The AI readiness checklist for businesses under 20 employees

"Should we be doing something with AI" is the wrong first question. The right one is "would AI have anything solid to stand on here." This checklist answers that in about ten minutes. Count your yes answers as you go. No trick questions, no jargon.

Part 1: Process clarity

AI amplifies your processes. If the process only exists in your head, there's nothing to amplify.

1. Could a new hire figure out your three most common tasks from written instructions, without asking you?
2. Do you know which task eats the most hours in your week? (If not, do our 10-minute busywork audit first.)
3. Can you name the three questions customers ask most often?
4. When something goes wrong repeatedly, do you change the process, not just fix the instance?
5. Is there at least one task you do the exact same way every single time?

Part 2: Data hygiene

AI works with what you can hand it. A shoebox of receipts hands it nothing.

6. Is your customer information in one system, not spread across a phone, a notebook, and three inboxes?
7. Could you find any given customer's history in under two minutes?
8. Do your important documents live somewhere searchable, not just in email attachments?
9. If two systems store the same information, do you know which one is the truth?
10. Could you export your customer list right now if you had to?

Part 3: Team and time

Tools don't adopt themselves.

11. Is there one person, maybe you, who would own trying new tools?
12. Could that person spend two hours a week on it for a couple of months?
13. Has your team adopted a new tool successfully in the past two years?
14. When you introduce a change, does it usually stick?
15. Are you willing to run a new tool alongside the old way for a few weeks before switching?

Part 4: Security basics

AI adds new doors to your business. Lock the existing ones first.

16. Does your team use a password manager, not a shared spreadsheet of passwords?
17. Is two-factor authentication on for email and banking?
18. When someone leaves, is there a routine for removing their access?
19. Do you know whether your industry has rules about customer data? (Health, finance, and legal usually do.)
20. Would you know within a day if an important account was compromised?

Part 5: Economics

You can't measure improvement without a starting point.

21. Do you know roughly how many hours a week your business spends on admin?
22. Do you know what a new customer costs you to acquire, even roughly?
23. Do you know your busiest and slowest recurring bottleneck?
24. Could you say what an hour of your own time is worth to the business?
25. If a tool saved five hours a week, do you know what you'd do with them?

Your score

18 or more yes answers: ready for workflow automation. Your foundations can support real integration work, connecting AI to the systems you already run. Start with the workflow that scored worst on the busywork audit.

10 to 17: start with assistive tools. Use AI to help people do tasks, not to run tasks alone. Drafting, summarizing, answering questions. Meanwhile, fix the no answers in Parts 1 and 2. They're your ceiling.

Under 10: fix foundations first. This is genuinely good news, because it means the cheapest improvements available to you aren't AI at all. Get customer data into one system and write down your top three processes. Do that and you'll leapfrog competitors who bought tools instead.

Want this as a printable worksheet, or want a second pair of eyes on your score? Email us or use the contact form. If your score says you're not ready, we'll say so too. That's free.