Ask what happens to your data if you leave
Can you export your patient records, prescriptions and billing in a usable format? Get the answer before you start, not after.
If the answer is vague, that is the answer.
Ask who does the work on day one
Someone has to enter your existing patients, services and pricing. Find out whether that is you, your staff, or the vendor, and how long it takes.
Ask about the claims you actually file
Generic software handles bookings and billing. Whether it handles the schemes and insurers you deal with is a different question, and it is the one that costs your staff hours every week.
Ask what it does when the internet drops
Clinic internet is not reliable everywhere. Find out what happens to a consultation in progress.
Ask to see it on a phone
Your front desk may be on a desktop, but you will check things on your phone between patients. Software that only works properly on a large screen gets used less.
Ask what it does not do
A vendor who cannot name a limitation either does not know their product or is not being straight with you. Every system has gaps. You want to know which ones you can live with.
In short. Buy for month three, not for the demo. Ask about exit, setup, your specific claims, and what it cannot do.