Choosing the Right Roofing Contractor – 7 Questions to Ask

May 5, 2026

Choosing the Right Roofing Contractor – 7 Questions to Ask

Worker kneeling on a steep roof, using a tool near the edge on an overcast day.

Hiring the wrong roofing contractor can cost you more than just money — it can lead to poor workmanship, delays, hidden fees, or even water damage down the line. Whether you’re replacing an old roof or just need minor repairs, choosing a qualified, trustworthy roofing company is essential.


To help you avoid costly mistakes, this guide breaks down the 7 most important questions to ask before hiring a roofing contractor in Massachusetts. With these tips, you’ll feel confident you’re hiring the right pro for your home.


Why Hiring the Right Roofer Matters

Roofing is one of the most expensive — and important — home projects. A poorly installed roof can:

  • Leak within months of installation
  • Void your manufacturer’s warranty
  • Lead to mold, rot, and interior damage
  • Reduce your home’s resale value
  • Require expensive rework later


In contrast, a skilled and honest contractor will deliver a roof that’s durable, energy-efficient, and built to last.


7 Questions to Ask Before Hiring a Roofing Contractor

1. Are You Licensed and Insured in Massachusetts?

Why it matters: A licensed contractor follows state codes, permitting, and safety standards. Insurance protects you in case of worker injuries or property damage.


Ask to see:

  • A copy of their Massachusetts contractor license
  • Proof of liability insurance and workers' compensation


At DGL Construction Inc, we’re fully licensed and insured — so you're protected from day one.


2. What Type of Roofing Work Do You Specialize In?

Why it matters: Not all contractors specialize in the same types of roofs or services. Ask if they handle:

  • Asphalt shingle systems (most common)
  • Flat or low-slope roofs
  • Commercial or residential roofing
  • Storm damage or insurance claims
  • Chimney flashing, skylights, or attic ventilation


Look for a roofer who’s experienced in the specific type of project you need.


3. Can You Provide Local References or Recent Jobs?

Why it matters: A reliable contractor should have a strong local reputation and completed work in your area. Ask for:

  • Recent job addresses or photos
  • Customer references you can contact
  • Reviews on Google, BBB, or Facebook


Pro Tip: Drive by a few recent installs to see the quality for yourself.


4. Do You Provide a Written Estimate and Contract?

Why it matters: Verbal quotes can lead to confusion or surprise charges. Always get a detailed written estimate that includes:

  • Scope of work
  • Materials being used
  • Estimated timeline
  • Cleanup procedures
  • Warranty details
  • Total price and payment terms


At DGL Construction Inc, we provide clear, itemized estimates with no hidden fees.


5. What Kind of Warranties Do You Offer?

Why it matters: A roof is only as good as the warranty behind it. Ask about:

  • Manufacturer warranties on materials (often 20–50 years)
  • Workmanship warranties on installation (commonly 5–10 years)


Make sure you get both in writing and understand what’s covered — and what’s not.


6. What Is Your Process for Weather Delays or Unexpected Issues?

Why it matters: New England weather is unpredictable. Your contractor should have a plan for:

  • Rain or snow delays
  • Protecting your home mid-project
  • Handling surprises like rotted decking or hidden leaks


A quality roofer communicates clearly and keeps you updated throughout the job.


7. Do You Handle Permits and Cleanup?

Why it matters: In many Massachusetts towns, a permit is required for roof replacement. Also, roofing creates a lot of debris — nails, shingles, flashing.


Ask if your contractor will:

  • Pull the necessary permits for your town
  • Use tarps and protection during tear-off
  • Perform magnetic nail sweeps after cleanup
  • Haul away old materials


At DGL Construction Inc, we handle all permits and cleanup from start to finish — you don’t lift a finger.


Red Flags to Watch Out For

  • Door-to-door contractors after a storm
  • Large upfront deposits (more than 30%)
  • Vague or missing contracts
  • Poor communication or pushy sales tactics
  • No online presence or reviews


These are all signs to keep looking for a more reputable company.


Why Homeowners in Massachusetts Choose DGL Construction Inc

With 16+ years of hands-on roofing experience and hundreds of satisfied clients across Massachusetts, we offer:

  • Licensed and insured roofing crews
  • Expert installation using top-rated materials
  • Clear estimates and job timelines
  • Excellent reviews and local references
  • Competitive pricing and warranty protection

See what makes us different – https://www.dglconstructioninc.com


FAQs – Choosing a Roofing Contractor

What’s the average deposit for a roofing project?

A typical deposit is 20%–30% of the total cost. Be wary of contractors asking for full payment upfront.


Can I get multiple quotes before choosing?

Yes — and you should. Just be sure you’re comparing apples to apples in terms of materials, scope, and warranty.


Should I choose the cheapest bid?

Not always. The cheapest quote may mean lower-quality materials or cutting corners. Focus on value, not just price.


Are manufacturer certifications important?

Yes. Some roofers are certified by manufacturers (like GAF or CertainTeed), which can offer better warranties and installation standards.


How soon can you start?

This depends on the season and demand. During spring and fall, booking early ensures your spot. We always try to accommodate urgent needs.


Ready to Hire a Roofing Contractor You Can Trust?

If you're planning a roof replacement or repair in Massachusetts, don’t settle for anything less than the best. At DGL Construction Inc, we’re committed to quality, transparency, and protecting your home — rain or shine.


Call today to schedule your free roofing estimate: (774) 248-3122
Or
request a quote online – https://www.dglconstructioninc.com/contact



Don’t risk your roof — hire a contractor who earns your trust.


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