What to Ask a Roofing Contractor — 12 Questions Most Homeowners Forget

Most homeowners spend more time researching a $400 dishwasher than they do interviewing the contractor about to install a $14,000 roof. The questions below take twenty minutes to ask in person and another twenty to verify afterward. Skipping them is the single most expensive mistake homeowners make in roofing.

1. What’s your TN contractor license number?

Tennessee requires a state-issued contractor’s license for any project of $25,000 or more. Most full roof replacements clear that threshold. Get the license number, then verify it yourself at verify.tn.gov — see our license verification guide. If they can’t produce a number on the spot, walk.

2. Can I see your Certificate of Insurance?

Ask for a Certificate of Insurance issued directly by the contractor’s carrier showing both general liability ($1M minimum) and workers’ comp. Reputable contractors send this within 24 hours. Anyone offering a copy of an insurance card or a marketing one-sheet is dodging.

3. Is your business locally owned and operated?

This is the question that most often exposes storm-chaser contractors. Get a physical office address. Verify it on Google Street View. If it’s a UPS Store or a vacant lot, you’re talking to an out-of-state operator who’ll be unreachable when the workmanship warranty matters in two years. Local roofers have an actual physical presence in the Tri-Cities.

4. What shingle brand and product line are you quoting?

“Architectural shingle” can mean a 25-year builder-grade product or a 50-year premium impact-rated product. The price difference is enormous. Get the specific brand (Owens Corning, GAF, CertainTeed) and the specific product line (Duration, Timberline HDZ, Landmark) on the quote. Don’t accept generic descriptions.

5. What’s included beyond shingles?

A complete quote should include line items for:

• Underlayment (synthetic, not felt)
• Ice and water shield at eaves and valleys
• Drip edge
• New flashing (chimney, valleys, walls)
• New vent boots and pipe collars
• Ridge vent if applicable
• Permit fees
• Tear-off and disposal

The cheapest quote is almost always missing two or three of these — the contractor plans to add them as “surprise charges” on the final invoice or skip them entirely.

6. Is your install crew employed by you or subcontracted?

Many roofing companies sell jobs and then sub the actual install to independent crews. That’s not always bad, but it changes the accountability. If subbed:

• Does the sub crew carry their own workers’ comp?
• Will the same crew be on your roof for the entire job?
• Who’s on site supervising?
• Does the contractor warranty workmanship even when subbed?

Some of the best roofers use their own employees. Some excellent ones use vetted long-term sub crews. The wrong answer here is “whoever’s available the day of.”

7. What’s your workmanship warranty?

Materials warranties come from the shingle manufacturer (typically 25–50 years prorated). Workmanship warranties come from the contractor and cover install errors. A real workmanship warranty:

• Is in writing
• Covers at least 5 years; 10+ is better
• Specifies what counts as covered (leaks, blow-offs, install defects)
• Survives if the company is sold or rebrands

A 1-year workmanship warranty is a red flag. So is a verbal warranty.

8. What does your tear-off and cleanup process look like?

Tear-off is messy. Reputable contractors use:

• Tarps to protect plants and AC units
• Plywood to protect siding
• Magnetic sweepers for nails (run multiple times)
• Daily cleanup, not just final cleanup
• Dump trailers, not piles in the driveway

9. How do you handle deck repairs if you find rot?

Deck rot is the most common “surprise” on a re-roof. The right answer:

• Per-square-foot pricing for replacement decking, listed on the original quote
• Photo documentation of any rot found
• Customer notification before replacement begins

The wrong answer: “we’ll let you know what we find.” That’s how a $13,000 quote becomes a $19,000 invoice.

10. What’s your timeline?

A typical 2,000–2,500 sq ft re-roof takes 1–3 days of actual work, with a 2–6 week lead time during peak season (April–October). A contractor offering “tomorrow” in May is either lying about scheduling or running an empty book — neither is reassuring.

11. What’s your payment schedule?

Reputable TN contractors collect:

• 0–10% deposit at contract signing
• Balance on completion or net-30 from completion

Anyone demanding more than 30% up front is a red flag. Anyone demanding payment in full before work starts should be walked away from immediately. This is the question that most often exposes contractors planning to take the deposit and disappear or do shoddy work without recourse.

12. Can I see three references from jobs in the last 12 months?

Recent references matter more than testimonials. Old testimonials are easy to fake; a phone number for a homeowner whose roof was done last spring is much harder to fabricate. Call the references and ask:

• Did they show up when they said they would?
• Was the final invoice close to the original quote?
• How was the cleanup?
• Has the roof had any issues since?
• Would you hire them again?

The hire-or-walk decision

After all 12 questions and verification, you should be able to fill out this checklist:

• License verified at verify.tn.gov
• COI received and confirmed with carrier
• Local physical address confirmed
• Specific shingle brand and product line on the quote
• Complete scope of work itemized
• Crew arrangement disclosed
• Workmanship warranty in writing, 5+ years
• Tear-off and cleanup process described
• Per-sq-ft deck repair pricing listed
• Realistic timeline given (not “tomorrow”)
• Payment schedule reasonable (under 30% up front)
• Three recent references provided and called

If you can check 11 or 12 of these, you have a hire. If you can check fewer than 9, get more quotes.

What to do next

Use this checklist on every contractor that quotes your roof. The whole process — three quotes, three verification rounds — takes a few hours and pays for itself many times over. The license verification guide walks through questions 1 and 2 in detail, and the insurance vs out-of-pocket guide covers the financial decision once you have the quotes in hand.