Questions to Ask Your Roofing Contractor: How to Choose a Trusted Roofing Professional

Choosing the right roofing contractor is one of the most important decisions a homeowner can make when facing a roof replacement, repair, or solar installation. A quality roof is a long-term investment, and working with a reliable, experienced roofing contractor ensures the job is done right the first time. But not all roofing companies offer the same level of professionalism, service, or value. Before signing your roofing contact, here are the questions to ask your next roofing contractor.

Is My Roofing Contractor Licensed and Properly Insured?

Ask this question first, as it is one of the most important. If a contractor doesn’t have proper insurance and something goes wrong—like a worker getting injured or a major water intrusion during installation—you, the homeowner, could be held financially responsible. Always ask for proof of insurance and make sure it’s up to date. You can also verify licenses through the Wisconsin Department of Safety and Professional Services.

Is It Better to Hire a Local Roofing Contractor?

Local roofing companies have more at stake.

They live and work in the same communities as their customers, which means reputation, follow-through, and long-term service actually matter.

Roofing is not a one-day transaction.

Local contractors understand Wisconsin weather, local permitting, and neighborhood expectations, and they are still around when you need service, documentation, or warranty support years later. This is why we recommend selecting a local roofing company.

It is also worth understanding who actually owns the company you are hiring. Many national brands and franchises market themselves as local, but are owned by large holding companies or private equity firms. That ownership structure can influence pricing, sales pressure, and long-term accountability.

When evaluating whether a contractor is truly local, ask:

• Who owns the company?

• Where is their office located?

• Will the same team handle service if issues arise later?

Sun Vault Roofing is independently owned, Wisconsin-based, a member of Dane Buy Local, and maintains a rating with the Better Business Bureau.

What Roofing Certifications Should a Contractor Have?

Roofing manufacturers offer certifications to identify contractors who meet high standards for product expertise, installation quality, and business ethics. For example, CertainTeed’s contractor credential program includes:

• Shingle Quality Specialist™

• Master Shingle Applicator™

• ShingleMaster™

• SELECT ShingleMaster™ (top-tier)

  
  

Ask what certification level your contractor holds and how that compares to the available options. Sun Vault Roofing is a SELECT ShingleMaster™ - CertainTeed’s highest designation—allowing us to offer their most comprehensive warranties, including the SureStart™ PLUS 5-Star Warranty with up to 50 years of coverage on materials, labor, tear-off, and disposal. Fewer than 1% of roofing contractors nationally hold this distinction.

What Roofing Materials and Brands Will Be Used on My Home?

Make sure your contractor uses an established brand such as CertainTeed, GAF, or Owens Corning. At Sun Vault Roofing, we use CertainTeed—one of the most respected names in the industry, with over 100 years of experience. Many of their products are manufactured domestically. A reliable contractor will also offer strong, long-term warranties that stand behind the materials used.

Some of the most expensive roofing failures start in places homeowners never see once the job is finished. These next questions focus on hidden components that directly affect leaks, longevity, and warranty coverage. Yet they're often skipped or downplayed in low-cost estimates.

Will My Old Shingles Be Removed or Covered Over?

Skipping the tear-off step is cheaper, but it comes with serious consequences. Roofs installed over old shingles won’t last as long, and manufacturer warranties are typically invalidated. There are very few situations where skipping the tear-off is recommended, and a trustworthy contractor will explain your best option honestly.

Will Flashing and Edge Metal Be Replaced With the Roof?

Flashing refers to metal installed around chimneys, vents, and valleys to prevent water infiltration. Edge metals protect the roof's perimeter. These components are essential to a watertight roof. Ask whether your contractor plans to replace these materials. In most cases, the answer should be yes—unless they’ve been thoroughly inspected and are in excellent condition. If a contractor recommends leaving them in place, they should be able to explain why and confirm they’re still expected to last the full lifespan of your new roofing system. Otherwise, you risk premature leaks, costly repairs, and problems with warranty coverage. 

How Thorough Is Your Roof and Attic Inspection Process?

Make sure the contractor will get on the roof for their inspection. A proper inspection should go beyond the surface. In addition to checking shingles and flashing, a reputable contractor will evaluate the attic ventilation, roof decking, and the overall structure for signs of wear, moisture buildup, or poor airflow. 

Ventilation is especially important. Without it, heat and moisture can build up in your attic, shortening the life of your roof and potentially causing mold or rot. Ask whether your contractor will check intake and exhaust vents, assess airflow, and make recommendations for improvement if needed.

