Don’t Work With a Contractor Before Asking These 5 Questions


Working with any expert can be intimidating – just think of the last time you got your oil changed. The mechanic could probably tell that you aren’t a car person and immediately tried to upsell you on things you don’t need.

It may seem like a good idea to choose a cheap contractor just because they’re less expensive than a luxury contractor, but you should always be careful when making decisions around projects as important as your home.

So, how do you know if you can trust your contractor to do a good job? Getting the answers to these 5 questions can help you protect against fraud and make sure that the final result is what you were imagining.

Here are the top 5 important questions to ask a contractor:

  1. Are you licensed?

    Thankfully, most construction, electrical, and plumbing work is regulated by the Massachusetts government. Licenses are only given after the contractor attends classes and passes a state examination to assure that the contractor has at least the minimal required amount of training, education, and experience. They also ensure that the contractor you’re working with is registered and regulated, allowing you to take complaints to the Massachusetts contractor’s licensing board. Sleeping Dog Properties, Inc. is proud to be a licensed contractor in Massachusetts.

  2. Are you insured? If so, how?

    Most licensed contractors are insured as well. There are, however, multiple kinds of insurance so you’ll want to make sure that your contractor has the kind of insurance relevant to the work being done. The first kind of insurance your contractor should have is workers’ compensation insurance. Without workers’ compensation insurance, you as the homeowner may be on the hook for paying for any medical costs incurred on the job. Homeowner’s insurance might help some of the cost, but this could result in your rates increasing and it being more difficult to become insured in the future. The other most important kind of insurance for contractors is liability insurance. Liability insurance helps contractors cover the costs of repairing any mistakes or damages to your house. Imagine a contractor accidentally bursting a water pipe – this would cause almost instant flooding!

  3. Do you have the experience in the work type I’m seeking?

    This question should almost be a no-brainer. Make sure your contractor has done the type of project you’re asking him or her to complete. You wouldn’t want your kitchen remodel to be a practice project for an amateur contractor eager to gain experience. Taking a look at your contractor’s portfolio of previous work can help you get a picture of their experience with your type of project.

  4. Do you have the capacity?

    You want your project done as efficiently as possible. Oftentimes, cheaper contractors can charge less for their services because they have fewer resources and therefore take longer on their projects. Ask your contractor for their schedule of upcoming projects to get a better idea about whether you’ll actually meet your target deadline or not.

  5. Do you have references?

    Finally, you want to make sure there are no skeletons hiding in your contractor’s closet. Doing this little bit of homework can give you valuable insight into the contractor you’re trying to work with. Maybe they do a stellar job, but require daily calls to keep them on track. This is the type of information that you’d only get from references. To be sure you’re getting the complete picture, we also recommend checking out online reviews from websites like Houzz.

These are just the first steps to finding a great contractor.

We’ve heard plenty of horror stories from clients who rushed into a construction project with a cheap contractor only to have to scrap it.

Investing the time and money in a qualified and trusted contractor can actually cost less in the long run. Make sure you get exactly what you’re looking for by finding a licensed, insured, and experienced contractor for your next project.


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