakes when you ask AI for this

  • Generic questions. The AI asks 'Have you considered authentication?' without pointing at a component. Try: Say: "Each question names a component from the doc."
  • Asking what's answered. The AI asks about TLS and rate limits, which the doc already settles. Try: Add: "Skip anything in 'What's decided'."
  • Missing the open items. Without being pointed at the gaps, the AI spreads questions over everything. Try: Ask: "Focus on the trust boundaries the doc leaves open."
  • Questions plus essays. The AI adds a paragraph of explanation under each question. Try: Be exact: "Exactly 4 numbered questions, each under 20 words."
  • Letting markdown in. AI adds bold and headings by default, and in the doc comments they show up as stray symbols. Try: Add: "Plain text only, no bold, no headings."

What a strong prompt includes

  • Asks for specific components
  • Targets the open items
  • Skips settled items
  • Says exactly how many
  • Asks for plain text

Practice this now ↑

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