18 Questions to Ask a Roofing Contractor | With Good and Bad Answers

Homeowners are often handed a list of questions to ask a roofer without any guidance on how to interpret the replies, which means a confident wrong answer passes as easily as a correct one. This page pairs each question with the answer you want and the answer that should disqualify the company. Use it as an interview script during the estimate.

Credentials and Coverage

1. What license do you hold that covers my specific address?

Good: A specific answer naming the authority. On the Illinois side, a state IDFPR roofing license number you can look up. On the Missouri side, the city or county credential that applies to your address, with an acknowledgment that Missouri has no statewide license.

Disqualifying: "Missouri doesn't require a license" offered as a reason not to hold anything at all. The absence of a state license does not mean the absence of local requirements.

2. Do you carry workers' compensation, and can your agent confirm it to me directly?

Good: Yes, with the agency name and number offered without friction.

Disqualifying: Hesitation, a forwarded PDF instead of carrier contact, or "my crews are subcontractors, so it's on them." If an uninsured worker is hurt on your roof, that can reach your homeowners policy.

3. How long has this company operated under this name?

Good: A year you can verify in the Secretary of State registry.

Disqualifying: A long history claimed under one name with an entity registered shortly after the last major hailstorm. Serial re-registration is a way to shed warranty obligations and complaint history.

4. Who pulls the permit, and which authority issues it for my address?

Good: They pull it, and they name the correct authority - which in this metro means knowing the City of St. Louis permits separately from St. Louis County, and that individual municipalities and St. Charles County have their own requirements.

Disqualifying: An offer to skip the permit to save money, or not knowing who issues it.

The Crew and the Work

5. Are the installers your employees or subcontractors?

Good: A straight answer either way, with a clear explanation of who carries the insurance and who is accountable.

Disqualifying: Evasion. You are entitled to know who will be on your property.

6. Who is my point of contact on install day, and will they be on site?

Good: A named person, reachable, with someone on site who can make decisions.

Disqualifying: The salesperson disappears after signing and you are routed to a general office line.

7. Will you photograph what you find and show me?

Good: Photographs of specific conditions - a failed pipe boot gasket, rusted step flashing, granule loss on the storm-facing slope, soft decking at a located spot.

Disqualifying: A verdict with no evidence, or generic stock photos that are not of your roof.

8. Is the old roof coming off, or going over?

Good: Clear specification either way, with the local code position on layovers.

Disqualifying: Vagueness. A layover quoted against competitors' tear-offs is not the same product at a better price.

9. Are you replacing the flashing or reusing it?

Good: New step and counter flashing at walls and chimneys, new pipe boots.

Disqualifying: Reuse presented as standard. Reused flashing is among the most common reasons a brand-new roof leaks.

10. What are you doing about ventilation?

Good: An assessment of intake and exhaust, and a correction if the existing setup is inadequate.

Disqualifying: Silence on the subject. Poor ventilation cooks shingles from underneath and shortens the life of the roof you are about to pay for.

11. What happens if it rains mid-job?

Good: A described process for drying the roof in overnight and mid-storm.

Disqualifying: Improvisation, or an implication that it will not happen. In this market, it will.

Money

12. Can I see the estimate itemized?

Good: Line items for tear-off, underlayment, ice-and-water shield, flashing, ventilation, penetrations, decking with a per-sheet price, disposal, and permit.

Disqualifying: One number, or an itemization refused as proprietary.

13. How is rotted decking priced if you find it?

Good: A stated per-sheet price in the contract and a change order requiring your written approval.

Disqualifying: "We'll let you know" - which means an open-ended charge discovered at the worst moment.

14. What is the deposit and what triggers the balance?

Good: A modest deposit, balance on completion, written into the contract.

Disqualifying: Full payment up front, or a deposit sized to fund the entire job.

15. If I am on an insurance claim, how does payment sequence?

Good: A clear explanation of actual cash value released first and depreciation held back until completed work is documented.

