Start with billing. Fee collection in an independent school is more involved than a single termly invoice. There are sibling discounts, bursaries, staggered payment plans and add-ons to account for. A dedicated billing module, such as the one Compass Education offers, is built to handle that structure, so the finance office is not rebuilding invoices by hand each term. Ask any provider to show a realistic fee run, with discounts and part-payments applied, before you judge whether it fits.
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Beyond hosting location and certification, a few further questions round out proper due diligence: how often is the system independently penetration-tested, what is the vendor's data breach notification process, and does the school retain the ability to export its full data set on request rather than being dependent on the vendor for access.
None of these five questions guarantees a good outcome on their own, but a vendor unwilling or unable to answer any of them plainly before a contract is signed is worth treating as a warning sign, whatever the rest of the proposal looks like.
Data mapping comes first. List every type of record your current system holds, from pupil details and attendance to finance and communication history. For each one, agree where it will live in the new platform and what format it needs to be in. This is where problems surface early, because two systems rarely store the same information in exactly the same way. Run a test import on a sample before the full move, check the results field by field, and
Pulse fix the mapping before you commit real data.
Finally, ask how the vendor handles onboarding for the specific transition the school is making, whether that is a first MIS, a migration from a previous system, or a rollout across several schools in a trust. A vendor with a clear, specific answer to this question, rather than a generic implementation timeline, is usually the one that has done this particular kind of transition before.