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How to ThinkIn the Age of AI

Four-category automation triage

Classify workflow steps as 'automate now' (well-defined, no judgment, high frequency), 'automate later' (well-defined, no judgment, low frequency), 'assist' (requires judgment but tools handle mechanical portions), or 'keep manual' (requires judgment, taste, or values only you provide).

When This Fires

  • When reviewing a workflow and deciding which steps to automate
  • When evaluating a new automation tool and identifying where it applies
  • When automation has produced poor results — likely a "keep manual" step was automated
  • When prioritizing automation investments for maximum return

Common Failure Mode

Binary thinking: either fully automate or keep fully manual. This misses the "assist" category, which is where most knowledge work lives. A writing workflow isn't "automate" or "don't automate" — it's "automate the formatting and distribution, assist the drafting with templates and outlines, keep the voice and argument manual."

The Protocol

(1) List all steps in your workflow. (2) For each step, answer two questions: "Does this step require human judgment, taste, or values?" (Yes/No) and "How frequently is this step executed?" (High/Low). (3) Classify: No judgment + High frequency → Automate now. No judgment + Low frequency → Automate later. Judgment required but has mechanical sub-steps → Assist (automate the mechanical, keep the judgment). Judgment is the entire step → Keep manual. (4) Prioritize automation in order: automate-now first (highest ROI), then assist (highest complexity-reduction), then automate-later (when convenient). (5) Apply Sovereignty check before automation — if the automation…'s sovereignty check to every automation decision before implementing.