1. Ask what happens to your data before you ask what the software does
Where does the membership data physically sit, and whose agreement covers it? The answers vary more than people expect: the supplier's cloud account, a shared database with a tenant column, or your own infrastructure. All three are legitimate; they are not the same thing.
Who holds the underlying licences? If the platform is built on Microsoft, Salesforce or similar, ask whether you hold that relationship directly or whether it is resold to you. It changes what happens if the supplier relationship changes.
A good answer names the location, the agreement and the licence holder without hedging, and does not need to check.
2. Make them show you the product, not describe it
This is the question that separates suppliers fastest. Ask for a screen — not a slide, not a diagram, not an animation of a dashboard nobody uses.
Ask specifically for: a member record with grade history; a subscription showing a mid-year change and the resulting pro-rata; a renewal run with failed collections in it; and the member portal on a phone.
A poor answer is a demo environment with three perfect members in it. Ask to see something that went wrong.
3. Bring your most awkward membership rule to the first demo
Every organisation has one. Joint membership where one party is invoiced. A concession that requires annual re-certification. A CPD cycle that does not align to the membership year. Grade progression that requires a panel. Employer-paid cohorts where the payer is not the member.
Do not describe it in advance — bring it to the session. What you are testing is not whether the platform can do it, but whether the supplier recognises it immediately or has to think about what you mean.
4. Establish what is standard, what is configured and what is a build
Every platform has all three, and the boundary is where budgets move. Ask for the boundary in writing, per requirement, before contract — not "yes we can do that", which is true of any software given enough days.
The requirements most often quoted as standard and delivered as builds: member-facing upgrade and regrade journeys, anything involving a panel or assessor, complex pricing structures, and integrations with systems the supplier has not met before.
A good answer volunteers where the boundary falls before you ask.
5. Ask about the data migration in detail, early
Most difficult implementations are difficult because of data, and most timelines move for the same reason.
Ask: how many source systems, who does the cleansing, how many trial loads before go-live, what reconciliation is run and who signs it off, and what happens to twenty years of history where the rules changed three times.
A good answer includes a trial load reconciled before anyone commits to a go-live date.