At Precision Exteriors, we've been serving homeowners across Maryland's Eastern Shore for years. As a family-owned business with offices in Cambridge and Salisbury, we've seen it all—from contractors who cut corners to homeowners who wished they'd asked more questions before signing a contract. We wrote this guide because we believe informed homeowners make better decisions, and we want you to get the roof you deserve, whether you choose us or not.

The roofing industry has a reputation problem. Consumer protection agencies receive thousands of complaints about roofing contractors every year. Maryland, like many states, has minimal regulations governing who can call themselves a roofing contractor. The barrier to entry is low, which means the market includes everyone from highly trained professionals to people who learned to roof last week—and a few bad actors who never intended to do right by you in the first place.

This creates a genuine "buyer beware" situation. Even when you do your homework, you can still end up with a contractor who doesn't supervise their crews properly or cuts corners when you're not watching. The best protection you have? Knowledge. Ask questions. Ask lots of them. If a contractor gets annoyed by your questions, that tells you everything you need to know. Walk away. A professional contractor welcomes your curiosity because they have nothing to hide.

We've organized these 44 questions into three categories: general questions about the contractor's business, specific questions about your project, and final questions you should ask after you've had time to evaluate your roof yourself. Use this as a checklist. Print it out. Bring it to every estimate. Your roof is one of the most important investments you'll make in your home—it deserves this level of attention.

Part One: Questions About the Roofing Contractor

Before you discuss your specific project, you need to know who you're dealing with. These 13 questions will help you understand whether the contractor has the experience, stability, and professionalism to handle your roof properly. Don't skip this step—many homeowners jump straight to "how much will it cost?" and regret it later.

1.    How long have you been in business? Longevity matters. A company that's been around for years has a track record you can verify. New companies aren't automatically bad, but they haven't proven they can stand behind their warranties.

2.    How local is your operation? Storm chasers follow severe weather from state to state, sign contracts, do questionable work, and disappear. A local company with a physical office is invested in the community and its reputation. At Precision Exteriors, our offices in Cambridge and Salisbury aren't just addresses—they're where you can find us when you need us.

3.    Who owns the business, and how long have they owned it? Ownership stability indicates a company that's built to last. Frequent ownership changes can signal financial problems or instability.

4.    Can I see examples of your completed work in person? Photos are helpful, but nothing beats seeing actual roofs the contractor has installed. Pay attention to the details—how do the flashings look? Are the shingles aligned properly? Does the overall appearance suggest care and craftsmanship?

5.    Who will actually be installing my roof? Are they your employees or subcontractors? Can I visit a current job site to watch them work? Some contractors sell the job but hire unknown crews to do the work. You want to know exactly who will be on your roof. Visiting an active job site tells you volumes about their work practices, safety standards, and attention to detail.

6.    What training and experience does your installation crew have? Have they been trained and certified by the manufacturer of the roofing materials they'll be installing? Manufacturer training ensures the crew knows the specific requirements for your roofing system. Without it, installation errors can void your warranty.

7.    Can you provide references from past customers I can contact directly? Online reviews help, but talking to actual customers gives you deeper insight. Ask about the entire experience, not just the finished product.

8.    When could you schedule my project? This tells you about their workload and availability. Be cautious of contractors who can start immediately—it might mean they're not busy for a reason. Also be wary of those with wait times so long that your roof might not survive the delay.

9.    How long will my project take from start to finish? A professional can give you a realistic timeline. They should also explain what factors might cause delays, such as weather or unforeseen structural issues.

10. Can you provide proof of proper licensing, certification, insurance, and workers' compensation coverage? Don't just ask—verify. Call the insurance company directly to confirm coverage is active. If a contractor is unlicensed or uninsured and someone gets hurt on your property, you could be held liable.

11. Is a building permit required for my project, and will you handle pulling it? Permit requirements vary by location. A reputable contractor knows local codes and handles permitting as part of the job. Skipping permits can create problems when you sell your home.

12. What safety measures do you take to protect your workers? Roofing is dangerous work. A contractor who cuts corners on safety is probably cutting corners elsewhere too. Look for OSHA compliance, fall protection, and proper equipment.

13. What precautions do you take to protect my home, family, and property during the project? Roofing creates debris, noise, and disruption. Professional contractors have systems to protect your landscaping, siding, windows, and outdoor living areas. They should also have protocols for keeping children and pets safe.

