Most roofing decisions are made on the front porch, in the first ten minutes, with a clipboard and a contract. The pattern that lets you beat that pressure is having the right questions ready before the contractor arrives. Not a long list. A short one, in the right order, that takes thirty minutes total across two phone calls and one inspection. Here is the list, the order, and what to listen for in the answers.
This is a spoke under the broader how-to-hire-a-roofer guide. Read the pillar first if you have not, then come back here for the exact phrasing.
Before you call: what to have on hand
Three pieces of information make the call substantially better. None of them are about your house. They are about how you want to evaluate the contractor.
Your insurance policy declaration page. You do not need to share it with the contractor. You need to know your deductible, your coverage type (ACV versus replacement cost), and whether your policy has a separate wind/hail deductible. A contractor who tries to pressure you into a specific scope without seeing the policy is reading off a script.
The contractor's website open in a tab. Look at the office address, the state license number, and the manufacturer certifications listed. You are about to verify each of these against an independent source during the call.
A pen and a single sheet of paper. You will write down four things: the office address they give you on the call, the license number they recite, the names on the COI they promise to send, and the permit pull policy. Notes prevent the "I-think-they-said" problem when you compare contractors a week from now.
The four disqualifying questions
Ask these in the first three minutes. If any answer comes back vague, evasive, or angry, end the call. You have not lost anything. There are other contractors.
"What is your physical office address?" Then look it up in Google Maps Street View while they answer. A real address resolves to a building with signage. A UPS Store, a Regus suite, a residential address in another state, a short-term rental: walk away.
"What is your state license or registration number, and which regulator issued it?" Real contractors recite it from memory. They name the issuing body without prompting. They expect you to verify. Anyone who pushes back ("you don't need that, just trust me") is the wrong contractor.
"Will you pull the building permit in your own name?" The answer is yes. Storm-chasers ask the homeowner to pull the permit because the contractor does not intend to be the licensed party on record when something goes wrong. Any answer other than yes ends the call.
"Will you email me a current Certificate of Insurance with your agent's name and direct number?" Yes, within twenty-four hours. Not a screenshot. Not a PDF that expired last quarter. A current COI with a callable agent. Then you call the agent and confirm the policy is active. Real agents pick up the phone.
Questions during the on-roof inspection
The contractor shows up. They get on the roof for thirty to forty-five minutes. They come down with photos and notes. These are the questions to ask in the next ten minutes, before they leave.
"Walk me through what you photographed." They should have fifteen to thirty photos: flashing at each penetration, valleys, ridge cap, drip edge, attic ventilation, decking condition, granule wear, hail strikes if relevant. A contractor who took five photos was not on the roof for forty minutes.
"What condition is the decking in, and how much will you need to replace?" A real answer includes a per-sheet estimate. "I won't know until we open it up" is fine if paired with a written per-sheet rate. Storm-chasers say "it's fine" because they have not actually looked.
"What does your ventilation calculation come out to?" Code requires one square foot of ventilation per 150 to 300 square feet of attic, balanced between intake and exhaust. A real contractor has done this math before quoting. A storm-chaser waves at the existing turbines.
"Will you remove the existing layer, or install over?" Most municipalities allow a maximum of two layers, and many ban layered installs entirely. A contractor who proposes installing over an existing two-layer roof is proposing code violation.
"What shingle line are you quoting, and why that one for my house?" They should name a specific product (GAF Timberline HDZ, Owens Corning Duration, CertainTeed Landmark, Malarkey Vista) and explain the choice based on your climate, your existing roof pitch, and your wind-rating needs. "We use whatever the supplier has" is not an answer.
Questions to ask after the written estimate
The estimate arrives within forty-eight hours. You read it. These are the questions to ask before you sign.
"Why is the decking allowance line set at X?" Decking replacement is the variable cost on every job. A real contractor will explain how they arrived at the allowance based on what they saw on the roof and what the typical pattern is for homes of similar age in your area.
"What is your in-house workmanship warranty, and what does it cover?" Separate from the manufacturer warranty. Real contractors offer one to five years on workmanship in writing. The warranty document should specify what is covered, what voids it, and how to make a claim. "Lifetime" warranties from contractors who have existed for sixty days are not warranties.
"Are you certified by the shingle manufacturer, and what does that unlock for me?" GAF Master Elite, Owens Corning Platinum Preferred, CertainTeed SELECT ShingleMaster, and Malarkey Emerald Premier each unlock extended labor warranties (commonly twenty-five to fifty years). Verify the certification on the manufacturer's own contractor-locator before you sign. A surprising number of websites display lapsed certifications.
"What is your payment schedule?" Standard is a small deposit (10 to 25 percent) at signing or material delivery, with the balance due at completion. A contractor who requires 50 percent or more up front is either undercapitalized or planning to walk. Either way, not your problem to solve.
"How many homes have you re-roofed at this address in the last twelve months?" Real local operators do thirty to two hundred residential re-roofs per year depending on crew size. A contractor who cannot give you a rough number, or quotes a number that does not match their crew capacity, is improvising.
Questions specific to storm and insurance work
If you are filing an insurance claim, these questions land on top of the previous ones. The insurance-claim guide covers the full process; these are the contractor-facing pieces.
"Will you meet my insurance adjuster on the roof at no charge to me?" Yes. That meeting is the single highest-leverage conversation in the entire claim. A contractor who refuses to meet the adjuster is either not licensed to do the work or not confident in their scope. Both are problems.
"How do supplements work in your process, and who files them?" Supplements are documented requests to raise the claim based on damage found during work. The contractor files them with photos and written justification. They do not need an Assignment of Benefits to file a supplement. Anyone who insists on an AOB to handle supplements is a hard no.
"Will you absorb my deductible?" No. The correct answer is no, and a contractor who volunteers that absorbing a deductible is illegal under §707 of the Texas Insurance Code without you having to ask is the right kind of contractor.
"What does the depreciation check look like for my claim?" Most policies pay actual cash value (cost minus depreciation) up front, with the recoverable depreciation released after the work is complete and the invoice is submitted. A contractor who pretends not to understand this is reading a script. Real contractors walk you through it before you sign anything.
Red-flag answers and the patterns they reveal
The same wrong answers come back in storm market after storm market. Recognizing the pattern saves hours of due diligence.
"We've been in roofing for thirty years." Usually true (about the owner personally), usually paired with an LLC formed sixty days ago. Ask the precise question: how long has this entity, at this address, operated.
"We're booked solid, but we can fit you in if you sign today." Time pressure tactic. Real contractors are honestly booked four to eight weeks out after a major event. They will say so, and they will not move you up by signing faster.
"Your neighbor already signed with us." Social-proof manipulation. Your neighbor's decision is information about your neighbor, not about whether this contractor belongs on your roof.
"We don't need an inspection, we can see the damage from here." A contractor quoting from the curb has not inspected your roof. No exceptions.
"We'll waive the deductible if you sign now." Insurance fraud. Federally and state-illegal in most jurisdictions. The contractor is offering to commit a felony with you. End the call.
"Just sign here and we'll handle everything with the insurance company." Assignment of Benefits. The storm-scam guide covers the patterns in detail. Walk away.
The questions are the filter. Ask them in this order, write the answers down, and the wrong contractors will sort themselves out before they ever get on your roof. The ones who survive are the ones worth talking to. If we cover your market, our coverage page lists the roofers in your city who have already cleared every check on this list.