The estimate meeting is your best chance to size up a roofer before any money changes hands. The right questions do two things: they surface the practical facts you need, and they reveal how the contractor thinks and communicates. Below is a checklist you can bring to every bid, grouped by topic, along with what a good answer sounds like.
The short version
Confirm licensing, liability insurance, and workers’ compensation first.
Ask who actually does the work — employees or subcontractors.
Pin down the material, warranty, timeline, and cleanup in writing.
Understand the payment schedule and never pay in full up front.
How they answer matters as much as the answers themselves.
Credentials and insurance
Start here, because nothing else matters if the basics are missing. You want a contractor who is properly licensed for your area and carries the right coverage.
Are you licensed to do roofing here, and can I see it? Requirements vary by state and city; a pro will not be offended by the question.
Do you carry general liability and workers’ compensation insurance? Ask for a certificate sent directly from their insurer, not a photocopy.
How long have you worked in this area? Local roots mean easier warranty service and a reputation they need to protect.
The crew and the work
Who climbs onto your roof, and how the job is run, has a direct effect on quality.
Will your own employees or subcontractors do the work? Either can be fine, but you should know and confirm the subs are insured too.
Who is my point of contact during the job? A named person beats a general phone line.
Will someone be on site supervising? Especially important on larger or complex roofs.
How do you protect my landscaping, gutters, and siding during tear-off? A thoughtful answer shows experience.
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Materials, scope, and timeline
Get specific here. Vague answers now become disputes later.
Exactly which material and product line will you install? Brand and line, not just “architectural shingles.”
Is the old roof being torn off or covered over? Tear-off reveals and fixes hidden problems.
What happens if you find rotted decking? You want a clear per-sheet price agreed in advance.
Are flashing, underlayment, and ventilation included? These details decide whether the roof lasts.
How long will the job take, and what is your weather plan? A realistic window beats an optimistic promise.
Question
What a good answer sounds like
Who does the work?
Named crew or vetted, insured subs — and they say so plainly
Tear-off or cover?
Recommends tear-off and explains why for your roof
Bad decking?
A set price per sheet, documented before work starts
Warranty?
Separate material and workmanship terms, both in writing
Pro tip — ask the decking question every time
The single most common cost surprise in roofing is rotted decking found after tear-off. Ask every contractor how they price it before the job starts. A pro gives you a clear per-sheet number and photographs what they replace. A vague “we’ll let you know” is how small jobs turn into big, unexpected bills.
Warranty, payment, and paperwork
Finish with the terms that protect you after the crew drives away.
What warranty do I get on materials and on your workmanship? Ask how long each lasts and whether the workmanship coverage transfers if you sell.
What is the payment schedule? A modest deposit with the balance on completion is normal; full payment up front is not.
Will everything be in a written contract? Material, scope, price, timeline, cleanup, and warranty should all be on paper.
How do you handle a callback if something leaks later? A confident answer here is reassuring.
Ready to start asking?
Line up estimates from licensed local roofers on Roofers At Your Service and bring this checklist.
Proof of insurance, especially workers’ compensation. If a worker is injured on your roof and the contractor lacks coverage, you could be exposed. It is the question most likely to protect you financially.
Is it rude to ask for references?
Not at all. A reputable roofer expects it and can provide recent local references. Call a couple and ask about timeliness, cleanup, and how problems were handled.
Should the answers be in writing?
Yes. Verbal promises are hard to enforce. Anything that matters — material, price, timeline, decking pricing, warranty — belongs in the written contract before you sign.
What if a roofer dodges these questions?
Treat evasiveness as an answer in itself. A contractor who is vague or defensive at the sales stage, when they are trying to win your business, rarely improves once they have your deposit.
General information for homeowners — not professional advice. Roofing costs, materials, codes, and insurance rules vary by location and change over time; confirm with a licensed local roofer.