Part Two: Contractor Questions About Your Specific Roofing Project

Once you're satisfied with the contractor's credentials, it's time to dig into the details of how they'll handle your particular roof. These 20 questions separate contractors who know their craft from those who are winging it. The answers will reveal whether they've thought through your project carefully.

1.    How will you access my roof? Different access methods affect your property differently. Will they use ladders? Scaffolding? Will equipment need to be staged on your lawn? Understanding this helps you prepare.

2.    How will you handle debris removal? Will there be a dumpster on site? Where will it be placed? Old roofing materials have to go somewhere. A dumpster in your driveway for several days is common—know in advance where it will be and for how long.

3.    How will you protect my gutters during the tear-off and installation? Gutters can easily be damaged during roofing work. A careful contractor has a plan to prevent this.

4.    What's your plan if bad weather arrives during the project? How quickly can you respond, and how will you protect my home? Weather on the Eastern Shore can change quickly. Your contractor should have a clear plan for tarping and protecting your home if rain threatens during tear-off.

5.    Will you provide written warranties for both your workmanship and the roofing materials? When will I receive these documents? Verbal promises mean nothing. Get everything in writing before work begins, including what each warranty covers and for how long.

6.    Are you using manufacturer-approved fasteners? How do you ensure the correct number of fasteners are used in the right locations? Fastener type, quantity, and placement directly affect your roof's wind resistance and longevity. Manufacturers specify these requirements precisely—deviating from them can void your warranty.

7.    How will you protect my driveway, landscaping, and other property from damage? Expect boards over flower beds, tarps on shrubs, and protection for hardscaping. Professional crews leave your property as clean as they found it.

8.    What is your cost for replacing damaged plywood or decking if you discover problems underneath? You won't know the true condition of your decking until the old roof comes off. Get a per-sheet price in writing so there are no surprises.

9.    Who will be my point of contact during the project, and how can I reach them? You shouldn't have to track down the crew chief when you have a question. There should be one person responsible for communication, and they should be easily reachable.

10. Can you provide the manufacturer's specifications and installation instructions for my roofing system? A contractor who follows manufacturer specs will have no problem sharing them. This documentation also helps you verify the installation was done correctly.

11. Besides the installers themselves, who oversees the installation for quality control? The best contractors have supervisors or project managers who inspect work in progress. Installation errors caught early are easier and cheaper to fix.

12. Will you install all new flashings, or do you plan to reuse any existing ones? Flashings are critical for preventing leaks. New flashings with a new roof is the standard practice. Be skeptical of any plan to reuse old flashings unless there's a compelling reason.

13. Are there any areas you plan to seal with caulk rather than properly flash? Caulk is a temporary solution at best. Proper flashing provides lasting protection. A contractor who relies heavily on caulk is cutting corners.

14. How will pipe penetrations, vents, and other roof protrusions be handled? Every penetration through your roof is a potential leak point. The contractor should explain their approach using proper boots, flashings, and sealants.

15. What is your payment schedule? How much is due when? Be cautious of contractors who want significant payment upfront. A reasonable deposit followed by payment upon completion is standard. Never pay in full before the work is done.

16. What circumstances could cause the final price to differ from the estimate? Legitimate reasons include hidden deck damage, code-required upgrades, or changes you request. The contract should specify how change orders are handled and priced.

17. How will you evaluate the condition of my roof decking? Will you perform fastener pull-out resistance tests? Decking evaluation is critical. Some contractors just eyeball it; others use testing to verify the deck can hold fasteners properly. Understand what you're getting.

18. What's your assessment of why my current roof is failing? Is there evidence of problems I should address beyond just replacing the shingles? A good contractor doesn't just see a sale—they diagnose problems. Issues like poor ventilation, inadequate flashing, or structural concerns should be identified and discussed.

19. Will you inspect my attic and evaluate whether ventilation needs to be improved? Can you identify any evidence of past leaks or moisture problems? Attic inspection reveals a lot about roof health. Moisture stains, mold, inadequate insulation, and ventilation issues all affect your new roof's performance. There's no better time to address these than during a re-roof.

20. Are there any tax credits, manufacturer rebates, or utility incentives available for my new roof? Energy-efficient roofing options may qualify for incentives. Your contractor should know what's available and help you take advantage of any savings.

Part Three: Final Contractor Questions After Evaluating Your Roof

Before making your final decision, take time to personally evaluate your roof. Walk around your home several times. Use binoculars to get a close look at details. Check satellite imagery to spot unusual areas from above. If you have upper-story windows overlooking lower roof sections, use them to your advantage.

