Testing organizational brittleness requires modified approaches accounting for complexity and politics:
Cascading Team Tests Have each team test their area, then combine results to see system-wide brittleness. Local brittleness often seems manageable until you see cumulative effects.
Anonymous Brittleness Reporting People may hesitate to highlight brittleness they're responsible for. Anonymous reporting systems surface hidden vulnerabilities.
Brittleness War Games Run scenarios where teams attempt to "break" other departments' systems. Competitive elements make brittleness discovery engaging rather than threatening.
External Brittleness Audits Outside perspectives see brittleness that insiders miss through familiarity. Regular external testing provides fresh insights.