When it’s time to replace your roof, choosing the right contractor can feel overwhelming. With every company claiming to be the best, how do you know who to trust? The truth is, a new roof is one of the biggest investments you’ll ever make in your home. Selecting the wrong roofer can result in leaks, wasted money, and ongoing frustration.
Warren Ropp, owner of Roofs by Warren, has seen it all, including quick fixes, hidden costs, and “too good to be true” deals that leave homeowners paying twice. His advice? Ask the right questions before you sign.
“Cheaper is not always better. When a price is low, something important is often missing.” – Warren Ropp
Here are five questions every homeowner should ask a roofing contractor to protect their home, their money, and their peace of mind.
1. Can I see proof of your insurance and workers’ compensation? And, how can I verify it?
One of the first questions to ask a roofer is simple but critical, “Can I see your insurance?”
A legitimate roofing company should have both liability insurance and workers’ compensation coverage. This protects you if something happens during the job, whether that’s a worker getting hurt or a piece of equipment damaging your property.
“Ask for the policy number. You can check online and make sure it’s current,” says Warren. “Just go to the Ohio BWC website and verify it there.”
When you’re reviewing bids, don’t just take a contractor’s word for it. Ask for a Certificate of Liability Insurance and their Bureau of Workers’ Compensation (BWC) policy number. Take five minutes to verify that both are active.
Quick checklist:
- Copy of Certificate of Liability
- Workers’ Compensation policy number
- Company address and office line
If a roofer hesitates to share these, that’s a red flag. A trustworthy contractor won’t mind you checking.
2. Will you do a complete tear-off and replace all flashings and metals?
This is one of the most important questions to ask, and one of the easiest ways to spot a questionable bid.
A proper roof replacement begins with a complete tear-off, which involves removing all old shingles, nails, and underlayment down to the wood deck. This allows the roofer to inspect for rot, replace any damaged boards, and begin with new materials.
Unfortunately, some companies skip this step to save time and money. They might reuse old flashings, drip edge, or even put new shingles over the old ones, called a “roof over.”
“A lot of guys reuse the flashings and drip edges. That saves them thousands of dollars, but it costs you later,” Warren warns. “You want to make sure nobody is doing what’s called a ‘roof over’.”
When a roof is installed over existing materials, there’s no way to inspect what’s underneath. Any soft wood or moisture damage gets trapped, and that can lead to leaks and mold.
Pro tip: Always confirm that your contract includes:
- Full tear-off
- Replacement of all metals and flashings
- New drip edge and pipe boots
- Per-sheet pricing for wood replacement
Real-life story: Warren’s team recently tore off a roof that had been done only five years earlier. “The shingles kept blowing off,” he said. “The last guy finally dropped off a bundle of shingles and told the homeowner, ‘You’re on your own.’ We tore it off, fixed it the right way, and even got the insurance approved.”
3. What shingles, ridge caps, and warranties will I get?
Shingles may all look the same from the ground, but what’s underneath the brand name matters. Homeowners should ask three questions about materials:
- What type of shingle are you installing?
- What ridge caps will you use?
- What warranties are included?
“We use a shingle-over ridge vent and buy ridge shingles made for high winds,” Warren explained. “Be sure to ask about the upgraded warranty. If they know shingles, they’ll know that answer.”
A reliable contractor will specify a laminated 30-year or lifetime shingle and explain whether the warranty is standard or upgraded. Some roofers cut corners by using cheap three-tab shingles for ridge caps, which are prone to blowing off in storms.
Here’s the difference:
- Three-tab ridge caps: $30/bundle, lower wind rating
- High-wind ridge caps: $80/bundle, built to last
That $50 difference per bundle might sound small, but it adds up and protects your roof in high winds.
4. What’s your plan for ventilation and underlayment?
This is one of the most overlooked parts of a roofing job. Ventilation affects your roof’s lifespan, your attic’s temperature, and even the comfort of your home.
“Looking at ventilation is critical,” Warren says. “Some rooms show signs of condensation because they don’t have enough airflow.”
