This is the operations-focused companion to the AI implementation roadmap — the week-by-week checklist for the operator (COO, Chief of Staff, Head of Ops) actually running the rollout. Less strategy, more checklist.
Your CEO has said yes to AI. Now you have to make it happen. This checklist is the version you can print, tape to your monitor, and check off as you go.
The rollout fails the same way the strategy fails — too many things tried at once, nobody owning execution. If you have to choose between doing all of this and doing the first 30% well, choose the 30%.
| Risk | Signal | Response |
|---|---|---|
| Adoption stalls at the AI lead | Only the AI lead uses the tools. Workflows have not transferred to owners. | Schedule pair-sessions: AI lead works alongside the workflow owner until owner is solo for 3 consecutive uses. |
| Quality drift | Customer complaints, brand voice slips, factual errors in outputs. | Add a human-review checkpoint before any output ships. Audit 10 random outputs weekly. |
| Data leakage | Confidential information appears in shared chats or non-approved tools. | Suspend access. Notify owner. Issue refresher on data classifications. Document incident. |
| Cost overrun | Per-seat or per-token costs growing faster than usage value. | Move from per-token model to a fixed-seat tier. Audit which seats are actually used. |
| Team pushback | Visible resistance, "I prefer doing it myself" comments. | Investigate. Usually a sign the tool is being forced into a workflow it does not fit. Adjust scope, not pressure. |