Apply & Commit: Run a 20-Minute Prompt-Risk Tabletop on One Workflow
Commit to a short tabletop exercise that exposes the highest-risk AI failure path in a real workflow.
Prompt-Risk Tabletop Worksheet One real AI workflow to tabletop this week A retrieval assistant that reads PDFs, webpages, or tickets and can send or post output externally. A support or ops workflow where people regularly paste logs, notes, or customer records into AI tools under time pressure. A multi-turn assistant where repeated reframing could slowly wear down a safety boundary. We will tabletop [workflow] with [roles]. We will test one prompt-injection path, one data-leak path, one jailbreak path, and one guardrail failure path. Our success metric is one concrete control change with an owner. When the next product or engineering…
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