Written by Kiwi Dynamics Team 1What exact workflow will this fix first
Ask the agency to name the one specific workflow, phone bookings, reviews, rostering or something else, that gets fixed first, and why that one. If the answer is vague or tries to cover everything at once, that is a sign of a sales pitch rather than a real scoped plan.
2Will this run in production, not a demo
Ask directly whether what gets built will run live in the business, handling real calls or real bookings, or whether the engagement ends at a proof of concept. A lot of AI projects stall exactly at the demo stage, and it is worth knowing upfront which one this will be.
3How is success measured, in hours or dollars
Ask how success will be measured, and push for a number: hours saved per week, no-shows prevented, calls answered that would otherwise be missed. An agency that cannot commit to a measurable outcome is not confident the system will actually work.
4Does this integrate with our current systems
Ask whether the new system plugs into the booking platform, POS and roster tools already in use, or whether it requires ripping out and replacing what already works. Integration is usually the hardest and most important part of the build, and it is where a lot of projects quietly fail.
5What happens when the AI gets it wrong
Ask what happens when the AI gets something wrong, a missed detail on a booking, an incorrect allergen answer, or a badly timed review reply. A serious agency will have a clear answer involving human review points and fallbacks, not a claim that it will never happen.
6Who owns the data this system touches
Ask exactly who owns and can access the customer, booking and review data the system touches, and where it is stored. This matters both for privacy compliance and for making sure the venue is not locked into the agency's platform indefinitely.
7How fast can the first version ship
Ask how long it takes to get the first working version live, not the final polished system, just something real handling real tasks. An agency that talks in months before anything ships is optimising for a long contract, not a fast result.
8What does ongoing support actually look like
Ask what happens after launch: who fixes issues, who updates the system as the menu or hours change, and what that costs ongoing. A system that is not maintained will quietly degrade, and it is worth knowing that cost before signing anything.
9Can we see it working for a similar venue
Ask to see or hear about a comparable hospitality venue the agency has actually built for, ideally with a real number attached to the result. Vague case studies or logos with no specifics are a warning sign; a strong agency will happily share what changed and by how much.
10What is the real cost against the return
Ask for the full cost, not just the build fee, against the actual return in hours or dollars saved, so the decision is a real business case rather than a leap of faith. If the agency cannot help build that case with real numbers, that itself is useful information.
These are the exact questions we expect to be asked, because the answers are straightforward when the work is real: a specific workflow, live in production, measured in hours and dollars. That is the whole Kiwi Dynamics approach, and we would rather earn the work by answering these than by outselling the alternative.