AI Readiness Checklist for $1–10M Businesses

1.Can you pull a clean P&L for any month in under 10 minutes?

2.Does your chart of accounts match how the business runs today?

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

4.Could you produce gross margin by product or service line today without building a new spreadsheet?

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

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.Do people use and trust the fields in your systems, instead of ignoring ones that are usually wrong or blank?

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

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

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

2.Do those systems share data automatically, without someone moving it by hand?

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

4.If the person who knows your systems best left tomorrow, would documentation keep that knowledge in the business?

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 reviews every week that changes decisions?

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?

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.Has it been at least 90 days since a process broke because someone did it their own way?

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

1.In the last 24 months, have you automated something that held up without constant fixes?

2.Do the AI tools you've deployed pull from a single clean data source? (No AI tools yet? Mark No.)

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

1.Does data quality have a named owner, not just a department?

2.When a system breaks, does monitoring or its owner catch it before the downstream damage does?

3.Has your leadership team agreed in writing on what good data looks like?

4.Are you willing to spend 60–90 days fixing the foundation before adding AI?