Too many small teams rush automation and discover failure modes in production. This episode teaches a compact, practical Automation Tabletop you can run in seven days to surface the top risks, build immediate rollback and comms playbooks, and harden one high‑value automation without heavy engineering. Bob interviews an operations lead who ran a real tabletop after a costly activation incident and an SRE/AI‑ops engineer who shows lightweight monitoring and alert patterns suitable for non‑engineers. Listeners get a reproducible agenda (stakeholder map, failure catalog, test cases), three incident scripts (client notice, partner escalation, internal postmortem), a one‑page rollback checklist, and a conservative pilot plan to harden one automation in a week. The episode keeps solutions pragmatic: human gates, canary runs, short retention logs, and clear go/no‑go criteria so advisors can scale safely and keep client trust intact.