|Business Categories||Cleaning, Painting, Tile Work in Boston, MA|
You'll certainly want to ask them this. Steer clear of any company that is not insured in Massachusetts, because that means that any incidental damage they may do on your property will be a real hassle to recover compensation for. It is never wise to work with uninsured tradesmen of any kind. Most states also require that someone have insurance in order to be issued a trade license. If they say they're licensed but not insured, they're being less than truthful.
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 Boston contractor will know how much they need for a deposit when they've given you the estimate, so ask early.
You'll always want to ask how long the company has been in business in Boston. 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.
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.