Choosing the right roofing contractor is one of the most important decisions you’ll make as a homeowner or commercial property owner. Whether you're installing a new roof, replacing an old one, or simply making repairs, the skill and integrity of your roofer can directly impact the quality, longevity, and performance of your roofing system.
With so many contractors offering services in the Massachusetts area — and horror stories about shoddy workmanship or disappearing deposits — how can you ensure you’re hiring the right team?
At Associated Roofing, we’ve proudly served Braintree and surrounding communities for decades. We’ve seen what can go wrong when property owners work with underqualified or dishonest contractors — and we want to help you avoid the same fate. That’s why we created this detailed guide to help you navigate the hiring process and ask the right questions from the start.
WHY CHOOSING THE RIGHT ROOFING CONTRACTOR MATTERS
Roofing is not just another home improvement project. It’s one of the largest, most complex, and cost-intensive repairs or upgrades you can make. A roof protects everything underneath it — your family, belongings, equipment, and the very structure of your property.
Here’s why the contractor you choose makes all the difference:
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Workmanship directly affects roof lifespan. Even the best materials will fail prematurely if installed incorrectly.
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Poor installation can void warranties. Many manufacturers only honor product warranties if certified installers perform the work.
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Hidden damage or corner-cutting can cost thousands. Missed flashing, improper underlayment, or rushed repairs lead to water intrusion, rot, and energy loss.
In short, hiring a trustworthy, qualified roofing contractor isn’t just smart — it’s essential.
RED FLAGS TO WATCH FOR
Before diving into what to ask, let’s cover what to avoid. Be cautious of any contractor who:
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Pressures you to sign immediately.
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Offers a “limited-time deal” or demands large deposits upfront.
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Lacks a physical business address or verifiable contact information.
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Refuses to provide a written estimate or contract.
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Cannot show proof of insurance or licensing.
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Uses vague language or dodges questions.
Unfortunately, fly-by-night roofers often appear after major storms, offering “quick fixes” at suspiciously low prices — and disappearing before problems arise.
KEY QUESTIONS TO ASK ANY ROOFING CONTRACTOR
1. Are you licensed and insured in Massachusetts?
Make sure your roofer holds the appropriate licenses for the state and carries both:
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General liability insurance (to protect your property)
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Workers’ compensation insurance (to protect you from liability if someone is injured on your property)
Ask for documentation, and verify it with the provider if necessary.
2. How long have you been in business?
Longevity in business is often a sign of consistency and reliability. Contractors who have been serving the local area for many years are more likely to deliver quality work and stand behind it.
3. Can you provide local references or reviews?
Ask for recent references — preferably within the last 12 months — and check online reviews through platforms like Google, Yelp, or the Better Business Bureau. A reputable contractor will have a proven track record of satisfied customers.
4. What roofing materials do you recommend and why?
A knowledgeable contractor should be able to explain the pros and cons of different materials (asphalt, architectural shingles, metal, etc.) based on:
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Your home’s architecture
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Local climate in Massachusetts
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Budget and long-term goals
Beware of anyone who pushes one option without understanding your needs.
5. Do you offer manufacturer certifications or warranties?
Top roofing manufacturers (like GAF or CertainTeed) certify contractors who meet specific standards. Certified roofers can offer enhanced warranties that non-certified installers cannot. This is especially important for protecting your investment long-term.
6. What is included in the estimate?
The estimate should clearly outline:
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Material costs
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Labor
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Removal of old roofing
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Cleanup
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Permit handling
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Any potential additional charges
Request a written, itemized estimate and avoid contractors who provide only vague ballpark numbers.
3. How will you protect my property during the job?
Replacing a roof is messy. Ask how the crew will protect:
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Landscaping
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Windows and siding
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Driveways and walkways
They should also outline how they’ll handle the cleanup and disposal of old materials.
8. Who will be on-site during the work?
It’s important to know:
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Who is managing the crew?
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Are subcontractors involved?
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Will a foreman or project manager be present daily?
You want a reliable point of contact to handle communication and ensure quality control.
9. What's the project timeline?
While weather can affect scheduling, your contractor should still give you:
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A projected start and finish date
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Working hours
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A clear explanation of what happens if delays occur
This helps you plan around the project and hold the team accountable.
10. Do you offer a workmanship warranty?
In addition to manufacturer warranties on materials, a trustworthy roofer will offer a workmanship warranty on labor. This means they’ll come back and fix any installation issues at no cost within a specified time (typically 5–10 years).
11. What is your payment schedule?
Be cautious of any contractor who demands full payment upfront. A typical payment schedule might be:
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10–20% deposit
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Progress payment during work
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Final payment upon completion and inspection
Make sure all terms are clearly outlined in the contract.
12. How will you handle unexpected repairs or hidden damage?
Roofing projects often reveal surprises (like rotted decking or inadequate ventilation). Ask how the contractor will communicate additional findings, provide updated estimates, and get your approval before proceeding.
13. Will you obtain permits and ensure code compliance?
The contractor should handle permitting and ensure the work meets all Massachusetts building codes and local ordinances. Failing to pull permits can result in fines and problems with future home sales.
14. What is your cleanup process like?
After the job is complete, your contractor should:
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Remove all debris
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Use magnetic tools to collect nails
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Leave your property as clean as they found it
A thorough cleanup is a sign of a professional, customer-focused contractor
15. Can I see examples of your work?
A portfolio of past projects can help you evaluate the quality of their craftsmanship and see how different roofing materials look once installed.
What makes a roofing contractor stand out?
While many contractors may have similar pricing or offer the same products, the experience of working with them can vary greatly.
Here’s what sets the best apart:
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Clear, honest communication
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Detailed estimates and contracts
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Punctuality and professionalism
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Local reputation and involvement
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Respect for your time and property
At the end of the day, trust your instincts. If a contractor makes you feel rushed, uncomfortable, or confused, they’re probably not the right fit.
Closing tips before signing a contract?
Before you hire your roofer, make sure you:
✔ Have a signed, written contract that outlines scope, timeline, materials, warranties, payment schedule, and more.
✔ Understand what happens in case of delays, weather issues, or unexpected findings.
✔ Know who to contact with questions during the project.
✔ Have verified licenses and insurance coverage.
✔ Have received and verified references or reviews.
Need a roofer you can trust in Massachusetts?
If you're looking for a licensed, experienced, and highly rated roofing contractor in the Braintree or South Shore area, Associated Roofing is here to help. We've been protecting homes and businesses across Massachusetts for decades with expert installations, honest advice, and quality you can count on.
Call us today at (781) 512-6773 or reach out through our contact form at https://www.associatedroofing.com/contact/. We’re happy to answer your questions, provide a free estimate, and help you feel confident in your roofing investment.