Ask to see something that actually happens to you
Choose a same-day turnover, a guest message and an intervention. Ask to find the information, follow up and check who can see what. A feature list does not tell you how many screens your daily work will require.
Ask what the connection actually retrieves
Properties, bookings, conversations, reviews and financial amounts may have different coverage. Clarify imported information, update frequency and write capabilities. Include your existing channel manager or pricing tool in the discussion.
Look at how the team works
A personal inbox should be able to stay private. A service inbox should be shareable without handing over a password. Check role permissions, then review the same journey on a phone with the person doing the field work.
Calculate the cost for your portfolio
Count properties, users, options and any connected-provider charges. Ask for an example using your current setup and your planned setup. Keyful publishes PMS and option prices; the total is confirmed before subscribing.
Check what you can take with you
Look at data and workflow exports, account revocation and access handling when a team member leaves. Software should help structure your operation, not make it difficult to understand without the software.
Your 30-minute demo: a practical script
Prepare a property, an upcoming stay and a fictional conversation. Ask to perform the actions yourself. Look at the actual work: number of steps, permissions, result and how to undo a mistake.
| Time | Action | Expected result |
|---|---|---|
| 0–5 min | Find a stay and its messages | Unambiguous property and dates |
| 5–10 min | Move a test booking | Old and new dates remain consistent |
| 10–15 min | Give a teammate access | Only authorized screens and inboxes |
| 15–20 min | Prepare a task and a reply | Stay context preserved |
| 20–25 min | Compare and export a period | Clear dates, units and scope |
| 25–30 min | Test a failing workflow | Visible error, owner and recovery path |
The important detail: what writes your rates?
If you use dynamic pricing, draw the route from pricing tool to manager to booking platform. Ask which system is authoritative and what happens after a manual calendar edit.
Test one night, a range of dates, minimum stay and a stop sell. Compare the platform’s received state with the PMS action. An attractive grid is not enough: both the rule and delivery of the update must be understandable.
Make the decision in three columns
Classify needs as essential now, useful soon or optional. A planned feature is not an available one. Base the decision on work your team will perform in the first week.
Record pre-migration checks too: listing IDs, room types, rate plans, occupied dates, sample booking amounts and team permissions. Keep exports and name the person who owns the switch.
Prepare my decision worksheet