How do you read a vendor who will not name a weakness?
Question D2 of the twelve. Every piece of software is bad at something. You will find out what, in week three, on a Tuesday. The only question is whether the vendor told you first.
This article goes deeper than the sheet: what a real weakness sounds like, the four fake ones, where the weak spots genuinely sit, and how to turn the answer into a test.
Ask any AI vendor what their product does badly and make them name one thing. Every tool has a weak spot, so a vendor who cannot name theirs either does not know the product or will not be straight with you. Then ask which forwarder should not buy it.
Why does the answer matter more than the weakness?
Because you will meet the weakness either way. The only variable is whether you meet it before you sign.
A product is a stack of choices, and every choice buys one thing by giving up another. Software that reads any format takes longer to set up than software that only accepts a form. A tool tuned for ocean groupage will be clumsy on one air shipment of dangerous goods. None of that is a scandal. It is arithmetic.
So D2 is not really about the product. It is about the vendor, and there are three things they can do with it. Name a real weakness. Dress a strength up as one. Or say there is not one.
The first tells you they know their product and expect you to still be here in two years. The second tells you somebody has been trained. The third tells you nothing about the software and a great deal about the relationship.
- 01Ask D2“What does your product do badly? Name one thing.”
- 02The pauseHow long they take is part of it.
- 03They name somethingOr nothing, which counts too.
- 04Ask the follow-up“What kind of forwarder should not buy this?”
- 05They describe a bad fitA size, a trade, a way of working.
- 06Send an enquiry through itThe one that sits inside the weakness they named.
- GATEYou decideAgainst a rule you wrote before the meeting.
Most buyers stop at the third step. The value is in the fourth. “Name one thing” invites a sentence, and a sentence can be prepared. “What kind of forwarder should not buy this” asks them to describe somebody real, in front of a person who knows those firms. Much harder to invent.
What does a real weakness sound like?
It costs the vendor something to say out loud. That is the whole test.
A real one has a shape. It names a situation rather than a quality, it comes with a rough size, and it ends with what people do about it today.
| What to ask | What a fair answer sounds like |
|---|---|
| What does your product do badly? Name one thing. | One named thing, in a situation you recognise. “We are weak where the rate lives only in an agent’s head” is an answer. “We can always be faster” is not. |
| How often does that come up? | A rough share of enquiries, or a lane type, or a mode. A vendor who has hit the weak spot at volume knows roughly how often it lands. |
| What do your customers do about it today? | A workaround, in the customer’s words. Somebody keys it in, or the enquiry goes to a person. If nobody has worked around it, nobody has hit it. |
| What kind of forwarder should not buy this? | A recognisable firm. A size, a trade lane, a mode, a way of working. If the answer is “nobody”, the product has no shape, and everything with a shape excludes somebody. |
| Is it being worked on, and what if it is not? | Either an honest “not soon, and here is how people live with it”, or a description of the change. Neither needs a date, and you should not ask for one. |
- What does your product do badly? Name one thing.
- What a fair answer sounds like
- One named thing, in a situation you recognise. “We are weak where the rate lives only in an agent’s head” is an answer. “We can always be faster” is not.
- How often does that come up?
- What a fair answer sounds like
- A rough share of enquiries, or a lane type, or a mode. A vendor who has hit the weak spot at volume knows roughly how often it lands.
- What do your customers do about it today?
- What a fair answer sounds like
- A workaround, in the customer’s words. Somebody keys it in, or the enquiry goes to a person. If nobody has worked around it, nobody has hit it.
- What kind of forwarder should not buy this?
- What a fair answer sounds like
- A recognisable firm. A size, a trade lane, a mode, a way of working. If the answer is “nobody”, the product has no shape, and everything with a shape excludes somebody.
- Is it being worked on, and what if it is not?
- What a fair answer sounds like
- Either an honest “not soon, and here is how people live with it”, or a description of the change. Neither needs a date, and you should not ask for one.
One note on that last row. Do not push for a delivery date on a weakness. You will get one, it will be sincere, and it will move. What you want is the version of your operation that works whether or not it lands.
Public buying guidance treats this as your job, not a favour. The UK government’s guidelines for AI procurement tell buying teams to “try to establish any limitations of the model” and to ask suppliers “to describe their strategies on how to address these shortcomings”. D2 is that instruction in one sentence.
Article 13 of the EU’s AI Act shows what a written limitation contains. Instructions supplied with a high-risk AI system must state its “characteristics, capabilities and limitations of performance”. A freight quoting tool is not a high-risk system, so this binds nobody you are meeting. Borrow the shape: the circumstance, the size, the effect.
What are the fake weaknesses, and how do you spot them?
Four answers sound like candour and carry none of it. You will hear at least one.
One. The strength in a costume
“We are probably too thorough.” “Our setup is more hands-on than people expect.” Each of those is a compliment wearing a coat. Send it back with the follow-up, unchanged: what kind of forwarder should not buy this?
Two. The weakness that belongs to you
“We do not always get clean data from customers.” That is your data and your job, and it is true of every vendor, so it separates nobody. The version worth accepting names what the product does when the data is bad, which is usually to ask rather than guess.
Three. The weakness that is already mended
“Reporting used to be thin, we rebuilt it in the spring.” A weakness with a resolution attached is a case study. Ask for a current one: what is weak today, on the version you would give me?
Four. The price answer
“Honestly, we are expensive.” It may be true, and it is not a product weakness. Price is a negotiation, not a limit. Ask again about the work: I mean an enquiry it handles badly.
None of the four ends a meeting. Each is a reason to ask again in different words. A vendor who answers properly on the second ask is fine. One who hands you a second costume has shown you how the next two years will go.
What kind of weakness did the vendor just name?
