Hiring a Roofing Contractor: 10 Questions to Ask Before You Sign

When your roof springs a leak or a storm tears shingles away, time feels like it’s running out. You want the right fix—fast. But who do you trust with your home, your business, or your peace of mind? Roofing isn’t just a patch job. It’s a shield over everything you value.

At Gregory’s Custom Roofing, we know emergency roofing calls test your confidence. Our experience has taught us that asking the right questions makes all the difference. Here’s how you can find a contractor who’s worth your trust.

Why Choosing the Right Roofer Matters 🏡

Picking a roofer isn’t like choosing a paint color or a new couch. It’s more like trusting someone to fix the brakes on your only car. If they get it wrong, the consequences can be costly—or even dangerous.

• A poor installation may void your warranty.
• Shoddy work can lead to hidden leaks, mold, or structural damage.
• Unqualified roofers may disappear when the job gets tough—leaving you with the mess.

The National Roofing Contractors Association (NRCA) and Occupational Safety and Health Administration (OSHA) both stress the importance of proper licensing, insurance, and safety training. A reputable roofing pro should be able to walk you through every step, answer your questions, and put everything in writing.

10 Essential Questions to Ask Before Signing

Don’t just nod along. These questions are your seatbelt. Buckle up before you sign.

1. Are You Licensed to Work in My Area?

Ask to see their license and verify it with your local building department. Different states and municipalities have specific rules. No license? Walk away.

2. Do You Carry Insurance?

A professional roofer carries both general liability and workers’ compensation insurance. Always request a certificate of insurance with your name and address on it. This protects you if an accident happens on your property.

3. What Warranty Do You Offer?

There are two types: manufacturer’s warranty (on materials) and workmanship warranty (on labor). Reliable roofers put both in writing. Ask for details—how long, what’s covered, and what voids the agreement.

4. Can You Provide Local References?

Call at least two recent customers. Ask about the crew’s punctuality, cleanliness, and how they handled surprises. A solid roofer has a track record in your community.

5. What Roofing Materials Do You Recommend, and Why?

Materials matter for everything from leak repair to new roof installation. Ask why they suggest shingles, metal, or tile for your property. Get details about brands and quality.

6. What’s the Estimated Timeline for My Project?

A clear schedule helps you plan—especially for emergency roofing. Ask about start and finish dates, possible weather delays, and how they’ll keep you updated.

7. Who Will Be Onsite Each Day?

Will it be the same crew, or different subcontractors? Who supervises the project? You should know who has access to your property.

8. How Will You Protect My Property?

From gutter installation to chimney flashing near you, the right contractor protects landscaping, siding, and walkways. Ask about tarps, magnetic nail sweepers, and daily cleanup practices.

9. What’s the Process for Handling Change Orders?

Sometimes hidden damage is found—like rotten decking or bad flashing. How will changes be communicated and approved? Get it in writing.

10. How Do You Handle Cleanup and Disposal?

Will they haul away old shingles and debris? What happens if a nail is left in your driveway? Ask for details about their cleanup plan.

Red Flags and Warning Signs 🚩

Sometimes, a roofer’s answer is all you need to hear. Watch for these warning signs:

• Frequent “We don’t need permits here.”
• High-pressure sales or “today only” discounts.
• Vague or verbal-only estimates.
• No physical address or unmarked vehicles.
• Insistence on large up-front payments.

If your gut says something’s off, listen. It’s better to wait an extra day than pay for a mistake.

Comparing Bids and Contracts

When the quotes start rolling in, it’s tempting to go with the lowest bid. But roofing isn’t like shopping at a discount store. Low bids can mean:

• Cheaper materials (not always visible until it’s too late)
• Cutting corners on safety or cleanup
• No written warranty

A reputable bid should be detailed and clear. Here’s what to look for:

• Full breakdown of labor, materials, and permit fees
• Start and end dates
• Payment schedule tied to project milestones
• List of included and excluded work (decking, gutters, skylight repair, etc.)
• Details on emergency roofing response time if needed

Ask for a written contract. Read it. Ask questions about anything that’s unclear.

How Gregory’s Custom Roofing Delivers Peace of Mind

At Gregory’s Custom Roofing, we treat your property as if it’s our own. Our crews are trained, certified, and insured according to state and OSHA guidelines. We handle everything from storm damage restoration and leak repair to eco-friendly options and preventative maintenance.

Here’s what you can expect when you work with us:

• Detailed written proposals for every job—no surprises
• Clear communication from first call to final inspection
• Local references and documentation available on request
• Transparent processes for chimney flashing, new roof installation, gutter repair, and all emergency roofing needs
• A commitment to safety, timely cleanup, and professional conduct

We believe you deserve a roof—and a roofer—you can count on. Download our free “10 Questions for Roofing Contractors” checklist before you interview your next pro. Take your time. Ask the hard questions. Your peace of mind is worth it.

Practical Tips for Homeowners & Property Managers

• Check with your local building department for any special permits or requirements.
• Look up your contractor on the Better Business Bureau and state licensing board.
• Take photos of your property before and after work starts.
• Keep copies of all documents and receipts for your records.
• After a storm, beware of “storm chasers” or out-of-town crews.

For more on roofing safety, see OSHA’s Residential Fall Protection guidelines and the NRCA’s Homeowner Resources.

Closing Thoughts

Choosing a roofer means putting your trust in someone’s hands. Don’t rush. Don’t settle for less. Your roof is the armor that keeps your family, your business, and your future safe.

Call Gregory's Custom Roofing now — or reach us anytime at  888-991-2840 .