The demo is not evidence.
A demo is a rehearsed path through a clean dataset run by someone who uses the product daily. It tells you the software can do the thing. It tells you nothing about how long it takes, how it behaves with your data, or what your least technical technician will do with it in a crawlspace.
Insist on a trial with your own jobs in it. If that is not available, treat the gap as information about how the relationship will go.
Test the messy job, not the clean one.
Everyone can handle a job that is quoted, scheduled, performed and paid in one visit. Take the job that went wrong: a change order mid-work, a partial payment, a return visit, a warranty callback, a customer who disputes part of the invoice.
That is where platforms diverge, and it is where your team will spend a disproportionate share of its time.
Four questions the sales process will not volunteer.
What exactly does the data export contain? Not "you can export your data" — a sample file. There is a large difference between a full relational export and a CSV of customer names.
Which integrations are live today, with which versions, and can I speak to a customer using that specific one? "Integrates with QuickBooks" covers a wide range of realities.
What does implementation require from my team, in hours, from which roles? Implementation failure is far more common than software failure, and it is almost always under-scoped.
What happens at renewal if my seat count drops? The answer shapes what growth costs you later.
Then ask whether you need to switch at all.
A meaningful share of platform migrations are triggered by a problem the current system could already solve. Modules that were never switched on, a configuration nobody revisited since onboarding, an integration that was never finished.
Migration is expensive in a way that is easy to underestimate — the licence is the small part, and the disruption lands on the same people who are already busy. Establish that the current system genuinely cannot do the job before concluding that a new one will.