The strongest answer in part D. Find it in the trial, because they told you where to look.
Usually a young product rather than an evasive vendor. Ask what their customers do when it happens, then carry that into D3.
Ask the follow-up once. If the second answer has the same shape, treat D2 as unanswered and lean on A1 and A3.
An unanswered D2 is not a rejection on its own. It is a reason to trust only what you have watched happen.
Where are the real weak spots in software that reads freight enquiries?
You cannot grade an answer to D2 without knowing where this job is genuinely hard.
None belongs to any product. They are the places the work resists software, and where honest answers cluster.
- Rates that live in a person, not a system. The agent who quotes on WhatsApp when you ask, and only when you ask. Nobody has solved this, and a vendor who says they have is answering a different question.
- The lane you run once. Software priced from your own history is confident on the trade you move weekly and thin on the one asked about this morning.
- The enquiry that is not one enquiry. “Sort out last month’s invoice, and quote me Nhava Sheva to Hamburg.” Two jobs, two departments, one subject line.
- Attachments that are pictures. A rate sheet photographed at an angle, a packing list scanned like a fax, a screenshot pasted under three forwarded signatures.
- Cargo that needs a person to look at it. Dangerous goods where the class changes the routing, out-of-gauge that needs a survey, temperature-controlled with one customer’s own tolerance.
- Anything with a customs decision inside it. Classification, duty, the filing. That work stays with your broker and your own filing system, and a vendor who implies otherwise is worth a second look.
- The rule your firm has that nobody else has. This customer never sees a surcharge line. This agent is quoted at cost. Real, written nowhere, and software meets it late.
Five of those seven are about the input, not the intelligence. That is the shape of this job, and a filter on the answer you got. A vendor who names a weakness from this territory has been inside a forwarder’s mailbox. One whose weakness is abstract may only have been in the demo.
How do you turn the answer into a test?
Put it on paper before the day ends, in their wording, on one line. By next week you will remember the tone of the room and nothing else.
| Column | What goes in it |
|---|---|
| The weakness | What they named, in their words, with the date you heard it. |
| Who should not buy | The forwarder they described when you asked the follow-up. If they described nobody, write that instead. |
| Does it touch us | Yes, no, or partly, judged against your own lanes and your own week. |
| Tested | Yes or no. Did you put a real enquiry through the weak spot before you signed. |
- The weakness
- What goes in it
- What they named, in their words, with the date you heard it.
- Who should not buy
- What goes in it
- The forwarder they described when you asked the follow-up. If they described nobody, write that instead.
- Does it touch us
- What goes in it
- Yes, no, or partly, judged against your own lanes and your own week.
- Tested
- What goes in it
- Yes or no. Did you put a real enquiry through the weak spot before you signed.
Agree what a pass looks like before you walk in. A workable rule: the weakness is current, you can picture the forwarder who should not buy, and it does not sit on top of the work that made you go shopping. The third clause decides.
The last column is the reason to ask at all. A named weakness hands you a test you would never have designed. Take ten enquiries that live inside it and run those, not ten easy ones. The vendor gave you the test.
Then do the uncomfortable half. Answer D2 about the system you already run. Ask the two coordinators who touch it most what it is bad at, in the same four columns. A longer list than the vendor’s is worth knowing before you sign.
What if the vendor genuinely does not know?
That happens, and it is not the same thing as hiding it.
A young product with a handful of live forwarders may not know where its edges are, because nobody has pushed it hard enough. The honest version is “we think it is this, and here is why we are not certain”, and it is worth accepting.
What is not worth accepting, at any size, is “nothing really”. A vendor with three live forwarders who names two weak spots is more useful than one with three hundred who names none.
It cuts the other way too. Be fair to a long-established product. When a mature tool names a weakness you can live with, it has told you something precise, learned in somebody else’s operation. That is experience, not decline, and it should not lose to a newer product that has less to confess.
D2 and D3 sit next to each other for a reason. D2 asks what the product cannot do. D3 asks whether the company will be around when it can. Read the two together, because a weakness only matters for as long as the vendor lasts.
Common questions
Is it fair to expect a salesperson to criticise their own product?
Yes, and the good ones do it unprompted, because a weakness you find in week three costs them the renewal. If the person in front of you does not know, ask to put it to somebody who builds the thing. How that request is handled is informative on its own.
What if the weakness they name is the exact thing I need?
Then you have the answer in the first meeting rather than the fourth month, which is what a five-minute question is for. Ask what their customers with the same need actually do, because the workaround is sometimes fine and sometimes a person keying things in all afternoon.
Should I ask D2 before or after the demo?
After. Asked first, it is answered in the abstract and costs nothing. Asked afterwards, the weakness has to be consistent with what you both just watched, and inconsistency is easy to hear.
Do I ask this about the whole product or one part of it?
One part, the part you are buying. “What is your quoting weak at” gets a sharper answer than “what is the product weak at”. Ask again for each job that matters, and expect the answers to differ.
- FreighAI Playground — programme outline and the twelve-question checklist (internal document; question D2, its four answer aids, and the article angle that every tool is bad at something)verified 2026-09-03
- UK Government — Guidelines for AI procurement (buying teams should try to establish any limitations of the model, and ask suppliers to describe their strategies on how to address these shortcomings)verified 2026-09-03
- European Union — Artificial Intelligence Act, Regulation (EU) 2024/1689, Article 13, read on the AI Act explorer (instructions for use must state the characteristics, capabilities and limitations of performance of a high-risk AI system). A freight quoting tool is not a high-risk system under that lawverified 2026-09-03
Take question D2 into your next vendor call
Ask it after the demo, not before. Make them name one thing, ask which forwarder should not buy the product, then send an enquiry straight through the weak spot they described. Ask us D2 as well.