Top 10 Questions to Ask Roofers and Siding Contractors Near Me Before Hiring

Hiring a roofing or siding contractor shouldn’t feel like a gamble. Your home is your biggest investment, and whoever touches it should treat it that way. Yet too many homeowners skip the most important step: asking the right questions before signing a contract.

Whether you’re dealing with a leaky roof or outdated siding, the search for trusted roofing contractors in Connecticut starts with curiosity—and confidence. At JS & R Roofing, we believe smart homeowners ask smart questions. And we’re here for every one of them.

Here are the Top 10 Questions you should always ask before hiring roofers or siding contractors near you.

This might seem obvious, but never assume. Licensing shows they meet state standards. Insurance? That’s your safety net. If something goes wrong—on your roof or on your lawn—you want to be protected.

JS & R Roofing is fully licensed and insured throughout Connecticut. No cutting corners, no risk on your part.

Experience is great. But local experience is gold. Connecticut’s climate, building codes, and neighborhood styles are unique. You want someone who’s navigated ice dams, humid summers, and unpredictable Nor’easters.

JS & R has been helping Connecticut homeowners for years. We know the towns. We know the weather. We know what works.

Any contractor worth your time should be proud to show off their work. Ask for photos, reviews, or drive-by addresses of recent jobs. A good track record speaks volumes.

Need proof? We’ve got satisfied customers across the state who would be happy to tell you about their JS & R experience.

Not all shingles, siding panels, or underlayments are created equal. Great contractors will walk you through options and explain what fits your home, budget, and style best.

We take pride in offering high-quality materials from trusted brands—because your home deserves better than “basic.”

Connecticut towns can have very specific permitting rules. Some contractors leave that headache to the homeowner. JS & R Roofing? We take care of all necessary permits and schedule inspections when required.

Because you’ve got better things to do than navigate the town hall.

You need a written plan. That means:

• What’s being done
• How long it will take
• What happens if the weather delays us

A clear timeline eliminates confusion and sets expectations from day one.

Ask about both material warranties and labor guarantees. One without the other is a red flag.

JS & R Roofing offers strong warranties that back up our work, because we stand by every nail, seal, and panel we install.

Here’s a detail most homeowners forget—until their lawn is covered in nails, shingles, and old siding.

We treat your property with respect. Our crews clean up every day and do a final sweep before we leave. Your yard will look just as good as your new roof or siding.

It’s important to know who’s in charge. Meet your project manager before work begins. That’s your go-to for updates, questions, and anything unexpected.

At JS & R, we don’t outsource oversight. You’ll always know who’s on your team.

Don’t be shy—ask about payment. Understand what’s due upfront, when progress payments happen, and how to pay your final balance.

We believe in clear, upfront pricing, and we’ll walk you through every dollar.

From the shoreline to the quiet suburbs, JS & R Roofing is known for honest work, expert craftsmanship, and neighborly service. We don’t just want to earn your business—we want to earn your trust.

Looking for reliable roofing contractors in Connecticut who also do top-tier siding? You just found them.

Use this list when talking to any contractor, but know that when you work with JS & R Roofing, we’ve got every answer covered.

✅ Local experts
✅ Full exterior solutions
✅ Licensed, insured, and fully transparent

📞 Contact us today to schedule your free consultation.
📍 Proudly serving communities throughout Connecticut