Every demo looks good. The pipeline is full of tidy jobs, the estimate builds in four clicks, and the presenter never loses signal. Here is what to ask instead.
About the handoff
1. When a contract is signed, what happens automatically? If the answer involves someone retyping the sale into a work order, your office is the integration layer and will stay that way.
2. Can production see what was sold, line by line? Not a total. The actual items the customer agreed to.
3. What happens when a change order is approved? It should reach the invoice without anyone remembering to add it.
About the money
4. Where does per-job cost come from? "You enter it" is a real answer, but it means you will not do it consistently and the margin figure will be fiction.
5. Does labor include burden? If wage and job-cost labor are the same number, job cost is understated.
6. Is revenue net of sales tax? If not, every margin percentage they show you is inflated.
About the field
7. What happens with no signal? Ask specifically: can a rep log a knock, shoot a photo and fill a form with the phone in airplane mode? What does the app show them about work that has not synced?
8. If two people edit the same record offline, who wins? "Last write wins" means someone's work is silently deleted. The honest answer is that a person is asked.
9. Can a photo go from the roof to the job without a laptop? This sounds trivial. It is the single most common reason damage photos are lost.
About ownership
10. Whose brand is on the customer's contract? If the software's name and colors appear on a document your customer signs, you are advertising for them at your own expense.
11. Can you export your data? All of it, in a usable form, without a support ticket.
12. What is the pricing per user? Per-seat pricing punishes you for hiring. If you plan to grow, a flat price is worth paying more for.
One more
Ask what it does not do. A vendor who cannot name a limitation has either not thought about it or is not telling you. Every product has a boundary; the useful question is whether that boundary sits somewhere that matters to your business.