How to choose AI software

1. Ignore benchmark charts; test your actual work

Every vendor claims leadership on some leaderboard, and every claim is true on Tuesday and stale by Friday. Take three real tasks from your week — a summary, a draft, an analysis — and run them on two or three free tiers. An afternoon of testing beats a month of reading reviews, including ours.

2. Decide between a tool and a layer

ChatGPT and Claude are destinations: you go to them to work. Gemini and Copilot are layers: they come to where your work already is. Neither is better in the abstract, but buying the wrong model for your workflow guarantees shelfware. Start from where your documents and email live.

3. Context window is the spec that quietly matters

If your work involves contracts, research archives, codebases or books, context size changes what is possible. A 200K to 1M token window ingests entire projects; a small one forces you to chop work into pieces. For short tasks it is irrelevant — know which user you are.

4. Free tiers are real; paid tiers are about headroom

Every product in this category is usable free, with paid plans (~$20–25/mo) buying higher limits, better models and features like deep research. One caution: some rivals meter usage by credits rather than flat rates, which makes heavy-use costs far less predictable — model your real workload before paying. Business plans add admin and data controls, not magic.

5. Ask the data question before the company standardises

Check each vendor's policy on training data, retention and regional processing — business and enterprise tiers generally exclude your data from training; consumer tiers vary. If you handle client-confidential material, this decision should happen before the first prompt, not after.

6. Assume you will switch, and stay portable

This market reprices and reshuffles quarterly. Keep your prompts, templates and workflows in plain formats you can carry between assistants, and avoid building critical processes on vendor-specific features until they have survived a year.

Next steps

With the criteria clear, the fastest route to a confident shortlist is our category research: