Your roof is the most consequential system on your home. It protects everything beneath it — your structure, your insulation, your belongings, your family. When it fails, the damage cascades fast and wide. And yet most homeowners hire a roofer the same way they’d hire someone to mow their lawn: whoever is available, whoever answers the phone, whoever has a sign on a nearby street.
Roofing also attracts a disproportionate number of storm chasers, unlicensed operators, and fly-by-night companies that collect a deposit and disappear. The questions in this guide are designed to protect you from a bad hire — and to help you understand what you’re paying for when you make a good one.
“Roofing is the trade where I see the most homeowner regret. Not because roofers are worse than other tradespeople — most are skilled and honest — but because the consequences of a bad roof are so expensive and so slow to reveal themselves. A leak that starts in year two of a bad installation can cause tens of thousands in damage before it’s visible on the ceiling. The questions you ask before signing protect you from that.”
— Tony Allaraj from Four Seasons Roofing, licensed roofing contractor with 24 years of experience in residential roofing across Toronto and Southern your region
“The best roofing questions aren’t about getting the lowest price — they’re about understanding how the work will protect your home over time. Ask who will be on-site, what materials are being used, how ventilation and flashing will be handled, and what happens if unexpected issues are found. A contractor who welcomes those questions is usually a contractor who stands behind their work.”
— Astrit from Innovation Roofing, roofing contractor with 10+ years of experience helping Toronto homeowners with roof repairs, replacements, and exterior roofing solutions
Table of Contents
Before You Call Anyone
Is this a repair or a replacement?
Before inviting a roofer to quote, have a sense of what you’re dealing with. A few missing shingles after a storm is a repair. A roof that’s 20+ years old with granule loss, widespread cracking, and interior water stains is likely a replacement. Getting this wrong costs you — a repair on a failing roof is money spent delaying the inevitable.
For help making this determination: Repair vs Replace: How Do I Know If I Need a New Roof?
Is this an insurance claim or an out-of-pocket job?
If your roof was damaged by a storm, hail, or a fallen tree, your homeowner’s insurance may cover part or all of the cost. File a claim before getting quotes — your insurer will send an adjuster, and the adjuster’s report will inform what work is covered. Be cautious of roofers who approach you unsolicited after a storm and offer to “handle the insurance claim” — this is a common storm-chaser tactic that often ends badly.
Questions to Ask Before Hiring
Are you licensed to work as a roofer in this region?
Roofing licensing requirements vary by region. In many regions, roofers working on residential projects above a certain threshold should be registered with the relevant trade licensing body as a Residential Roofing Mechanic. In other regions, check the relevant trades authority. An unlicensed roofer has no regulatory accountability and may not know — or follow — current installation standards.
Ask for the licence or registration number and verify it.
What a good answer looks like: A specific registration or licence number offered without hesitation, with the issuing body named.
Do you carry liability insurance and workers’ compensation coverage?
These are two separate and essential protections. Liability insurance covers damage the roofer causes to your property — or a neighbor’s — during the job. Workers’ compensation coverage (or equivalent workers’ compensation) covers their crew if someone falls. Roofing is one of the most physically dangerous trades. If a worker is injured on your roof without proper coverage, the liability may fall to you as the property owner.
Ask for a certificate of insurance and a workers’ compensation clearance certificate. Verify both.
For a full breakdown: Questions to Ask a Roofer About Licensing and Insurance
What a good answer looks like: A current certificate of insurance and workers’ compensation coverage clearance provided within 24 hours of asking.
How long have you been in business under this name?
Roofing is notorious for companies that appear after major storms, collect deposits, and disappear. A company that has operated under the same name for five or more years, in your area, with verifiable reviews and references, is significantly more accountable than a newcomer. Ask directly how long the company has been operating and verify it.
What a good answer looks like: An established local business with a verifiable history, identifiable ownership, and a fixed address.
Will you or your crew be doing the work, or will it be subcontracted?
Many roofing companies subcontract the actual installation to crews they don’t directly employ. This isn’t automatically a problem, but you need to know. If the work will be subcontracted, ask: who is the crew, are they licensed, are they covered under the roofing company’s insurance, and has the company worked with them before?
What a good answer looks like: A named crew with clear accountability, whether direct employees or a known subcontractor.
Questions About the Quote
Is this a full-replacement quote or a repair quote?
Make sure you and the roofer are quoting the same scope. A quote for a “roof job” that turns out to be a patch repair on an otherwise failing roof is not the same as a full replacement. Get the scope in writing.
What materials are included?
