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When storms leave damage behind or water stains begin creeping across your ceiling, the next step is obvious: you need a reliable roofing contractor. But with every company calling themselves the best, sorting through the noise becomes a challenge. You don’t need flash — you need real experience, clear communication, and honest answers. We've created a free downloadable checklist to help you separate the true professionals from the fly-by-night operators.
Where to Start Your Search: Building Your Contractor Shortlist
Before diving into specific questions, let's talk about how to create your initial list of potential roofing contractors:
Ask People You Trust
Talk to neighbors, friends, and family who’ve had roofing work done in the past year or two. Honest feedback from people who’ve paid for the service is one of your most valuable tools. You’ll get clear insights on who followed through and who didn’t. If you’re in an HOA, they may also have a contractor list based on past experience.
Check Review Sites the Right Way
Don’t rely on just one platform — look at Google Reviews, Yelp, and the Better Business Bureau. Reading the reviews is more helpful than just counting stars. Focus on:
- A few negative reviews among many positive ones are normal.
- Look at how the company responds to criticism.
- Watch for patterns in complaints (like communication issues or unexpected costs).
- Be skeptical of companies with only perfect reviews — they might be curated.
Get Multiple Quotes
Aim for at least three written estimates. This gives you a better sense of pricing and how each company approaches the job. While they’re on site, pay attention to:
- How thoroughly they inspect your roof
- Their explanations of material options and installation processes
- Their professionalism and communication style
- Their willingness to answer questions without pressure tactics
A low bid might sound tempting, but it often comes at the cost of rushed work or low-end materials. Look at the full picture — materials, process, communication, and long-term value.
10 Power Questions That Separate Great Roofers from the Rest
1. “Can You Show Me Your License and Insurance?”
Never settle for a verbal promise — ask to see proof of coverage. A qualified roofer carries both general liability and workers’ compensation insurance. Without it, you could be held responsible if someone gets hurt or your home is damaged during the job.
When we meet with homeowners at Greater Midwest Exteriors, we bring our insurance documentation to every consultation. We’ve seen too many cases where homeowners ended up with bills after an uninsured worker fell off a ladder. Don’t put yourself in that position.
2. “Who’s Actually Going to Be on My Roof?”
A lot of homeowners assume the person giving the quote will be involved in the installation, but that’s often not the case. Many companies outsource to subcontractors you've never met.
Ask pointed questions about:
- Who will be on-site during the installation?
- How long have they worked with the company?
- What quality checks are in place?
- Who handles issues if something goes wrong later?
At Greater Midwest Exteriors, we maintain long-term relationships with our installation teams. They're not strangers — they're partners who understand our exacting standards.
3. “Can You Provide Local References?”
A reputable contractor should offer recent references without hesitation. And you shouldn’t stop at collecting names — reach out and ask meaningful questions:
- Did they clean up thoroughly?
- Were there any surprise costs?
- How did they handle setbacks?
- Would you work with them again?
Even better, ask for addresses of completed projects in your neighborhood, then drive by to inspect their work firsthand. We proudly showcase our completed projects throughout Chicagoland.
4. “What Roofing System Do You Recommend, and Why?”
This question quickly reveals whether you’re speaking with someone knowledgeable or just a salesperson. A good contractor explains why a specific roofing system fits your home, weather conditions, and budget.
Listen for discussions about complete roofing systems (not just shingles), including underlayment, ice and water shields, flashing details, and proper ventilation. At Greater Midwest Exteriors, we work with leading manufacturers like CertainTeed and Owens Corning, but we'll help you understand all your options.
5. "What's Your Guarantee? Tell Me About Your Workmanship Warranty.”
Material warranties come from the manufacturer, but what about the installation itself? A reliable contractor backs up their workmanship with a clear warranty, often ranging from 5 to 10 years.
Get specifics in writing about:
- What the workmanship warranty covers (and doesn’t).
- Whether it stays valid if ownership changes.
- If it transfers to the next homeowner.
- How claims are handled if you ever need to use it.
Our workmanship warranties are a reflection of the quality we promise, and we’re still around years later if you ever need to use them.
6. “How Do You Handle Hidden Repairs or Structural Issues?”
