An AI readiness checklist I built for SMBs (5 pillars, 20 questions)

SMB agent pilots work fine in controlled demos, then fall apart the moment you point them at production. The failures cluster around the same five things. I built this pre-flight checklist for SMBs thinking about delegating workflows to agents. 5 pillars, 20 yes/no questions, about 3 minutes. **The 5 pillars and what breaks for each:** 1. **Data**: Agent treats a customer with three CRM IDs as three different customers and updates the wrong one 2. **Integrations**: Sync fails silently overnight, agent acts on stale state at 7am, you find out from the customer 3. **Process**: Workflow has undocumented exceptions only Sarah knows about; agent runs the standard path, angry emails follow 4. **Tools**: Shadow AI usage in your team puts company data into vendor training sets you never agreed to 5. **People**: Verifier is too busy to verify properly, rubber-stamps the output, mistakes reach customers **The agent-specific gotchas:** * Irreversible actions (sent emails, posted invoices) need to be scoped out of the agent's tool surface, not "wrapped in rollback" * Pipeline monitoring catches obvious failures (loops, runaway cost) but not slow drift on edge cases. You need to sample what the agent is producing, not just whether it's producing * Per-agent spending cap + kill switch holder named before you turn it on **Scoring:** * **0–7**: not there yet, fix the foundation first * **8–14**: assistive-AI patterns only (suggest-and-approve, human in the loop) * **15+**: you can start delegating bounded work to agents Full interactive scorecard in the comments. What's the most expensive SMB agent failure you've seen? Particularly curious about data-quality issues. That's where I keep seeing pilots fail.