The 90-Day AI Playbook: measurable ROI without the $400K executive hire.
Eighty-five percent of AI projects fail with the same signature: no owner, no ROI target, no kill switch, a vendor demo mistaken for a strategy. This field manual fixes that in ninety days: seven steps, in order, each ending in a written artifact you can hand your leadership team tomorrow. No platform purchase in the first sixty days.
Built from the same method used across 100+ implementations — the readiness score, the five-pillar governance framework, exit-cost vendor evaluation, and the honest ROI subtraction.
Score your readiness by your weakest dimension.
AI payoff is decided by four things, and companies grade themselves two levels too high. Score each 0–9 using the tells below. The rule that makes this useful: your readiness is your lowest score, not your average. A 9 in enthusiasm and a 2 in governance is a 2.
| Dimension | 0–3 Not ready | 4–6 Foundations | 7–9 Ready |
|---|---|---|---|
| Data | Records live in inboxes and spreadsheets; duplicates everywhere | Core systems hold most of it; nobody owns cleanliness | One source of truth, actively maintained |
| Process | The process is whatever each person does | A few outdated checklists | Core workflows documented, followed, reviewed |
| People | Nobody owns AI decisions; use is invisible | A leader owns it off the side of their desk | A named owner with time, budget, and authority |
| Governance | No policy; people paste anything anywhere | An informal "be careful" | A written policy people can recite; an approval path |
Trap to avoid: scoring this in a room full of your most AI-enthusiastic people. Score it with your ops lead and your controller. Prefer the interactive version? Three minutes, no email.
Run it alone, or with the person who wrote it.
The $750 Strategy Intensive works through your single highest-stakes AI decision in ninety minutes, written assessment within 24 hours, credited toward the Fractional Chief AI Officer retainer if we continue.