10 Questions to Ask Before Hiring a Contractor in Massachusetts The answers that separate contractors who know what they’re doing from those who don’t.
You can check reviews, browse portfolios, and compare prices all day — but the single most revealing thing you can do when evaluating a contractor is ask the right questions and listen carefully to the answers.
Good contractors answer immediately, specifically, and confidently — because they do this work every day. Bad contractors dodge, generalize, or pivot to something else. The questions below are designed to expose the difference. They’re Massachusetts-specific, meaning they test knowledge of MA building code, licensing, and construction practices that out-of-state or inexperienced contractors won’t have.
Ask every one of these during the estimate visit. The answers tell you more than any Google review ever will.
“What’s your CSL number and HIC registration number?”
Massachusetts requires two separate credentials for general contractors: a Construction Supervisor License (CSL) issued by the Board of Building Regulations, and a Home Improvement Contractor (HIC) registration issued by the Office of Consumer Affairs. They are not interchangeable. A contractor needs both to legally perform renovation work on your home.
A good contractor provides both numbers immediately — they’re on their business card, their website, their truck. They expect this question. A contractor who hesitates, says they’re “getting their license,” or claims they “don’t need one for this type of work” is not legally allowed to do the work.
Red flag answer
“I have a license but I don’t have it on me.” / “I’m in the process of getting licensed.” / “You don’t need a license for this kind of work.”Good answer
“My CSL is #______ and my HIC is #______. You can verify both on the state’s website. Here’s my card with both numbers.”“Do you carry general liability and workers’ compensation insurance?”
General liability insurance covers damage to your property caused by the contractor’s work. Workers’ compensation covers injuries to workers on your property. If a contractor doesn’t carry workers’ comp and a worker is injured at your home, your homeowner’s insurance may be responsible for their medical bills.
Ask for a certificate of insurance (COI) — not just a verbal confirmation. Then call the insurance company listed on the certificate to verify it’s active. Policies can lapse between the time the certificate was printed and the time you see it.
Red flag answer
“I don’t need workers’ comp — it’s just me working.” (In MA, sole proprietors with no employees are exempt, but this means zero protection for you if they’re injured.) / “I’m insured” without providing a certificate.Good answer
“Yes, I carry both general liability and workers’ comp. Here’s my current certificate of insurance. You can verify with [insurance company] at this number.”“Was my home built before 1978? And if so, what does that mean for this project?”
This is a test question — you already know when your home was built, but you want to see if the contractor brings up lead paint without prompting. Any renovation in a pre-1978 home that disturbs painted surfaces legally requires EPA RRP (Renovation, Repair, and Painting) lead-safe practices. This is federal law plus additional MA requirements under 105 CMR 460.000.
A contractor who doesn’t mention lead paint on a pre-1978 home is either uninformed about federal law or planning to ignore it. Both are disqualifying. Lead-safe practices add cost — but they protect your family from lead exposure and protect the contractor (and you) from EPA fines up to $37,500 per day.
Red flag answer
“Lead paint isn’t really an issue anymore.” / “We don’t worry about that for small projects.” / No mention of lead paint at all.Good answer
“Yes, pre-1978 means lead paint is likely present. We’re EPA RRP certified. The project will include containment, HEPA cleanup, and proper disposal. Here’s our RRP certification number.”“Who pulls the permits — you or me?”
The contractor should pull the permits. Always. Pulling permits is part of what you’re paying a general contractor to do. It means they’re putting their license number on the project, accepting responsibility for code compliance, and coordinating inspections.
A contractor who asks you to pull the permit is doing one of two things: they’re not properly licensed (pulling a permit requires a CSL in MA), or they’re trying to distance themselves from accountability for the work. Either is a deal-breaker.
Red flag answer
“You’ll need to pull the permit yourself.” / “We don’t really need a permit for this.” / “Permits just slow things down.”Good answer
“We handle all permits — building, electrical, plumbing. We schedule inspections and coordinate with your town’s building department. Permit fees are included in the scope.”“What happens if you find hidden damage behind the walls?”
This is the most important question for older Massachusetts homes. Hidden conditions — water damage, mold, outdated wiring, corroded plumbing, asbestos, lead paint layers — are not rare. They’re common. What matters is how the contractor handles them.
