Choosing the Right Roofing Contractor
Candle Sampley • February 20, 2026
10 Questions to Ask Before Signing Anything

Why Choosing the Right Roofing Contractor Matters
Your roof is one of the biggest investments in your home, yet many homeowners rush the hiring decision when repairs or replacements feel urgent. Unfortunately, choosing the wrong contractor can lead to poor workmanship, denied insurance claims, hidden costs, and even safety risks.
The good news is that most roofing disasters are preventable. Asking the right questions upfront puts you in control, helps you spot red flags early, and ensures you are working with a contractor who will stand behind their work.
Here are the ten most important questions to ask before you sign any roofing contract:
1. Are You Licensed and Insured?
This should always be the first question you ask. A legitimate roofing contractor should have no hesitation in providing proof.
A properly licensed and insured contractor protects you from liability if something goes wrong during the project. Without insurance, you could be financially responsible for accidents, injuries, or property damage.
Always ask to see documentation, not just verbal confirmation.
2. How Long Have You Been in Business Locally?
Experience matters, especially in areas with unique weather challenges.
A contractor with a long local history is more likely to understand regional building codes, common roofing issues, and insurance requirements. They are also easier to track down if you need warranty support later.
Be cautious of companies that appear only after major storms and disappear soon after.
3. Do You Have Recent References or Reviews?
Before you hire a contractor, it’s important to know how they’ve performed for other homeowners. Checking references and reviews gives you insight into their reliability, work quality, and professionalism, helping you avoid costly mistakes.
- Ask for recent references, not just older testimonials.
- Look for consistent reviews that mention communication, cleanliness, and follow-through.
- Pay attention to how the company responds to negative reviews, if any exist.
Social proof is one of the strongest indicators of reliability.
4. Will You Provide a Written Estimate and Contract?
Never rely on verbal agreements when it comes to roofing.
A detailed written estimate should clearly outline the scope of work, materials, timeline, payment schedule, and warranties. This protects both you and the contractor by setting clear expectations from the start.
If a contractor avoids putting details in writing, that’s a major warning sign.
5. What Materials Will Be Used and Why?
Not all roofing materials are created equal, and cheaper is not always better.
A trustworthy contractor should explain:
- Why are specific materials recommended for your roof?
- How those materials perform in local weather conditions.
- What kind of lifespan and maintenance to expect.
This shows they are focused on long-term value, not quick profits.
6. How Will You Protect My Property During the Project?
Roofing can be messy, and a professional contractor plans for that.
Ask how they will protect landscaping, siding, windows, and outdoor areas. Cleanup procedures should also be clearly explained, including nail removal and debris disposal.
Attention to property protection often reflects overall workmanship quality.
7. Who Will Be On Site Managing the Job?
Knowing who is responsible on site prevents miscommunication.
You should understand whether the work is handled by in house crews or subcontractors, and who your main point of contact will be. Clear supervision helps ensure the job stays on schedule and meets quality standards.
Lack of clarity here can lead to mistakes and delays.
8. How Do You Handle Insurance Claims if Needed?
Roofing and insurance often go hand in hand, especially after storms.
An experienced contractor can help you understand whether damage may qualify for a claim, document findings properly, and communicate effectively with insurance adjusters.
This guidance can significantly improve the outcome of your claim and reduce stress.
9. What Warranties Are Included?
There are usually two types of warranties involved in roofing.
- Manufacturer warranties cover the roofing materials.
- Workmanship warranties cover the quality of the installation.
Make sure both are clearly explained in writing so you know exactly what is protected and for how long.
10. What Is the Payment Schedule?
Be cautious of contractors who demand full payment upfront.
A professional payment schedule typically includes a deposit, progress payments if applicable, and final payment after completion and inspection. This structure protects you and encourages accountability throughout the project.
Clear payment terms help avoid disputes later.
Why These Questions Can Save You Thousands
Many homeowners only learn these lessons after something goes wrong. Taking time to ask these questions upfront helps you avoid poor workmanship, unexpected costs, and future headaches.
The right contractor will welcome these questions and answer them confidently. The wrong one will rush, deflect, or pressure you to sign quickly.
Work with a Roofing Contractor You Can Trust
If you’re looking for a contractor who values transparency, experience, and homeowner education, Keeler Roofing will guide you through every step of the process, from inspection to completion.
Speak with a Keeler Roofing professional today to make sure your next project is done right. Our team provides expert guidance, quality workmanship, and peace of mind from inspection to completion.













