Guide

How to choose a TMS: 12 questions to ask the supplier

August 17, 2026
4 min read
How to choose a TMS: 12 questions to ask the supplier

Short answer: The most important thing when choosing a TMS is not the feature list - most systems can do "everything" on paper. What matters is how the system works in your everyday operations: Does it talk to your accounting system? Can the drivers handle the app? Do you get help in your own language when it is urgent? And can you get out again with your data if you want to switch? Ask the 12 questions below, and demand concrete answers - not "yes, we support that".

Why demos lie a little

A TMS demo is like a viewing of a flat: everything is tidied, the light is perfect, and you don't get to see the neighbour. Every system looks good when the supplier is steering the mouse through a pre-rigged example.

Your job in the selection process is to get behind the demo. You do not do that by asking for more features, but by asking questions the supplier cannot answer smoothly. Here are the twelve that matter most - with an explanation of what to listen for.

The 12 questions

1. "Show me a whole order - from booking to paid invoice"

Do not look at modules one by one. Ask to follow one specific order through the whole cycle: received, planned, driven, signed for, invoiced, booked. It is in the handovers between the links that systems differ - and that is where your hours disappear today.

2. "Which accounting systems do you integrate with - and how many customers use the integration today?"

"We have an API" is not an answer. Ask specifically about Tripletex, PowerOffice, Visma or whatever you use - and whether the integration is in daily use with other customers, or something that "gets set up during the project".

3. "Can I try the driver app myself - now?"

The driver app is where the system wins or dies. Ask to have it in your hand and complete a delivery yourself. If it needs explaining, it is going to need explaining to every single driver you hire.

4. "What happens when the driver loses coverage?"

In a country like Norway, coverage gaps are not a theoretical challenge. The app must be able to record deliveries, photos and signatures without coverage - and synchronise when the network is back. Ask them to show it, with flight mode on.

5. "Where is support based, what hours is it open - and who answers?"

Friday at 2.30pm with a payroll run on Monday is not the time for a contact form in a foreign language. Ask whether support is in your language, how you reach it, and whether the people answering know transport - not just the software.

6. "How does the system handle extras - waiting time, extra stops, wasted trips?"

The extras are where margins leak. Ask specifically how an extra is recorded out with the driver and how it ends up on the invoice. If the answer involves "you note it down and enter it afterwards", you have found the leak.

7. "Can the system document CO2 emissions per customer and job?"

Transport buyers and public tenders increasingly require emissions figures. Ask whether the report exists ready-made in the system and is based on actual driving data - not on a standard estimate.

8. "How much time and help does it take to get started - and who does the work?"

Ask for a concrete onboarding plan: who enters customers and prices, who trains the drivers, how long it takes for a company of your size. "You get a consultant" and "you get a video" are very different answers.

9. "How is the system priced - and what triggers extra costs?"

You don't need the lowest price; you need a predictable price. Ask what happens to the cost when you add a user, a vehicle or an integration - and whether support and updates are included or billable.

10. "How often do updates come - and what was in the last three?"

A cloud-based system should develop continuously. Ask to see the changelog. Three-month-old "news" tells you where the product is heading.

11. "Who owns my data - and how do I get it out if we leave?"

The uncomfortable question that separates serious suppliers from the rest. The answer should be: the data is yours, and you get it out in a readable format without drama. Hesitation here is a red flag, no matter how good the demo was.

12. "Can I call two of your customers who are similar to us?"

Not the references on the website - two customers of your size and your type of work. Ask them about the support experience and what they wish they had known before they chose. Ten minutes on the phone is worth more than ten demos.

Three traps to steer clear of

The feature hunt. The system with the longest feature list wins the comparison in the spreadsheet and loses in everyday use. Choose the system your team is actually going to use - it is the three or four core flows that decide the gain.

"We customise everything for you". Unlimited customisation sounds like service, but often means you pay to maintain a special version nobody else tests. A good standard system with well-thought-out settings beats a bespoke patchwork over time.

Choosing alone. Bring a dispatcher and a driver to the demos. They see different things from management - and they are the ones who will live in the system from six in the morning.

Frequently asked questions

What is the most important thing to look for in a TMS?

That the whole flow hangs together - from order to paid invoice - and that the system fits your local conditions: accounting integrations, support in your language and a driver app that works without coverage. Individual features can be taught; a poor core flow cannot be repaired.

How long should a TMS procurement take?

For a small or mid-sized transport company: weeks, not months. Look at two or three systems, ask the questions above, call references and make a decision. The biggest cost in most procurements is the time the company keeps operating manually while it "evaluates".

Should we choose a local or an international system?

What matters is not the flag, but the everyday reality: support in your language during your working hours, integrations with your accounting systems and an understanding of local requirements such as transport licences, driving and rest time rules and environmental documentation in tenders. Ask about it - the answer quickly reveals how well the supplier knows your market.

What if we already have a system we are unhappy with?

Ask question 11 to your current supplier first: how do we get our data out? After that, the process is the same as for first-time buyers - but with the advantage that you now know exactly what you don't want.

FleetX is happy to answer all 12 - including number 11. Try FleetX, and let a dispatcher and a driver test it with you.

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