Ask what happens to the accounting, specifically
Most field service tools do not keep books. They push data to an outside accounting package on a schedule. That works until the push fails, and then you are reconciling by hand months later.
There are two honest answers a vendor can give: 'we sync to your accounting package' or 'we keep a general ledger'. Both can be fine. What is not fine is a vague answer. Ask which one it is and ask what happens when the sync breaks.
- Does an invoice write a ledger entry, or does it wait for a sync?
- Where do vendor bills live? Where does payroll post?
- If I close a month in your system and in my accountant's system, do the two agree?
Read the renewal, not the price
Published monthly prices are the cheapest part of the deal. Setup fees, minimum term, per-technician charges as you hire, and the renewal increase are where the real cost lives.
Contractors routinely report enterprise field service platforms costing several hundred dollars per technician per month with multi-year terms and substantial implementation fees, and price increases at renewal. Ask for all of it in writing before the demo ends.
- What is the minimum term, and what does it cost to leave early?
- What happens to the price at renewal? Is there a cap?
- What does adding a technician mid-term cost?
- What does implementation cost, and how long before we run a real job?
The technician test
Software that the office loves and the truck hates will fail, quietly, over about four months. The notes get thinner, the photos stop, and eventually somebody is retyping paper tickets again.
Here is a test that predicts it: hand the app to your least patient technician, on his own phone, in a parking lot, and ask him to complete a job without instructions. If he needs help, the office will be doing his data entry forever.
- Can he do it one-handed?
- Can he read it at arm's length in daylight?
- What happens in a basement with no signal. Does the work queue, or does it vanish?
Count the taps to a finished job
Ask the vendor to run one complete job during the demo: take the call, dispatch it, work it on a phone, price it, get it signed, invoice it, collect it. Watch the clock and count the screens.
If the vendor will only show you modules and dashboards rather than one job end to end, that is the answer to your question.
Ask what is not built yet
Every product has holes. A vendor who names theirs without flinching is telling you the truth about the rest of it too. A vendor whose answer is 'that is on the roadmap' for everything is telling you something as well.