25 Questions to Ask a Roofing Contractor Before Hiring (2026)

Your roof is the most critical structural component of your home. In Pinellas County, where hurricanes, tropical storms, and intense summer thunderstorms are a fact of life, the quality of your roofing contractor directly affects your home's safety and your family's protection. A well-installed roof can last 25 to 50 years and withstand Category 4 winds. A poorly installed one can fail in the first moderate storm.

Before you sign a contract or hand over a deposit, ask these 25 questions. Each one is designed to reveal the contractor's qualifications, professionalism, and trustworthiness. We have organized them into categories and included the answers you should expect from a legitimate, qualified Pinellas County roofing professional.

Licensing and Insurance Questions (Q1 to Q4)

These are the most important questions you will ask. A contractor without proper licensing and insurance exposes you to enormous financial and legal risk.

Question 1: What Is Your Florida Roofing License Number?

Why it matters: Florida requires all roofing contractors to hold a state-issued license. There are two types:

• CCC (Certified Roofing Contractor): A statewide license that allows the contractor to work in any Florida county. This is the higher-level license and requires passing a state exam
• CRC (Registered Roofing Contractor): A county-specific license that restricts the contractor to approved counties. The contractor must have a local competency card

What to expect: A legitimate contractor will readily provide their license number. It should start with "CCC" or "CRC" followed by a series of numbers.

How to verify: Visit the Florida Department of Business and Professional Regulation (DBPR) website at myfloridalicense.com. Enter the contractor's name or license number to verify it is active, the license holder matches the person you are dealing with, there are no disciplinary actions, and the license covers roofing specifically.

If a contractor cannot or will not provide a license number, end the conversation immediately. Unlicensed contracting is a felony in Florida, and hiring an unlicensed contractor voids your protections under the Florida Construction Lien Law.

Question 2: Do You Carry General Liability (GL) Insurance?

Why it matters: General liability insurance protects you if the contractor or their crew damages your property, a neighbor's property, or if someone is injured on your property during the project. Without GL insurance, you could be personally liable for these costs.

What to expect: The contractor should carry a minimum of $1 million per occurrence in general liability coverage. Ask for a Certificate of Insurance (COI) directly from their insurance provider, not just a copy from the contractor (which could be outdated or falsified).

Question 3: Do You Carry Workers Compensation (WC) Insurance?

Why it matters: Roofing is one of the most dangerous occupations in the United States. If a worker is injured on your property and the contractor does not carry workers compensation insurance, you, as the property owner, could be held liable for medical bills and lost wages. In Florida, roofing contractors with one or more employees are required to carry workers compensation insurance.

What to expect: The contractor should provide proof of active workers compensation coverage. Verify this independently through the Florida Division of Workers' Compensation at myfloridacfo.com.

Red flag: Some contractors claim they do not need workers comp because they are a "sole proprietor" or "use only subcontractors." While there are limited exemptions, any roofing crew working on your home should be covered. If someone falls off your roof and has no coverage, the liability falls on you.

Question 4: Can I Verify Your License and Insurance Independently?

Why it matters: Fraudulent contractors sometimes present fake or expired documents. Independent verification through state databases eliminates this risk.

What to expect: A legitimate contractor will encourage you to verify their credentials. They have nothing to hide. Be wary of anyone who discourages independent verification or becomes defensive when asked.

To learn more about verifying contractor credentials and avoiding fraud, read our guide on roofing scams in Florida.

Experience and References Questions (Q5 to Q8)

Credentials get a contractor in the door. Experience and references tell you whether they will do good work on your specific project.

Question 5: How Long Have You Been Roofing in Pinellas County?

Why it matters: Local experience matters enormously in Florida roofing. A contractor who has been working in Pinellas County for years understands the local building codes, knows the permitting process for each municipality (Clearwater, St. Petersburg, Largo, Dunedin, Safety Harbor, and others), and has experience with the specific weather challenges of the Tampa Bay area.

