Questions to Ask Before You Hire a Roofing Contractor
The right questions do not test whether a contractor is friendly. They test whether the answers can be verified, whether the work has been thought through, and what happens when something goes wrong.
Most homeowners hire a roofer based on how the estimator came across. That is not irrational — trust matters — but likeability is the easiest thing in this industry to fake and the hardest thing to verify. The questions below are chosen for a different reason: each one produces an answer you can either check independently or judge on its substance.
Who Am I Actually Hiring?
Ask for the full legal business name, the business address, and how long the company has operated under that name. Companies that have been rebranded repeatedly, or that operate from a name different from the one on the contract, are worth a second look. Ask who will be on your roof: direct employees or subcontracted crews. Neither answer is disqualifying, but if it is subcontracted, you need to know whose insurance and whose warranty applies, and who is responsible if the crew damages something.
Can I Verify Your Coverage?
Ask for a certificate of commercial general liability insurance and a WSIB clearance certificate, and ask for the information you need to verify both directly with the insurer's broker and with WSIB rather than accepting a PDF at face value. A contractor who deals with this routinely will not find the request unusual. One who reacts badly to it has told you something useful.
Have You Done This Specific System Before?
Metal roofing is not asphalt with different material. The panel handling, the trim detailing, the flashing methods, the allowance for thermal movement and the eave detailing are all different skills. Ask how many roofs of the specific system you are buying the company has installed, whether they roll-form panels on site or install factory-supplied panels, and which manufacturer's system they work with most. Then ask to see addresses — not photographs — of jobs you can drive past.
Can I See Work That Is Several Years Old?
This is the question that separates the serious from the plausible. Anyone can show you a roof finished last month. Ask to see work from five or more years ago, and ask to speak to those owners. What you want to know is not whether the roof looked good on the last day — it is whether anything went wrong afterward, and what the company did about it.
Process Questions Worth Asking
- ✓How do you measure the roof, and will I see the measurements?
- ✓What happens when you find rotten sheathing — how is it priced and who approves it?
- ✓Will you assess the attic ventilation and insulation, or only the roof surface?
- ✓How is the roof kept watertight overnight and if weather comes in mid-tear-off?
- ✓Where does the bin go, and how is the driveway protected under it?
- ✓What is protected on the ground — landscaping, air conditioner, deck, pool, windows?
- ✓How often is a magnetic nail sweep done, and is it included on the final day?
- ✓Who is my day-to-day contact, and how do I reach them if something comes up?
- ✓What happens to satellite dishes, solar panels or anything else attached to the roof?
What Exactly Does the Warranty Cover?
There are two warranties and they cover different things. The manufacturer's warranty covers the product. The contractor's workmanship warranty covers the installation. Ask for both in writing, ask what each excludes, ask whether the manufacturer's coverage requires registration and who does that, and ask what would void either. Then ask the harder question: what is the process if I have a problem in year six, and what happens to the workmanship warranty if the company is sold or closes.
Who Handles the Permit?
Whether a permit is required depends on your municipality and on what the work involves, so the first correct answer is that it will be confirmed with the local building department. The second thing to establish is who is responsible for obtaining it, who deals with inspections if there are any, and whether that cost is in the quote. You do not want to discover on day one that the permit was assumed to be your job.
The best single question to ask any contractor: what could go wrong on this job, and how would you handle it? A contractor with real experience will name two or three specific things — rotten sheathing, a hidden layer, a chimney flashing that needs rebuilding, weather. Someone who says nothing ever goes wrong has either not done many roofs or is not being straight with you.
Payment Questions
Ask for the payment schedule in writing and tied to progress rather than to dates. Ask who cheques are made out to — it should be the company on the contract, not an individual. Ask for a receipt for every payment. Be wary of any request for a large payment before materials are on site, of cash-only arrangements, and of pressure to pay the balance before the walkthrough and deficiency list are complete.
Communication and Change Orders
Ask how changes are handled. The answer should be: in writing, described, priced and approved by you before the work happens. Verbal change orders are how a project ends in a dispute. Ask how you will be told about a weather delay, how much notice you get before the crew arrives, and what hours they work — that last one matters more than people expect when a tear-off starts early on a Saturday.
What the Contract Must Contain
Before signing, confirm the contract includes the full scope and specification, the total price and payment schedule, start and completion expectations, the warranty terms, an exclusions list, the change order process, and the cancellation terms. If any of those are missing, they are missing on purpose or by neglect, and either way you want them added before you sign rather than discussed afterward.
Frequently Asked Questions
How many quotes should I get?
Three is a reasonable number. Fewer and you have no basis for comparison; many more and the process stalls. What matters more than the count is that all three are quoting comparable scope — same tear-off assumption, same panel system, same underlayment coverage, same trim list.
Is it rude to ask for insurance and WSIB documents?
No. It is standard practice, and every legitimate contractor is asked for them regularly. The request is about protecting you if someone is hurt or something is damaged on your property. A contractor who is offended by it is telling you how they will handle the next reasonable request.
Should I hire a contractor who subcontracts the crew?
Subcontracting is common and not inherently a problem — plenty of excellent work is done by long-standing subcontracted crews. What you need is clarity: whose insurance and WSIB coverage applies, who holds the workmanship warranty, who supervises daily, and who is accountable if something goes wrong.
What if a contractor pressures me to decide today?
Decline. A real quote for real work is still valid tomorrow. Time pressure exists to prevent you from comparing, verifying and reading — which is exactly why it is used. No legitimate roofing project requires a same-day signature.
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