Questions to Discuss with Your Roofing Contractor
Selecting the Right Roofing Contractor
Critical Questions Every Homeowner Must Ask
Choosing who will install your new roof is one of the most important decisions you will ever make as a homeowner. A roof is not just a cosmetic upgrade—it is a structural system that protects your home, your investment, and your family for decades. The quality, longevity, and performance of your roof depend largely on the experience, integrity, and professionalism of the contractor you choose.
To help you make a confident and informed decision, we have created this guide: “Critical Questions You Must Ask Your Roofing Contractor.” These questions are designed to reveal whether a contractor is qualified, transparent, and truly committed to quality workmanship.
Before diving into the checklist, start with three simple—but powerful—preliminary questions:
A) Was it easy to contact the company and schedule an appointment, either through their office staff or website?
B) Was your estimator on time, knowledgeable, and able to clearly explain what they were proposing?
C) Is your estimator properly licensed, allowing them to provide a roofing or renovation proposal legally?
If you answered “No” to any of these, you should strongly consider selecting a different contractor and beginning the checklist again. Roofing is a technical trade that requires communication, accountability, and professionalism from the very first interaction.
The Critical Questions You Must Ask Your Contractor
1) Does the contractor provide a comprehensive written proposal?
A professional roofing contractor should never provide only a verbal quote or a vague one-page estimate. Your written proposal should clearly define what you are purchasing and how the work will be performed.
A complete proposal should include:
- Materials being proposed: product type, brand, style, and grade
- Warranties and documentation: manufacturer brochures and written warranty terms
- Options and pricing: multiple choices at different price points when available
- Detailed roofing specifications, including:
- How many layers will be removed (ideally all existing layers)
- Whether debris will be hauled by truck or placed in dumpsters
- Confirmation that all dumping fees are included
- How decking repairs are priced (per sheet, per foot, or per hour)
- How your yard, landscaping, and property will be protected
- Whether gutters are protected and cleaned
- If new decking is needed, the type and thickness being installed (avoid OSB where possible)
- Flashing details: replacement vs. reuse, installation areas, metal gauge, and finish
- Underlayment type
- Ice and water shield placement
- Ventilation design to meet manufacturer and local code requirements
- Fastener type, quantity, and wind ratings
Every roofing project is different, but a high-quality proposal should include a detailed specification sheet. Review it line by line with your contractor and ask questions. A knowledgeable estimator will be happy to explain each item clearly.
Cascade Roofing provides a detailed six-page bid and complete proposal packet outlining all roofing specifications and options. They also take the time to walk homeowners through every detail.
2) How many years has the company been in business?
Roofing problems often do not appear immediately. Leaks, ventilation failures, and flashing issues can take years to become visible. That is why longevity matters.
Choose a company that is well established and financially stable. Many roofing companies disappear long before their warranties expire.
Cascade Roofing has served homeowners since 1959, providing long-term accountability and peace of mind.
3) Are they licensed with the State of Oregon?
In Oregon, every contractor is assigned a CCB (Construction Contractors Board) number, which can be verified with the state to confirm that the company is compliant with licensing and regulatory requirements. You can also review any complaints filed with the board.
Cascade Roofing holds Oregon CCB License #104430.
4) Can they provide proof of insurance?
Ask to see current copies of the following four insurance coverages:
- General Liability Insurance
- Auto Insurance
- Workers’ Compensation Insurance
- Performance Bond
Some contractors fail to carry adequate insurance because they cannot qualify or because of the high cost of roofing insurance. This puts homeowners at risk.
Cascade Roofing provides written documentation of $2,000,000 in liability insurance, auto insurance, workers’ compensation insurance, and a $15,000 performance bond.
5) If a worker is injured, how is my property protected from liability?
Homeowner insurance typically excludes injuries to contractors and workers on your property. The only way to protect yourself is to verify that your roofing company carries proper workers’ compensation insurance for employees and subcontractors.
Cascade Roofing carries workers’ compensation through SAIF on all employees and does not use roofing subcontractors.
6) Does the company use employees or subcontractors?
