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Playbook·4 min read

An AI readiness checklist for Caribbean small businesses

Islandpreneur Team·May 28, 2026

AI isn't magic — it's leverage applied to a system that already works. Before you sign up for a single tool, run your business through these five questions.

1. What do you do more than 10 times a week that follows the same pattern? That's your first automation candidate.

2. Where does information get stuck — in your head, in WhatsApp, in a notebook? AI can only help what it can read.

3. What does a great customer interaction sound like? Document it. That becomes the prompt.

4. Who on your team is curious enough to test things? Give them two hours a week.

5. What would you measure in 60 days to know it worked? If you can't answer, don't start yet.

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