Questions Every Homeowner Should Ask Before Hiring a Roofing Company

Every year, we meet homeowners who learned the hard way that not all roofing contractors are created equal. Some ended up with new roofs that leaked within 5 years. Others struggled with warranty claims, finding it difficult to reach their contractor once problems appeared. These aren’t rare cases, but they are preventable. In an industry littered with rushed sales tactics and vague contractor promises, how do you protect yourself from subpar contractors?

At Happy Roofing, we’ve inspected and replaced hundreds of roofs across the greater Naperville area, and have noticed a big disconnect between homeowners and contractors. We believe that you shouldn’t be left feeling uncertain, overwhelmed, or confused after receiving your quote.

Clarity is crucial before deciding on a contractor to partner with, but if you’ve never been through the roof replacement process before, how would you even know what to ask? This article will walk you through exactly why asking detailed questions matters. Our goal is to help you ask smarter questions, avoid costly mistakes, and feel confident in your decisions every step of the way. By the time you’re done reading, you’ll have what you need to help choose a trustworthy roofing contractor.

Why You Should Ask Questions Before Hiring a Roofing Contractor

Every roofing contractor approaches jobs very differently. Some prioritize long-term quality, thorough inspections, and clear communication. Others are playing a numbers game, focused on selling jobs fast and keeping costs low, often at the expense of quality. Asking the right questions could help you make a more informed decision when choosing a contractor to partner with for your next roofing project.

Asking detailed questions helps homeowners:

• Spot red flags before agreeing to any work: Avoid hiring a contractor who cuts corners, uses subpar materials, or leaves out key parts of the job.
• Understand what they’re paying for and why it matters: Ensure every line item in the estimate has a purpose and protects the roof’s longevity.
• Confirm any warranty information: Avoid surprises by knowing exactly what’s covered and for how long, so you’re not stuck paying out of pocket for an issue you assumed was included.
• Accurately compare roofing estimates: Make sure you’re comparing apples to apples instead of being swayed by a low price that leaves out critical work.
• Ensure they’re getting quality work: Have confidence that the materials, installation methods, and final result will stand up to weather, time, and manufacturer requirements.

A reputable roofing contractor won’t dodge your questions. They’ll take the time to understand your situation, walk you through what they found during their inspection, and explain your options clearly. In other words, a contractor should educate you rather than overwhelm you with industry jargon or vague promises. By the time they leave you with a quote, you should have a clear understanding of what options are best for your home.

So what types of questions should you ask before deciding on a roofing contractor that’s right for you? We’ve highlighted the most important topics to cover below.

3 Questions To Help Determine The Legitimacy Of a Roofing Company?

You may think it shouldn’t need to be asked, but it’s essential to verify that your contractor is legally allowed to provide their services. Here are some questions to ask about their credentials:

Are you licensed, bonded, and insured in my state?

A roofing license is non-negotiable. Holding a valid license shows that the company is legally allowed to work in your area. A lot of contractors provide their license number somewhere on their website, but they should be happy to provide it when asked if you can’t find it.

You can check the authenticity of their license number on the official IDFPR License Lookup site if you’re in Illinois, or by visiting your state’s contractor license lookup page. It’s also important to verify the contractor’s insurance coverage. Valid insurance protects both the contractor and you from liability if someone is injured on your property or if any damage occurs during construction.

How long have you been in business?

Years in business often reflect experience, stability, reliability, and a proven track record of standing behind their work. When a roofing company has been in the industry for years, it tells prospective customers that they've likely refined their processes, built a reputation through word of mouth, and weathered the ups and downs of the market. That kind of consistency builds trust, especially when it comes to long-term investments like a new roof or major repairs.

Can you show me recent roofing jobs you've completed nearby?

Look for recent work on their website, Google profile, or social media pages to get a real sense of their consistency and quality. You can also ask the contractor directly if they’ve completed any past projects similar to yours (whether it’s the same roof pitch, materials, or structural challenges) and request photos or homeowner references from those jobs.

Whatever the method you choose to review their past work, it’s important to look at both finished and in-progress photos. Progress photos allow you to evaluate a contractor’s attention to detail during installation.

What to look for in past projects:

New flashing: Flashing is the thin metal material installed around roof features like chimneys, roof-to-wall intersections, skylights, vents, and other vulnerable areas to direct water away from seams. When reviewing past projects, check whether damaged, rusted, or bent flashing is present, especially at roof transitions and around chimneys. Poor or reused flashing is a common cause of leaks, and any quality contractor should treat proper flashing replacement as non-negotiable.

