AI Readiness Checklist for Small Businesses

Before you spend a dollar on any AI tool, work through these ten questions. They'll tell you where you actually are — and where to start.

1. Do you have a repeatable process?

AI works best on tasks you do the same way, again and again. If the process changes every time, automate the process first.

2. Can you describe the task in plain language?

If you can't write it down clearly, you can't prompt it clearly. Spend 20 minutes documenting the task before touching any tool.

3. Where does your team lose the most time?

List the top three time sinks. The best AI investment is almost always in the one with the highest volume — not the most glamorous.

4. Do you have examples of good output?

AI tools learn from examples. Three solid examples of "what good looks like" are worth more than hours of prompt tweaking.

5. Who will own this after launch?

Every AI system needs a human owner. If there's no one to review outputs, catch drift, and improve the prompts — wait until there is.

6. What's the cost of a mistake?

A draft email that's slightly off is fine. An invoice with the wrong number is not. Match your oversight level to the risk.

7. Can your team see the benefit?

Adoption fails when people feel replaced, not supported. Make sure the team understands what they gain — not just what changes.

8. Is your data accessible?

Most AI tools need text. If your knowledge lives in someone's head, or in scanned PDFs, extract it first.

9. What does "good enough" look like?

Define a clear bar before you start. Chasing perfection with AI is expensive and slow. Ship when it's good enough.

10. Can you measure improvement?

Baseline the current state — time, error rate, volume handled. Without a baseline, you can't prove the win.

Next step: Score yourself. If you answered yes to seven or more, you're ready to move. Fewer than five? Focus on the questions you couldn't answer — that's where the real work is.