What to expect: Look for a minimum of 3 to 5 years of local experience. Longer is generally better, as it means they have survived multiple hurricane seasons and maintained their business reputation over time. Be cautious of contractors who appear in the area only after major storms ("storm chasers") and disappear when warranty issues arise.

Question 6: Can You Provide Local References I Can Contact?

Why it matters: References from recent Pinellas County customers give you real-world feedback about the contractor's work quality, communication, timeline adherence, and cleanup.

What to expect: Ask for at least three references from projects completed within the last 12 months. When you contact references, ask about:

• Did the project stay on schedule and on budget?
• How was the crew's professionalism and cleanup?
• Did the contractor communicate well throughout the project?
• Were there any surprises or hidden costs?
• Would you hire this contractor again?
• How did the contractor handle any issues or callbacks?

Also check online reviews on Google, the Better Business Bureau (BBB), and Angi (formerly Angie's List). Look for patterns in reviews rather than focusing on individual positive or negative comments.

Question 7: Do You Have Experience with My Type of Roof?

Why it matters: Different roofing materials require different installation techniques. A contractor experienced with asphalt shingles may not be the best choice for a concrete tile or metal roof installation.

What to expect: The contractor should describe specific experience with your roof type, including the number of similar projects completed, any manufacturer certifications they hold for that material, and specific installation techniques they use. For example, tile roofing in Pinellas County requires knowledge of hot-mopping, mechanical fastening, and Florida's specific wind-uplift requirements for tile.

Question 8: Can I See Photos of Recent Completed Projects?

Why it matters: Visual proof of work quality is invaluable. Photos show the contractor's attention to detail, material quality, and finished appearance.

What to expect: A proud contractor will have a portfolio of recent projects readily available on their phone, website, or in a physical binder. Look for clean lines, proper flashing details, and consistent quality across multiple projects. If possible, ask to drive by a recently completed job to see the work in person.

Estimate and Pricing Questions (Q9 to Q13)

Understanding the financial details prevents surprises and protects your budget. A transparent contractor will welcome these questions.

Question 9: Will You Provide a Detailed Written Estimate?

Why it matters: A written estimate is your foundation for understanding what you are paying for and comparing bids from multiple contractors. Verbal estimates are meaningless and unenforceable.

What to expect: The estimate should include:

• Total project cost with itemized line items
• Material specifications (brand, product line, color)
• Labor costs broken out from materials
• Tearoff and disposal costs
• Permit fees
• Any anticipated code upgrade costs
• Decking repair estimates (or a per-sheet price for any discovered damage)
• Timeline for start and completion
• Payment schedule

Get estimates from at least three contractors to compare. Be cautious of any estimate that is significantly lower than the others, as it may indicate corners being cut, inferior materials, or hidden costs that will appear later. Learn more about expected pricing in our guide to roof replacement costs in Florida.

Question 10: What Is Your Payment Schedule?

Why it matters: The payment schedule is one of the most important indicators of a legitimate contractor versus a potential scam. Payment structure reveals a lot about a contractor's financial stability and intentions.

What to expect: A fair payment schedule for a Pinellas County roof replacement typically looks like this:

Red flags: Demanding 50% or more upfront. Requesting full payment before work begins. Cash-only payment requirements. No written receipt for payments. Pressure to pay immediately for a "discount."

Question 11: What Materials and Brands Will You Use?

Why it matters: The quality of roofing materials directly affects longevity, storm resistance, and warranty coverage. Not all shingles, tiles, or metal panels are created equal.

What to expect: The contractor should specify exact brand names and product lines (for example, "GAF Timberline HDZ" or "Boral concrete tile"). Ask about the material's wind rating, warranty terms, local availability, and whether the contractor is a certified installer for that manufacturer. Manufacturer-certified installers often provide enhanced warranty options. In Pinellas County, all roofing materials must be rated for the appropriate wind zone under the Florida Building Code.

