Questions to Ask a Roofing Contractor (Before You Sign a Contract)

Hiring a roofing contractor is a big decision. Your roof protects everything underneath it—your family, your belongings, and the structure of your home. Whether you need a small repair or a full replacement, choosing the right contractor can make the difference between a smooth experience and a costly headache.

Before you sign anything, here are the most important questions every homeowner should ask a roofing contractor—and why each one matters.

1. Are You Licensed and Fully Insured?

This is the first question to ask, and it’s non-negotiable. A legitimate roofing contractor should be able to confirm licensing requirements in your area and provide proof of insurance.

What to ask:

• Are you licensed to perform roofing work in this state?
• Do you carry general liability insurance?
• Do you have workers’ compensation insurance?

Why it matters:
If someone gets injured on your property and the contractor isn’t properly insured, you could be held responsible.

2. How Long Have You Been in Business?

Experience matters in roofing. Every roof system is different, and it takes real knowledge to identify issues, recommend the right solution, and install everything correctly.

What to ask:

• How many years have you been installing and repairing roofs?
• Do you specialize in residential roofing, commercial roofing, or both?

Why it matters:
Established roofers are more likely to have proven processes, strong local relationships, and consistent workmanship.

3. Can You Provide Local References or Recent Projects?

A reputable roofer should be able to show examples of recent work and provide references. It also helps to see projects similar to your roof style.

What to ask:

• Can you share recent customer reviews or references?
• Do you have photos of similar roofs you’ve completed?

Why it matters:
Good contractors stand behind their work and can prove it with satisfied customers.

4. Will You Provide a Written Estimate?

Always get a written estimate. It should clearly outline the scope of work, materials, labor, and what’s included.

What to ask:

• Can you provide a detailed written estimate?
• Is your estimate itemized or bundled?
• Does it include labor, materials, disposal, and cleanup?

Why it matters:
A written estimate protects you from surprise charges and makes it easier to compare quotes fairly.

5. What Roofing Materials Do You Recommend and Why?

Not every roofing material is right for every home. The right choice depends on your roof slope, ventilation, budget, design preferences, and local weather conditions.

What to ask:

• What type of shingles or roofing system do you recommend?
• Why is that the best option for my home?

Why it matters:
A contractor should guide you based on your needs—not just sell the most expensive product.

6. Will You Replace the Underlayment and Flashing?

Shingles are only part of a roof system. Underlayment, flashing, vents, and drip edge all play a huge role in preventing leaks.

What to ask:

• Are you replacing the underlayment?
• Will you replace flashing around chimneys, vents, and valleys?
• Is drip edge included?

Why it matters:
Many roof leaks happen because of flashing issues—not shingles.

7. What Happens If You Find Rotten Wood or Deck Damage?

Sometimes the roof decking underneath the shingles is damaged due to long-term moisture. This can’t always be seen until the old roofing is removed.

What to ask:

• How do you handle rotted decking or damaged plywood?
• Will you show me photos before replacing anything?
• How is that cost calculated?

Why it matters:
You want transparency if repairs are needed once the roof is opened up.

8. Who Will Be On-Site Doing the Work?

Some roofing companies use their own crews, while others subcontract the work out. Neither option is automatically bad—but you should know who is responsible.

What to ask:

• Will your own crew install the roof, or subcontractors?
• Who is the on-site supervisor or project manager?

Why it matters:
Clear accountability helps ensure quality control and better communication during the project.

9. What Is the Timeline for the Job?

Knowing how long the work will take helps you plan for noise, parking, pets, kids, and normal daily routines.

What to ask:

• When can you start?
• How long will the job take?
• What happens if weather delays the project?

Why it matters:
A reliable contractor provides a realistic timeframe and communicates changes clearly.

10. How Will You Protect My Property During the Job?

Roof replacement can be messy if the contractor doesn’t take precautions. You want your landscaping, driveway, and exterior protected.

What to ask:

• How do you protect plants, siding, windows, and gutters?
• Where will debris land?
• Will you use tarps and plywood protection?

Why it matters:
Professional roofers treat your property with care and clean up thoroughly.

11. How Do You Handle Cleanup and Disposal?

A good roofer doesn’t leave nails behind, and they don’t leave a dumpster in your driveway longer than necessary.

What to ask:

• Is old roofing removal included?
• Will you use a magnetic nail sweep?
• Do you haul away all debris?

Why it matters:
Cleanup is part of the job, and it should be handled professionally.

12. What Kind of Warranty Comes With the Work?

Roofing warranties typically include two parts:

• Manufacturer warranty (materials)
• Workmanship warranty (installation)

What to ask:

• What warranty comes with the shingles or roofing system?
• What workmanship warranty do you provide?
• What can void the warranty?

Why it matters:
Even great materials won’t perform properly if they’re installed incorrectly.

13. Do You Handle Permits and Inspections If Needed?

Some towns require permits for roof replacement. A contractor should know what’s required locally and handle it correctly.

What to ask:

• Do you pull permits if required?
• Will inspections be scheduled if needed?

Why it matters:
Permits protect homeowners and help ensure the job meets code.

14. Do You Offer Financing Options?

Roof projects often aren’t planned—they’re unexpected. Many homeowners need flexible payment options.

What to ask:

• Do you offer financing?
• What payment methods do you accept?
• What is the deposit amount and payment schedule?

Why it matters:
Clear payment terms reduce stress and prevent misunderstandings.

15. What Should I Expect on Installation Day?

A good contractor prepares you for what the day will look like so you aren’t surprised.

What to ask:

• Will I need to move vehicles from the driveway?
• Will there be loud noise or vibration?
• Should I keep pets inside?

Why it matters:
A professional roofing company communicates clearly and helps the project run smoothly.

Choose a Roofer You Can Trust

The best roofing contractor isn’t just the one with the lowest price—it’s the one who is transparent, experienced, and willing to answer your questions clearly. Asking the right questions upfront helps you avoid scams, reduce risk, and feel confident about your investment. Contract JVW Contracting to discuss your roofing options.