1. What experience does your contractor have with this type of project?
How much experience does the home improvement contractor have in doing projects like yours? Does s/he specialize in this type of project, or will s/he be using your home as a learning project? Typically, contractors who have done several projects like yours will have a better idea of the actual costs and production issues involved in your project. Remember, however, that every remodeling project is a little different, and it is doubtful that any contractor has ever done a job EXACTLY like yours.
2. Who will be doing the actual work?
Will the individual you're talking to be doing the work himself, or will they be using subcontractors or employees? Each scenario has its own advantages and disadvantages, but make sure you know what to expect on your job. Who will you ask questions once the project begins? Should you talk to the subcontractors, a jobsite manager, or the owner of the business? It is very important you have one person who will consistently answer your questions and not give you the run around.
3. What happens if changes are required to the initial bid?
What is the contractors' process for making changes in the middle of the project? Most times you would like to avoid making changes mid-project but there can be unforeseen obstacles that arrive and it is good to know ahead of time how your contractor will deal with those obstacles. Most contractors use some sort of change order form that details the exact work and cost involved in changes once work has begun.
4. Am I prepared to be flexible when the unexpected arises?
Invariably, every job has something that wasn't planned on come up. Delays due to weather, unforeseen conditions which present themselves once walls are torn down, changes to design or material choices, and problems with employees or subcontractors can all upset the planned flow of the project. Are you prepared to be flexible and work with your contractor to find solutions when these problems arise?
5. How do I feel about working with this contractor?
What is your gut feeling on working with this individual? Do you trust him or her? How do you feel about their design ideas as compared to your own? Can you communicate openly and clearly with this person? If it's a remodeling project, how do you feel about this person being in your house for several days or weeks at a time often when you are not home? This is a really important factor to consider if you don