Questions to Ask Before Hiring a Contractor in Ontario
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Seven Questions That Separate a Good Contractor From a Risk. Ask All of Them Before You Hire.
Most Ontario homeowners ask one question before hiring a contractor: "What's it going to cost?" That's not enough. These seven questions take ten minutes and tell you far more about what you're actually getting into.
The contractor conversation feels awkward for most homeowners. You don't want to seem like you don't trust them. You don't want to come across as difficult before the job even starts. So you ask about price, nod at the number, and sign.
That reluctance is understandable — and it's also one of the most consistent predictors of contractor disputes. Not because the contractor is dishonest, but because the homeowner and contractor have different assumptions about scope, timeline, materials, and what happens when something goes wrong. The pre-hire conversation is where those assumptions either get aligned or don't.
These seven questions take ten minutes. They're not confrontational — they're the same questions a general contractor would ask when vetting a subcontractor. Asking them tells a legitimate contractor you're a prepared client. If a contractor reacts badly to any of them, that reaction is itself information worth having before you sign anything.
The Pre-Hire Conversation Is When You Have the Most Leverage
Once you've paid a deposit and work has started, your options narrow significantly. If the contractor doesn't have WSIB coverage and a worker is injured, you're dealing with that problem after the fact. If the scope was vague and the contractor interprets it differently than you did, you're negotiating mid-project when you have the least leverage.
"The best time to evaluate a contractor isn't after they've finished the job. It's in the ten minutes before you agree to hire them."
The pre-hire conversation costs nothing and creates no obligation. A contractor who provides clear, confident answers to the questions below is demonstrating exactly the kind of professionalism you want on your project. A contractor who deflects, delays, or reacts with frustration to reasonable questions is giving you a preview of what the project will look like when something goes wrong.
What to Ask Every Contractor Before You Sign in Ontario
These questions apply to any trade and any project size — roofing, decks, windows, basement finishing, landscaping, HVAC. Adjust the specifics for your project, but ask all seven.
"Can you provide your WSIB clearance certificate?"
A current WSIB Clearance Certificate confirms the contractor is registered and in good standing with the Workplace Safety and Insurance Board. Without it, you may be personally liable for workplace injury costs on your property. A legitimate contractor can provide this within 24–72 hours. What to watch for: Evasion, excuses about "just renewing," or confusion about what WSIB is. Any of these are red flags before work starts.
"What does your general liability insurance cover, and what's the limit?"
General liability insurance covers damage to your property caused by the contractor or their workers. The minimum you should accept in Ontario is $2M coverage. Ask for the certificate of insurance directly — not just a verbal confirmation. What to watch for: A contractor who says they have insurance but can't produce the certificate, or whose coverage is below $2M.
"Who will be doing the work — your own crew, or subcontractors?"
Many contractors operate as project managers and subcontract the actual work. That's not inherently a problem, but you need to know. If subcontractors are involved, ask whether they carry their own WSIB and insurance — or whether they fall under the GC's coverage. What to watch for: Uncertainty about who is covered or vague answers about sub arrangements.
"Have you pulled permits for this type of work before? Who handles that?"
Many renovations in Ontario require a building permit — decks over 24 inches, structural work, electrical, plumbing, HVAC. Ask directly whether a permit is required and who is responsible for pulling it. A contractor who says "you don't need a permit for this" on a project that clearly requires one is either uninformed or hoping you don't check. What to watch for: Dismissing permit requirements or saying permits are "the homeowner's job" on a contracted renovation.
"Can you provide references from a similar project in the last 12 months?"
References are more useful when they're recent and relevant to your project type. A roofer's deck reference from four years ago tells you something — a roofing reference from six months ago tells you more. Ask for contact details, not just names — and follow up. What to watch for: Contractors who can only offer vague references, who ask you to look at online reviews instead, or whose references are friends or family.
"What's your warranty on workmanship, and how do I make a claim?"
Ask for the warranty in writing before signing. A legitimate workmanship warranty covers defects in the contractor's installation for at least one year — ideally two. Ask specifically how to make a claim: who to contact, what the response time is, and what the remedy is. A contractor who gives you a vague verbal answer or says "we stand behind our work" without specifics isn't offering you a real warranty. What to watch for: No written warranty, very short warranty periods, or warranty language that excludes the most likely failure points.
"What's your payment schedule, and what does each payment correspond to?"
A reasonable payment schedule for most Ontario renovation projects runs: 10–25% deposit at signing, one or two progress payments tied to milestone completion, and the final 10–15% held until the job is done and inspected. Anything that asks for more than 33% upfront on a job over $5,000 is a yellow flag. A contractor who asks for 50%+ before work starts, or who won't tie payments to deliverables, is shifting all financial risk onto you. What to watch for: Large upfront deposits, payment schedules not tied to milestones, or resistance to any holdback on the final payment until job completion is confirmed.
What Each Question Is Designed to Catch
Use this table as a reference when you're in the conversation. If any answer triggers a flag, note it — it doesn't need to be a dealbreaker, but it should be resolved before you sign.
| The Question | What It Catches | Flag If... |
|---|---|---|
| WSIB clearance certificate | Personal liability for on-site injuries | Can't Produce It |
| General liability insurance | Property damage coverage, minimum $2M | Below $2M or Unverified |
| Own crew vs. subcontractors | Coverage gaps, accountability chain | Unclear Coverage |
| Permit responsibility | Unpermitted work, future resale issues | Dismisses Permit Need |
| Recent references | Track record on similar, recent work | No Verifiable References |
| Written workmanship warranty | Post-completion protection if work fails | Verbal Only or Vague |
| Milestone payment schedule | Deposit risk, leverage after work starts | >33% Upfront or No Milestones |
If You're Unsure How to Interpret the Answers — That's What Contract Link Is For
Some contractor responses are clearly fine. Some are clearly not. Many fall in the middle — a partial answer, a hesitation, a "we can figure that out once work starts." If you've had a pre-hire conversation and you're not sure whether the answers you got were good enough, Contract Link can review the quote and flag what's missing before you commit.
Got the Answers. Not Sure What They Mean? We'll Tell You.
Contract Link reviews contractor quotes and pre-hire documentation for Ontario homeowners — so you know whether what you've been told is actually what you need before you sign.
Serving Kitchener · Waterloo · Cambridge · Guelph and surrounding areas — contractlink.ca
A Good Contractor Welcomes These Questions. That's How You Know.
None of the seven questions above are unusual, aggressive, or unreasonable. They're the standard pre-hire checklist any informed homeowner should run through before committing money and access to their property. A contractor who takes them seriously — who answers clearly, produces documents without drama, and explains their process — is demonstrating exactly the professionalism that makes for a smooth project.
"The question isn't whether asking these things is awkward. The question is whether skipping them is worth the risk."
If you're working through the contractor selection process in Kitchener, Waterloo, Cambridge, Guelph, or anywhere in Southern Ontario and want an independent review of the quotes and documentation you've received, contractlink.ca is built exactly for that.