Start with the workflow, not the feature list
Write down the work that takes your team the most time. Who performs it? What information do they need? Which mistakes happen repeatedly? A useful software shortlist starts with these answers, then maps each workflow to a feature. Separate must-haves from improvements you can add later.
Ask to see your own use case
A polished demo is a starting point. Ask the provider to walk through a realistic scenario: adding a student, processing a refund, changing a staff role or exporting a report. Include the people who will use the system every day, and ask what happens when data is missing or a connection fails.
Understand the full cost of ownership
Compare the initial project cost with recurring hosting, licences, messaging, payment fees and maintenance. Check what is included in support and what becomes a separate change request. A transparent proposal should help you understand both your launch budget and your ongoing commitment.
Agree on ownership and exit
Clarify source-code licensing, administrative access, account ownership and data export before signing. Ask how you would move your data or hand maintenance to another provider. These questions make the working relationship clearer from the beginning.