If you run a trades company, you have probably been pitched by an AI consultant already. Maybe more than one. The pitches blur together: "AI strategy," "transformation roadmap," "workflow audit." Some of these people can build and some cannot. From the buyer's chair they sound identical for the first 30 minutes.
The questions below sort them out. They are written for owners, GMs and ops leads at HVAC, plumbing, electrical, roofing and general contracting companies, but they work for any small business. Use them with anyone, including us. We would rather you ask than guess.
If you have not yet worked out where AI should touch your business, read AI for contractors: where to start first. It makes these answers easier to judge.
The ten questions
1. What exactly will be live, and by what date?
A builder names a deliverable and a date: "After-hours calls are answered and qualified, texts go out to missed callers, and leads land in your field service software, live in 30 days." A talker names a phase: "Discovery will take six to eight weeks, followed by a roadmap."
Discovery is fine if it is short and ends in something you can use. Be wary if the first deliverable is a document about the work rather than the work.
2. How will you measure success, and in what unit?
The answer you want is booked jobs and revenue against a baseline. The answer you do not want is "engagement," "conversations handled," "tasks automated" or "hours saved." Those are activities. For the full method, see how to measure AI ROI in a contracting business.
Follow up with: "Who sets the baseline, and when?" If the answer is "we will figure that out after launch," you will never be able to tell whether it worked.
3. Who will actually build it, and will I talk to them?
Sales calls are often handled by one person and delivery by another, sometimes by a subcontractor you never meet. Ask for the names of the people doing the work, their roles and whether they will be on your kickoff call. A firm that cannot tell you this either has no stable team or does not want you to know.
4. What does it connect to in my software, and how?
Ask which field service platform you use (ServiceTitan, Housecall Pro, Jobber or something else) and what the system reads and writes: customers, jobs, estimates, lead source, notes. A vague answer like "we integrate with everything" is a flag. Real integrations have specific limits, and a good consultant will tell you what they are. Our overview of AI integration with ServiceTitan, Housecall Pro and Jobber lists what to verify.
5. What is the full cost, including usage fees and ongoing support?
The quote should separate one-time work, monthly fees, usage costs (voice minutes, texting) and maintenance. If the number given is only the build, ask what happens in month four. We walk through the drivers in what AI implementation costs a trades business.
Also ask: "Is the first project fixed-scope?" A fixed scope with a clear end beats an hourly meter that runs until you stop it.
6. What tools and vendors do you recommend, and do you get paid by them?
Many consultants resell software or earn referral fees. That is not automatically bad, but it should be disclosed up front. Ask whether the recommendation would change if you used a different field service platform or phone system. A vendor-neutral firm can say "use X for this, Y for that, and here is why." A reseller tends to recommend the thing it resells.
7. What happens when it makes a mistake?
AI systems misunderstand callers, double-book jobs and say things they should not. Ask how errors are caught (call transcripts, flagged exceptions, weekly review), who reviews them, what the system does when it is unsure and how fast problems get fixed. The right answer includes a human handoff and a log you can read.
8. How do you handle texting, call recording and consent rules?
Automated texts and AI-handled calls touch federal and state rules on consent, registration and recording. A consultant does not have to be your lawyer, but should know the basics and tell you what you need your counsel to confirm. Our guide to TCPA texting rules for contractors is a starting point, and it is general information, not legal advice. If the answer is "that is not our department" or "do not worry about it," that is a problem.
9. Who owns the work if we part ways?
Ask who owns the call flows, prompts, scripts, workflows and data, and what you get if you leave. You should be able to export your call recordings, transcripts, contact lists and the logic of what was built. Lock-in is easy to miss in a contract and expensive to discover later.
10. What would make you tell me not to do this project?
This is the best single question. A consultant with something to sell will rarely say no. A good one will tell you when a project is too early, when your biggest leak is somewhere else or when your software cannot support it. If every answer you hear ends in "yes, we can do that," you are talking to a salesperson.
Red flags
Walk away, or at least slow down, when you hear any of these.
- Guaranteed results. "We guarantee 30% more revenue." Nobody can promise that without knowing your business.
- Statistics with no source. If a consultant quotes a number about missed calls or lead response, ask where it comes from. Many popular figures have no traceable original study.
- No named people. A firm that will not say who builds the work.
- A roadmap before a first deliverable. Months of planning with nothing live.
- Metrics that count activity. Conversations, messages and automations in place of booked jobs.
- Pressure. "The price goes up Friday" is a sales tactic, not a project requirement.
- "Our proprietary AI." If you cannot learn what it does or how it connects, you cannot judge it.
- No baseline. If they do not want to measure before they start, they do not want to be measured after.
- Case studies with no checkable detail. Ask whether you can speak to the client. A case study that cannot be verified is a story.
- Silence on trade-offs. Every approach has a downside. If you hear only upsides, you are not getting the full picture.
How to run the conversation
Send the questions in advance, or bring them as a list. Ask for answers in writing, and compare two or three firms side by side. Note not just what they say but how: whether the answers are specific, whether they mention limits and whether they are comfortable saying "I do not know yet, but here is how we would find out."
Then ask for the same thing from each: a one-page scope, a fixed price for a first project and a way to measure it. Differences in these three things tell you more than any demo.
Ask us the same questions
We would rather be tested than trusted on faith. Di-Hy is an AI implementation firm, senior built and founder led, run by three founders: Charles Holmes IV (strategy and AI systems), Amadou Sidibe (product management and delivery) and Charles DeShazer (technical architecture and build). We sell no software product, so we can stay vendor-neutral. Our flagship offer, the Booked-Jobs Recovery System, is a fixed-scope engagement, live in 30 days and measured in booked jobs. Pricing is scoped on a call.
Bring these ten questions to that call and hold us to the answers. You can start with AI strategy consulting or book through our contact page, and if you want the numbers before the conversation, size your leak with what a missed call really costs.
Frequently asked questions
What should I ask an AI consultant before hiring them?
Ask what will be live and when, how success is measured in booked jobs, who builds it, what it connects to, the full cost, who gets paid by which vendors, how errors are handled, how consent rules are handled, who owns the work and what would make them advise against the project.
What are red flags when hiring an AI consultant?
Guaranteed results, unsourced statistics, no named team, a long roadmap before any deliverable, activity metrics instead of booked jobs, pressure tactics and no baseline.
Should a first AI project be fixed price?
A fixed scope with a clear end date and a defined outcome keeps the risk limited and makes the result easy to judge. Open-ended hourly work makes it hard to say when you are done.
Do I need a consultant at all?
Not always. If your leak is clear and a self-serve tool fits your stack, you may be able to do it yourself. A consultant makes sense when integration, call design or follow-up logic is beyond your team's time.