12 Questions to Ask a Roofer Before Hiring a Contractor
Print this checklist. Ask every contractor these twelve questions before you sign - and know which answers are red flags.
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12 Questions to Ask a Roofer Before Hiring
Hiring a roofer isn’t like hiring a plumber. A roof replacement is a full-scale construction project that happens over your head, around your life, and with your largest asset sitting underneath it.
Here’s what most homeowners don’t realize until it’s too late: the materials matter, the price matters, but the contractor you choose is the biggest factor between a roof that lasts thirty years and one that leaks in three.
The contractors who do good work don’t dodge questions. They welcome them, because their answers separate them from the guys who show up with a truck and a prayer.
Print this list. Ask every contractor these twelve questions. Write down the answers. Compare them side by side, and the right choice will be obvious.
Questions 1-4: Verify the basics
Before you talk shingles or pricing, confirm you’re dealing with a legitimate business. Skip this step and nothing else matters.
1. What’s your license number, and how do I verify it?
A legitimate roofer knows their license number the way they know their own phone number.
Good answer: They give you the number unprompted and tell you which state board website to check.
Red flag: “We’re licensed, don’t worry about it.” No number. No verification.
Every state handles licensing differently. Some require a specific roofing license. Others use a general contractor license. A few - Missouri, Wyoming - don’t license at the state level at all. Know what applies in your area and verify the number against the actual database. Paper can be copied. The state database doesn’t lie.
2. Can I see your certificate of insurance?
This is the most important question for protecting yourself, and most homeowners skip it. You need proof of two policies:
- General liability - covers damage to your property if the crew drops a bundle through your sunroom.
- Workers’ compensation - covers injuries to workers on your property. Without it, you can be held personally liable if someone falls off your roof.
Good answer: They produce a certificate of insurance (COI) within 24 hours and agree to name you as an additional insured.
Red flag: “We’re fully insured, trust me.” Verbal insurance claims are worthless. Paper or it didn’t happen.
Call the insurance agency listed on the COI to verify the policy is active. It takes five minutes and can save you a nightmare.
3. How long have you been in business at this address?
A roofer with five years at a physical address has something to lose. A roofer with a P.O. box and a two-year history has nothing anchoring them to your community.
Good answer: Five years or more, a local street address, and references from jobs completed near you in the last year.
Red flag: “The owner has thirty years of experience. We just started this company last year.” That’s not the same thing. Experience as an employee doesn’t prove the business can handle payroll, permits, and subcontractor quality.
Take ten minutes to search their name plus “complaint” or “lawsuit.” A clean record isn’t a guarantee, but a dirty one tells you everything you need to know.
4. Who will be on-site every day, and how do I reach them?
The friendly estimator who sells the job is rarely the person who manages the installation. You need to know who has authority when things go sideways.
Good answer: A named project manager who’s on-site daily and carries a phone they answer. “Your project manager is Jake. He’ll be here every morning at 7:30, and his direct number is [number].”
Red flag: “The crew lead handles everything.” Crew leads can quit or just not care the way a salaried project manager does. You need someone with decision-making authority who’s accountable to you, not just the crew.
Questions 5-8: Understand the scope
Once you’ve confirmed they’re legitimate, it’s time to understand exactly what you’re paying for.
5. Full tear-off or overlay - and what happens when you find rot?
A full tear-off (stripping to the deck, inspecting, then installing new underlayment and shingles) is the right approach for nearly every home. Overlaying hides problems, adds weight, and usually voids manufacturer warranties.
Good answer: “We tear off to the deck, inspect everything, and replace any rotten sheathing before we install new materials.”
Safety note: A tear-off also lets the crew check that your attic ventilation, drip edge, and flashing are intact under the old material. These aren’t upgrades - they’re what prevent moisture buildup, which is the leading cause of premature shingle failure.
Red flag: “Overlay saves you money.” It does - upfront. But it hides deck damage that causes leaks down the road and guarantees a more expensive tear-off next time.
6. Can I see a line-by-line estimate?
A real estimate isn’t a single number on a scrap of paper. It’s a document you can compare against other bids.
Good answer: A two-to-four-page estimate with itemized lines for tear-off, disposal, decking repair, underlayment, flashing, shingles (brand, line, color), ventilation, and warranty.
Red flag: “$12,500 for a new roof.” That’s not an estimate - it’s a prayer. Without a breakdown you can’t compare across bids or tell what’s missing.
7. What exact shingles are you installing - brand, line, and color?
“Architectural shingles” is a category, not a product. There’s a world of difference between a GAF Timberline HDZ and a no-name brand from a discount warehouse.
Good answer: “GAF Timberline HDZ in Weathered Wood. Here’s a sample.” Brand, line, color, and any add-on features.
Red flag: “We’ll use a quality 30-year shingle.” That means “I haven’t decided, and it’ll be whatever’s cheapest at the supply house the morning we start.”
8. What’s your rate for decking replacement?
Bad decking is the most common surprise during a tear-off. A good contractor prices this upfront.
Good answer: “$85 per 4x8 sheet. We’ll photograph everything we find and get your approval before we replace anything.”
Red flag: “We’ll figure it out when we get up there.” That’s a blank check. Without a pre-agreed rate, you’re authorizing them to name their price once the old shingles are off and you have no bargaining power.
Questions 9-12: Protect yourself
The work is agreed upon. Now protect your money and your rights if something goes wrong.