Question 12: What Is Included in the Price?

Why it matters: Hidden costs are a common source of disputes. Clarify exactly what is included before signing.

What to expect: A comprehensive quote should include tearoff and disposal of existing roofing, new underlayment, all flashing and drip edge, ridge cap or ridge vent, all penetration boots (pipe jacks), permit fees, code-required upgrades, cleanup and nail sweep, dumpster rental, and all labor.

Question 13: Are There Potential Additional Costs?

Why it matters: Some costs cannot be determined until the old roof is removed. Understanding what could change helps you budget accurately.

What to expect: The most common additional cost is rotted or damaged decking that is discovered during tearoff. Ask the contractor how much they charge per sheet of replacement plywood or OSB (typically $75 to $150 per 4x8 sheet installed). Other potential additions include unforeseen structural repairs, additional code requirements, fascia board replacement, and soffit repairs.

Project Detail Questions (Q14 to Q19)

These questions help you understand the logistics and set proper expectations for the work process.

Question 14: When Can You Start and When Will You Finish?

Why it matters: A clear timeline helps you plan around the disruption and sets expectations. Delays are costly and frustrating.

What to expect: The contractor should provide specific start and completion dates in writing. Factor in permit processing time (3 to 10 business days in Pinellas County), weather contingencies, and material delivery lead times. A typical asphalt shingle roof replacement takes 1 to 3 days of actual work. Tile roofs take 3 to 7 days. Ask what happens if the project runs over schedule and whether there are any penalties or provisions in the contract for delays.

Question 15: Who Is Responsible for Pulling Permits?

Why it matters: In Pinellas County, a building permit is required for all roof replacements. The contractor, not the homeowner, should be responsible for pulling the permit.

What to expect: The only acceptable answer is: "We handle all permits." If a contractor suggests that you pull the permit yourself or that a permit is not needed, walk away immediately. Working without a permit is a code violation that can result in fines, forced removal of the new roof, insurance claim denial, and problems selling your home.

Question 16: How Large Is Your Crew?

Why it matters: Crew size affects project speed, quality, and supervision. Too few workers means the project drags on. Too many without proper supervision can lead to quality issues.

What to expect: A typical residential roof replacement in Pinellas County uses a crew of 4 to 8 workers, depending on the size and complexity of the roof. There should be a designated crew leader or foreman on-site at all times who is responsible for quality control and communication. Ask if the same crew will work on your project from start to finish.

Question 17: Do You Use Subcontractors?

Why it matters: Some contractors use their own employees while others subcontract the labor. Subcontracting is not inherently bad, but it adds a layer of complexity to accountability, insurance coverage, and quality control.

What to expect: If the contractor uses subcontractors, verify that the subcontractors are properly licensed and insured. The general contractor should provide certificates of insurance for all subcontractors working on your property. Understand who is responsible for quality and warranty claims if subcontractors perform the work.

Question 18: What Is Your Cleanup Process?

Why it matters: Roofing generates significant debris, and stray nails are a real hazard for vehicle tires, bare feet, and pets.

What to expect: Professional cleanup should include running a magnetic roller across the yard, driveway, sidewalks, and street multiple times. All debris should be collected and hauled away in the dumpster. Gutters and downspouts should be cleared. Landscaping should be restored to pre-project condition. The contractor should include cleanup in the written contract.

Question 19: Who Is Liable for Property Damage During Work?

Why it matters: Roof replacement can damage landscaping, pool screens, fences, windows, air conditioning units, and other property. Knowing who pays for repairs is important.

What to expect: The contractor's general liability insurance should cover property damage caused by their crew. Get this confirmed in writing in the contract. Document the condition of your property before work begins with photos so you have evidence if damage occurs. Reputable contractors will address any damage promptly and at their expense.

