The demo is not the product
Demos show the happy path on clean data with a practised operator. Everything that decides whether a tool works for you — your data, your volume, your integrations, your exceptions — is outside the demo by construction.
1. How do I get my data out?
Full export, on demand, in a usable format, including history and attachments. A vendor who makes leaving hard is charging a switching cost that never appears on the invoice, and it decides whether you can build on that data later.
2. What does it cost at three times this volume?
Per-seat, per-record, and per-transaction pricing behave very differently as you grow. Ask for the number at the size you expect to be, not the size you are.
Ask what it costs when you succeed. That is the price you will actually pay.
3. Which parts are on the roadmap rather than shipped?
Anything demonstrated that does not yet exist should be identified explicitly and, if you are relying on it, written into the contract with a date.
4. What happens to my exceptions?
Every business has cases that don’t fit the standard model. Ask how the product handles yours; the answer “you can use a custom field” usually means you will run the real process in a spreadsheet beside the tool — which is itself the specification for what you should have built.
5–8. The ones people forget
Who owns the integration work and how long has it taken others; what the support response time is contractually rather than aspirationally; where data is stored and under whose jurisdiction; and what the last two years of incident history look like. All four are answerable, and reluctance is itself an answer.
Ask a current customer, not a reference
References are selected. Find a user of comparable size through your own network and ask what they would do differently. That conversation is worth more than the entire evaluation process around it.