What a free AI assessment should include

A good one leaves you with something useful even if you never hire anyone. A bad one is a sales pitch with a clipboard. Here’s how to tell them apart.

“Free AI assessment,” “free AI audit,” “free strategy session”: lots of people offer them, and they vary wildly. Some are genuinely useful. Some are an hour-long pitch for a product that was decided before anyone walked in.

Full disclosure: I offer one too. This page is the standard I try to hold mine to, and a checklist you can use on anyone’s, including mine.

What a good one includes

1. Someone looking at your actual work. Not a questionnaire, not a slide about “the AI landscape.” They should ask to see the real thing: your inbox, the spreadsheet that holds the business together, the folder of quotes. People describe their process as it should be; the screen shows what it is. The most useful findings almost always come from watching one ordinary task being done.

2. Findings in your words. You should recognize your own business in what they tell you. “You rebuild the same quote from scratch about eight times a week” is useful. “Your workflows have automation potential” is not.

3. Something you can use right away, for free. A good assessment teaches you at least one thing you can use tomorrow, with no strings attached: an instruction to give ChatGPT, a template, a setting you didn’t know about. If the only way to get value is to buy something, it wasn’t an assessment.

4. What they wouldn’t do. This is the best sign of honesty there is. Someone looking out for you will name at least one thing you could pay for and shouldn’t, because it’s not worth it for a business your size, or the tool you already have does it fine.

5. Prices, in writing. You should leave with (or receive within a day or two) a short summary: what they’d fix, what changes, roughly how much time it gives back, and what it costs. Clear prices, not “let’s scope it on a follow-up call.”

6. No pressure. “Take your time” is the right tone. A good recommendation is still a good recommendation next month.

Red flags

It’s a demo. If they open a laptop and show you their product in the first ten minutes, it’s a sales call.
Every answer is the same tool. Real advice depends on your business. If every problem is solved by the one thing they sell, be careful.
They recommend everything. Five projects, all urgent, all expensive. Real businesses have one or two things worth doing first.
Jargon you can’t follow. If you don’t understand what they’re proposing, that’s their failure, not yours. Ask them to explain it like they would across a counter. If they can’t, walk away.
No price until the next meeting. Or the price changes depending on how much you seem to want it.
A long contract. Especially for something that should take days, not months.
They make you feel behind. Most of what people think they should already know, nobody knows. Anyone using that feeling to sell to you isn’t on your side.

How to get the most out of it

A little preparation makes an hour much more useful:

Think about last Tuesday. Walk through a normal day in your head. Where did the time go? What did you do at night that you wish you hadn’t?
Have the real things handy. Be ready to open your inbox, your quote template, your job list, whatever you actually use.
Bring your worst job. The task you’d hand off tomorrow if you could. That’s usually the best place to start.
Include whoever does the admin. If someone else in the business does the paperwork, they know where the time really goes.
Ask anything. Including the questions you think are basic. Especially those.

Questions worth asking them

What would you not recommend for us, and why?
Who owns what you build? Does it run on our accounts or yours?
What happens if we stop working with you?
What goes into these tools, and what never should?
How would we know, in a month, that this was worth it?

Clear answers to those five tell you most of what you need to know.

How mine works

Since I’m writing this: my free hour happens at your place. I ask about your week, you show me a couple of things on your screen, and I teach you one thing you can use the next day. Within a day, I send a one-page report with three things that would improve your business, how I’d do each one, and what it costs. It’s yours either way, and if you don’t need me, I’ll tell you.