The questions to ask a roofing contractor fall into five stages: before the estimate, about the estimate and materials, before you sign the contract, during the job, and at the final walkthrough. Ask them in that order and you’ll know who you’re hiring, what you’re paying for, and what happens if something changes halfway through.
We’ve been replacing and repairing roofs for Pittsburgh homeowners since 2003, and we answer these questions every week. For each one below, we tell you what a good answer sounds like and what a red flag sounds like, so you can compare roofing contractors in Pittsburgh side by side, including us.
Short answer: Ask for the HIC number and insurance first, an in person inspection and a written estimate that names the materials second, and a contract with payment terms, change order rules and a written warranty before you sign. A good roofer answers all of it without hesitating.
Questions to ask a roofing contractor, stage by stage
| Stage | Ask about | Good sign | Red flag |
|---|---|---|---|
| Before the estimate | HIC number, insurance, office, who does the work | Answers right away and hands over paperwork | No number, no certificates, only a cell phone |
| Estimate and materials | Inspection, repair or replace, shingle line, tear off, what’s included | Walks the roof and writes everything down | A price from a satellite photo or the curb |
| Before signing | Contract contents, payment terms, change orders, warranty, cancelling | Every promise from the estimate is in the contract | Pressure to sign today, large cash deposit |
| During the job | Your contact, weather, protecting the yard | One named contact and a daily plan | You have to chase anyone for an update |
| Final walkthrough | Inspection, cleanup, paperwork | Walks the job with you before the balance is paid | Wants full payment before you see the work |
Questions to ask a roofer before the estimate
These decide whether the company is worth an hour of your time. You can ask most of them on the phone.
1. Are you registered in Pennsylvania, and what is your HIC number?
Good answer: A number that starts with “PA,” given right away and printed on the estimate and contract. Ours is PA#126638. You can check any number on the Attorney General’s HIC search, and our guide to the Pennsylvania HIC number shows how.
Red flag: “We don’t need one for roofing,” or a number registered to a different business name.
2. Do you carry liability insurance and workers’ comp?
Good answer: “Yes, I’ll send the certificates.” Then call the agent listed to confirm the policies are current. Our post on licensed vs unlicensed roofers explains why this matters on tear off day.
Red flag: “Your homeowners policy covers my guys,” or a promise to send paperwork that never shows up.
3. Where is your office, and how long have you been in business?
Good answer: A real street address and a history you can check. We’re on Stanley Street in the 15207 zip code and have served Pittsburgh since 2003.
Red flag: Only a cell number, no address, or a crew that appeared in your neighborhood the week after a windstorm.
4. Who will actually be on my roof?
Good answer: A named crew lead and a clear answer about whether the company uses its own crew or subcontractors. At our company, crew lead Fernando runs installs.
Red flag: “We’ll find someone when your date comes up.”
Questions about the estimate and materials
5. Will you inspect the roof in person?
Good answer: Someone walks the property, measures, checks for soft decking, and looks at flashing, fascia and gutters. A roof like this one, with a hip and several dormers, has far more flashing and cutting than a simple gable, and nobody can price that honestly from above.
Greg J. noticed the difference: “Alan construction was the only company that actually came to our house to give us an estimate, not just driving by or looking at google images.”
Red flag: A firm price over the phone or from a satellite image.
A hip roof with several dormers in underlayment in Pittsburgh, Alan Construction.
6. Does my roof need a repair or a full replacement?
Good answer: A reasoned recommendation with photos of what the roofer saw, and an honest repair option when one makes sense. Our guide to roof replacement vs repair covers how to judge it, and you can see what each job involves on our roof repairs and roof replacement pages.
Red flag: Every roof needs replacing, every time, with no photos to back it up.
7. What material and product line will you use?
Good answer: A brand and line by name, plus the underlayment and flashing that go under it. We install Atlas shingles, including Pinnacle Pristine, and the estimate says so. For flat sections we use rubber EPDM, and we also work with metal, slate and tile.
Red flag: “Architectural shingles” with no brand, or a material swap you only find out about when the bundles arrive.
Synthetic underlayment covering a roof deck with shingle bundles staged on top in Pittsburgh, Alan Construction.
8. Are you tearing off the old roof, and how are bad boards handled?
Good answer: Strip to the deck, inspect the boards, replace soft wood, and write how that wood is priced into the contract.
Red flag: Shingling over the old roof without explaining the tradeoffs, or “we’ll see” about the decking with nothing in writing.
9. What exactly does the estimate include?
Good answer: Line items for tear off, underlayment, flashing, drip edge, ventilation, cleanup, haul away and any permit. Our guide to understanding your roofing estimate walks through each line.
Red flag: One number on a business card, or a price that’s only good if you sign tonight. Marti S. chose us for the opposite reason: “His price was his price. It was not going to increase it if I waited till another day to make my decision.”
10. Will you work with my insurance on storm damage?
Good answer: “Yes, and we’ll meet the adjuster at the house.” That’s how we handle storm claims.
