Question two: “Who owns the integration, and who do we call if it breaks?”
“Do you integrate with X?” is a yes-or-no question, and every vendor will say yes. It tells you almost nothing.
The more useful questions sit underneath it. Who owns the integration: What can your team manage directly, and what requires a support team? Is that support provided by the vendor, or by a third-party integration provider? When something breaks mid-service on a Saturday, who do you contact?
Data flow matters here too, and this is often underestimated. If you are currently with a provider that pushes stock data every 15 minutes and a new vendor updates daily, that is a material change to your planning and operations. It might not come up unless you ask. Ask how often data is pushed, who manages the mapping between systems, and what the process is if that mapping breaks.
A good answer to these questions volunteers something you did not think to ask. It reveals a limitation or nuance you would not have seen in a demo. That is a signal that the vendor has real experience of how integrations behave in practice, not just in a sales environment.
Question three: “What does going live actually look like, from signing to being live across the estate?”
Operators tend to focus on the product decision and move quickly past the rollout detail. This is where a lot of the harder discoveries happen.
Ask for a clear picture of the milestones between signing and being fully live across the estate. What needs to happen before go-live? Do you test in one site first? What does the cutover itself look like? What resource will the vendor need from your team, and across which functions?
This matters especially when hardware installs, network requirements, and multi-site scheduling are involved. A rollout across six sites looks different from one built for 40. Ask which scenario the vendor has more experience with, and ask for a timeline.
Also ask: What happens if something does not go to plan during cutover? Can you run two systems in parallel if you need to?
At Vita Mojo, we aim to test so thoroughly that parallel running is not necessary. But we do not discourage clients from having the option. How a vendor answers this question tells you a great deal about how they think about operational risk.
Question four: “If you were going to do this process differently, what would you change?”
This one is for the reference call. Vendors will connect you with their happiest existing client. That is not dishonest, it is just how reference calls work. Your job is to get past the prepared answer.
Do not ask “Are you happy with the product?” Ask: “If you were going to go through this whole process again, what would you do differently, knowing what you know now?” That question invites the reference customer to share something specific and useful: something they did not know going in, a step they would handle differently, a conversation they would have had earlier.
Two other questions worth asking on the same call. First: What do your on-site team think of the product? You may have a positive view as the person who drove the decision, but the general managers and front-of-house staff using the Point of Sale (POS) every day may have a different experience.
Second: How often are you actually in contact with the vendor’s team, whether that is the support team or your account manager? You can be promised a great deal of contact during the sales process. An existing client can tell you what it looks like in practice, once the project is closed and the attention moves on.
Question five: “What customers are not a good fit for your solution?”
A vendor who has a clear sense of their ideal customer, and the confidence to say honestly where they are not the right fit, is a very different business from one that will sign anyone willing to pay a monthly fee. Ask directly: Which types of operators does your product not serve well? What does your roadmap not currently cover?
Listen carefully to the answer. A confident, specific response tells you the vendor knows what they are building and for whom. It tells you whether your needs sit within that picture today, and over the next two to three years.
If a vendor will not give you a straight answer, that is a signal. The best partnerships work because there is a genuine match between what an operator needs and what a vendor is actually built to deliver. A vendor willing to walk away from the wrong deal is one worth working with.
One more thing: Get it in writing
If any technical commitment has been made during the sales process (a custom build, a roadmap feature you have been told will be live by the time you go live) make sure it is documented in the contract and agreed by both parties.
Verbal commitments made in a sales conversation are easy to lose. If a feature or integration matters to your operation at launch, it belongs in writing.
