12 questions to ask before buying an AI solution for freight forwarding

Do not read it out like a survey. Twelve questions asked flatly get twelve rehearsed answers.

Send the twelve to each shortlisted vendor before the call, in writing, in the same wording for everyone. What you are testing is whether the answers change once somebody has to say them out loud.

In the call, ask them in order. Parts A and B belong in the first conversation. Parts C and D belong in the second, once you can see that the product is real.

Write each answer down in one line, in the vendor’s own words, the same day. A week later you will remember the tone of the meeting and none of the substance.

There is no form and no email gate on this page, on purpose. The job of a checklist is to travel. Forwarded, quoted, printed and carried into meetings the people who wrote it will never attend.

Twelve questions, in four parts. Each part settles a different worry, and they are ordered the way a real evaluation moves.

Part A is about evidence. Part B is about effort. Part C is about risk. Part D is about the company behind the software. A vendor can pass one part and fail another, and the part they fail tells you what the next six months look like.

Nothing here is scored. If a vendor gives you nine straight answers and three evasions, the three evasions are the finding.

Every question below carries four aids. They exist because the hard part is not asking. The hard part is knowing, in the room, whether the answer you have just heard was any good.

Read the aids before the meeting, not during it. The follow-up in the fourth aid is the one that does the work, and it only works if you ask it in the same breath as the question itself.

This part is about evidence. Every vendor can show a product working. Very few can show it working on your enquiries, put a defined number on how often it works, and describe the day it did not.

Measurement is a discipline of its own. The NIST AI Risk Management Framework, which is intended for voluntary use, puts measure alongside govern, map and manage. Carry that into A2. A percentage nobody can define is not a measurement.

A1. Run it on twenty of my real enquiries from last week. Can I watch, and can I pick which twenty?

A2. Out of 100 real enquiries, how many quotes go out with nobody editing them, and how do you count that?

A3. Show me one it got wrong, and tell me what happened next.

This part is about effort, and not the vendor’s effort. Yours. Three things decide whether the project starts at all: where the rates come from, whether your TMS has to move, and what the first weeks actually ask of your people.

B1. Where do you get partner and carrier rates from, and what happens when the rate is not there?

B2. Do I have to change or replace my TMS or ERP?

B3. From signing to my team sending a real quote, give me a date, and tell me what would push it.

This part is about risk. It is the part buyers skip, because by then the meetings are going well and nobody wants to sound suspicious.

One rule is worth knowing about. The EU Data Act, which applies from 12 September 2025, sets out a framework for customers to switch effectively between providers of data processing services. It does not settle who owns your rate cards, and it does not decide what happens to your quote history. Your contract does. This checklist explains what to ask. It is not legal advice.

C1. Who owns my rate data and my customer list? Can I export all of it, today, without asking you?

C2. If I stop paying next year, what happens to my quote history?

C3. Does this replace anyone on my team? Answer straight.

This part is about the company rather than the product. You are putting a daily process on somebody else’s software. Can they introduce you to a forwarder like you, will they name a weakness out loud, and are they going to be here in three years.

D1. Introduce me to a forwarder my size, in my market, who uses this. Not a logo, a phone call.

D2. What does your product do badly? Name one thing.

D3. How long have you been doing this, how many forwarders are live on it, and who funds you?

Put the twelve answers from each vendor side by side on one page. Read down the columns, not across your meeting notes.

Two of them carry more weight than the other ten. A1, because a vendor who ran your own twenty enquiries in front of you has shown you the product rather than described it. D1, because a forwarder your size, in your market, who has lived with the thing for a year will tell you in ten minutes what a year of demos will not.

A vendor who answers all twelve well is not the finish line. Check the answers. Ask for the export they described in C1. Make the reference call they offered in D1. Both are easy to verify and hard to fake.

Then run the same twelve questions on whatever you are already paying for. It is an uncomfortable hour, and it is usually the most useful one in the whole process.