Start with your working week
List the recurring work your team performs: updating records, reviewing applications, sending reminders, managing registrations, and publishing content. Ask vendors to demonstrate these exact tasks.
Test the member journey
Review joining, signing in, registering for an event, and finding member resources on a phone as well as a desktop. Invite someone unfamiliar with the software to try the process.
Make migration concrete
Ask which records can be imported, how columns are mapped, what a dry run shows, and who resolves duplicates. Keep a copy of your source data and validate a representative sample before importing everything.
Understand the full cost
Ask about subscriptions, billable units, payment fees, email allowances, AI usage, migration assistance, and contract terms. Request a written explanation of what happens when usage grows.