10 Critical Questions to Ask a Roofing Contractor Before Hiring Them

You have 3-4 bids. All seem legit.

But one contractor will do quality work with integrity, and another will cause you nightmares.

Here's how to tell them apart.

Question 1: "What's your Virginia DPOR contractor license number?"

This should be the easiest question they answer.

Virginia requires Class A or B contractor license for roofing work over $1,000 (which is every roof job).

Right answer: They give you the license number immediately. "2705-123456A" or similar format.

Wrong answer:

• "It's on my truck" (go look, then verify it)
• "I don't have it with me" (red flag, they should know their own license)
• "My boss has that" (you're talking to unlicensed salesperson)
• "We don't need one for roofing" (absolutely false)

How to verify: Virginia Department of Professional and Occupational Regulation website (dpor.virginia.gov). Search contractor name or license number.

Check for:

• License is active (not expired or suspended)
• No disciplinary actions
• Correct business name matches who you're talking to

We've had Richmond homeowners call us after hiring unlicensed contractors. Contractor vanishes mid-project. No recourse. Money gone. Half a roof.

Don't skip this step.

Question 2: "Do you carry liability and workers' comp insurance?"

If an uninsured worker gets hurt on your roof, you're liable. Your homeowner's insurance might cover it, might not. Either way, your rates go up.

Right answer: "Yes, let me get you certificates from our insurance company."

They should provide:

• General liability certificate ($1-2 million minimum)
• Workers' compensation certificate (if they have employees)
• Contact info for insurance company

Critical step: Call the insurance company directly. Verify policies are current, not expired.

We've seen fake certificates. Photoshopped. Expired ones contractors keep using.

Wrong answer:

• "We're bonded" (not the same as insured)
• "Our insurance is included in the price" (doesn't answer the question)
• "You don't need to worry about that" (you absolutely do)
• Resistance to providing proof

No current insurance? No hire. Period.

Question 3: "Can I see 3 recent local references with addresses?"

Specific request: Recent (last 6 months), local (Richmond area), addresses included (so you can drive by).

Why addresses matter: Anyone can give you their brother-in-law's phone number. Addresses let you verify real projects.

Drive by the addresses. Look at the roofs. Do they look good?

When you call references, ask:

"How was the quality of work?" (Look for specifics, not generic "fine")

"Did they finish on time?" (Weather delays are understandable. Chronic lateness isn't.)

"How was cleanup?" (Nails in your driveway for 6 months? No thanks.)

"Were there any surprises with cost?" (Change orders happen, but constant upcharges are red flag.)

"Any issues after installation? How did they respond?" (Good contractors fix problems promptly.)

"Would you hire them again?" (Simplest question, most telling answer.)

Wrong answer:

• Only provides phone numbers, no addresses
• References are from 3 years ago
• Projects are all in North Carolina (storm chaser)
• "We don't give out customer info" (privacy is valid, but good contractors have willing references)

Question 4: "What's included in your warranty, and who stands behind it?"

Roofing has two warranties: manufacturer (materials) and workmanship (installation).

Manufacturer warranty:

Covers defective shingles. Typical: 25-50 years for materials, prorated after 10 years.

Doesn't cover installation errors. Doesn't cover storm damage. Doesn't cover normal wear.

Requires registration (usually within 60 days of installation).

Workmanship warranty:

Covers installation errors. Leaks from improper flashing, missed nails, poor ventilation design.

Good contractors: 10+ year workmanship warranty.

Average contractors: 5 years.

Bad contractors: 1 year or "manufacturer warranty only."

Critical questions about warranty:

Is workmanship warranty transferable if you sell house? (Good ones are.)

How do you file a claim? (Process should be simple.)

Are there exclusions? (Read fine print. "Act of God" exclusions can be abused.)

What happens if your company goes out of business? (Manufacturer warranty remains, workmanship warranty dies with company.)

Red flags:

"Lifetime warranty" with no written details.

Vague answers about what's covered.

No mention of workmanship warranty at all.

Question 5: "Will you be using subcontractors?"

Not inherently bad. Many companies use subs. But you need to know.

Follow-up questions if they use subs:

Are subcontractors also insured? (Get their certificates too.)

Will the same crew be there every day? (Consistency matters.)

Who supervises the work? (Your contractor or the sub?)

Who handles warranty claims? (Prime contractor should, regardless of who installed.)

Red flag answers:

"It depends" (on what?)

"Sometimes" (when?)

Evasive non-answers.

Good contractors using subs:

"Yes, we use a 4-person installation crew we've worked with for 8 years. They're fully insured. I'm on-site daily to supervise. All warranty claims go through me."

Bad contractors using subs:

"We might sub out parts of it." (Which parts? To whom? No idea.)

Question 6: "What's your payment schedule?"

Industry standard in Virginia: deposit, progress payment, final payment.

Reasonable schedule:

10-20% deposit to order materials and secure your spot.

30-40% after tear-off when you can inspect decking.

Remaining balance after completion and your approval.

Unreasonable schedule:

50%+ upfront before work starts.

100% before work starts (absolute scam).

Cash only, no checks or cards (why? tax evasion? money laundering?)

"Pay the crew directly at end of each day" (you don't know these people)

Good contractors explain payment timing:

"We take 15% deposit when you sign. This covers materials and gets you on schedule. Progress payment of 40% after tear-off and decking inspection. Final 45% when project's complete and you're satisfied."

Clear. Reasonable. Protects both parties.

Red flag contractor:

"We need 60% to start work and the rest halfway through."

Why 60%? If they vanish with your money, you're out $9,000+ with partial work.

Never pay more than 50% before completion. Preferably less.

Question 7: "How do you handle unexpected issues?"

Rotted decking gets discovered during tear-off. Happens constantly.