Disqualifying: Any offer to waive, absorb, or "work around" your deductible. That is insurance fraud, and you are the one on the policy.

After the Job

16. Can I read the workmanship warranty before I sign?

Good: The document, handed over, with exclusions and transfer terms in it.

Disqualifying: A verbal "lifetime warranty" with no paper behind it.

17. Does the warranty transfer if I sell the house, and is there a fee?

Good: A direct answer. Transferability is a real resale asset, and the terms vary legitimately.

Disqualifying: Not knowing the terms of their own warranty.

18. Can you give me references from completed jobs in my municipality?

Good: Recent addresses or customers in your own city or an adjacent one.

Disqualifying: References only from forty miles away, which suggests they have not worked your area or your permitting authority.

How We Answer These

We would rather be asked all eighteen. The short version of our answers: founded 1947 and family-run through three generations under the same name; we hold what each jurisdiction requires and will give you the number for your address; general liability and workers' compensation with carrier confirmation available; we pull the permit and meet the inspector; the inspection is free and photographed; the estimate is itemized; the limited lifetime workmanship warranty is on every roof we install and readable before you ever speak to us; and we will give you references from work in your own municipality. More than 50,000 customers across the Midwest, and winner of the Better Business Bureau Torch Award for Ethics.

Common Questions

What is the most important question to ask a roofing contractor?

If you only ask one, ask whether their agent can confirm workers' compensation coverage to you directly. It is the question that most reliably separates established companies from temporary ones, because carrying workers' comp is expensive and uninsured operators cannot fake a call to a real agency. It also protects you from the worst financial exposure in the whole transaction, since an injury to an uninsured worker on your roof can end up reaching your homeowners policy.

Is it rude to ask a roofer for proof of insurance?

No, and a contractor's reaction to being asked is diagnostic in itself. Established companies are asked constantly and have the certificate and agent contact ready. Take the request one step further than most homeowners do: rather than accepting a PDF from the contractor, ask for the agency's name and number and call to confirm the policy is active, since a document can be altered or kept past its expiration date.

What should I ask about a roofing warranty?

Four things. Whether the workmanship warranty exists as an actual document you can read before signing rather than a verbal promise. What specifically voids it. Whether it transfers to a buyer if you sell the house, and at what fee. And separately, what the manufacturer's product warranty covers, since the shingle warranty and the installation warranty are two different instruments and most roof failures are installation failures rather than product defects.

How can I tell if a roofer is overcharging me?

Price alone will not tell you, because three estimates are often describing three different jobs. Get every estimate itemized across the same lines - tear-off versus overlay, underlayment type, ice-and-water shield placement, new versus reused flashing, ventilation work, pipe boots, decking price per sheet, disposal and permit - then compare row by row. A high price with a complete scope and a low price with reused flashing and no ventilation correction are not the same product, and the low number frequently becomes the higher one by the end.

Should I ask for local references from a roofing company?

Yes, and specify your own municipality rather than accepting references from anywhere in the metro. A company with recent completed jobs in your city has worked your permitting authority and knows the housing stock, which matters more than it sounds - the roofs and the permit process in the City of St. Louis are meaningfully different from those in St. Charles County. References clustered far from you can indicate a company that does not actually work your area.

What questions should I ask about an insurance roof claim?

Ask how the contractor handles the two-stage payment structure, since carriers typically release actual cash value up front and hold depreciation until the finished work is documented. Ask whether they will meet your adjuster on the roof. Ask what happens if the carrier's scope is narrower than theirs. And treat any offer to waive, absorb or discount your deductible as a reason to end the conversation - it is insurance fraud, and the policy is in your name, not the contractor's.

Keep Reading

How to Read Roofing Reviews How to Choose a Roofing Contractor How to Verify a Roofer Longevity and Warranty Survival Best Roofing Companies in St. Louis: The Comparison Framework

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