Look for areas where debris accumulates, extreme wear patterns, streaking, staining, or biological growth like moss and algae. Note any "dead valleys" where water might pool instead of draining properly. Know whether your chimney has a cricket—that's the ridge structure behind it that diverts water. If you have skylights, know how old they are.

This self-evaluation gives you the knowledge to ask these 11 final questions, which will reveal whether your contractor truly understands your roof's unique challenges.

1.    For roof protrusions like walls, skylights, and chimneys, can you show me photos or sketches of exactly how these areas will be flashed and finished? This question separates experts from amateurs. A knowledgeable contractor can explain that flashings need to be inserted behind or into most roof protrusions. Skylights need to be curbed above the roof plane. Vague answers here are a red flag.

2.    My skylights are [X] years old. What's your recommendation? Skylights older than ten years should generally be replaced during a re-roof. Replacing them later means disturbing your new roofing—and risking leaks. Get your contractor's professional opinion.

3.    Does my chimney have a cricket, and if not, do you recommend installing one? Chimneys 18 inches or wider generally need crickets to divert water around them. Without one, water pools behind the chimney and eventually finds its way inside.

4.    I've noticed [describe unusual features you observed]. How will you handle these areas? Every roof has unique characteristics—dead valleys, unusual angles, multiple roof levels connecting. Make sure your contractor has a specific plan for each challenge you've identified.

5.    Are there any areas where structural modifications should be made to prevent future problems? Sometimes the best solution to a chronic problem area is changing the roof structure—not just replacing the roofing. A good contractor will identify these opportunities.

6.    My roof has significant streaking and staining. What causes this, and how can we prevent it in the future? Algae growth causes those black streaks common on Eastern Shore roofs. Solutions include algae-resistant shingles, zinc or copper strips, and improved airflow. Your contractor should have recommendations.

7.    My roof has low-pitch areas. Can you provide manufacturer documentation that your proposed roofing material is approved for these slopes? Different roofing materials have minimum slope requirements. Using the wrong material on a low-slope area leads to leaks. Don't take their word for it—ask for documentation.

8.    Let's discuss attic ventilation. What exhaust vents will be installed, and how will they be balanced with intake vents? Proper ventilation extends shingle life, reduces energy costs, and prevents moisture problems. Understand exactly what's being installed and why. There's no better time to upgrade ventilation than during a re-roof.

9.    Does my old roof need to be completely removed, or could a second layer work in my situation? In some cases, roofing over existing shingles is acceptable and can reduce costs. In other cases, it's a terrible idea. Local codes, existing roof condition, and weight limitations all factor in. Get your contractor's honest assessment.

10. I've had ice dam problems in the past. What can be done differently to prevent them? Ice dams form when heat escapes through the roof, melts snow, and the water refreezes at the eaves. Solutions include improved attic insulation, better ventilation, and ice and water shield at vulnerable areas. Address the root cause, not just the symptoms.

11. I'm interested in environmental considerations. What options exist for energy efficiency, recycled content in roofing materials, and recyclability at end of life? If sustainability matters to you, discuss cool roofing options that reflect heat, materials with recycled content, and what happens to the old materials. Some contractors recycle old shingles; others send everything to the landfill.

The Bottom Line

Forty-four questions might seem like a lot, but your roof is a significant investment that protects everything underneath it—your family, your possessions, and your home's structure. Taking the time to thoroughly vet your roofing contractor is one of the smartest things you can do as a homeowner.

At Precision Exteriors, we welcome these questions. As an Owens Corning Platinum Preferred Contractor—a designation held by less than 1% of roofing contractors nationwide—we've earned our reputation through transparent communication, expert craftsmanship, and standing behind our work. We're proud of our BBB A+ rating and the relationships we've built with homeowners across Cambridge, Salisbury, Ocean City, Easton, and throughout Maryland's Eastern Shore.

When you're ready to discuss your roofing project, we're ready to answer every one of these questions—and any others you might have. Because you deserve to know exactly what you're getting before you sign on the dotted line.

Ready to Talk About Your Roof?

Contact Precision Exteriors today for a free, no-obligation consultation.

Cambridge Office: 443-675-6485

Email: office@precision-exteriors.com

Owens Corning Platinum Preferred Contractor | BBB A+ Rated | Family-Owned