A demo is designed to look good. These are the questions that tell you whether the thing will still be in use in March.
A demo is a performance. It is run by someone who knows the product perfectly, on clean data, along the path that works best. Nothing about that is dishonest, and almost none of it predicts what your school will experience in March. The questions below are the ones that do.
Start with who has to change their habits. Software only the leadership team touches will be adopted. Software that asks forty teachers to do something new every week will not, unless it replaces something they already do. Count the people whose daily routine has to change, and be suspicious of any answer claiming nobody's does.
Then ask what week three looks like. Almost anything gets used in week one, when it is new and someone is watching. The honest question to put to a supplier is: what do schools stop using, and why? One who cannot name a single thing their customers abandoned has either never asked or will not say.
Ask where your data lives, in specifics - which country, which company, and who at that company can read it. Ask whether you can export all of it, in a usable format, on the day you decide to leave. A supplier confident in their product answers this immediately; one who treats it as an odd question has told you something.
Ask what it costs when you grow. Per-student pricing that is comfortable at 200 students can be painful at 600, and the moment to discover that is not the renewal after you have built your reporting around it. Ask what is not included: training, support, data import, the integration you assumed came as standard.
Ask to speak to a school like yours - same size, same curriculum, ideally the same country - and ask them what went wrong rather than what went well. Every implementation has something. What you are listening for is whether the supplier stayed present when it did.
The final test is not a feature list. It is whether a teacher would keep using the thing if nobody checked. Everything that survives in a school passes that test, and everything that fails it becomes another login staff resent, however good the demo was.
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