What to ask an AI company, and what the answers tell you

The short answer: ten questions, in four groups

Ask about the work, the people, what you have to supply, and the ending. In that order, because the last two are the ones vendors are least prepared for and the ones that decide how the second year goes. Here is the whole list, so you can stop reading and take it with you.

None of these are trick questions and a good supplier will enjoy most of them. What you are listening for is not confidence. It is whether the answer contains specifics that could later be checked.

• Walk me through a process like mine that you have built. What broke, and what did you change?
• What would you need to see before you could give me a number?
• Which parts of this will you refuse to automate, and why?
• Who exactly does the building, and will I meet them or only you?
• How many people at your firm would be able to work on my system?
• What do you need from us, in hours, and from which people?
• What runs where, in whose account, and who holds the credentials?
• What happens in month four, when the build is done and nobody is looking at it?
• If we stopped working with you, what would we still have running in ninety days?
• What would make you tell us not to do this?

Questions about the work itself

The first question is the one that separates people who have built things from people who have sold things. Ask for a process resembling yours, then ask what broke. Anybody can describe a success. A supplier who can describe the thing that went wrong, what they had missed, and how the design changed afterwards is describing a build they were actually present for.

The second question is about pricing behaviour rather than price. A supplier who will quote before walking your process end to end and listing every system it touches is quoting a sales number.

Three things move the size of any of this work more than the feature list does: how many systems have to be connected and whether they have a usable interface, whether the process is written down or has to be mapped from how people actually work, and how many exceptions the process really has. Exception handling is usually most of the build.

The third question, about what they will refuse to automate, is the fastest way to find out whether you are talking to someone with a view. Every honest answer sounds similar in shape: anything that moves money without a person looking, anything where the process changes every time, anything where the one person who understands it is never available to explain it.

Questions about the people who will actually do it

In a small firm the person selling is often the person building, which is an advantage as long as it is true. Ask it directly. If the answer is that a delivery team takes over after signing, ask to meet one of them before signing rather than after, and ask how many hours a week they will actually be on your work.

Then ask how many people at the firm could work on your system if the first one were unavailable. Every supplier has a number. Large firms answer with a rota, and the follow-up worth asking there is how many people on that rota have ever opened your system. Small firms answer with a small number, and the follow-up worth asking is what happens to you if that number becomes zero for a fortnight.

Neither answer is disqualifying. What matters is whether the risk is reduced structurally, by documentation you can read and access you hold, or reduced verbally, by reassurance.

Questions about what you have to supply

This is the group most buyers skip, and it is where projects actually go wrong. Every system of this kind runs on things only your business can provide: the real process, the exceptions, the price list that is current, the login to the tool that one person set up four years ago, and the decisions nobody has made yet about what the system is allowed to say.

Ask for the requirement in hours and names. How many hours of whose time, over how many weeks, and at what points. A supplier who says almost none has either built something like this before and knows it needs less than you fear, or has not thought about it and will discover in week two that the person who knows the process is on leave until the end of the month.

Ask what happens if you cannot supply it on time, because you probably will not. The good answer is a sequenced plan where the build proceeds on the parts that are ready. The bad answer is a payment schedule that continues regardless while the work waits.

• Hours of your team's time, by person and by week
• Which accounts and credentials have to exist, and in whose name they will sit
• What has to be written down before building starts, and who writes it
• Which decisions only you can make, and by when
• What happens to the schedule and the invoices if your side runs late

Two questions a small firm answers worse

A checklist that only asks questions the author answers well is an advertisement wearing a clipboard. Two of these are genuinely uncomfortable for a firm the size of Wobble, and a large incumbent will answer both better.

The first is procurement. Can you complete our supplier onboarding, our security questionnaire, our insurance requirements and our legal review before work starts? A large firm has a function for that, with completed questionnaires on file and lawyers who negotiate paper for a living.

A small firm answers slowly, sometimes has to ask what a clause means, and occasionally cannot meet a requirement at all. If your organisation cannot buy from a supplier who is not already on an approved list, that is a real constraint and no amount of technical fit resolves it.

