You've gotten two or three roofing quotes. The prices are in the same ballpark, the contractors seem professional, and now you have to choose. How do you tell the difference between a roofer who'll do the job right and one who'll cut corners you won't discover until water is coming through your ceiling?
Ask these questions before you sign. A confident, specific answer to each one signals a contractor who knows their business. Vague answers, deflections, or pressure to sign quickly signal the opposite.
1. Will You Pull the Metro Nashville Building Permit?
This is the first question — not because it's the most dramatic, but because the answer immediately reveals whether a contractor is operating legitimately. Your roofer should pull the permit under their Tennessee contractor's license without hesitation. If they suggest you handle it, or claim a permit isn't required for a full replacement, that's a disqualifying answer.
For a full explanation of why this matters, see our guide on finding a Nashville roofer who handles the permit process.
2. Can I Have Your Tennessee Contractor License Number?
Tennessee requires a Home Improvement license (TDCI) for residential roofing projects over $3,000. Ask for the number and verify it at verify.tn.gov before signing. Active license, no disciplinary history — that's the baseline. Any contractor who resists this request is telling you something important.
3. Are You Insured — and Can I See the Certificate?
You need two types of coverage confirmed in writing: general liability (if they damage your property) and workers' compensation (if a worker is injured on your roof). Ask for a certificate of insurance naming you as the certificate holder. If they can't produce one within a day, move on.
4. Who Will Actually Be on My Roof?
Some Nashville roofing companies use their own trained employees. Others are essentially brokers who subcontract the actual labor to whoever is available. Neither is automatically bad — but you deserve to know. If subcontractors are involved, ask whether they're covered under the same insurance and whether the primary contractor guarantees their workmanship.
5. What Specifically Are You Installing?
Ask for the exact shingle brand, product line, and grade. "30-year architectural shingles" is not a sufficient answer. The difference between Owens Corning Duration and a builder-grade 3-tab shingle is significant — in cost, performance, and warranty. Get the manufacturer name and model in writing, in the contract.
6. Are You a Certified Installer for That Shingle Brand?
Most major shingle manufacturers — GAF, Owens Corning, CertainTeed — offer certification programs to contractors who meet installation training and quality standards. Certified installers can unlock extended warranties (50-year vs. 30-year) for their customers at no additional cost. Ask whether they're certified and what warranty tier that unlocks for your project.
7. How Many Layers Are on My Roof Currently, and What's Your Plan?
Metro Nashville code limits most roofs to two shingle layers. If you already have two layers, tear-off is required — no overlay allowed. Ask how many layers exist and what the contractor plans to do. If they propose overlaying onto two existing layers to save money, that's a code violation and a future problem you'll pay for.
8. What Happens If You Find Damaged Decking?
Once old shingles are off, damaged OSB decking sometimes appears. Ask upfront: what's the per-sheet cost to replace damaged decking, and how do they communicate this discovery before proceeding? A legitimate contractor will call you with a photo and a per-sheet price before adding cost. Contractors who just replace it and add it to the final bill without notification should be avoided.
9. What Does Your Workmanship Warranty Cover and How Long Is It?
The manufacturer warrants the shingles. The contractor warrants their installation. These are separate. Ask for the workmanship warranty in writing — what it covers, how long it lasts (2–10 years is typical), and whether it transfers to a new owner if you sell. A contractor who can't explain their workmanship warranty clearly may not intend to be reachable if problems arise.
10. What Is the Payment Schedule?
A reasonable payment structure for a Nashville roofing project is roughly 10–30% upfront to cover material deposits, with the balance due upon completion. Contractors who demand 50% or more upfront — especially in cash — are a risk. Full payment before work begins is never appropriate. Get the payment schedule in the contract, not just verbally agreed upon.
One More Thing: How We Pre-Vet Contractors at US Home Renovations
If you'd rather start from a list of contractors who've already cleared the licensing and insurance bar, our Nashville roofing directory screens for active Tennessee licensure before listing. That doesn't replace your own questions — every project has specifics a directory can't know — but it removes the first layer of risk from the search.
Use the questions above on any contractor you speak with. The good ones will answer every single one without blinking.
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