Core insight: small, time-boxed adversarial probes—run as a microhabit—catch high-leverage failure modes before they compound. This episode gives you a repeatable, five-check red-team ritual you can run solo or with one colleague in under ten minutes. Supporting moves: (1) assume the worst credible outcome and name the single weakest link; (2) hunt proxies and perverse incentives that will distort behavior; (3) test data and provenance on one critical claim; (4) run a quick role-reversal—what would a competitor or regulator do; (5) define the smallest mitigation that would have changed your call. You’ll get exact prompts and a two-line template to log findings so learning compounds. Finish with one immediate action: run the red-team microhabit on a decision you’ll make this week, apply the simplest mitigation, and subscribe. Stay agentic.