Guides · Updated 5 November 2026

How to choose an AI tool: a checklist before you pay

There are more AI tools than anyone can test. This checklist is how we narrow them down for our buyer's guides, and it works for any category.

1. Name the one job you need done

"An AI tool" is too broad. Write down the task, such as drafting client emails, summarising meetings or explaining code. A general assistant may cover it; a specialised tool only earns its price if it does that job clearly better.

2. Start on the free plan with real work

Most major assistants offer a free tier or trial. Test it on a task you actually do this week, not a toy example, and compare two tools side by side on the same input.

3. Read the data and privacy settings

Check whether your conversations may be used to improve the vendor's models, and whether you can switch that off. Some vendors offer this as a setting on consumer plans and different defaults on business plans. Read the vendor's own privacy page rather than relying on a summary.

4. Find the real limits

Free and paid plans usually cap messages, uploads or minutes in some way, and the caps can change. Look for the limits on the pricing page and in the help centre, and notice whether they reset daily, weekly or on a rolling window.

5. Check that you can get your work out

Can you export transcripts, documents or chat history in a standard format? Tools that make leaving hard cost more over time.

6. Check billing and cancellation before you subscribe

Note whether the price shown is monthly or billed annually, and whether tax is included.
Find out how to cancel and whether the plan auto-renews.
Set a reminder before any trial ends.

7. Re-check prices on the vendor's page

AI pricing changes often. Our buyer's guides list the date we checked each vendor's pricing page; always confirm on the vendor's site before paying.

Questions

Is a paid plan always better?

Not for everyone. If the free plan handles your task within its limits, upgrading mainly buys higher limits and extra features you may not use.

Should I pay annually?

Only after you have used the tool monthly long enough to know you will keep it.

Sources and further reading

Written by the AI Week Daily editors. Spotted an error? See our corrections policy.