Software decisions are usually made at the moment of adoption. Buyers compare features, prices and onboarding. The more expensive moment can arrive years later, when the organization wants to leave and discovers that the product has become woven into everyday operations.
Data portability is the obvious first check
Find out what you can export and in which formats. A CSV export may be enough for a simple contact list but almost useless for a complex workspace containing comments, relationships, files and permissions. Test an export early if the data matters. Do not wait until you are already unhappy with the vendor.
Workflows can be harder to move than data
The database may transfer cleanly while the automations, templates and team habits do not. If staff have spent years building a process around one platform, migration involves retraining as well as technical work. That does not mean you should avoid powerful software; it means the switching cost should be acknowledged as part of the purchase.
Integrations create invisible dependencies
A tool can begin as a standalone app and gradually become the center of dozens of integrations. Before replacing it, you need to know which systems send data in, which systems depend on data going out and which automations assume a particular field or workflow exists.
The sensible approach is not to fear lock-in so much that you never commit to useful software. It is to keep ownership of critical data, document important processes and understand how you would leave. A product is easier to trust when you know the exit is possible.