45 questions to ask in a TMS demo

Before the demo: set it up so you learn something

A vendor's standard demo is built to show the product at its best. That is fair, but it tells you little about how the system handles your freight. Send the vendor two or three real loads a few days ahead: one simple, one with multiple stops or a split, and one with an accessorial such as detention or a lumper. Ask them to use those loads in the demo. Bring the people who will live in the system, not only the owner: a dispatcher, whoever bills customers and whoever keeps driver files will each spot gaps the others miss.

Write down your must-haves before the call and score every vendor against the same list afterward. The TMS requirements checklist gives you a ready-made scorecard you can print or fill in on screen.

Dispatch and load management (questions 1 to 8)

1. Can you enter one of my loads from scratch while I watch? Watch how many screens and fields it takes. A good system builds the load from the customer, lanes and rates it already knows.
2. How do multi-stop loads work? Ask to see stop order, appointment times per stop and what the driver sees for each stop.
3. Can a rate confirmation create the load for me? If the system reads emailed rate confirmations, have them forward one of yours and show the load it produces, including what a person still has to check.
4. How does the dispatcher see which trucks and drivers are free? Look for one board that shows assigned, available and out-of-service equipment without switching screens.
5. What does the driver receive when a load is dispatched? Ask to see it on the driver's phone: stops, references, documents and how the driver confirms.
6. How are proof-of-delivery documents collected? Make them show a POD going from the driver to the load and onto the invoice.
7. How do you handle a load that changes after dispatch? Change an appointment or add a stop live and see who gets notified.
8. Can I see every change made to a load and who made it? An audit trail settles disputes with customers and drivers.

Billing and getting paid (questions 9 to 15)

9. How does a delivered load become an invoice? The best answer is that the invoice is built from the load, with the POD attached, in one or two clicks.
10. How are accessorials added and approved? Detention, layover and lumper charges need a clear path from the driver's report to the invoice.
11. Do you work with my factoring company? Ask what is sent to the factor, in what format, and how payments from the factor are recorded.
12. How do I see what is owed to me and how old it is? Ask for the receivables aging screen.
13. Which accounting systems do you sync with, and what moves? Invoices, payments, customers, bills? One way or both ways? See it, do not take it on trust.
14. Can I invoice in batches and email invoices with documents attached? Batch work is where billing time is saved.
15. How do credits, short pays and rebills work? Every carrier gets short-paid. See how the system records it.

Driver pay and owner-operator settlements (questions 16 to 22)

If you lease on owner-operators, your settlements have to follow the federal leasing rules in 49 CFR 376.12. A TMS cannot make your lease compliant, but it can make it easy or hard to pay people the way the lease says.

16. Which pay methods can you handle? The leasing rule allows pay as a percentage of gross revenue, a flat rate per mile, a rate that varies by direction or commodity, or another method the parties agree on (49 CFR 376.12(d)). Make sure yours is supported as written in your lease.
17. How do recurring deductions work? Insurance, equipment payments, fuel advances. Charge-backs must be listed in the lease with how each is computed, and the owner-operator must get the documents behind them (376.12(h)). Ask how the settlement shows each one.
18. Can a percentage-pay settlement include the rated freight bill? When pay is a percentage of revenue, the lease must give the owner-operator a copy of the rated freight bill or equivalent documentation (376.12(g)).
19. How is escrow tracked? Where escrow is required, the carrier must account for every transaction on the settlement or in a separate monthly accounting (376.12(k)).
20. How fast can settlements go out after delivery? The lease must provide payment within 15 days after the required delivery documents are submitted (376.12(f)). Ask how the system tracks that clock.
21. Can company drivers be paid by mile, by load, by percentage or by hour? See one of each.
22. Can drivers see their pay statements themselves? A driver who can read their own settlement calls the office less.

US compliance records (questions 23 to 30)

23. Show me a driver qualification file. Under 49 CFR 391.51 it holds the employment application, the motor vehicle record from each state at hire, the road test certificate or equivalent, the annual MVR, the note of the annual review, the medical examiner's certificate and, where it applies, a medical variance. Ask to see each item and its expiry date.
24. Where do previous-employer safety inquiries live? They belong in a separate driver investigation history file with restricted access (49 CFR 391.53).
25. How long are driver files kept after a driver leaves? The file must be kept while the driver works for you and for three years after (391.51(c)). Ask whether the system keeps files of former drivers.
26. Which documents get expiry warnings, and how far ahead? CDL and medical certificate at a minimum.
27. Does the system use US or Canadian document sets, and how do I switch? Some platforms serve both countries. Make sure your account uses the US set.
28. How are drug and alcohol testing records stored? Ask who can see them and how access is limited.
29. How are hours-of-service records used? Carriers must keep records of duty status and supporting documents for at least six months (49 CFR 395.8(k)). Ask whether the system pulls logs from your ELD and what it does with them.
30. Can I store authority and permit documents with their renewal dates? USDOT and MC records, UCR, IRP, IFTA license, insurance certificates.

IFTA, fuel and ELD (questions 31 to 36)

31. Where do IFTA miles come from? The strongest answer is jurisdiction miles from your ELD, matched against fuel purchases.
32. Show me a finished IFTA quarter. Miles and gallons by jurisdiction, ready to enter in your base state's portal.
33. How are fuel purchases imported? Fuel card files or feeds save hours of receipt entry.
34. Which ELD providers do you connect to today? Ask for the list of providers live in production, not ones "on the roadmap".
35. What comes over from the ELD? Trucks, drivers, locations, hours of service logs, miles by jurisdiction. Each one is a separate question.
36. What happens when the ELD connection fails? Ask how you would find out.

Your data, security and access (questions 37 to 41)

37. Can I export all of my data, at any time, in a usable format? Loads, customers, invoices, driver files and documents. Ask for a sample export.
38. What happens to my data if I cancel? How long is it kept and how do you get it back?
39. Who at the vendor can see my data? And how is access logged?
40. How do user roles work? A dispatcher should not see payroll; a driver should see only their loads.
41. Is there a charge per user or per driver? Pricing models differ a lot. Get the model in writing even if you do not discuss figures on the call.

Onboarding, support and contract terms (questions 42 to 45)

42. Who sets up my account, and what do you need from me? A clear answer names the data they import for you and the data you enter yourself.
43. How do I reach support, and when? Phone, chat, email, hours. Trucking runs nights and weekends.
44. What is the contract length and the notice period? Monthly or yearly, auto-renewal, and how to cancel.
45. What is changing in the product over the next year, and does it cost extra? Features you are buying today should not become add-ons later.

Extra questions if you also broker freight

If you hold broker authority, add these. A broker must keep a record of each transaction, including the shipper, the carrier and its registration number, the bill of lading number, the compensation received and the freight charges paid to the carrier, for three years (49 CFR 371.3). Ask how the system keeps that record, how carriers are tendered and how they respond, how carrier insurance expiry is tracked, how margin is checked before a load is tendered, and whether shipper EDI (load tenders, status updates and invoices) is available. Our guide to carrier TMS vs broker TMS covers the differences in more depth.

After the demo

Score each vendor on the same list the same day. Ask for written answers to anything that was promised rather than shown. If two systems are close, ask each for a short supervised pilot on a few real loads with your own dispatcher at the keyboard. The system your team can run without the vendor on the call is the right one.