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How to ThinkIn the Age of AI

Handoff workflows need finer granularity than personal…

When documenting workflows for handoff or future self, use finer granularity than workflows written for immediate personal use, calibrating the competent stranger to match the least experienced actual executor.

When This Fires

  • When documenting a workflow you'll hand off to someone else
  • When creating documentation for your future self (anything you won't execute for 30+ days)
  • When a handoff recipient keeps asking questions that "should" be answered by the docs
  • Complements Competent stranger test for workflow steps — could someone… (competent stranger test) by adjusting who the "competent stranger" is

Common Failure Mode

Writing handoff documentation at the same granularity as personal notes: "Run the deploy script." You know which script, where it lives, what flags it needs, what to check after. The recipient knows none of this. Every unstated element is a support request that interrupts you or a mistake that requires cleanup.

The Protocol

(1) Identify who will actually execute this workflow — the specific people or roles, not a theoretical audience. (2) Calibrate to the least experienced among them: what do they know? What don't they know? (3) Apply Competent stranger test for workflow steps — could someone…'s competent stranger test using this specific calibration: could the least experienced executor complete each step with zero clarifying questions? (4) Include elements you'd normally skip for yourself: exact file paths, specific tool names, output formats, success/failure indicators, and "what to do if X goes wrong." (5) Test if possible: have the actual least-experienced executor follow the documentation cold. Every question they ask is a documentation gap to fill.