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.
A multi-academy trust or independent school signing a multi-year contract with a school
Compass Billing Management information system vendor is making a decision that is expensive and disruptive to reverse. A short list of direct questions, asked before signature rather than after, reduces the risk of discovering a gap once the school is committed.
Spreadsheets are where many multi-academy trusts start, and for a single form entry they can just about cope. Run several schools from them and the cracks show quickly. Versions multiply, formulas break, and no one is quite sure which file is current. For a trust accountable to governors, the Department for Education and parents, that is a real risk rather than a minor annoyance.
A centralised school management information system fixes the core problem: one source of truth. When every school in the trust works in the same platform, attendance, admissions and reporting follow a shared structure. Trust leaders can see figures across all sites without emailing round for the latest workbook, and central teams stop rekeying the same data three times.
None of this needs to become an exhaustive audit for every school, but a business manager or IT lead signing off on a cloud MIS contract should be able to answer, with evidence rather than assumption, where data is hosted and which certifications back that hosting. That is the baseline, not an optional extra.
Finally, weigh support and continuity. Ask about the support model, response times and where the support team is based, and ask to speak with schools in the same sector. The UK and Irish market has several established providers, so compare on governance, reporting fit and total cost rather than the demo alone. Set your sector requirements down first, score each provider against them, and the right system for a government or Catholic school becomes far clearer than a general feature comparison would suggest.