Roofing is not just shingles. A complete roof installation includes: underlayment, ice and water shield (especially in Canadian climates), drip edge, flashing around penetrations (chimneys, skylights, vents), ridge cap, and starter strips. Ask the roofer to list every component and specify the brand and grade of each.
For a deep dive: Questions to Ask a Roofer About Materials and Shingles
What a good answer looks like: A written materials list with brand names, grades, and quantities — not just “architectural shingles.”
What is and isn’t included in the price?
Ask specifically: does the quote include tear-off and disposal of the old roof? Replacement of damaged decking if found? Flashing replacement? Cleanup and magnet sweep for nails? Each of these can be excluded, and each can add hundreds or thousands of dollars to the final bill if they surface mid-job.
How are price changes handled?
Rotted or water-damaged decking, discovered after tear-off begins, is a legitimate and common reason for additional cost. Ask how this is handled: will the roofer stop and show you the damage before proceeding? Is there a per-sheet price for decking replacement established upfront? Will there be a written change order?
What a good answer looks like: A clear process, with a pre-agreed per-sheet decking price and a commitment to show you any damage before repairing it.
For more on quotes: Questions to Ask When Getting a Roofing Quote
Questions About the Job
What is the timeline?
A standard residential roof replacement typically takes one to two days for an average-sized home. Ask specifically: when will work start, how long will it take, and what would cause delays? Weather is the most common legitimate delay in roofing — know their policy.
For more: How Long Does a Roof Replacement Take?
Will you protect my property during the job?
Tear-off generates significant debris — old shingles, nails, underlayment. Ask how the roofer will protect your landscaping, windows, siding, and air conditioning unit during the job. Will tarps be used? Will a magnetic sweeper be used after to collect fallen nails? Who is responsible for any incidental damage?
What a good answer looks like: A clear site protection plan, with specific mentions of tarps, nail sweeping, and damage responsibility.
Do you pull permits if required?
In many jurisdictions, a full roof replacement requires a building permit. The permit must be pulled by the roofing contractor, not the homeowner. Ask whether your job requires a permit and who is responsible for pulling it.
Questions About Warranties
What manufacturer warranty comes with the shingles?
Quality shingles carry manufacturer warranties of 25 to 50 years, and some carry lifetime coverage. But those warranties are often voided if the shingles aren’t installed by a certified installer using all required components. Ask whether the roofer is a certified installer for the shingle brand they’re recommending, and what the manufacturer warranty covers.
What workmanship warranty do you offer?
Separate from the manufacturer warranty, the roofer should offer their own workmanship warranty covering defects in how the roof was installed. Industry standard is at least two years; reputable companies offer five or more. Get it in writing.
For a full breakdown: Questions to Ask a Roofer About Warranties
What a good answer looks like: A written workmanship warranty of at least two years, with clear terms on coverage, exclusions, and the claims process.
Red Flags to Watch For
Door-to-door solicitation after a storm. Storm chasers are real and actively target post-storm neighborhoods. A company that approaches you unsolicited, pressures you to sign quickly, and offers to “handle your insurance” is a high-risk hire.
Requesting a large deposit. A deposit of 10–25% is reasonable. Anything more than 30–40% upfront — especially in cash — is a warning sign.
Significantly lower quote than everyone else. A dramatically lower quote usually means inferior materials, missing components, or an unlicensed crew. Ask specifically what’s different.
No local address or verifiable presence. A company with no fixed local address, no verifiable business history, and no reviews is an unknown quantity. Don’t hire them.
Pressure to decide immediately. No roofing job requires a same-day signature unless there is an active leak and emergency conditions. Take the time you need.
For a complete guide: Red Flags When Hiring a Roofer
Before They Start: A Quick Checklist
- Licence or trade registration verified independently
- Certificate of insurance received and confirmed current
- Workers’ compensation clearance certificate received and verified
- Written quote with full materials list and exclusions
- Decking replacement policy confirmed and priced upfront
- Warranty terms — both manufacturer and workmanship — in writing
- Timeline and start date confirmed
- Site protection plan discussed
Related Questions
- Questions to Ask a Roofer About Licensing and Insurance
- Questions to Ask a Roofer About Materials and Shingles
- Questions to Ask When Getting a Roofing Quote
- Questions to Ask a Roofer for References and Past Work
- Questions to Ask a Roofer During the Job
- Questions to Ask a Roofer About Warranties
- Questions to Ask After a Roof Replacement Is Complete
- How Much Does a Roof Replacement Cost ?
- Red Flags When Hiring a Roofer
- Repair vs Replace: How Do I Know If I Need a New Roof?
- How Long Does a Roof Replacement Take?
- What to Do If a Roofer Does Bad Work
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