Hiring a contractor for roofing or siding is one of the most important decisions a homeowner can make. These are not small projects. They protect your home, influence your property value, and determine how well your house stands up to Wisconsin’s unpredictable weather. Yet many people choose a contractor based only on price or a quick online search. That is how problems begin.
As a company that has worked with thousands of homeowners, GL Construction of Madison knows that asking the right questions can prevent stress, unexpected costs, and long-term damage. Whether you are planning a full replacement or a simple repair, here are 10 essential questions you should ask before hiring anyone for roofing or siding.
1. “Are you fully licensed and insured?”
*A foundation of trust and safety*
This may be the most important question of all. A trustworthy contractor should carry proper licensing that meets local and state requirements. They should also have insurance, including liability insurance and workers’ compensation, to protect you if something goes wrong on the job. If a contractor hesitates or cannot show proof, move on. Professionals are always transparent about their credentials.
2. “How long have you been in business?”
*Experience matters more than many people realize*
For large exterior projects, experience is everything. Contractors with years of work behind them know how to navigate unexpected challenges, handle Wisconsin’s climate, and choose materials that are proven to last. A newer company can still be capable, but longevity often reflects skill, consistency, and community trust. Companies like GL Construction of Madison earned their reputation through decades of hands-on work.
3. “Can you walk me through your process from start to finish?”
*You should always know what to expect*
A good contractor should be able to explain their workflow in clear and simple language. This includes site preparation, removal of old materials, installation of new materials, crew management, and clean up. If their explanation feels rushed or vague, that may be a sign that communication will be inconsistent during the project. A responsible contractor wants you to feel confident from beginning to end.
4. “What materials do you use and why did you choose them?”
*Quality materials create long-term savings*
Roofing and siding materials vary widely in durability, performance, and cost. A knowledgeable contractor should be able to explain why certain materials are better for your home and for Wisconsin’s climate. You want someone who focuses on long-term value, not someone who simply uses the cheapest supplies to increase their profit margin.
5. “Do you provide a written estimate and contract?”
*Verbal promises are not enough in construction*
Every detail of your project should be in writing. This includes the scope of work, materials, costs, and timeline. A written estimate protects you and the contractor by preventing misunderstandings. A reputable company will offer a detailed contract that outlines everything clearly. Avoid anyone who relies on handshake agreements or vague numbers.
6. “Who will be doing the work?”
*Not all companies use in-house crews*
Some contractors use their own trained teams. Others rely on subcontractors. Both can be acceptable, but you should know who will be on your property. Ask if the crew is experienced, insured, and supervised. A company that takes pride in its work will make sure you know who is responsible for the project and will ensure accountability at every stage.
7. “What is your timeline and how do you handle delays?”
*Wisconsin weather can interrupt any project*
Construction projects do not always go exactly as planned. A qualified contractor will be honest about timelines and realistic about potential delays. They should also have a plan for weather issues, supply shortages, or other unexpected situations. Good communication matters. You want a contractor who keeps you updated, not one who disappears for days at a time.
8. “Do you offer warranties on materials and labor?”
*Protection after the project matters just as much*
The best contractors stand behind their work long after the job is complete. There are two types of warranties to ask about. Material warranties are provided by manufacturers, and labor warranties are provided by the contractor. Both are important. Without them, you may pay for repairs that should have been covered. Companies that care about quality will always provide strong warranties.
9. “Can I see examples of your recent work or talk to past clients?”
*Reputation tells you everything you need to know*
A reputable contractor will gladly show you photos, videos, or in-person examples of recent roofing or siding projects. They should also be willing to connect you with past customers who can provide honest feedback. If a contractor cannot provide references or refuses to do so, that is a sign they may not have a strong track record.
10. “What makes your company different?”
*The answer reveals their values and commitment*
This final question helps you understand the contractor’s approach, priorities, and philosophy. Some companies focus on speed. Others focus on low prices. Companies like GL Construction of Madison focus on craftsmanship, communication, and long-term durability. When a contractor can clearly explain what sets them apart, you gain insight into the type of experience you will receive.
Why These Questions Matter
When you hire someone for roofing or siding, you are trusting them with your home’s structure and long-term protection. Asking the right questions helps you compare companies, avoid scams, and choose a contractor who cares about your home. The best contractors welcome questions and appreciate informed customers. This leads to better communication, stronger trust, and higher quality results.
A Smart Approach to Choosing the Right Contractor
Roofing and siding projects have a major impact on the safety, durability, and value of your home. By asking these 10 questions, you can quickly separate true professionals from contractors who may cut corners or lack experience. Whether you need a full roof replacement, new siding, or work on a new build, these questions will help you choose a company that will deliver quality results and a smooth experience from start to finish.