1. What happens when it does not know the answer?
The only acceptable answer is: it says so and escalates on a defined path. A system that guesses is worse than a voicemail, because a voicemail does not confidently tell your customer the wrong thing under your brand.
Ask to see the escalation rules written down. If they do not exist in writing before launch, they do not exist.
The short versionAsk for the escalation path in writing. Vagueness here predicts everything else.
2. Who writes the triage rules, and are they from your industry?
Triage is the whole product. Deciding that "no heat, elderly occupant, minus twenty outside" is an emergency while "noisy fan" is a Tuesday appointment is trade knowledge, not software.
Ask who wrote the urgency rules and what they did before they wrote them.
The short versionA generic agent triages by keyword. A useful one triages by consequence.
3. Can it see live availability, or does it promise a callback?
"Someone will call you back" is a voicemail with extra steps. The commercial value of an answering agent is almost entirely in converting the call into a booked slot while the customer is still on the phone.
That requires a real, two-way integration with your scheduling or dispatch system, which is an integration project rather than a setting.
The short versionIf it cannot book, it is deflecting calls rather than capturing jobs.
4. What does it do with a safety issue?
Gas, carbon monoxide, an electrical burning smell, water where it should not be. The correct behaviour is a scripted safety response and an immediate human escalation, never a diagnosis.
In regulated trades this is not a service-quality question. It is a liability question, and the answer should already be written into the contract.
The short versionIt should never attempt a diagnosis on anything safety-related.
5. Which of my systems does it actually integrate with?
Ask for names, and ask whether that integration has been built before or would be built for you. Those are very different risks and very different timelines.
Ask specifically what happens when the third-party API is down at 2am: a good integration has error handling, logging and alerting, so a failure is visible immediately rather than discovered weeks later as missing jobs.
The short versionAsk what happens when the integration fails, not whether it can be built.
6. Can I read the transcripts?
You should be able to read every conversation the system had with your customers, without asking. If transcripts are unavailable, summarised, or behind a support request, you cannot audit what is being said in your name.
Transcript review is also how the system gets better. A vendor that will not show you them is a vendor who is not tuning it.
The short versionNo transcripts, no deal. This is the audit trail for your own brand.
7. What happens to my data, and who owns the configuration?
Ask where customer data is stored, under whose accounts the system runs, and what you receive if you leave: the configuration, the knowledge base, the call records.
Plenty of vendors will hand you nothing, which turns a service problem into a migration problem later.
The short versionOwnership on exit is much cheaper to negotiate before you sign than after.
8. How is it priced as we grow?
Per-minute, per-call, per-seat and flat-rate pricing behave very differently in a seasonal trade. A per-call model is comfortable in October and painful during the first cold snap, which is precisely when the system earns its keep.
Model the cost against your busiest week, not your average one.
The short versionPrice it against your peak week. That is the week it exists for.
9. What does it sound like to a customer who is annoyed?
Every demo uses a patient caller. Ask to hear a recording of an impatient one, or an accent the system was not trained on, or someone who interrupts.
Ask what happens when a caller says "I want a human". The correct answer is that it hands over immediately, without a negotiation.
The short version"Let me speak to someone" should end the automation instantly.
10. Will it replace my office staff?
If the vendor says yes, they are selling to the wrong problem and will disappoint you. These systems cover the hours nobody is at the desk, absorb the seasonal spike, and take the repetitive questions off a team so it can handle the work that needs judgement.
A vendor pitching staff replacement is describing a product they have not operated.
The short versionThe honest pitch is coverage and triage, not headcount reduction.