Ep 146 AI: Premortems, Because A.I. Won't Wait for a Retrospective

The "ship it, fix it later" playbook was already broken. AI just made it catastrophic. Post-mortems assume you have time to observe, adjust, and course correct. AI has collapsed those timelines, and the damage isn't waiting for a retrospective. In this episode, Stephen argues that pre-mortems aren't a luxury anymore. They're the only way responsible teams can keep pace with and scale AI-assisted work. He walks through six questions every team needs to answer before any project where AI touches the workflow — not as a checklist, but as the conversation you have before the pressure hits. Stephen anchors the argument in a core frustration he's named on the show before: most teams are in the consequence business without ever acting like it. From the Pokémon Go failures to the output-obsessed cultures that celebrate shipping as success, the episode makes the case that individually good decisions can still add up to collectively disastrous outcomes. This one is for any team using AI in their work who hasn't yet had a real conversation about what happens when it goes wrong. In this episode: Why the post-mortem era is over — and what has to replace it The six pre-mortem questions every AI-assisted project needs answered upfront How to map the blast radius before you're in a war room during a crisis The headline test: writing the failure story before the project starts Why agreeing on non-negotiables is the easy part — and holding to them under pressure is the real work Why AI is a culture problem, not a technology problem — and why this episode is the proof Send us Fan Mail SHOW NOTES AND MORE: https://thecrazy1.com/ WATCH MORE CONTENT ON YOUTUBE: https://www.youtube.com/@StephenGates WORK WITH CRZY: http://crzydesign.com/ FOLLOW THE CRAZY ONE: LinkedIn, Instagram, Facebook