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The Three Questions To Ask Before Any New AI Tool

By Nigel Guy · 2 min read

A new AI tool gets recommended to you and the instinct is to sign up and poke around — see what it does, decide later whether it's worth keeping. That's how you end up with a dozen half-used accounts, three of them holding data you'd forgotten you'd given them, and no clear memory of why you picked any of them.

The rule: ask what it costs, what it does with your data, and what it's actually for, before you create the account — not after.

The three questions

  1. What does this actually cost, once you use it properly? The free tier is rarely the story. Check what the next tier up costs, and check what triggers the upgrade prompt — a message limit, a feature gate, a file-size cap. If you can't find pricing in under two minutes, that's itself useful information about how the product wants you to sign up first and find out later.
  2. What happens to what you put into it? Specifically: is your input used to train their models by default, and can you turn that off? Is there a retention period, or does it keep things indefinitely? A vague privacy page that talks about "improving our services" without specifics is answering a different question than the one you asked.
  3. What is this actually for, and is that your actual task? Not "AI tool for productivity" — the specific job. A tool built for summarising meetings and a tool built for writing code are both "AI tools," and using the wrong one for your task usually means you're fighting the interface more than the model.

What to skip

Skip reading a full terms-of-service document end to end — the data-handling question above is answerable from the privacy policy summary or a search within the page, and most of the rest is generic legal boilerplate. Skip comparing every plan tier in detail before you've decided you'll use the tool at all; you only need the tier you'd actually land on. And skip taking a sales page's own claims about accuracy or capability at face value — that's a marketing document, not a spec sheet.

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