7 Questions to Ask a Contractor Before You Hire Them

Most homeowners ask contractors about price and timeline. Those matter, but they're not what separates good contractors from bad ones. Here are the questions that actually reveal what you're dealing with.

1. "Are you licensed and insured? Can I see the certificates?"

In Massachusetts, any contractor doing home improvement work over $1,000 must have a Home Improvement Contractor (HIC) registration. Ask for the registration number and verify it yourself at mass.gov. Ask to see their certificate of insurance — general liability and workers' comp. A legitimate contractor will hand these over without hesitation. If they hesitate, that's your answer.

2. "Who will actually be doing the work?"

Many contractors use subcontractors for most or all of the actual labor. That's not inherently bad, but you should know. Ask: are your workers employees or subs? If subs, do you vet them? Are they also licensed and insured? You want to know who's in your home, not just who you're signing the contract with.

3. "What's your payment schedule?"

A legitimate contractor will typically ask for 30% upfront, a draw at a defined midpoint, and the balance on completion. Any contractor who asks for more than 1/3 upfront is a red flag. Contractors who ask for 50% or more before starting work are often either in financial trouble or planning to disappear. Massachusetts law limits deposits to 1/3 of the contract price for good reason.

4. "Walk me through a project that didn't go as planned. What happened and what did you do?"

This is the most revealing question on this list. Every contractor has had a project go wrong — unexpected conditions, material delays, design changes. What you're evaluating is not whether problems happened but how they handled them. Did they communicate proactively? Did they own the issue or blame the homeowner? Good contractors have specific, honest answers. Bad ones give vague deflections.

5. "What will the project timeline look like, and what's your current availability?"

Get a start date in writing. Ask what their typical crew looks like — are they running multiple projects simultaneously? Will they be on your job every day or weekly? A contractor who can start in two weeks when everyone else is booking out three months is either underbooked (ask why) or planning to juggle you with other jobs.

6. "Can you provide five references from the last 18 months?"

Not two, not three — five. And from the last 18 months, not from their best job five years ago. Call the references. Ask specifically: did they finish on time, did the final cost match the quote, would you hire them again without hesitation, and — critically — was there anything you wish you'd known before hiring them?

7. "What happens if you find something unexpected mid-project?"

Old Boston homes hide a lot — mold, asbestos, outdated wiring, structural issues. A good contractor will tell you they'll stop work, document what they found, and give you a written change order before proceeding. Red flag: any contractor who says "we'll figure it out as we go" or who you suspect would just keep going and add it to the bill at the end.