We wrote these for our own discovery meetings, then realised the list is more useful to the buyer than to us. Ask them of any firm you are considering, this one included.
Ask who owns the intellectual property, what happens to the system if the firm disappears, and what the run cost looks like in year three. Most engagements that go wrong go wrong on one of those three, and all three are answerable before you sign.
Below are twelve questions, each with why it matters and what a worrying answer sounds like.
If the answer involves a licence, a platform fee or anything that renews, you are buying access rather than an asset. Both are legitimate, but they are very different purchases and the difference should be explicit before you sign, not discovered at renewal.
Ask to see the documentation standard they hand over, not a promise that documentation will exist. A worrying answer is that everything lives in a platform only they can access.
In your repository, under your account, from the first week, is the answer you want. If it lives on their machines until the end, you are relying on goodwill at exactly the point where a relationship is most likely to have soured.
A proposal that arrives before any measurement is a proposal about their capability rather than your business. Ask what the number was and where it came from.
A firm that says everything can be automated has not looked closely. Judgement, relationship and risk usually should not move. A good answer names specific steps they deliberately left alone.
Every system is wrong sometimes. The question is whether that is designed for. Ask where a person approves things, what gets logged and how you would find out afterwards which decision was made on what basis.
A demonstration proves a firm can build. Something still in daily use proves somebody wanted to keep using it, which is a much harder test and the only one that matters.
Build cost is the easy number. Running cost is where the surprise lives, and it usually grows with usage. Ask for it modelled at three times today's volume.
A firm that cannot describe a smaller version is selling a programme rather than solving a problem. There is nearly always a smaller version.
If nothing would, be careful. Every honest practitioner has a list of conditions under which their own service is the wrong purchase, and they should be able to say it out loud.
This is a question about you, not about them, and it is the single best predictor of whether anything survives. If the answer is nobody, the honest move is to fix that first or to price a support arrangement deliberately.
Certifications are often described loosely. Ask which are issued and which are in progress, and expect a straight answer. For our part, Laveeka's SOC 2 Type 2 and ISO/IEC 27001 programmes are underway with Oneleet and are not complete, so we do not describe ourselves as certified in either.
Can you name, in one sentence, the decision that gets made better because this exists? If nobody in your business can, the project has no target, and no amount of good engineering will give it one.