9. What’s the payment schedule?
The golden rule: the contractor should never be paid in full before the work is done to your satisfaction.
Good answer: A small deposit (10-30%) when materials arrive on-site, with the balance due after a final walkthrough where you sign off.
Red flag: “We need 50% down to book your date” or “Full payment when materials drop.” These are cash-flow red flags. A well-capitalized contractor doesn’t need your money to buy materials.
Never pay in cash. Pay by check or credit card so you have recourse if the work isn’t completed.
10. What does your workmanship warranty cover, in writing?
Manufacturer warranties cover defective shingles. Workmanship warranties cover installation errors - and the mistakes that cause most leaks are installation errors.
Good answer: A written warranty with a specific duration (5, 10, or 25 years), a clear list of what’s covered and excluded, and a process for filing a claim.
Red flag: “We stand behind our work.” That’s not a warranty. Get it in writing with terms and a duration.
11. Will you pull the permit, or do I need to?
In almost every jurisdiction, the contractor pulls the permit. It’s part of their job.
Good answer: “We handle all permitting. We’ll post the permit on-site before we start and schedule the final inspection.”
Red flag: “You can save money if you pull it yourself.” Translation: “I don’t want the inspection because I’m not confident the work would pass.”
Safety note: Permits are not bureaucracy - they’re a safety net. A permitted roof has been inspected for proper nailing, flashing, ventilation, and structural compliance. When you sell, unpermitted work can delay the sale and reduce your property value.
12. Can I speak with three homeowners you’ve worked for in the last six months?
Not a Yelp page. Not Google reviews. Actual homeowners with actual roofs you can call.
Good answer: Three names, phone numbers, and addresses without hesitation. Bonus if one of them had a complication (rotten decking, weather delay) and can tell you how the contractor handled it.
Red flag: “We respect our customers’ privacy.” Or they can only give you one name from two years ago.
When you call, ask: Did they show up on time? Did they clean up every day? Would you hire them again? That last question tells you more than any review ever could.
Red flag cheat sheet
Keep this handy during your contractor meetings.
| Red flag | What it actually means |
|---|---|
| ”Sign today to lock in this price” | They’re afraid you’ll get a better bid |
| ”We’ll give you a verbal estimate” | They don’t want written accountability |
| ”We don’t have a local office” | Storm chaser or transient operator |
| ”We need 50% down” | Cash flow problem - possibly insolvent |
| ”Our work speaks for itself” | They won’t put a warranty in writing |
| ”We’ll figure out decking costs later” | They want a blank check |
| ”You can pull the permit yourself” | They’re unlicensed or expect to fail inspection |
| ”I worked for [big company] before” | That’s not a company reference |
What to bring to the meeting
When contractors show up to walk your property, come prepared.
- This list, printed. Hand them a copy - it signals you’re serious.
- A tape measure or your last appraisal dimensions. Keeps you from being quoted for a roof 30% bigger than yours.
- Photos of water stains or ceiling cracks. Helps estimators scope accurately and avoids surprises.
- A notebook. Write every answer down. After three contractors, the details blur.
The bottom line
The cheapest quote is never the best value - it’s the one where the contractor is cutting something you can’t see. The contractor who pressures you to sign today isn’t confident they’ll win on merit. And the one who dodges questions about licenses, insurance, and permits isn’t someone you want on your roof.
Get three estimates. Ask all twelve questions. Compare the answers. The difference between a pro who does good work and someone who’ll cause you years of headaches will be visible in the first fifteen minutes - if you know what to ask.
For a deeper dive on comparing estimates, see how to read a roofing estimate. If you are still building your shortlist, start with how to choose a roofing contractor before the sales calls. If the warranty language feels vague, compare it against what roof replacement warranties actually cover.
Frequently asked questions
How many estimates should I get before hiring a roofer?
Three. One estimate gives you no context. Two gives you a high and low but no middle. Three shows you the range and helps you spot the outlier - whether it’s suspiciously cheap or inexplicably expensive.
Should I tell one roofer what the others quoted?
Not until you’ve chosen one. If you reveal numbers during bidding, some contractors will undercut to win the job and then inflate the price with “unexpected issues” later.
What if a contractor won’t answer one of these questions?
That’s your answer. A contractor who hesitates on licensing, can’t produce insurance, or gets defensive about permits is telling you something. Move to the next name on your list.
Can I use the roofer my insurance company recommended?
You can, but get independent estimates too. Insurance-preferred contractors have volume relationships with carriers. An independent contractor may scope and price differently - and may work harder to earn your business directly.
What’s more important - the shingle brand or the installer?
The installer, by a wide margin. Top-tier shingles installed by a mediocre crew fail faster than mid-grade shingles installed by a crew that knows what they’re doing. Shingle defects are rare. Installation errors are common. The person holding the nail gun matters more than the logo on the wrapper.
When should I walk away from a contractor mid-conversation?
When you hear: no license number, no COI, demand for a large cash deposit, refusal to put a warranty in writing, pressure to sign immediately, or inability to name a specific project manager. You don’t owe them an explanation - you owe yourself the protection of finding someone better.
Is it worth paying more for a manufacturer-certified contractor?
Usually, yes. Certifications like GAF Master Elite or Owens Corning Preferred Contractor require the contractor to maintain proper licensing and insurance, pass training, and meet volume thresholds. Certified contractors also get upgraded manufacturer warranties. It’s not a perfect guarantee, but it’s a strong screening filter.