Sometimes a tear-off reveals problems you couldn’t see from the outside — rotted wood, damaged decking, or structural concerns. A good contractor has a clear process for handling these discoveries.
Ask how they’ll:
- Communicate any additional problems
- Price out necessary extra work
- Get your approval before moving forward
Beware of contractors who dodge this question — they might be planning to hit you with expensive change orders or cut corners by ignoring problems.
7. “How Will You Protect My Home During the Project?”
Roof replacements involve heavy materials, debris, and high-traffic work zones. A reliable contractor has clear systems to protect your property throughout the job. Ask about:
- Tarping over landscaping, HVAC units, and patios
- How debris will be managed and where it's stored
- Daily cleanup expectations
- Magnetic sweeps for nails around your yard and driveway
- How they avoid damaging gutters, siding, or walkways
At Greater Midwest Exteriors, we take the same precautions we’d want at our own homes. Your property is treated with care and respect from the first day on-site.
8. “Who Handles Permits and Inspections?”
Professional roofing contractors manage all permitting requirements. They should:
- Know local building codes inside and out
- Obtain necessary permits (not ask you to pull them)
- Schedule required inspections
- Ensure all work passes final inspection
If a contractor suggests skipping permits to "save money", run the other direction. They're setting you up for potential fines, insurance issues, and complications when selling your home.
9. “How Do You Structure the Payment Schedule?”
You should never be asked to pay in full before work begins. A fair and professional payment plan typically includes:
- A deposit of 10-30% to get started.
- Clearly defined milestones tied to progress.
- A final payment is only made after the project is completed and inspected.
We structure our payment schedules to give homeowners confidence while allowing us to secure premium materials for their projects.
10. “Will You Give Me a Detailed Written Estimate?”
The estimate should do more than just show a final number. A thorough proposal outlines every part of the job, including:
- Exact materials, including brands and product types
- A clear description of the full scope of work
- Line-item breakdowns for labor and materials
- Timeline expectations from start to finish
- Cleanup and disposal plans
- Warranty coverage and documentation
Verbal agreements aren’t enough if problems come up. A written estimate keeps both sides aligned and avoids confusion later.
Run from These Red Flags: Warning Signs of Trouble
When you're talking to roofing contractors, trust your gut — some red flags are too big to ignore:
- Too-low pricing: An unusually cheap bid often means they’re planning to cut corners on materials or labor.
- Hard sales pressure: If someone’s pushing you to “sign today”, that’s a tactic, not professionalism.
- No real office: If all they list is a P.O. box, they might be gone the moment there’s a problem.
- Cash up front: Reputable companies have supplier relationships. They don’t need your full payment before starting.
- Storm chasers: Be cautious of out-of-towners knocking after a storm. Many don’t plan to stick around.
- Avoiding questions: Vague responses, dodging details, and refusing to provide things in writing? That’s a major red flag.
Why Going Local Makes All the Difference
Working with a roofer who knows your community offers clear advantages that national chains can’t match:
- Local climate knowledge: Roofers based in your area understand how to build for Chicagoland’s weather — hot summers, ice, wind, and everything in between.
- Reputation on the line: Local companies rely on referrals and community trust. Poor work isn’t something they can hide from.
- You know where to find them: If there’s ever an issue, they’re nearby, not unreachable in another state.
- Supporting the local economy: Choosing a neighborhood contractor helps keep money in your community and supports local jobs.
At Greater Midwest Exteriors, we live where we work. We’re not just contractors — we’re your neighbors, and our name is tied to every job we complete.
The Greater Midwest Exteriors Difference
Beyond just getting a roof, homeowners who choose us are choosing a company that takes every part of the process seriously:
- No shortcuts: We use top-grade materials and experienced crews who focus on quality from start to finish.
- Hands-on oversight: A dedicated project manager stays involved in your job, not just a name on paper.
- We protect your home: Your landscaping, siding, and outdoor spaces are treated with care throughout the job.
- Clean job sites: We clean up daily and use magnet sweeps to keep your property safe and tidy.
- Clear, honest updates: We explain the work in simple terms and keep you updated every step of the way.
