New business software usually gets chosen by the people who will use it: a finance manager, an operations manager, sometimes the owner. They sit through the demos, compare the features and pick the one that looks best. The problems tend to show up later, in the parts the demo skipped: how the data comes across, how the software connects to everything else, and who fixes it when a connection breaks.
Those parts are where most of the cost and frustration sits after go-live. The good news is that you can test them before you sign, by asking the right questions and insisting on specific answers.
Integrations
"Yes, we integrate with that" can mean anything from a well-supported connector to a spreadsheet export someone uploads each week. Pin it down.
1. Is it a standard connector, or custom work? Ask who built it, who maintains it, and whether it is included in the price. A connector listed on a marketplace page is not the same as one that handles your setup.
2. What data flows, in which direction, and how often? For example: do invoices go from the new system to Xero, or do payments also come back? Is it real time, hourly or nightly? Ask them to show you, with a record like one of yours.
3. What happens when it fails? Every integration fails sometimes, when a password expires, a field is missing or the other system is down. Ask who gets told, how, and whether failed records are retried or quietly dropped.
4. What changes on our side? Some integrations need you to change how you code accounts, name items or set up customers. Find out before you are committed.
Your data
5. Exactly what comes across from the old system? Opening balances only, open transactions, or years of history? Customers, suppliers, items, jobs, attachments? Get it in writing.
6. Who does the mapping and cleaning? Many quotes assume you will deliver clean data in their template. If your data has duplicates or gaps (most does), someone has to fix it. Find out who, and what it costs.
7. How will we know it came across correctly? Ask how balances will be reconciled back to the old system, and whether there will be at least one trial load your team can check before the real one.
8. What happens to the old system? Keeping it read-only for look-ups is often cheaper than migrating every old transaction. Make sure you will still have access, and for how long.
Reports
9. Which of our current reports exist out of the box? Bring the reports people rely on today, including the spreadsheets built on exports. For each one, ask whether it exists, needs configuring or has to be built.
Custom work and support
10. What has to be customised, and what does that do to upgrades? Customisation is sometimes necessary, but every change has to be kept working through future versions. Ask who is responsible for that.
11. Who fixes problems after go-live, and what does it cost? The implementation team often moves on once the system is live. Ask what support looks like in month three, not week one: response times, hourly rates or support blocks, and whether integrations are covered.
12. Can we talk to a customer with a setup like ours? Not a hand-picked reference that uses the software on its own, but one that runs the same integrations you need.
Getting straight answers
Vendors aren't being dishonest when they answer these loosely. Their demo is built to show the software at its best, and the integration and data detail often belongs to someone else: a partner, an app developer, or you. Clear answers in writing protect both sides.
If the answers are vague, treat that as information. The parts nobody can explain clearly are the parts most likely to cost you later.
Frequently asked questions
When should we ask these questions?
Before you sign anything, ideally while you still have two or three options. Answers to the integration and data questions often separate products that look similar in a demo.
Who in our business should be involved?
Whoever owns the data today: usually finance for the accounts and payroll side, and operations for jobs, stock or orders. Include the person who maintains your current integrations or exports, even if that's an outside contractor.
Do we need an independent adviser?
Not always. If the new system replaces one product and connects to nothing else, these questions are usually enough. If several systems, entities or years of history are involved, an independent check is worth considering, because the vendor's team is focused on its own product.
If you are choosing new software and want the integration and data claims checked against your actual systems, book a free initial chat. We don't resell software, so we have no reason to push one product over another. See also ERP integration and data migration.