Start with the work that costs you money
School software demos look similar. Ask instead which daily job each system removes: chasing fee balances, re-entering marks, reconstructing attendance, or answering parents by phone. Score vendors on those jobs, not on the length of the feature list.
Insist on one record per student
Admissions, fees, attendance and results should hang off the same student record. If a vendor proposes separate systems “integrated later”, you will maintain the join by hand in spreadsheets.
Ask where the data lives and how you get it out
Ask who hosts the database, which country it sits in, what happens at the end of the contract, and how you export students, balances and payment history. Get the export answer in writing before you sign anything.
Check the boring rules: roles, receipts, audit trails
Who can approve a refund? Who can edit a mark after publication? Every payment should get a numbered receipt, and every change should record who made it and when. These details matter more after a dispute than during a demo.
Trial with the people who do the work
Let the bursar, a form teacher and the front office use the system for two weeks on real tasks. Their list of blockers is the only due diligence that counts.