Five questions to answer before you buy any AI tool

By Keith Myers · August 2026

Every week a new AI tool promises to transform your business. Most of the subscriptions bought that way are dead within six months: nobody uses the tool, someone notices the charge, it gets cancelled, and the company concludes AI does not work for them.

The tool was rarely the problem. The buying process was. Five questions fix it.

1. What task does this replace, and who does that task today?

Not "what can it do." What will it do, in your business, starting which week, replacing whose work. If you cannot name the task and the person, you are buying a demo, not a tool. The tools that stick are attached to a job someone already hates doing.

2. Where does your data go?

Read the answer to three specific things: is your data used to train the vendor's models, where is it stored, and can you delete it when you leave. Any vendor that makes these answers hard to find has answered them. If you handle client data, health data, or financial records, this question comes first, not fifth.

3. Does it work inside the software you already use?

A tool your team must open in a separate tab loses to a worse tool that lives inside Outlook, Gmail, or whatever they already have open. Adoption beats capability. Check for a real integration, not a logo on a partners page.

4. What does it cost at your real headcount, next year?

Per-seat pricing looks cheap at the trial stage. Multiply by everyone who would actually need it, add the tier you will really need (the useful features are rarely in the cheapest one), and compare that annual number against the hours saved. If the math needs a spreadsheet to look good, it is not good.

5. Who owns it after the first month?

Every tool needs one named person who sets it up properly, shows others, and decides in 90 days whether it stays. Tools without an owner die quietly. If nobody wants to own it, that tells you what the team really thinks of it.

The pattern behind all five

Good AI purchases are boring. They name a task, a person, a monthly cost, and a review date. The exciting purchases, the ones bought off a keynote or a LinkedIn post, are the ones that get cancelled. Boring is the goal.