The short answer
Ask who will actually build it, what they map before recommending tools, whose accounts the system lives in, what they would tell you not to automate, what happens after go-live, what the escalation path is, and what happens if it does not work. Vague answers to any of the seven are the risk.
Everybody in this market can show you an impressive demo, because demos run on the best case and the best case is the easy part. What tells you whether a build will survive contact with your business is a different set of questions, and all 7 can be asked in the first call, before anybody opens a laptop.
1. Who actually builds this?
Find out whether the person in the meeting is the person who ships. Every handoff between a salesperson, an account manager and a builder is a place where the specific detail of your process gets rounded off, and the detail is the whole job.
At Otomatic the audit is with Natan Trolka, who is the founder and the person who does the build. The one who hears the problem is the one who scopes the fix.
2. What do you map before recommending a tool?
The answer should describe your workflow rather than their stack: who touches what, where data moves, what breaks when somebody is away, which steps repeat often enough to justify building around.
A supplier who names a platform in the first 10 minutes has decided the answer before hearing the question, and you will spend the project bending your process to fit it.
3. Whose accounts does the system live in?
The answer should be yours. Workflows and integrations built inside your own logins mean the system stays with you on the day the relationship ends, which is worth arranging while everybody is still friendly.
If it lives in the supplier's account, the switching cost is a full rebuild, and the power sits on the wrong side of the table for as long as the arrangement lasts.
If the system lives in their account, the power sits on the wrong side of the table.
4. What would you tell me not to automate?
This is the question that separates operators from sellers, and it is worth asking in exactly those words.
Some work looks automatable and is not, whether because the volume never justifies it, the exceptions arrive too often, or the client relationship depends on a person being the one who does it. A supplier who cannot name a single exclusion has not looked closely enough to have formed an opinion, and is describing a product rather than your business.
5. What happens after it goes live?
Ask what documentation you get, whether there is a recorded walkthrough, and how long somebody stays on the build after handover.
The first fortnight of live use always finds cases the mapping missed. That is the nature of the work rather than a failure, and every Otomatic build includes 30 days of monitoring for exactly that reason, with Ongoing Care optional and project-priced afterwards.
6. What does the system refuse to handle?
Every build needs a written list of what it must not decide alone, who those cases go to, and how quickly. Complaints, money already paid, anything outside the agreed scope.
Ask to see that list before the build rather than after. A supplier who treats it as a detail to sort out later has skipped the part where the risk lives, and it is the part you will be asked about if something goes wrong.
7. What happens if it does not work?
Get the answer in writing, and be specific about what you are asking. Not a promise to fix bugs, which is table stakes, but what happens if the finished system works exactly as specified and still does not change how you operate.
Every paid Otomatic build carries a full refund or continued work at no extra cost until it does, and the choice is yours. The Systems Audit is free, so it carries no guarantee, because there is nothing to refund.
What to do with the answers
Ask all 7 of everybody you shortlist, then compare what they said about your process rather than what they showed you on screen. The demos will look broadly similar to each other. The mapping will not, and the gap between the best and the worst answer to question 4 usually tells you the rest.
The Otomatic Systems Audit takes 30 minutes, costs nothing, and returns a written roadmap within 24 hours that is specific enough to take to any of them.