The right answer involves documentation, communication, and your approval before additional work. The wrong answer is either “that never happens” (it does, constantly) or “we’ll figure it out” (which means they’ll do the work and send you a surprise bill).
Red flag answer
“That doesn’t usually happen.” / “We’ll just take care of it.” / “That’s what the contingency is for” (without explaining the process).Good answer
“We stop work, document the condition with photos, explain the issue and the cost to fix it, and wait for your approval before proceeding. We never do additional work without your authorization. That’s why we recommend a 15% contingency budget.”“What’s the minimum ceiling height for a finished basement bedroom in MA?”
This is a code knowledge test. The answer is 7 feet (per 780 CMR). A contractor who works in Massachusetts regularly knows this instantly. A contractor who guesses, says “6 foot 8” (that’s door height, not ceiling), or says “I’d have to look it up” doesn’t do basement work frequently enough to trust with yours.
You can substitute other code questions depending on your project: “What’s the egress window size requirement?” (5.7 sq ft opening). “What thickness drywall goes on a garage-to-house wall?” (5/8″ Type-X fire-rated). The specific answer matters less than whether they answer confidently and correctly without looking it up.
Why this matters
A contractor who doesn’t know basic MA code answers will build your project wrong, fail inspections, and cost you time and money fixing mistakes. Code knowledge isn’t a bonus — it’s the minimum qualification.
“Have you pulled permits in my town before?”
Massachusetts building departments vary dramatically between towns. Permit turnaround times, inspector expectations, documentation requirements, and even inspection scheduling processes differ from Clinton to Worcester to Framingham. A contractor who has worked in your town knows the local inspector, understands the process, and can predict timelines accurately.
A contractor who has never worked in your town isn’t disqualified — but they should be honest about it rather than pretending familiarity they don’t have. Experienced contractors learn new towns quickly. Inexperienced contractors get stuck in unfamiliar permit processes.
Concerning answer
“Permits are pretty much the same everywhere.” (They’re not in MA.)Good answer
“Yes, we’ve done [number] projects in [your town]. The building department there requires [specific detail]. Inspector [name or description] is thorough about [specific thing]. Permit turnaround is typically [timeframe].”“What does your written estimate include — and what does it exclude?”
The items that are NOT in the estimate cause the most disputes. Permit fees, dumpster rental, debris removal, appliance delivery, final cleaning, landscaping repair, touch-up paint — if these aren’t explicitly listed as included, assume they’re not.
A good estimate is a document you can read line by line and know exactly what you’re paying for. Material brands and specifications should be named, not generic (“quartz countertop, Caesarstone, Calacatta Nuvo, 3cm, eased edge” — not just “new countertop”). Square footages, quantities, and per-unit costs make estimates comparable between contractors.
Why this matters
The $15,000 difference between two quotes might be real savings — or it might be $15,000 in excluded items that appear as “extras” once the project starts. The only way to know is to compare what’s included, item by item.
“What’s your payment schedule, and how much is the deposit?”
Massachusetts law (MGL Chapter 142A) caps contractor deposits at one-third of the total contract price or the cost of special-order materials, whichever is less. A contractor asking for 50% upfront is breaking MA law. A contractor asking for full payment before starting hasn’t read the statute — or is intentionally violating it.
Payment schedules should be tied to project milestones (rough completion, substantial completion, final walkthrough) — not arbitrary dates. The final payment should be withheld until after the walkthrough and punch list completion. This is your leverage to ensure everything is done right.
Red flag answer
“We need 50% upfront to start.” / “Full payment due before work begins.” / “We require payment before materials are ordered.”Good answer
“One-third at contract signing per MA law, one-third at rough completion, and one-third at final walkthrough after punch list is complete. The final payment is tied to your satisfaction with the finished work.”“Can I see a project you’ve completed that’s similar to mine?”
Photos on a website are a start, but the most powerful reference is a completed project you can visit or a past client you can call. A contractor who has done your type of project successfully will eagerly connect you with a past client — because that client will say great things about them.
A contractor who can’t or won’t provide references from similar projects either hasn’t done your type of work before or knows their past clients wouldn’t recommend them. Both are important information.