Good answer:

"We include an allowance in our bid for typical decking repair. If we find rot, I stop work, show you the damage, explain what needs fixing and the cost. You approve before we proceed. If it's within the allowance, no extra charge. If it's extensive, we have a set price per square foot in the contract."

Clear process. No surprises. You stay in control.

Bad answer:

"We fix whatever we find and bill you at the end." (How much? Who decides what's necessary?)

"That almost never happens." (It happens regularly.)

"Don't worry, we take care of everything." (Translation: We charge whatever we want, and you'll pay because your roof is torn off.)

Ask specifically:

"What's your price per square foot for decking replacement?" (Should be in writing.)

"Do you stop for approval or make decisions on the fly?" (Stop for approval is correct answer.)

"Can I see what you find before repair?" (Yes, via photos if you're not home.)

Question 8: "Who obtains the permit?"

Contractor should handle this. They know the requirements, have relationships with inspectors, understand the process.

Right answer:

"We pull all necessary permits. Cost is $X (itemized in bid). We schedule inspections and handle county requirements. You don't have to do anything."

Wrong answer:

"You don't need a permit for this." (Wrong. Henrico and Chesterfield require permits for full replacements.)

"Permits are optional." (No, they're not.)

"We can skip it to save money." (Saves them hassle, costs you later.)

Why permits matter:

Insurance claims can be denied for unpermitted work.

Home sale gets complicated. Buyer's inspector finds unpermitted roof, deal falls apart.

No recourse if work is shoddy. Code enforcement won't help with illegal work.

How to verify:

Both Henrico and Chesterfield have online permit lookup. Search your address after contractor says permit is pulled.

If they said they pulled it but nothing shows up? Call them out.

Question 9: "What happens if it rains during the project?"

Richmond weather is unpredictable. Rain happens.

Good answer:

"We watch weather forecasts closely. If rain is likely, we don't start tear-off that day. If we're caught by surprise, we have tarps ready to protect your home. We secure everything before leaving. If multi-day rain delay happens with roof open, we install temporary protection at no charge."

They have a plan. You're protected.

Bad answer:

"Hopefully it doesn't rain." (Hope is not a strategy.)

"We work in light rain." (Shingles shouldn't be installed on wet surfaces.)

Silence or uncertainty.

Ask specifically:

"Who pays if rain damages interior because protection failed?" (Should be covered by their insurance.)

"What temporary protection do you use?" (Tarps, plastic sheeting, secured properly.)

Question 10: "What's your cleanup process?"

Roof replacement creates debris. Thousands of nails. Shingle granules. Torn materials.

Complete answer:

"We put tarps down before starting to catch debris. Dumpster gets loaded throughout project. At end of each day, we do magnetic sweep for nails. After final completion, we do another magnetic sweep of entire property including driveway. We inspect gutters for debris. Everything gets hauled away, including dumpster."

Thorough. Professional.

Incomplete answer:

"We clean up when we're done." (How? How well?)

"Dumpster rental is extra." (Should be included in bid.)

Vague assurances without specifics.

Reality check:

We use magnetic rollers after every job. Still find nails we missed first pass.

Homeowner finding nails in driveway 6 months later? That's on the contractor.

Bonus Red Flags That Should End the Conversation

High-pressure tactics:

"This price is only good if you sign today."

"I have another customer who wants your time slot."

"Materials are going up next week, you'll pay more."

Run. Good contractors don't play these games.

Knocking on door after storm:

"I was driving by and noticed damage on your roof."

Storm chasers. Here today, gone tomorrow. Get local contractors.

Can't provide physical business address:

"We work out of our trucks."

No office = no accountability.

Online reviews that are all 5-star or all 1-star:

Either fake positive reviews or fake negative reviews from competitors.

Real companies have mix: mostly 4-5 stars with occasional legitimate complaint.

Willing to break rules for you:

"I can waive your insurance deductible." (Insurance fraud.)

"We don't need permits." (Code violation.)

"Pay cash and I'll give you discount." (Tax evasion.)

If they're willing to break the law for you, they'll break it against you too.

What Good Contractors Say (And Mean)

After asking these questions to 5 contractors, one stands out.

They answered everything directly. Provided license number, insurance certificates, references. Explained payment schedule and warranty clearly. Had process for unexpected issues.

That's your contractor.

The one who got defensive about insurance questions? Pass.

The one who couldn't explain warranty details? Pass.

The one offering huge discount for signing today? Run.

Our Answers to These Questions

Since we wrote this list, here's how we answer:

License: Virginia Class A, 2705-XXXXX (we give actual number)

Insurance: $2M general liability, full workers comp, certificates provided same day

References: 10+ recent Richmond projects, addresses included, customers willing to talk

Warranty: 10-year workmanship, transferable. GAF 50-year material warranty (with registration).

Subs: We use same crew for 95% of projects. They're insured. I'm on-site daily.

Payment: 15% deposit, 40% after tear-off, 45% on completion.

Unexpected issues: We estimate decking needs upfront, include allowance. If we find more, we stop and get approval at $4.50/sq ft.

Permits: We pull all permits. Cost is itemized. We handle inspections.

Rain: We watch weather, tarp if needed, never charge for weather protection.

Cleanup: Magnetic sweep twice, everything hauled away, dumpster included.

Any contractor should be able to answer like this. If they can't, keep looking.

Bottom Line

You're spending $10,000-25,000. Contractor will be on your property for days. Work will last decades (if done right) or fail within years (if done wrong).

These 10 questions separate professionals from scammers.

Ask every contractor. Compare answers. The right choice becomes obvious.

Want to hear how we answer these questions in person? Call (804) 238-7837 for a no-pressure consultation. We'll give you straight answers, a detailed bid, and references you can actually check.