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Free · one pageUpdated 2026-10-07

AI Discovery Cheat Sheet

Business discovery with the sponsor and users

  1. What decision or task should get better, and for whom?
  2. How is it done today, step by step, and how long does it take?
  3. How will we know it worked? What number, measured how, today's baseline?
  4. Who owns that number and will sign off on success?
  5. What happens if the AI is wrong? Who is affected and how badly?
  6. What has been tried before, and why did it stop?
  7. What is the deadline, and what is driving it?

Technical discovery with data, security and IT owners

  1. Which systems hold the data, and who can grant access?
  2. How is access controlled today (identity provider, groups, roles)?
  3. What regulation applies (privacy, health, finance, sector rules)?
  4. Where may data be processed and stored? Any residency rules?
  5. Which external AI services are already approved, if any?
  6. Where must the result appear: which app, channel or workflow?
  7. What logging and audit does security expect?

Red flags that should pause the project

  • Nobody can name a measurable outcome or owner.
  • The data needed does not exist, or nobody can grant access to it.
  • The AI would make an irreversible or regulated decision with no human review.
  • Security has not been told about the project.
  • Users were not consulted and the sponsor cannot name one.

Send the same day

  • A one-paragraph summary of the problem in their words.
  • The success metric and baseline you heard, for them to correct.
  • Open questions with a named owner for each.
  • The proposed next step and date.

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