Questions to Ask Before Hiring a Roofing Company
A few direct questions will tell you more about a roofing company than any sales pitch.
October 14, 2026 · 4 min read

Hiring a roofer feels risky because you can't easily judge the work. You're not going to climb up and inspect the nailing yourself. What you can do is ask good questions and pay attention to how they're answered. A solid contractor will answer them without fuss, and a shaky one will get vague. Here are the questions worth asking before you sign anything. They work for a homeowner in Yorktown and for a property manager with a building in Newport News.
Are you licensed, and can I verify it?
Ask for the company's contractor license number and look it up with the state yourself. It takes a few minutes. Roof Masters, for example, lists a Class A contractor license, number 2705169040, and a Class B contractor license, number 2705129793. A real contractor will hand over the number gladly, and you can confirm that what they say matches the record.
Ask about insurance too, and ask to see proof. If a worker is hurt or something gets damaged on your property, you want to know who's responsible before the job starts, not after.
What exactly does the estimate include?
A useful estimate is in writing and specific. It should name the materials and brand, describe what's being removed and replaced, mention flashing, vents and underlayment, and say what happens to the old roofing. If two quotes look very different, compare the line items before you compare anything else, because the difference is often in what's left out.
Ask how soon you can get an estimate. Roof Masters offers a free consultation and same-week estimates, which tells you something about how the company runs.
Which manufacturers do you work with, and are you certified?
Manufacturer certifications mean the company has met requirements set by the brand, and in some cases they open the door to better warranty options. Roof Masters is a GAF Certified Plus Contractor and an Owens Corning Preferred Contractor, and it works with brands including GAF, Versico, Owens Corning, Mule-Hide and IKO. It's also affiliated with the Better Business Bureau and the NRCA. You can ask any contractor for the same kind of detail, and then check it.
What warranties do I get, in writing?
There are two kinds. The manufacturer's warranty covers the materials. The contractor's workmanship warranty covers the installation. Roof Masters provides both, and it offers upgraded GAF warranty options. Whoever you hire, ask for the terms on paper and read what is and isn't covered. A warranty is only as good as the company that stands behind it, so ask how long they've been in business. Roof Masters has been roofing the Yorktown area since 2008.
Who will be on my roof, and who do I talk to?
Find out who manages the job, whether the crew is employees or subcontractors, and who answers the phone if something comes up. Communication is where a lot of roofing jobs succeed or fall apart. One Google reviewer, Peter Harris, wrote about a repair: "Derrick was excellent at communicating options and his progress on the work performed." That's what you want: someone who tells you what's happening without being chased.
How long will it take, and what if the weather turns?
Ask for a realistic timeline and a plan for rain. Most residential replacements at Roof Masters take one to two days, but weather can shift anything. A good crew protects the open roof at the end of each day and doesn't leave you exposed overnight.
What will the property look like when you leave?
Roofing is messy, and cleanup is a real part of the job. Ask about magnetic sweeps for nails, protection for landscaping and how debris is hauled away. A customer who hired Roof Masters for a client's home sale noted the crew "left the premises super clean!!" That sounds small until you've stepped on a roofing nail in your driveway.
Can you handle emergencies, and what about later?
Roofs fail on weekends and in the middle of storms. Ask whether the company offers emergency service and whether it will come back for repairs later. Roof Masters offers 24/7 emergency service and also handles gutters, chimney flashing, skylights and ventilation, so a single company can follow up on related issues.
A quick checklist
- License number you can verify, plus proof of insurance.
- Written estimate with materials, brands and scope spelled out.
- Manufacturer certifications and the names of the products to be used.
- Written warranty terms for both the materials and the workmanship.
- A named person to contact and a clear timeline.
- A plan for weather, cleanup and emergencies.
- Recent reviews from people in your area.
Your next step
Bring these questions to any roofer you're considering, including Roof Masters. Call (757) 219-2106 for a free consultation and a same-week estimate, and ask whatever you like. The answers will tell you plenty about how the job will go.
Roof Masters, (757) 219-2106
Call (757) 219-2106More articles
How Roof Repair Companies Fix Asphalt Shingle Damage
Most shingle damage can be repaired without a new roof, if it's found early and fixed the right way.
Why Shingle Roofs Remain So Popular With American Homeowners
Shingles keep winning the everyday roofing decision for practical reasons, and a few honest limits are worth knowing.