Written by Kiwi Dynamics Team 1What exactly will be in production, and by when
A vague pitch about transforming the practice with AI is a warning sign, ask instead for the exact workflow that will be live, working, and measurable, and a real date it will be running by. A good agency can answer this in one sentence, because they have scoped it already.
2How will we measure the hours or dollars saved
If an agency cannot tell you, before the project starts, how success will be measured, in hours saved, no-shows reduced, or dollars recovered, there is no way to know afterward whether it worked. Insist on a specific, numeric measure agreed before the build begins, not a vague sense of improvement afterward.
3What happens to client data, and where does it live
Client and patient data in a health and wellness practice carries real sensitivity, so ask exactly where it is stored, who can access it, and whether it ever leaves the country or gets used to train a model you did not agree to. A serious agency will have a clear, specific answer, not a shrug.
4How does this integrate with our existing systems
A workflow that does not connect to your actual booking system, calendar and client records becomes a second system for staff to check, which usually means nobody checks it. Ask how the new tool talks to what you already use, and insist it works with your existing practice management software rather than replacing it.
5Who owns the system once it is built
Ask directly who owns the code, the workflow, and the data once the engagement ends, because some agencies build systems that only they can maintain, which quietly locks you in. A good answer here is that you own it, and could, in principle, take it elsewhere.
6What does it do when it does not know the answer
Any tool touching bookings or client communication will eventually hit a question it cannot answer, and what happens next matters more than anything else. Ask whether it escalates cleanly to a real person with full context, or whether it guesses, especially for anything that brushes against clinical advice.
7Can we see a real, live example, not a demo
Ask to see a live system running in a comparable practice, not a slide deck or a canned demo video, and ask to speak to that client if possible. An agency confident in its work will happily show you the real thing, because that is the whole pitch.
8What is the actual cost, including ongoing
Get the full cost picture up front, build cost, monthly running cost, and any per-message or per-call fees that scale with your volume, because some pricing models look cheap until the practice gets busy. Ask what it would cost at double your current booking volume, not just today's.
9How do you handle clinical or sensitive information
Ask specifically how the agency handles anything that touches clinical information or advice, and be wary of anyone who is vague about the line between admin automation and clinical judgement. The honest answer is that AI should never give clinical advice, only handle the admin around it.
10What happens if it breaks on a Saturday
Ask what happens when the system goes down outside business hours, who gets alerted, how fast it gets fixed, and whether missed bookings during an outage are recoverable. A practice cannot afford a receptionist that disappears silently on a busy Saturday with no one noticing.
11How small can we start
A good agency will happily start with one narrow, well-scoped workflow rather than insisting on a full platform from day one, because that is how risk gets kept low and results get proven fast. If an agency only offers an all-or-nothing package, that is worth questioning.
These questions exist to protect the practice, not to make hiring harder, and any agency worth hiring will welcome them. Kiwi Dynamics answers all ten of these the same way every time: production systems, clearly scoped, measured in hours given back and dollars saved, never the size of the invoice.