Buying an AI Tool

Criteria: Buying an AI Tool

Five articles. Narrow first, then one criterion at a time in weight order. Then the Playbook, if you want to run it with your team.

Articles in this series

Choosing an AI Tool for a Small Business: Shape, Gates and the Bundled Test

Before you shop, prove you need a tool at all by running the job through the AI assistant you already pay for. Then write an eight-line shape, pick a rung on the ladder, and run every shortlisted tool through six pass-or-fail gates.

Testing an AI Tool on Real Work: 14 Questions Before You Pay

Run the real job with real inputs in the free trial. Time the job by hand first. Then rate fourteen questions from the trial. This is the weight-five criterion. Nothing else matters until it passes.

Why Employees Don't Use AI Tools: Score Adoption Before You Buy

The standard failure of an AI tool purchase is not that it does not work. It is that nobody opens it in week three. Score for adoption before buying. Twelve questions, weight four.

Can You Trust an AI Tool With Client Data? 12 Questions to Ask First

Trust has two halves. Accuracy on your job and data handling from the terms. Twelve questions, weight four. Read the data processing terms, not the marketing page.

AI Tool Pricing: Per Seat vs Usage, and One Annual Number

Normalise every option to one annual all-in number in Canadian dollars. Then ask which pricing model gets expensive if the tool works, what the bundled tool costs, and what the price is at double the seats. Eight questions, weight three.

The tool

The AI Tool Buyer's Playbook

Six gates. Four weighted criteria. Five tools. One room.

Get the Playbook

Case Study

The worked example

Fathom vs Copilot vs Fireflies for Client Meeting Notes: A 50-Person Agency Runs the Method

A 50-person marketing agency on Microsoft 365 and HubSpot runs Copilot, Fathom and Fireflies through the AI Tool Buyer's Playbook. Real prices, filled-in templates, a 1.2-point finish, and the tiebreaker that decided it.

Read the case study

Best AI Tool for Small Business in 2026? The Top-Rated One Is Probably Not Yours

The top-rated AI tool wins on someone else's job, seats and data. Here is why rankings fail small firms and the free method for finding the one that fits yours.

ChatGPT vs Copilot for Small Business (2026): Prices, Data, and Which Fits Your Job

ChatGPT Business and Microsoft 365 Copilot cost about the same per person. The difference is where the work lands and what you already pay for. A method, not a verdict.

ChatGPT Business Pricing (2026): What a Team of 5 to 50 Actually Pays

ChatGPT Business is USD 20 a seat annual or 25 monthly, 2-seat minimum, as of September 2026. What is included, what is not, and how to turn the sticker into one annual number before you buy.

Is It Safe to Put Company Data in ChatGPT? (2026) It Depends on the Plan, Not the Tool

On Free, Go, Plus and Pro, ChatGPT trains on what you type unless each person opts out. On Business and Enterprise it does not, by default. Which plan, what to check, and the four questions before any client file goes in.

AI Adoption in Small Business (2026): Why It Is Decided Before You Buy, Not After

Most AI tools go quiet by week three. Not because of training or change management, but because the people who do the job were not in the decision. How involving them in the choice fixes adoption before the invoice arrives.

AI Tools for Writing Proposals (2026): Three Kinds, One Job, and What a Real Firm Chose

There are three kinds of AI tool for writing proposals, not thirty products. The assistant in your office suite, a general assistant seat, and a proposal builder. What each does well, what one engineering firm found, and the questions to run before you buy.

The dispatch

One email a month. Just what we're working on.

A short note each month with every new criterion we've added. No promotions, no pitches, just a heads-up on what's in progress.