Questions to ask an AI vendor before you sign

Before you sign anything, you need answers to four questions. They are not technical. They are not about features. They are about whether this vendor actually understands your business or is just selling a template to every company that walks in.

1. Do you have references from businesses like mine

Ask for three to five references from Canadian businesses in your industry. Not case studies. Not testimonials on their website. Real names, real phone numbers, real people who will talk to you off the record.

Call them. Ask these things:

• How long did it take to get this tool working the way you wanted.
• What surprised you about the cost—either higher or lower than expected.
• What does the tool still get wrong, and how do you catch it.
• If you could go back, would you do it again.

If a vendor can't give you three references, that's a red flag. If they give you references and those people sound like they're reading from a script, that's another one.

A plumber in Richmond who tried document AI might tell you it saved her 3 hours a week on invoicing but still needs her to check the numbers. A Burnaby accounting firm might tell you their tool works great 95 percent of the time but they built a person-powered catch system for the other 5 percent. That's the real story you need to hear.

2. What does this cost, and what are the real numbers

Ask the vendor to give you a number per month. Not per transaction, not per "unit", not per "seat". Per month. A number you can put in your budget.

Then ask:

• Does that price go up if we use it more.
• What happens if we stop using it—do we pay to get our data back.
• Are there setup costs, training costs, or integration costs on top of the monthly fee.
• Do you charge differently if we add another location or another user.

A typical AI tool for a small business costs between $200 and $1,500 a month depending on what it does and how much you use it. A property manager in Surrey might pay $400 a month for a tool that screens tenant applications. A 12-person software company in Gastown might pay $800 a month for a tool that summarizes customer feedback. That's the range. Anything outside that range, ask why.

Write down the total cost for a year and a three-year period. That's what you're actually committing to.

3. When the tool gets it wrong, what happens

Every AI tool makes mistakes. The vendor who tells you theirs doesn't is lying.

Ask:

• How often does this tool make mistakes on the kind of work I do.
• What kinds of mistakes are most common.
• What happens when it gets something wrong—who catches it, and how.
• Can I reject a result and have a human review it.

A dental clinic in Kelowna using AI to transcribe patient notes might find that it misses medical terms 2 or 3 times per month. A distributor in Calgary using AI to forecast inventory might be right 92 percent of the time. Those are the real numbers you need.

Then ask yourself: can I live with that error rate. If the answer is no, this tool is not for you yet. That's okay. Honesty saves money.

4. Who stays in the loop

This is the most important question.

Ask the vendor: for every decision this tool makes that affects my clients, my money, or my reputation, does a human have to approve it first.

The answer should be yes. If it's no, walk away.

A tool that sends appointment reminders can run on its own. A tool that declines a customer's application, approves a quote, or makes a refund decision needs a person to sign off. Always.

Ask the vendor to show you exactly where and how a human gets involved. Is it easy to override the tool's decision. Does it take 30 seconds or 30 minutes. Who on your team has to do it. What happens if that person is away.

What to avoid asking about

Don't ask about the technology. You don't need to know how it works. You need to know what it does.

Don't ask for a free trial unless the vendor offers one. Most don't, and that's fine. Instead, ask for a short paid pilot—maybe $500 or $1,000 for a month—so you can test it with real work before committing.

Don't let them rush you. If a vendor says you have to decide this week, that's a sales tactic, not a real deadline. Good vendors will still be there next month.

Where to start

• Write down the three biggest repetitive tasks your team does each week, then ask the vendor if their tool handles any of them. Focus on the one that wastes the most time.
• Ask the vendor for three references and call all three this week. Take notes on what they say about mistakes and costs.
• Request a written quote that includes the monthly cost, setup costs, data retrieval costs if you leave, and how the price changes if you use more.