Six questions, one score, and an honest read on whether an AI project will take hold here or quietly die in month three.
Score your business readiness for AI in 6 questions. Get a personalized action plan and readiness score.
1. How much of your team's work is repetitive?
2. Is your business data digital?
3. How does your team handle new technology?
4. Monthly budget for AI tools?
5. Do you have a clear problem AI should solve?
6. Have you used AI tools before?
An MIT report widely cited through 2026 found roughly 95% of enterprise generative-AI pilots produced no measurable profit-and-loss return. That figure gets quoted carelessly, so here is the honest version: it measured P&L impact within six months, mostly in sales and marketing — the weakest category in the study. It is not evidence that AI does not work. It is good evidence that pilots get launched into businesses that were not ready for them.
Readiness is mostly not about technology. It is about whether repetitive work exists to automate, whether the data describing it is in a usable state, and whether anybody's job is genuinely allowed to change as a result.
| Question | What it is really asking |
|---|---|
| How repetitive is the work? | Is there enough volume for automation to pay back the effort of building it? |
| Is your data digital? | Can a system reach the information at all? Paper and people's inboxes are both "no". |
| How does the team handle new tech? | The strongest predictor of whether the tool survives past month three. |
| Monthly budget | Not whether you can afford it — whether you can afford to iterate after v1 disappoints. |
| Is there a clear problem? | "We should be doing AI" is not a problem. It is the most expensive sentence in this field. |
| Prior AI experience | Calibration. Teams who have used the tools have realistic expectations of them. |
A low score is a useful result, not a bad one. It costs nothing to discover you are not ready. Discovering it four months into a paid engagement costs a great deal.
The most common outcome is somewhere in the middle, and the most common mistake is treating that as permission to proceed at full scale. Fix the weakest of the six answers first — it is almost always data or team readiness, and both are cheaper to address before an implementation than during one. Then run the 90-day planner, which builds a roadmap around your specific obstacle.
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