A professional roofer should be able to explain:
- Whether they’ll install new ice and water shield underlayment
- What type of felt or synthetic underlayment will be used
- How your attic will be vented using ridge vent, box vents, or can vents
When homeowners skip this question, they risk moisture buildup, poor energy efficiency, and shortened roof life.
Ask these specifics:
- Are you replacing the underlayment?
- Will you inspect attic ventilation?
- What type of ridge vent will you use?
A little curiosity here can prevent big headaches later.
5. If I have an issue later, who do I call, and what happens next?
A new roof should come with confidence and a clear point of contact if something goes wrong.
“Eight years from now, if a chimney leaks, you want someone who says, ‘We’ll send our guys out right away,’” Warren says.
When hiring a contractor, it’s important to ask about their process for handling warranty or service calls. A reputable company will have a formal system in place. Typically, this involves the customer calling the office, logging the issue, and scheduling a technician to resolve the problem.
If the roofer says, “Just call my cell,” you should be cautious. That’s usually a sign they don’t have staff, a permanent office, or a proper warranty process.
“We tell customers to call our office,” Warren explains. “There’s a procedure in place that ensures that the message gets to the right person.”
A physical office also shows stability. “A physical location is a sign of security,” he says. “You want your roofing contractor to be there years from now if you need them.”
How to Compare Bids
Roofing quotes can be confusing. The key is to understand what each contractor includes in their estimate.
When reviewing multiple bids, ask these questions of each bidder.
- Are you doing a complete tear-off?
- Are all metals and flashings replaced?
- What ridge type and brand are listed?
- Is ventilation or underlayment included?
- How is rotten wood priced?
- What warranty is included, and who registers it?
- Can you provide references?
“Read the contract, then call each roofer and ask, ‘Is this included?’” Warren says. “That’s how you make sure you’re comparing the same thing.”
If one bid seems unusually cheap, dig deeper. It may skip essential steps that protect your roof in the long term.
Red Flags to Watch Out For
Warren has encountered some unbelievable situations in his career.
“I’ve seen contracts written on the back of a business card,” he says. “If the estimate is really cheap, that’s also a red flag.”
Here’s what to avoid:
- Vague, handwritten, or sloppy contracts
- Reused metals or “roof overs”
- No proof of insurance
- “We can start tomorrow,” promises
- Only a cell number, no office contact
A well-organized roofer with a proper contract and office isn’t hiding anything.
What a Quality Roofing Process Looks Like
When you hire Roofs by Warren, you get a clear, step-by-step process.
- Walk-around and roof inspection – including photos of problem areas.
- Detailed written proposal – everything itemized, no surprises.
- Scheduling – materials ordered, delivery confirmed, crew assigned.
- Full tear-off – old materials removed and wood inspected.
- Replacement of metals and flashings – done right the first time.
- Installation of underlayment and shingles – with high-wind ridge caps.
- Inspection and cleanup – including magnet sweep and final photos.
- Post-install inspection – a third-party inspector checks every detail.
“We have a third-party inspector look at the job when it’s done,” Warren says. “Then we collect the final payment.”
That’s the difference between a job that just gets done and one that gets done right.
Final Advice from Warren
Buying a roof can feel overwhelming, but Warren wants to offer homeowners this reassurance.
“There are several really good roofing companies out there. Most are trying to do a good job. Just do a little homework, make your decision, and have some faith in it.”
A good roofing company, he says, has three things:
- Good communication
- High-quality product
- Excellent warranty and reviews
Before signing any roofing contract, ask the five questions above and ensure you feel confident with the answers. When you find a company that meets all these criteria, you can sign the contract with assurance.
At Roofs by Warren, we believe in honesty, transparency, and craftsmanship that stands the test of time. We’re happy to walk you through your options, show proof of coverage, and explain our process from start to finish.
Ready to compare bids the smart way?
Call Roofs by Warren today or click here to schedule your free inspection and consultation.