Red flag answer
“Our work speaks for itself.” / “Check our reviews online.” / “We don’t give out client information.”Good answer
“Absolutely. We completed a similar [kitchen/bathroom/basement] in [town] last [month/season]. I can give you the homeowner’s number — they’d be happy to talk about their experience. I also have photos from the project.”Bonus: The One Question They Should Ask YOU
A good contractor should ask “When was your home built?” during the estimate visit — without being prompted. This single question reveals awareness of lead paint (pre-1978), asbestos (pre-1980), knob-and-tube wiring (pre-1930), balloon framing (pre-1940), cast iron plumbing (pre-1970), and dozens of other age-related construction issues that affect scope, cost, and safety.
If a contractor walks through a 1920s Worcester County home without asking the age, they’re not thinking about what’s inside the walls. And in Massachusetts, what’s inside the walls is half the project.
How JM All-Pro Answers These Questions
In the interest of transparency, here’s how we answer every question on this list — because if we’re asking you to hold contractors to this standard, we should hold ourselves to it publicly:
CSL #121166. HIC #214808. Both verifiable on state websites. General liability and workers’ compensation insurance current — certificate available on request. EPA RRP lead-safe certified. We pull all permits and coordinate all inspections. Hidden conditions are documented with photos, explained with cost implications, and never addressed without your written approval. We know MA code because we work in MA every day. We’ve pulled permits across Worcester County, Middlesex County, and MetroWest. Our estimates include material specifications, and our payment schedule follows MA law. And we’re happy to connect you with past clients from projects similar to yours.
If we can’t answer any of these questions confidently for your specific project, we’ll tell you that too — and refer you to someone who can. Honesty before the project starts is better than excuses after.
Frequently Asked Questions
How many contractors should I get estimates from?
Two to three is ideal. It gives you comparison points for pricing, scope, and communication style without overwhelming you with options. More than five is diminishing returns — you’ll struggle to remember who said what. Quality of the estimate matters more than quantity of estimates. One detailed, spec-specific estimate tells you more than three vague ones.
Is the cheapest estimate always a bad sign?
Not always — but usually. If three estimates are $42,000, $38,000, and $44,000, the $38,000 might just be a more efficient operator. But if three estimates are $42,000, $38,000, and $22,000, the $22,000 is either using dramatically cheaper materials, planning to cut scope, or expecting to make up the difference in change orders. Ask what’s different about the low bid — the answer reveals everything.
What if a contractor can’t answer all 10 questions perfectly?
Nobody expects perfection. A contractor who confidently answers 8 out of 10 and honestly says “I’d need to check on that” for the other 2 is being genuine. The red flags are contractors who dodge questions, get defensive when asked, or give vague non-answers to straightforward questions. Confidence and honesty — even when the answer is “I don’t know, but I’ll find out” — are good signs.
Should I tell the contractor I’m getting other estimates?
Yes — it’s expected and professional. Most reputable contractors assume you’re comparing bids. Telling them upfront sets honest expectations. A contractor who pressures you to “sign today” or claims the estimate is only valid for 24 hours is using high-pressure sales tactics. Good contractors let their work and their process earn your business.
What’s the most important question on this list?
Question 5 — “What happens if you find hidden damage?” — reveals the most about how a contractor operates under pressure. Hidden conditions create real-time decisions about scope, cost, and trust. A contractor who has a clear, documented process for handling surprises will manage the entire project well. A contractor who wings it when surprises appear will wing everything else too.
How do I verify CSL and HIC numbers?
CSL: Visit the Massachusetts Board of Building Regulations website or search “MA CSL lookup.” Enter the license number and confirm it’s active and in good standing. HIC: Visit mass.gov/hic or search “MA HIC lookup.” Enter the registration number and confirm it’s current. Both searches take about 60 seconds.
What if a contractor refuses to answer these questions?
That is your answer. A qualified, licensed, insured contractor with nothing to hide will answer every question on this list openly — because the answers make them look good. A contractor who gets defensive, dodges, or says “you don’t need to worry about that” is telling you something important about how they’ll communicate during the project. Trust that signal.
How do I get started with JM All-Pro?
Call (508) 925-0396 or submit the quote form. We’ll answer every question on this list during the estimate visit — and we’ll ask you some questions too, because understanding your project starts with understanding your goals. Free on-site consultation, written estimate with material specs, and no obligation. CSL #121166, HIC #214808.
Ask Us These Questions — We Welcome Them
Free on-site consultation where we answer every question on this list and more. CSL #121166, HIC #214808. Insured. EPA RRP certified. The answers that build confidence before you sign anything.
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