Most software evaluations start with vendor demos, which is exactly backwards. Start here instead. Work through this checklist before you talk to anyone, so you walk into every conversation knowing what you actually need. Tick items as you go.
0 of 15 completed
Document your real requirements first
List the specific tasks your current system cannot do, with real examples
Note every spreadsheet or workaround your team relies on to fill gaps
Identify which processes are manual today and how many hours they consume
Map how many entities, locations, and currencies you need to support
Pressure-test the fit before the demo
Write down three scenarios from your business to make every vendor demo live
Ask which capabilities are standard versus separately priced add-ons
Confirm the system handles your industry-specific needs natively, not by customization
Ask to speak with a reference in your specific industry and size
Understand the true cost
Get pricing modeled over five years, not just year one
Ask what renewal pricing looks like and whether increases are capped
Include implementation, data migration, and training in the total
Identify any hidden costs: extra users, storage, integrations, support tiers
Protect yourself on implementation
Ask for a realistic timeline and who is responsible for what
Understand what happens to your data if you ever leave
Confirm who supports you after go-live and how responsive they are
Want the full printable version?
Get this checklist as a printable one-pager you can bring to your evaluation, plus the questions vendors hope you will not ask. We will send it over and follow up personally, no automated spam.