How to Evaluate AI Tools - the framework that cuts through vendor hype.

Question 1: What specific workflow problem does this solve?

The most important evaluation question. 'AI for your business' is not a workflow problem. 'Reduces proposal writing from 4 hours to 45 minutes for our 10-person sales team' is a workflow problem. If you can't articulate the specific workflow the tool addresses and estimate the time currently spent on it, you're buying a solution before you have a problem definition. Every tool evaluation starts here.

Question 2: Can you test it on real work in 30 minutes?

The best AI tools have immediate, legible value. If you need an onboarding call, a demo, and a 2-week pilot before you can tell if it works, the tool has a usability problem. Test with real examples from your actual workflow - not the vendor's sample data. If Claude can draft a real proposal from your notes in 20 minutes, you know it works. If an enterprise AI platform requires 3 weeks of configuration before it does anything useful, that's integration cost you're paying, not tool value.

Question 3: What does it actually cost at your scale?

The pricing question most people ask too late:

• What's the per-seat cost when deployed to your full team?
• Are there API fees, usage-based costs, or data storage fees beyond the subscription?
• What's the annual contract commitment vs. monthly?
• What does the contract renewal look like - is the vendor known for aggressive price increases?

Question 4: What does it take to get your team using it?

The question that kills more AI tool purchases than anything else. A tool your team doesn't use is worth zero. Evaluate: Does it require significant IT setup? Does it change existing workflows or layer on top of them? What does the training requirement look like? What's the failure mode if it doesn't work as expected in production? The tools with the best adoption curves have low friction, clear value in the first session, and don't require employees to learn a new system - they slot into existing work.

The 30-day test protocol

Before committing to any AI tool subscription above $500/month:

• Week 1: Test with 3 real workflow examples. Document time before and after. Is the output usable with light editing?
• Week 2: Have 2–3 team members test independently. Is the quality consistent? Is the tool usable without the person who championed it?
• Week 3: Measure the edit overhead. AI tools that require heavy editing for every output don't save time - they shift where the time goes.
• Week 4: Calculate the real ROI. Hours saved × loaded hourly rate vs. monthly cost. If the ROI isn't at least 5:1, the tool isn't ready or the use case isn't right.