Red flag: Someone who wants your signature before anyone has looked at the roof. Our list of red flags when getting a new roof covers more of these.
Questions to ask before signing a roofing contract
This is where homeowners rush and regret it. Read the whole roofing contract, not just the total.
11. What should a roofing contract include?
Pennsylvania’s Home Improvement Consumer Protection Act spells out what a home improvement contract needs. At minimum, look for:
- The contractor’s HIC number, name, street address and phone number.
- Signatures from you and the contractor, and the date.
- An approximate start date and completion date.
- A description of the work and the materials, by name.
- The total price and the down payment.
- Any subcontractors known at signing.
- The amount of liability insurance the contractor carries.
- A notice of your right to cancel within three business days.
If anything you discussed at the estimate is missing, have it added before you sign.
12. What are the payment terms?
Good answer: A deposit at signing that follows the state limit on larger jobs, and the balance after the work is done and you’ve walked it. If you want to spread payments out, ask about financing now, not after the crew shows up.
Red flag: Most of the money up front, cash only, or payment demanded before the contract is signed.
13. How do you handle a contractor change order?
Good answer: “If we find something once the old roof is off, we stop, show you photos, and write a change order you sign before we go further.” On older Pittsburgh houses, soft boards under the shingles are common, and nobody can see them from the ground.
Pennsylvania law says the work in your contract can’t change without a written change order signed by both sides.
Red flag: “We’ll settle up at the end,” or extra work agreed with a nod on the driveway.
A row house roof stripped to bare boards in Pittsburgh, Alan Construction.
14. What warranty comes with the job, and is it in writing?
Good answer: A written workmanship warranty from the roofer, plus the manufacturer’s product warranty details for your shingle, and who you call if there’s a problem.
Red flag: A verbal promise, or a warranty that only appears after the final payment.
15. Can I cancel after I sign?
Good answer: “Yes, you have three business days to cancel without penalty, and it’s in the contract.”
Red flag: No cancellation notice at all, or a claim that the deposit is gone the minute you sign.
Questions to ask during the job
16. Who is my contact, and how will you keep me updated?
Good answer: One named person who calls before the start date and if anything changes. With us, owner Alan Landy still looks at jobs himself and James handles estimates and jobs. Marie K. wrote: “Alan was always responsive and kept me informed along the way.”
17. How will you protect my yard and my neighbors’?
Good answer: Tarps over shrubs and beds, and a plan for the dumpster on a tight city lot. Geneva C. noticed: “I appreciated that his team was considerate of my neighbors yard and put tarp on it.”
Drone view of a roof under work between neighboring homes in Pittsburgh, Alan Construction.
18. How long will it take, and what happens if it rains?
Good answer: A realistic estimate and a promise not to tear off with rain coming. Most of our roofing jobs are finished in one day. Our roof replacement timeline shows how the day goes.
Red flag: A roof left open overnight with no tarp, or a start date nobody confirms.
Questions to ask at the final walkthrough
19. Will you walk the job with me before I pay the balance?
Good answer: “Yes, and anything that isn’t right goes on a punch list we fix before closing out.” On the walk, look for straight shingle lines, neat flashing at walls and chimneys, gutters reattached and draining, and no debris in the beds.
20. How do you clean up the nails?
Good answer: A magnetic sweep of the yard, driveway and beds before the crew leaves. Kenny K. wrote after his job: “They left no nails in my rock bed or grass.”
21. What paperwork do I get at the end?
Good answer: The signed contract, any change orders, the written warranty, product warranty details, and a receipt marked paid in full. Ask for progress photos of the underlayment and any replaced boards too, since those layers are hidden for good.
If windows are part of the same project, our questions to ask a window contractor cover that side of it.
Frequently Asked Questions
Start with the essentials: what is your Pennsylvania HIC number, can I see your liability and workers' comp certificates, will you inspect the roof in person, which shingle line will you use, how do you handle change orders, what are the payment terms, and what warranty do I get in writing.
A good roofer has an active HIC number you can verify, carries insurance and shows you the certificates, inspects the roof in person, and puts the materials, price, payment terms and warranty in writing. They don't pressure you to sign the same day. Recent Google reviews and a local address are good signs too.
In Pennsylvania, a roofing contract should show the contractor's HIC number, name, address and phone number, the start and completion dates, a description of the work and materials, the total price and down payment, any known subcontractors, the liability insurance amount, and a notice of your right to cancel within three business days. Any later change needs a written change order signed by both sides.
Pennsylvania gives homeowners three business days after signing a home improvement contract to cancel without penalty, and the contract must tell you so. After that window, getting out depends on the contract terms. If a contractor has broken the agreement or the contract doesn't meet state law, the Pennsylvania Attorney General's consumer protection office is the place to ask.
You don't have to, but it helps to be reachable in case the crew finds soft boards or needs a quick decision. Tear off is loud and can shake top floor walls, so many people with young kids, pets or a home office plan to be out for the day.
Want straight answers to every question on this list? Request a free estimate and we’ll inspect your roof in person and put everything in writing.
