Most stalled AI projects did not fail because the tool was bad. They failed because nobody answered these five questions first. Work through them honestly and you will know whether you are ready — and where to start if you are not.
1. What business outcome are we actually after?
"Use AI" is not a goal. "Cut proposal turnaround from four days to one" is. Name the number you want to move. If you cannot, you are not ready to buy anything yet — you are ready for a strategy conversation.
2. Where does our information actually live?
AI is only as useful as the context you can give it. If your processes, pricing, and client history live in people's heads and scattered inboxes, that is the first thing to fix. Often the highest-value early work is simply writing things down.
3. Who on the team will own this?
Someone has to be responsible for the prompts, the templates, and the training. Not a committee — a person. Without an owner, tools get trialed and abandoned.
4. What are our guardrails?
Decide in advance what never goes into an AI tool — client financials, personal data, anything under a confidentiality agreement — and who reviews AI-assisted work before it goes out. Write it down in one page your team can actually read.
5. How will we know it worked?
Pick your measure before you start: hours saved, response time, error rate, revenue per client. Review it in 30 days. Anything you do not measure will quietly drift back to the old way of working.
If you answered "not sure" more than twice
That is normal, and it is fixable. A short AI readiness assessment answers all five in a structured way and leaves you with a roadmap instead of a shopping list.