Warranty Questions (Q20 to Q21)

Warranty protection is your long-term safeguard. Understanding what is covered and for how long prevents expensive surprises years down the road.

Question 20: What Manufacturer Warranty Do You Offer?

Why it matters: The manufacturer warranty covers defects in the roofing materials themselves. Different products come with vastly different warranty terms.

What to expect: Ask about the specific warranty tier. Most major manufacturers (GAF, Owens Corning, CertainTeed, Atlas) offer multiple warranty levels:

• Standard warranty: Typically 25 to 30 years, covers manufacturing defects only, prorated after the first few years
• Enhanced/System warranty: 40 to 50 years, covers materials and may include some labor for repairs. Requires use of a complete system from one manufacturer
• Premium/Lifetime warranty: Non-prorated coverage for the life of the original owner, includes materials and labor. Typically requires installation by a manufacturer-certified contractor

Ask whether the contractor will register the warranty with the manufacturer on your behalf. Unregistered warranties may default to the lowest tier of coverage. Also ask if the warranty is transferable if you sell your home, as this adds value to your property.

Question 21: What Is Your Workmanship Warranty?

Why it matters: The manufacturer warranty only covers material defects, not installation errors. The workmanship warranty covers problems caused by incorrect installation, such as improper nail placement, flashing failures, and sealing issues.

What to expect: Reputable Pinellas County roofers offer workmanship warranties of 5 to 10 years, and some offer even longer. Get the warranty in writing with clear terms about what it covers, what is excluded, and how to file a claim. The warranty should specify that the contractor will return to repair any installation defects at no charge during the warranty period.

Consider the contractor's longevity when evaluating a workmanship warranty. A 10-year warranty from a company that has been in business for 20 years carries more weight than the same warranty from a company that opened last year. If the company goes out of business, the workmanship warranty becomes worthless.

Florida-Specific Questions (Q22 to Q25)

These questions are specific to Florida's unique climate, building codes, and insurance requirements. A contractor who works regularly in Pinellas County should answer these confidently and thoroughly.

Question 22: Will My New Roof Qualify for Wind Mitigation Discounts?

Why it matters: A wind mitigation inspection evaluates your home for features that resist wind damage. The resulting report can save Pinellas County homeowners 10% to 45% on their windstorm insurance premiums, potentially saving hundreds or thousands of dollars annually.

What to expect: Your contractor should be knowledgeable about the wind mitigation form (OIR-B1-1802) and understand which features qualify for each discount. Key features that affect your wind mitigation credits include:

• Roof covering: FBC-compliant materials earn better credits than older non-compliant coverings
• Roof deck attachment: How the plywood is fastened to the trusses (8d nails at 6-inch spacing is the minimum for credits)
• Roof-to-wall connection: Hurricane clips, straps, or structural connectors (clips and straps earn significant discounts)
• Roof geometry: Hip roofs earn better credits than gable roofs
• Secondary water barrier (SWR): A sealed roof deck earns additional credits

Ask your contractor to explain which wind mitigation features your new roof will include and recommend scheduling a wind mitigation inspection after the project is complete. Learn more about Florida roof insurance and how wind mitigation saves you money.

Question 23: What Code Upgrades Are Required?

Why it matters: When you replace a roof in Florida, the new installation must meet the current Florida Building Code, even if your existing roof was built to older standards. Your contractor should know exactly what upgrades are required for your specific location in Pinellas County.

What to expect: Common required code upgrades in Pinellas County include:

• Sealed roof deck (secondary water barrier) using peel-and-stick or foam adhesive
• Proper nail patterns and spacing per the Florida Building Code
• Wind-rated starter strips and hip/ridge caps
• Code-compliant drip edge on all roof edges
• Proper ventilation meeting current code minimums
• Hurricane straps or clips at roof-to-wall connections (if not already present)

The contractor should include all required code upgrades in their estimate. These are not optional extras. They are legal requirements. A contractor who does not mention code upgrades either does not know the current code or plans to skip them, both of which are serious red flags.