Roof deck condition: Decking serves as your roof’s foundation, and is typically made up of plywood, oriented strand board, or planks if you have an older home. In our experience, nearly every project requires replacement of at least some roof decking. That doesn’t mean we’ve never seen a roof where all of the decking was in good shape, and it’s not necessary to replace unless the existing materials are worn. Photos of exposed decking should show clean, flat wood. If it’s warped or rotted, it could lead to leaks and more extensive damage.

Signs of property protection: During roof tear-off and installation, a lot of debris comes off the roof. A reputable contractor should take steps to protect your property throughout the process. You don’t want any stray nails left in your lawn or driveway. Look for tarps or coverings over siding, windows, landscaping, and flower beds. Driveways should be protected with plywood if heavy equipment or dumpsters are used, especially if they’re using a roll-off dumpster that could crack concrete or leave dents in asphalt. In-progress photos or customer reviews should reveal whether the crew kept the area clean and respected the homeowner’s property.

Consistent positive feedback: Take time to read customer reviews on Google, Facebook, and other platforms. Don’t just glance at the star rating, but find what people in your area are saying about the contractor. Look for patterns in the feedback that speak to their professionalism and reliability. Do homeowners mention clear communication, detailed estimates, or how the company handled unexpected issues? Are there multiple mentions of crews being respectful, tidy, and careful with the property? Positive feedback about quality workmanship, prompt follow-up, and a customer-first mindset are strong signs that the contractor takes pride in their work and will stand behind it, even after the job is done.

Progress photos like the one we've added below can signify that a contractor has a thorough and transparent work process:

Ask: Do You Use In-House Crews or Subcontractors?

Some roofing companies use their own in-house crews, while others rely on subcontractors. Both models can deliver quality work, but what truly matters is how those crews are selected, managed, and held accountable.

Ask your contractor:

• Are the installers employees or subcontractors?
• If they’re subcontractors, do they work exclusively with your company or for multiple roofing businesses?
• Will there be someone from the company directly overseeing the project while it’s in progress?

Why does this matter?

Subcontracting is common in the roofing industry, and there’s no problem with it, but not all subcontractors are created equal. Some roofing companies act as middlemen, hiring crews through labor brokers they have little to no relationship with. These subcontractors might be given jobs from multiple companies, each with different standards, materials, and methods, leading to inconsistencies and missed steps like flashing replacement or verifying proper ventilation setup. Additionally, these jobs may not be supervised by anyone from the roofing company at all, leaving nobody to hold the subcontractors accountable.

Legally, roofing companies can’t dictate exactly how subcontractors perform the work that they do. If there’s no employee-contractor relationship, critical details may be skipped, even if the homeowner was told otherwise. Many reputable companies choose to build long-standing relationships with dedicated subcontractors who work exclusively with them and follow their standards consistently. This is also a good indicator that the company will provide support should any issues arise later down the road, given that their subcontractors consistently work with them.

On the other hand, in-house crews give the contractor full control over every aspect of the roofing process. Because these crews are direct employees, the company can standardize processes across all jobs, reinforce quality expectations, and quickly correct any mistakes that arise. This level of oversight helps ensure consistent workmanship and accountability. However, maintaining a full-time in-house team comes with higher overhead costs, including payroll, training, insurance, and benefits, which could increase the cost of their projects. It can also be challenging for contractors to keep these crews busy year-round, especially in regions with harsh winters or slower seasons.

Consideration Factor

Ultimately, whether it’s a company employee or a subcontractor, there should always be someone accountable for the crew’s actions, the installation quality, and any issues that may come up later. The key takeaway is that a reputable contractor won’t shy away from explaining who is doing the work and how they’ll make sure it’s done right.

How Do You Select and Install Your Materials?

We choose roofing materials as part of a complete, integrated system with each component selected to work together for maximum durability and performance. From the underlayment to the shingles, every product is vetted for quality, compatibility, and manufacturer reputation. Our installation follows the manufacturer’s exact specifications so your roof performs as intended, lasts longer, and maintains full warranty protection.

Ask your contractor to walk you through every layer of the roofing system, including:

• Shingles: Why did they choose that particular brand or line? What makes it a good fit for your climate or roof design?
• Underlayment: Is it synthetic or felt? What level of protection does it offer against moisture and wind-driven rain?
• Flashing: Will old flashing be replaced during roof replacement?
• Roof ventilation: Do they evaluate ventilation? Can they upgrade ventilation if your home requires better airflow?
• Fasteners: What types of fasteners are they using? Will the underlayment be secured with staples or cap nails?