If a contractor relies on subcontractors, you must verify that each subcontractor carries all required insurance. Subcontracting can create gaps in accountability, safety standards, and quality control.
Cascade Roofing installations are performed exclusively by their own trained, professional employees.
7) How will the contractor protect you from liens?
Many homeowners are unaware that a lien can be placed on their home if a contractor disputes payment with a supplier, installer, or subcontractor—even if the homeowner has already paid in full. A lien can affect your credit, prevent refinancing or selling your home, or force you to pay a portion of the bill again.
Your best protection is:
- Obtaining a written lien waiver from the material supplier
- Working with an established company
- Minimizing the use of subcontractors
Cascade Roofing provides written lien waivers from their suppliers as part of their proposal packet.
8) Is the contractor reputable and well-reviewed?
Go beyond the references they provide. Do your own research:
- Check the Better Business Bureau (BBB)
- Read online reviews on Google and other platforms
- Review third-party sites such as Angie’s List
- Call suppliers
- Read recent testimonials
- Drive by completed projects to inspect workmanship
Every company may encounter an occasional unhappy customer, but consistent patterns in reviews tell the real story.
Cascade Roofing has extensive positive online reviews, and maintains strong supplier relationships.
Choosing a Professional
If you choose quality materials, you have only about a 1-in-4 chance of receiving a long-lasting roof if the installation is poor. Less than 25 percent of roofs meet manufacturer specifications—not because of the products, but because of who installs them. It truly is about the professionals on your roof.
9) Are the installers employees or subcontractors?
Cascade Roofing uses only their own trained employees.
10) How long have the installers been with the company?
Many Cascade Roofing installers have been with the company for 10, 15, and even 20 years—a strong indicator of training, stability, and craftsmanship.
11) How are installers trained?
Cascade Roofing requires extensive training before employees enter their apprenticeship program. With years of supervised experience, installers advance through certification programs and specialized training in advanced materials. Safety training is ongoing.
12) What certifications do the installers and company hold?
Cascade Roofing installers are Certified Master Applicators, and the company has earned the Master Roofing Company distinction through rigorous industry certification.
13) How is my project supervised?
Is there:
- No supervisor?
- A supervisor who stops by occasionally?
- Or a supervisor assigned full-time?
Cascade Roofing assigns a supervisor to one job at a time, present throughout the installation and available for homeowner questions.
14) What safety measures are in place?
Ask about harnesses, scaffolding, and safety procedures.
Cascade Roofing is NTI safety certified, uses OSHA-approved equipment, and is one of the few Northwest companies with its own scaffolding and safety trailers.
15) Are restroom facilities provided on-site?
Cascade Roofing provides a portable restroom on every job site.
16) How is my property protected?
Protection should include:
- Scaffolding for sensitive areas
- Tarps for landscaping
- Plywood for siding, windows, HVAC units, and ponds
Cascade Roofing implements all of these measures.
17) What about cleanup?
Cascade Roofing cleans gutters, clears walkways, and uses magnetic sweepers to remove nails and debris.
18) Are there smoking or music policies?
Cascade Roofing maintains smoke-free and music-free job sites.
19) Who will I communicate with, and is there a final inspection?
Cascade Roofing assigns a full-time foreman/supervisor as your point of contact and completes a final written inspection after the job.
20) Are warranties provided in writing?
Cascade Roofing includes written labor and material warranties and often extends manufacturer warranties at no additional cost.
21) What are the payment terms?
Cascade Roofing requires a modest down payment, with final payment due within 5–10 days. Multiple payment methods are accepted.
22) Is old roofing material recycled?
Cascade Roofing recycles the majority of removed roofing materials through environmentally responsible facilities in Portland.
Final Thoughts
By following this guide—and applying your own common sense—you transform one of the most expensive purchases you will ever make in one of the least trusted industries into a thoughtful, informed decision.
The right roofing contractor doesn’t just install shingles. They provide documentation, safety, accountability, craftsmanship, and long-term support. Ask the right questions, demand clear answers, and choose a professional who stands behind their work.