Question 24: Will You Install Hurricane Clips or Straps?

Why it matters: Hurricane clips and straps are metal connectors that secure the roof structure to the wall framing. They are one of the most important features for preventing roof loss during high winds. Many older Pinellas County homes were built with toe-nailed roof-to-wall connections, which are significantly weaker.

What to expect: If your home does not already have hurricane clips or straps, your contractor should recommend their installation during the re-roof. While adding clips/straps to an existing home can be challenging from the attic side, many contractors include this service. The types of connectors include:

• Hurricane clips (single wraps): Metal brackets that connect each truss to the top plate of the wall. Better than toe nails but less protection than straps
• Hurricane straps (double wraps): Metal straps that wrap over the truss and attach to both sides of the wall plate. The strongest standard connection
• Structural connectors: Heavy-duty engineered connectors for additional hold-down strength in high-wind zones

Hurricane straps can earn you the best roof-to-wall connection credit on your wind mitigation inspection, which translates directly to insurance savings. This is one of the most cost-effective upgrades you can make to your Pinellas County home.

Question 25: Do You Have Experience with Insurance Claims?

Why it matters: If your roof replacement is related to an insurance claim, working with a contractor who understands the claims process can significantly streamline the project and help you maximize your payout.

What to expect: An experienced contractor should be able to document damage in a format that insurance adjusters recognize, provide estimates using industry standard pricing software (like Xactimate), assist with supplemental claims when additional damage is discovered, coordinate with your adjuster or public adjuster, and understand the insurance claim process and timeline requirements.

Be cautious of contractors who promise to "handle everything" with your insurance or who ask you to sign an Assignment of Benefits (AOB). Under Florida's 2022 reforms, AOB agreements are heavily restricted, and you should maintain control of your own claim.

Contractor Evaluation Scorecard

Use this scorecard to compare contractors side by side. Rate each category from 1 to 5 based on the contractor's responses to these 25 questions.

Red Flags That Should Stop You From Hiring

During your conversations with contractors, watch for these warning signs that indicate an unprofessional or potentially fraudulent operator:

• No license or refuses to provide number: This is an immediate disqualifier. Unlicensed roofing is a felony in Florida
• Demands large upfront payment: More than 20% upfront is a red flag. Full payment before work begins is almost always a scam
• No written estimate or contract: Everything should be in writing. Verbal agreements offer zero protection
• Pressures you to decide immediately: "This price is only good today" is a high-pressure sales tactic, not a legitimate business practice
• Shows up unsolicited after a storm: Door-to-door solicitation after hurricanes is the hallmark of storm-chasing contractors
• Suggests skipping permits: This will cause problems with insurance, inspections, and home resale
• Cannot provide references: Every established contractor has satisfied customers willing to vouch for them
• Asks you to sign an AOB: Post-2022 reforms make AOBs risky for homeowners. Maintain control of your own claim
• Uses a P.O. Box as sole business address: Legitimate contractors have a physical business location
• Offers to waive your deductible: This is insurance fraud in Florida and can result in criminal charges for both the contractor and the homeowner

For a deeper dive into protecting yourself from fraud, read our comprehensive guide on roofing scams in Florida.

Printable Contractor Interview Checklist

Make an Informed Decision for Your Pinellas County Home

Asking the right questions before hiring a roofing contractor is the single most effective way to protect yourself from poor workmanship, financial loss, and fraud. A qualified, experienced Pinellas County roofing contractor will welcome these questions and answer them confidently with specific details.

Take your time. Get multiple estimates. Verify everything independently. The contractor you choose will install the barrier that stands between your family and Florida's worst weather. That decision deserves careful consideration.

Ready to start your search? Read our complete guide on how to find a roofer in Florida for a step-by-step process for finding, vetting, and hiring the right contractor for your Pinellas County roofing project.