AI Readiness Checklist for midsize businesses

The ten questions

1. Can you name one repetitive chore that costs your team a day or more every week?AI pays back on frequent, repeatable work. If you cannot name the chore, start there, not with the technology.
2. Is there a senior sponsor who wants this fixed and can approve a phased budget?Projects without an owner stall at the first data question. A sponsor keeps decisions moving.
3. Can you say how you would measure success in one number?Hours saved, cost per job, empty miles, win rate or data coverage. One number keeps everyone honest.
4. Do you know today’s value for that number?Without a baseline you cannot prove the result, and you cannot build a business case the CFO will sign.
5. Does the chore leave a data trail?Spreadsheets, ERP, TMS or CRM exports, invoices or emails all count. AI learns from what your team already records.
6. Can you export at least 12 months of that data without an IT project?Access is usually the first blocker. A simple export is enough to start.
7. Would a person trust that data to make the decision today?Imperfect data is normal. The question is whether it is good enough to act on, with a confidence rating.
8. Do you know where the answer needs to land?An email, a spreadsheet, a CRM field or your planning system. Tools that fit the workflow get used.
9. Will the people who do the chore today help test and check the output?The best results come when the team stays in control and the tool takes the repetitive work.
10. Do you know the rules around this decision?Customer, audit or regulatory requirements shape how the solution is built and documented.

What your score means