|Business Categories||Roofing in Chicago, IL|
This will be answered when you ask if all employees are licensed. The only way to obtain a legitimate tradesman's license is to be a legal or naturalized citizen of the US. The company may employ people in positions that don't require a license, however, so it's wise to inquire.
You'll always want to ask how long the company has been in business in Chicago. While this isn't a guarantee that the company will do good work, companies with longevity on their side must be doing something right. That being said, there are newer companies that do great work. If the company is under three years old, ask where the owner was employed before and for how long. If he/she has a long history of employment, it's reasonable to infer that he or she decided to go into business for themselves after so many years of experience.
Always ask for references, and always check them. Keep in mind though that the only references you'll get are people who the contractor is certain will give him a good review. You'd also be well advised to check online review sources in Chicago as well, which will give you a broader view of customer satisfaction for a given company.
This is important mostly for larger jobs. Clearly a two man operation is going to build a home much slower than a 15 man crew. This is also a good indication of the overall size of the Roofing company, if that's an area of concern for you. The reason you may want to ask about the fleet is that fleet size is a good indicator of the mobility of the company. Mobility may not sound important, but it's hard for the Chicago contractors to get to job sites if they lack appropriate vehicles.
Some companies may require a 10% deposit, some may not require any. For larger projects, you'll almost always need to give a deposit, and it's good to ask how much the deposit will be before going forward with a project. The Chicago contractor will know how much they need for a deposit when they've given you the estimate, so ask early.