Keep a simple checklist through the whole project: data mapped, test import verified, go-live date agreed, old system retained, staff trained, first reports produced and checked. Assign an owner to each item so nothing slips.

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 School MIS 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.

The cheapest headline price often is not the cheapest system to own. Ask for every cost in writing, model the full term, and compare providers on the total rather than the quote. That is the figure governors will ask about, so bring it to the table first.

Hosting location is the first thing worth confirming directly, in writing, rather than assumed. Where is student and financial data physically stored, and does that location bring specific regulatory obligations with it? A school should ask this plainly of any vendor rather than accepting a general answer about "secure cloud infrastructure," which describes almost every provider on the market and tells a procurement team nothing distinctive.

Do not skip references. Ask to speak to schools of a similar size and structure, and ask them the awkward questions: what went wrong during setup, how responsive is support, and would they choose the same system again. The UK and Irish market has several established providers, so you have room to compare rather than settle.

Data portability is the second essential question, and it should be asked before any enthusiasm about features clouds the discussion. If the school ends the contract in three or five years, can it export its full historical data, in a usable format, without additional fees or delay? Get this answer in writing as part of the contract itself, not as a verbal assurance during the sales process, since it is precisely the point where the balance of power shifts away from the school once a contract is signed.