AI Readiness Checklist for $1–10M Businesses

1.Can you pull a clean P&L for any given month in under 10 minutes, without adjustments after the fact?

2.Does your chart of accounts reflect how the business actually operates today — not a company you outgrew two years ago?

3.Do your bank feeds reconcile to the penny each month without manual corrections?

4.If someone asked for gross margin by product or service line right now, could you produce it from existing data — not a spreadsheet you'd have to build?

5.Are your books closed within 10 business days of month-end, consistently?

1.Do your customer, vendor, and product records use consistent naming conventions across every system?

2.When a deal closes in your CRM, does that data flow to accounting without manual re-entry?

3.Are the fields in your systems actually used — no fields everyone ignores because they're always wrong or always blank?

4.If you exported your customer list from three different tools today, would the records match?

5.Do you know exactly where each number on your dashboard comes from — which system, which field, which calculation?

1.Can you name every system that touches a customer transaction from first contact to cash collected?

2.Do those systems talk to each other automatically — without someone manually moving data between them?

3.When your business changed (new products, pricing, headcount), did your system configurations change with it?

4.If the one person who knows your systems best left tomorrow, would the critical knowledge stay behind — documented, not walking out the door with them?

1.When two people on your leadership team pull the same number, do they get the same answer?

2.Do you have at least one report your team looks at every week that actually changes a decision?

3.When something looks wrong in a report, can you trace it to its source in under 15 minutes?

4.Are your financial and operational reports built on the same underlying data — not separate sources that sometimes disagree?

1.Do the same transactions get processed the same way every time, regardless of who's doing them?

2.Are your recurring processes (month-end close, invoicing, collections, payroll) documented anywhere outside the heads of the people who run them?

3.Have the last 90 days been free of a process breaking because someone did it “their way” instead of the standard way?

4.If you had to onboard someone to a core operational role in two weeks, is there documentation that could carry half the load?

1.Have you attempted to automate something in the last 24 months — and had it hold without needing constant fixes?

2.Do the AI tools you've already deployed pull from a single clean data source — not just whatever data happens to be available? (No AI tools yet? Mark No.)

3.Do you know what you would automate first if your data and systems were in order?

1.Is there a named person accountable for data quality — not IT, not finance generally, a specific owner?

2.When a system breaks, do you find out because monitoring or a named owner caught it — not because a downstream consequence surfaced it?

3.Has your leadership team aligned on what “good data” looks like, in writing?

4.Are you willing to fix the foundation before adding AI — even if that takes 60–90 days?