You’re looking for a web project that meets your requirements, so make sure to do your due diligence and ask questions before diving in. This will help both parties get on the same page.
1) Your competition uses a particular Content Management System, what would they say it does better? After all, you are looking for the company that will best suit your needs.
2) How much time will this really take to get done? Often times schedules change as requirements get fleshed out and to arrive at an exact schedule, a development team needs to spec out the project.
3) How will my project be supported? There may be a ticket system, forum, 800 number, dedicated individual or even someone overseas as infamously pioneered by some big computer manufacturers. This is important since your websites will be a new piece of software to you and you will have questions.
4) How do you document the project? Projects are often planned in phases depending on complexity. A proposal starts the project and a technical specification gets into the details so that developers know what to do.
5) What’s the cost for the project? Here, on a project of moderate complexity, you actually don’t want an exact answer since the team you introduced the project to must get into the technical details, think through features, research APIs if that are being used, etc. and get their heads around the amount of work involved.
This list isn’t all encompassing, but should provide you with some common sense things to think about on your next web 2.0 development project.