A truly thorough inspection should also include soffit and fascia. These areas support your gutters, influence attic ventilation, and are common entry points for moisture and pests. If soffit or fascia boards are rotted, sagging, or compromised, installing a new roof on top of them can shorten the lifespan of the entire system. A reputable contractor should identify these issues early and explain whether repairs are necessary before roofing work begins.

What Should a Roofing Estimate and Contract Include?

A professional roofing estimate should clearly explain what is being done, how it will be done, and what happens if conditions change. Anything less creates room for confusion or unexpected costs.

At a minimum, your written estimate should include a detailed scope of work, specific materials and product lines, tear-off and disposal plans, ventilation and flashing details, permit handling, project timeline, and payment structure. Vague one-page quotes or verbal estimates often leave out critical components that later reappear as added charges.

The contract should also explain how change orders are handled, what warranties apply, and who is responsible if issues arise after installation. If a contractor can’t walk you through their estimate line by line, that’s a sign they may be cutting corners elsewhere too.

Will You Pull Roofing Permits and Schedule Inspections?

Roofing permits protect homeowners, even when they feel like paperwork.

In most Wisconsin cities, roof replacements require a permit and inspection. A reputable contractor should always pull the permit for you and close it out properly.

We’ve seen what happens when that doesn’t occur. A friend of ours backed out of buying a Madison home after discovering a recently replaced roof had no permit on file. With no inspection or public record, there was no way to verify the work.

Unpermitted roofing can complicate home sales, insurance claims, and warranties. The correct answer to this question should be simple:

“Yes, we’ll pull the permit and handle the inspections.”

Anything else exposes you to unnecessary risk.

Many Wisconsin municipalities use roofing permits to populate public records like the roof replacement year. If no permit is pulled, there may be no official record the work ever happened. This screenshot is from public property tax records in the City of Madison.

How Will My Roofer Communicate During the Project?

Roofing projects in Wisconsin rarely go exactly as planned. Weather shifts, material availability, and hidden conditions can affect timelines or scope. That’s why communication matters just as much as craftsmanship.

One of the most common surprises during a roof replacement is plywood decking replacement. Beneath your shingles is waterproof underlayment, and beneath that are sheets of plywood fastened to your attic rafters. Over time, especially near the end of a roof’s life, that decking can become damp or rotten. Shingles cannot be installed on wet or deteriorated plywood. Doing so violates building code, voids manufacturer warranties, and puts contractor certifications at risk.

The challenge is that decking condition cannot be confirmed with 100% certainty until the old shingles are removed. Even a thorough attic inspection may miss damage that exists on the top side of the plywood, directly under the shingles. That means a roof may be quoted at price X, then legitimately require additional decking once the roof is opened. At that point, replacement isn’t optional — the roof must be made sound before work can continue.

Where contractors differ is how this is handled.

Some crews replace decking as needed and inform the homeowner of the added expense only after the fact. At Sun Vault Roofing, we take a more transparent approach. We do our best to estimate potential decking replacement in advance, using roof walkability and inspection clues, and include that estimate in your proposal. We also explain upfront that additional decking may be required due to conditions that can’t be fully predicted. If more decking is discovered beyond the estimate, we communicate before costs escalate.

Ask your roofer:

• Who is my point of contact once work begins?

• How will you communicate unexpected findings?

• How are change orders approved and documented?

  
  

Clear answers protect your budget, your roof, and your peace of mind.

Does My Roof Need to Be Replaced Now or Can It Wait?

Deciding whether to repair or replace your roof isn't always straightforward. Like getting a second opinion from a dentist, you can ask five roofers and get five different answers. And while many contractors strive to be objective, roof replacements are more profitable than repairs, which can subtly bias recommendations of commissioned salespeople.

In most cases, it’s in a homeowner’s best interest to extend the life of a roof as long as it can be done safely. Not every aging roof needs immediate replacement. A knowledgeable, local contractor should be able to tell you whether your roof can make it through another Wisconsin winter and, if so, what short-term repairs or maintenance could reduce risk and buy time.

That said, there are situations where replacement is the responsible option. If a roof has reached the end of its serviceable life, shows widespread failure, or poses a high risk of leaks or structural damage, patching may no longer be viable. When that’s the case, your contractor should clearly explain why, pointing to specific conditions or failure points, not just offering a blanket recommendation.

Good advice is grounded in evidence, not urgency.

Why Choose Sun Vault Roofing?

Sun Vault Roofing is a certified Wisconsin roofing contractor offering both traditional roofing and solar-integrated roofing systems. We pride ourselves on honesty, craftsmanship, and clear communication. Whether you’re dealing with storm damage, normal wear and tear, or planning a full solar upgrade, we guide you every step of the way.

📞 Call 608-608-1082 or Schedule a Free Inspection to meet with a trusted roofing contractor today.