Before hiring anyone to work on your home, knowing the right questions to ask a contractor can protect you from unreliable work, poor communication, and expensive mistakes. Your roof is a major investment, so choosing a good contractor is just as important as selecting the right materials.
In this blog, we’ll cover the most important contractor interview questions and help you:
- Evaluate contractors with confidence before signing
- Understand how project timelines and budgets are managed
- Spot red flags that signal an unqualified or untrustworthy roofer
Use this roofer checklist to make sure you’re choosing someone who will treat your home with the care it deserves.
🏠 Why It Pays To Ask the Right Questions
Most roofing issues happen because of poor installation or unclear expectations, not just bad weather. Having an upfront conversation about experience, scheduling, and the inspection process can prevent delays and future stress.
- Clarify the project scope: Know exactly what work is being done, who’s doing it, and when.
- Protect your investment: Asking questions helps you avoid surprises with the payment schedule, change orders, or missed deadlines.
- Ensure accountability: You want a contractor who’s licensed, organized, and personally involved—not just passing your project off to someone else.
Whether you’re dealing with a small repair or a full replacement, a short contractor interview can go a long way.
✅ Ask These 9 Questions Before You Hire
Here’s a list of must-ask questions to include in your contractor interview. These will help you identify if you’re dealing with a general contractor who’s professional, reliable, and worthy of your trust.
1. Do You Have a Valid Business License and Insurance?
- Why it matters: A business license proves the contractor is operating legally, while insurance protects you from liability.
- What to ask: Can I see your business license, general liability insurance, and workers’ compensation coverage?
2. How Many Projects Like Mine Have You Completed?
- Why it matters: Past experience with residential roofing (not just general construction) is key.
- What to ask: How many projects like mine have you handled in the last year? Can you provide examples or references?
3. Who Will Be On-Site Managing My Roof Project?
- Why it matters: Some general contractors assign a project manager, while others leave the job site unattended for long periods.
- What to ask: Will you or a dedicated project manager be on the job site each day to oversee work and answer questions?
4. What Is Your Typical Payment Schedule?
- Why it matters: A clear payment schedule sets expectations and prevents billing surprises.
- What to ask: How do you structure your payment schedule, and what’s required at signing, during work, and at completion?
5. Can You Explain the Full Inspection Process?
- Why it matters: The inspection process affects permitting, code compliance, and final sign-off.
- What to ask: How do you handle inspections during and after the project? Who is responsible for scheduling inspections?
6. Will You Pull All Necessary Permits?
- Why it matters: A good contractor understands local requirements and pulls permits on your behalf.
- What to ask: Will your team handle permits, scheduling inspections, and meeting with local inspectors?
7. What Is the Timeline for This Job?
- Why it matters: Delays can impact your home, your schedule, and other projects.
- What to ask: What’s your expected start date, how long will the work take, and how will weather or material delays affect the timeline?
8. Who Will Be Working on My Roof?
- Why it matters: You should know if your general contractor is hiring subcontractors or using an in-house team.
- What to ask: Do you use your own crew, or do you subcontract? Are they licensed and trained?
9. How Do You Keep the Job Site Clean and Safe?
- Why it matters: A well-managed job site protects your family, pets, landscaping, and home value.
- What to ask: What steps do you take to maintain a clean and safe job site throughout the project?
These questions don’t just help you understand the process—they also give you a sense of the contractor’s communication style, professionalism, and attention to detail.
👉 Bonus Tips for Hiring a Good Contractor
Asking questions is the first step. Here are a few bonus tips to make sure you’re hiring someone who’s truly right for the job.
- Look for transparency: A good contractor won’t hesitate to answer your questions or provide references.
- Watch for red flags: Avoid anyone who avoids giving a written contract, rushes you into signing, or changes the price without explanation.
- Get it all in writing: Your estimate, payment schedule, project scope, and warranty terms should be clear and detailed.
Remember—if the contractor won’t put it in writing, they may not stand behind their work.
⭐️ Why Local Experience Matters
Not all general contractors understand Pennsylvania’s weather patterns, permitting rules, or roofing codes. That’s why it pays to work with someone who’s experienced in your region.
- Local references: Ask for recent work done near your neighborhood.
- Familiar with local inspectors: This helps streamline the inspection process and avoid unnecessary delays.
- Knowledge of roofing materials that work in your climate: Pennsylvania homes face snow, rain, and heat—your roof should be ready for all three.
At G. Cannon, we live and work where you do. We take pride in delivering high-quality craftsmanship with a commitment to customer satisfaction.
🤝 Trust G. Cannon for Transparent, Reliable Roofing Service
Knowing the right questions to ask a contractor helps you avoid stress, protect your home, and feel confident in your roofing project from start to finish. At G. Cannon, we welcome your questions and make sure you’re informed every step of the way.
Our team is experienced, licensed, insured, and focused on doing the job right—with honesty, cleanliness, and clear communication. Contact G. Cannon today to schedule your free roofing estimate and see the difference a good contractor makes.
