1. Start with five real scenarios.
A feature list tells you what a platform contains. A scenario tells you whether your team can use it. Choose a normal airport transfer, a multi-day itinerary, a last-minute change, a partner-covered job and an unpaid invoice.
Remove personal information before sharing examples with a supplier. Keep the complexity: several stops, luggage that changes the vehicle choice, or a pickup that overlaps another assignment. These details reveal the fit.
- Use one straightforward job and one difficult job.
- Include the person who quotes and the person who dispatches.
- Write down what a successful result looks like before the demo.
2. Follow one record all the way through.
Ask the demonstrator to turn your request into a structured enquiry, prepare a quote, show the customer’s acceptance and continue to the booking. Then assign a driver and generate the financial record.
Watch what has to be retyped. Check whether a changed date or price has a visible source, and whether the team can tell a draft, a confirmed booking and a paid invoice apart.
- Find the original request from the booking.
- Check that acceptance and payment have distinct states.
- Ask how a change reaches an assigned driver or partner.
3. Try it as each person who uses it.
The office workspace is only one part of the product. Open the driver view on a phone, a client’s quote and portal, and a partner’s invitation. A screen that works on a large monitor may still be awkward at a pickup.
For a growing team, ask how access is granted and removed. Confirm which client, partner and financial information each role can see. Use separate test identities instead of judging every screen through an administrator account.
- Read instructions on a phone without zooming.
- Inspect client and partner views with their actual roles.
- Check how an invitation becomes active access.
4. Compare the whole operating cost.
Record the vehicles, users, AI allowance and add-ons included in the plan you would actually use. Compare monthly and annual terms on the current pricing page and ask what happens when a limit is reached.
Separate the subscription from payment-provider charges, third-party services and the effort of moving data. A cheaper plan is not a saving if the essential workflow is missing; a larger plan is not automatically a better fit.
- List the features you need now versus later.
- Check allowances and paid add-ons, not just the headline price.
- Confirm which data you can import and export.
5. Make the trial a small operational test.
Choose a short set of representative records and a named person to check each handover. Test a known rate, one assignment conflict, a partner response and a partial payment. Compare the results with your expected outcomes.
Keep a scorecard with three answers: works, needs setup, or does not fit. Record evidence and unresolved questions. This makes a final decision easier than relying on how polished the demo felt.
- Reconcile a known price and invoice balance.
- Confirm support and setup questions before switching.
- Choose a controlled transition point for live work.