Independent Thinking
How to Evaluate AI Tools for Your Business
June 6, 2026
There are hundreds of AI tools that claim to save time. Most of them will cost you more than they save if you adopt them the wrong way. Here's the evaluation framework we use.
Most AI tool evaluations go wrong the same way: they start with the tool. Someone sees a demo, gets excited, and the question becomes “how do we use this?” That's backwards. The question is “what job needs doing, and is this the cheapest reliable way to do it?” — and sometimes the honest answer is a spreadsheet, or nothing at all.
You don't need to become an AI expert to evaluate AI well. You need a few questions that cut through the demo magic.
Start with the job, not the tool
Every worthwhile AI tool is doing a job you can name in plain language: drafting first-pass copy, summarizing calls, flagging anomalies, answering repetitive customer questions. If you can't state the job in one sentence — what goes in, what comes out, and how you'll know it's right — you don't have a use case. You have a tool looking for a problem.
“Earns its keep” is the only test that matters
Here's the test worth holding every tool to: does it earn its keep? Not “is it impressive” — does the value it creates clearly exceed everything it costs, including the part that isn't on the invoice. The subscription is the cheap part. The real cost is your team's time learning it, reworking around it, and checking its output.
The automation that earns its keep usually looks unglamorous in practice. A couple of years ago, a multi-site operation replaced its hand-assembled weekly numbers with automated reporting that gave leadership real-time visibility into figures they used to wait a week for. It earned its keep because the time saved was real, measurable, and larger than the time it took to build and maintain. That's the bar. A tool that saves four hours but costs five to babysit is a loss with good production values.
Build, buy, or skip
Once a job clears the “earns its keep” bar, there are only three honest answers — and most owners only consider one:
- Buy — a vendor already does this well and the price is fair. Usually the right call. Don't build what you can rent.
- Build — the job is specific to how you work, no tool fits, and the value is big enough to justify owning it. Rarer than people think.
- Skip — the honest answer more often than the AI conversation admits. Not every job is worth automating, and not every tool is ready. “Not yet” is a real, respectable result.
The skip option is the one a vendor will never offer you — which is exactly why it belongs on your list.
The questions that actually protect you
Before you commit, ask the unglamorous things the demo skips:
- Where does our data go, and who can see it? If you can't get a straight answer, that is the answer.
- What happens when it's wrong — and how will we catch it? Every AI tool is wrong sometimes. The question is whether your workflow notices.
- What's the exit? If you adopt this and it stops working — or triples in price — how hard is it to leave? Easy to enter and impossible to leave is a trap.
The mindset
Evaluate AI like you'd evaluate a hire: what's the job, can it actually do it, what does it really cost, and what's the plan if it doesn't work out. The businesses getting real value from AI right now aren't the ones using the most tools. They're the ones who picked two or three that clearly earn their keep — and skipped the rest without guilt.
Want to talk through what this means for your business?
Thirty minutes. No deck. An honest answer about whether we’re the right fit.