10 Questions to Ask Before Hiring an AI Service for Your Business

The market for AI services aimed at small businesses has exploded. A year ago there were a handful of options. Now there are hundreds of companies promising to "transform your business with AI." Some are excellent. Some are glorified chatbot templates with a nice landing page.

Before you hand over your credit card, ask these ten questions. The answers will tell you almost everything you need to know about whether a provider is worth your money.

1. How Do You Handle My Business Data?

This should be your first question, full stop. Your customer information, financial records, and internal processes are the lifeblood of your business. You need to know:

• Where is your data stored?
• Who has access to it?
• Is it used to train models that serve other clients?
• What happens to your data if you cancel?

Good answers sound like: "Your data is stored in encrypted, isolated environments. It's never used to train models for other clients. If you cancel, we delete everything within 30 days and provide you an export." Bad answers sound like vague reassurances with no specifics.

2. How Customized Is the Solution to My Business?

There's a massive difference between an AI that's configured with your specific pricing, services, policies, tone of voice, and business logic — and one that's a generic template with your logo slapped on it.

Ask to see examples of how the AI will be trained on your business. Will it know your service area? Your pricing tiers? Your cancellation policy? The answer should be specific, not theoretical. If the provider says "just give us your website and we'll figure it out," that's usually a sign of a shallow implementation.

3. What Ongoing Support Do I Get?

AI isn't a set-it-and-forget-it product. Your business changes — new services, new pricing, seasonal adjustments, staff changes. Your AI employee needs to change with it.

Find out what's included in the monthly fee. Does the provider handle updates and adjustments? Is there a dedicated point of contact? What's the response time for support requests? A good provider includes ongoing optimization as part of the monthly cost. A bad one charges extra every time you need something changed.

4. What Systems Does It Integrate With?

Your AI employee is only useful if it connects to the tools you already use. Calendar systems, CRMs, email platforms, phone systems, booking software, payment processors — the integration list matters.

Ask specifically about the tools you use. "We integrate with over 200 platforms" means nothing if yours isn't one of them. Get confirmation that your specific tech stack is supported, and ask what the integration process looks like. Some providers handle it end-to-end. Others hand you documentation and wish you luck.

5. What's Your Cancellation Policy?

This tells you how confident the provider is in their own product. Long-term contracts with heavy cancellation penalties are a red flag — they suggest the provider knows clients might want to leave and wants to make it painful.

Look for month-to-month agreements or short commitment periods (90 days maximum). If the service delivers value, you'll stay voluntarily. If it doesn't, you should be free to walk away without a financial penalty.

6. Can You Show Me Results from Similar Businesses?

Case studies, testimonials, or references from businesses similar to yours — in size, industry, or use case — are worth more than any sales pitch. Ask for them specifically.

"We've worked with hundreds of businesses" is marketing. "Here's a landscaping company with 8 employees that reduced their response time from 6 hours to 3 minutes and increased bookings by 28%" is proof. If a provider can't show you relevant results, they either don't have them or don't track them. Neither is a good sign.

7. What's the Timeline from Signup to Go-Live?

AI deployment isn't instant, but it shouldn't take months either. For a well-run managed AI service, you should expect:

• Discovery and scoping: 1–3 days
• Build and integration: 5–7 days
• Testing and tuning: 3–5 days
• Total: 2–3 weeks from signing to a live, functioning AI employee

If a provider tells you it'll take 2–3 months, they're either overcomplicating it or under-resourced. If they tell you it'll be live tomorrow, they're cutting corners that'll show up as quality problems later.

8. What Exactly Is Included in the Setup Fee and Monthly Cost?

Get an itemized breakdown. The setup fee should cover discovery, custom configuration, integration with your systems, testing, and go-live support. The monthly fee should cover hosting, maintenance, ongoing optimization, support, and a reasonable amount of usage.

Watch for hidden costs: extra charges for integrations, per-message fees that scale unpredictably, fees for updates or changes, charges for "premium" features that should be standard. If the pricing page is vague, ask for a written quote that covers every possible cost.

9. Are There Hidden Costs or Usage Limits?

This is different from question 8 and worth asking separately. Some AI services advertise a low monthly rate but charge per interaction, per message, or per API call. A $200/month plan that costs $0.05 per message sounds cheap until your AI handles 10,000 messages in a month and your bill is $700.

Ask: Is the monthly price truly all-inclusive? What happens if my usage doubles? Are there overage charges? Is there a cap on interactions, and what happens when I hit it? Predictable pricing matters — you need to know your costs won't spike unexpectedly.

10. Who Owns the Work Product?

If your AI service creates content, generates responses, builds workflows, or develops custom logic for your business — who owns that output? What happens to all the custom training and configuration if you leave?

You should own anything created specifically for your business. The provider can retain their underlying platform and general methodologies, but your custom configurations, content, and data should be yours. Get this in writing. If a provider won't commit to this, they're building lock-in, not value.

The Bonus Question: What Happens When It Makes a Mistake?

Because it will. Every AI system makes errors, especially in the first few weeks. The important thing isn't whether mistakes happen — it's how the provider handles them.

Ask about their error resolution process. How are mistakes flagged? How quickly are they addressed? Is there a human escalation path for sensitive situations? A provider that acknowledges AI isn't perfect and has a clear process for catching and correcting errors is far more trustworthy than one that promises flawless performance.

Use This List

Print these questions out. Bring them to every sales call. Email them to providers and see who gives direct answers versus who dodges. The providers worth working with will welcome these questions because they have good answers.

We're obviously biased, but we believe we have strong answers to all ten. Want to put us to the test? Book a free consultation and ask us anything on this list. We'll give you straight answers.