Each of these elements affects not just the durability of your roof, but also its warranty eligibility and long-term performance. Even industry-leading shingles can fail prematurely if installed with incompatible or low-quality components underneath. Manufacturers know this as well, which is why they often require the use of approved materials along with their shingles as a condition of their warranty.

A knowledgeable, trustworthy contractor won’t shy away from explaining their material choices. They’ll help you understand how those materials work together as a system and why their approach leads to long-lasting results.

Ask: What happens if you find hidden damage during the job?

Make sure your estimate includes a plan for the unexpected. Certain factors are almost impossible to verify before the tear-off begins. For example, it’s difficult to know the true condition of the roof decking before work has started. Without removing shingles, it’s anyone’s guess as to how many sheets of deck material need to be replaced.

A good contractor will:

• Consult with you before moving forward on additional repairs, making sure you understand pricing.
• Include a per-item price for the replacement of any variable components, like decking.
• Provide photos before and after the replacement.

Nobody likes surprises, so you must be informed of any variable costs before you partner with the contractor of your choice.

Here is an example of how we include variable cost factors, like decking replacement, in our quotes:

Ask: What Are Your Payment Terms and Financing Options?

Before signing any contract, it’s important to understand how and when your roofing contractor expects to be paid, and if there are financing options available.

Typical Payment Structure: Most roofing companies require a deposit of 25% to 50% upfront. This helps cover the cost of materials and secures your spot on their project schedule. The remaining balance is usually due upon completion. Be cautious of any contractor who demands full payment before work begins. If the deposit is higher than 50%, request a detailed reason before agreeing. Final payment should only be due once the work is finished.

Accepted Payment Types: Ask if they prefer checks, credit cards, bank transfers, or other forms of payment. Some companies also offer digital invoicing and payment portals for added convenience. Be cautious if a company insists on cash-only with no receipt, asks you to pay into a personal account instead of a business account, or pushes for untraceable payment methods. These can be signs the business isn’t operating transparently.

Financing Options: If paying out of pocket isn’t ideal, see if the contractor offers or partners with financing providers. Many reputable roofers have relationships with third-party lenders that allow you to break the cost into manageable monthly payments.

A contractor that’s transparent and flexible about payments is more likely to prioritize a smooth and respectful customer experience, while helping you get the roof you need without financial strain.

Ask: What Warranties Are Available, and How Do I Register?

Most roofing projects can come with two types of warranties: a workmanship and manufacturer's warranty. One is directly from the contractor, and other from the manufacturer. Both are important, but they cover very different things:

Workmanship Warranty:

This warranty is provided by the contractor and covers installation-related issues. If a leak or problem occurs due to improper installation or other labor mistakes, this warranty is what protects you. Coverage terms can vary widely, from 1 year to 25 years or even lifetime warranties. While they can be a direct reflection of the contractor’s confidence in their quality of work, these warranties are created and handled by said contractor and are only useful if the company is reliable. Make sure you ask what’s covered, for how long, and what happens if you need follow-up service.

Manufacturer’s Warranty:

This is issued by the roofing material manufacturer and covers defects in the materials themselves, like shingles that crack, blister, or fail prematurely under normal conditions. However, this warranty is often only valid if the roof was installed according to the manufacturer's specifications. That means proper ventilation, flashing, nail placement, and compatible system components must be in place. Some manufacturers also offer enhanced or extended warranties if the contractor is factory-certified or installs a full system using their brand’s products.

Who is responsible for registering the warranty?

The contractor should handle manufacturer warranty registration on your behalf and provide you with a certificate. For workmanship warranties, it’s best to ask the contractor directly, as these are handled differently depending on the company.

Important: Just because you receive a manufacturer’s warranty certificate doesn’t mean you’re protected. If the contractor ignored ventilation, reused flashing, or cut other corners, your claim can be voided if these are found during an inspection. Always ask for documentation that shows the roof was built to warranty specifications. A quality contractor will give you photos showing that key components were addressed.

How to Find the Right Roofing Contractor for You

A roofing company that deserves your trust will never rush you, dodge your questions, or gloss over important details. They’ll explain their recommendations clearly, explain how the work will be done, and back it all up with thorough documentation. The more clarity you have upfront, the fewer surprises you’ll face later, and the more confident you’ll feel about who’s working on your home.

If there’s something in your quote that you’re not sure of, or if you feel that anything is missing from the scope of your roofing project, ask for clarification. Your contractor should be willing to educate and guide you through the process.

If you’re still narrowing down your options, we’ve also put together a breakdown of local, reputable contractors worth considering. Check out our next article, Who Are the Best Roofing Replacement Companies in Naperville, Illinois for insight into some of the top contractors in the area.