Begin with the work
List who uses the system, where they work and which information they need. A workplace system used beside equipment has different needs from a portal used by a distributed team. Bring these examples to the first discussion.
Compare responsibilities and total cost
Look beyond a hosting bill. Include equipment, maintenance, support availability and the people who approve changes. Local, cloud and hybrid options can all work; the right choice depends on responsibilities your business can sustain.
Agree the data boundary
Identify which information must stay in your chosen environment and what external services are acceptable. Ask for an explanation in business terms before committing to a scope.
Define support before launch
Agree support hours, response expectations, recovery priorities and who to contact. Ask what is included, what requires additional work and what your own team will need to maintain.