The second is surge. If we needed four departments live by a fixed external date, could you staff it? A small firm cannot. It can sequence the work and be honest about the dates, but it cannot add six people in a month, and any small supplier claiming otherwise is describing a bench that does not exist. Ask this of everyone, including the large firms, and then ask the large ones how many of those six will have seen your system before they start.

What this question list cannot tell you

A list rewards whoever prepares for lists. A well drilled sales team will answer every one of these smoothly, and a small firm doing excellent work may fumble one because nobody has ever asked it before. Use the answers to start a conversation and weight what you are shown above what you are told.

None of these questions test whether the supplier can build the thing. Ownership, staffing and exit are commercial matters, and a company can be faultless on all three while being technically wrong about your problem. The test for that is different: hand over one real process, including its ugly exceptions, and watch whether the first response is a proposal or a set of questions about the exceptions.

There is also a limit to what a meeting can settle. If you cannot describe the process you want automated, no supplier can answer these questions well, because every answer depends on knowing what the work is. In that case the useful next step is a fortnight of writing down how the work actually happens, which costs nothing and changes every conversation afterwards.

This company's answers to its own ten questions

Taking the four groups in order. On the work: a process resembling yours, with the numbers attached and the unfinished write ups labelled as unfinished, sits on the work page. On the people: the person selling is one of four co-founders and so is the person building. Moiz Khan owns automation architecture, Haad owns growth and client solutions, Ibrahim owns build and workflows, Ali owns marketing and sales, and there is no delivery team behind them who has not been named. The published work includes more than 500 calls a day at Big Texas Land Buyers and a delivery line rebuilt as one audited automation at Quillon.

The two groups vendors are least prepared for are what you have to supply and what happens at the end. What you supply is set out on a page of its own rather than raised in month two. On price there is no price published anywhere on this site, because what moves the number is your volume, your tool count, how much of the process exists in writing and who maintains it afterwards, and a figure quoted before those four is a guess with a decimal point on it. On timing the shape is published instead: the audit in the first week, one named system live inside a fortnight, the second and third across month two.

The ending question has two halves and only one of them usually gets asked. What you keep is the accounts, the workflows, the documentation and the data, in your name. What you carry is the stop: money, pricing, anything published in your name and any serious complaint wait for human approval, and a case outside the rules hands it to a person. That hour a week is yours on every model, and it is also why a build kept in-house is sometimes the better answer, because your own team is already standing there. Wobble works from Karachi, bills month to month rather than annually, and is answerable for what it operates across 25 engagements in six countries.

Common questions

What is the single most useful question to ask an AI company?

Ask for a build resembling yours and then ask what broke. Anybody can narrate a success. A supplier who can describe what they had missed, how they found out, and what changed in the design afterwards is describing work they were present for rather than a case study they read.

How do I know if a quote is real or invented?

Ask what they needed to see before producing it. A number that arrives before anyone has walked your process end to end and listed the systems it touches is a sales number. The three things that move the price are how many systems connect, whether the process is documented, and how many exceptions it really has.

Should I ask about ownership in the first meeting?

Yes, and ask it as a location question rather than a legal one. Whose account does the system run in, who holds the credentials today, and could you export the workflow and read it without the supplier present. An ownership clause matters much less than who is holding the keys during a disagreement.

What questions is a small AI firm worse at answering?

Procurement and surge. A large incumbent has a compliance function, prepared security questionnaires and lawyers, and can put several people on a deadline at once. A small firm answers procurement slowly and cannot staff four departments in a month. Both are real constraints and should be weighed rather than argued away.

How much of my team's time will a project like this need?

Ask for it in hours and names, by week. Every build of this kind depends on things only your business has: the real process, the exceptions, current prices, and old logins. A supplier who has not estimated your side of the effort has not planned the project, they have planned their part of it.

Can a list of questions replace a proper evaluation?

No. Lists reward suppliers who prepare for lists, and a rehearsed team will answer all of them well. Use the answers as conversation starters, then test capability separately by handing over one real process with its real exceptions and watching what the first response is.