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How to ThinkIn the Age of AI

Automate only fully-specifiable tasks — if it needs…

Automate only tasks where the rule can be stated completely (fixed rule, known inputs, predictable outputs) and execution requires no judgment about exceptions or novel cases.

When This Fires

  • Evaluating whether to automate a recurring task
  • Designing automation for a process with known edge cases
  • When an existing automation starts producing incorrect outputs (it hit an un-specified case)
  • Any time someone says "we should automate this" about a judgment-heavy process

Common Failure Mode

Automating the 80% of cases that are straightforward while the remaining 20% require judgment — and forgetting that the automation will process the 20% identically to the 80%. The automation confidently handles edge cases wrong because it can't distinguish them from normal cases. The silent failures accumulate until someone discovers them, often too late.

The Protocol

Before automating any task: (1) Write out the complete rule: every input condition, every branch, every output. (2) Check: does any branch require judgment, evaluation, or assessment of ambiguity? (3) If the rule is completely specifiable with no judgment → automate. (4) If some branches require judgment → automate the judgment-free branches and route the rest to human processing. (5) Never automate the judgment step itself — that's where automation fails silently.