21 Questions To Ask Your Contractor

Written by Tina Wu, Founder of Smart Renovations – a licensed, WSIB-certified renovation contractor serving the GTA since 2017, with 1,000+ completed kitchen and bathroom projects across Toronto, Richmond Hill, Vaughan, Mississauga, and beyond.

In nearly a decade of running a renovation company in the GTA, I’ve spoken with hundreds of homeowners who came to us after a bad experience with a previous contractor. When I ask what went wrong, the answers cluster around the same few patterns: the contractor stopped showing up without explanation, the final cost was approx 20-30% higher than the quote, or the work was never finished properly.

In almost every case, the warning signs were there in the first conversation. The homeowner just didn’t know what to listen for.

This checklist is built from those patterns. Use it before you sign anything – in your first phone call, your site visit, or your quote meeting. A contractor who runs a legitimate business will not be bothered by these questions. The ones who get defensive or vague when you ask them are telling you something important.

How to Use This Checklist

Work through the sections naturally in conversation – this isn’t an interrogation script. Think of it as a job interview, because that’s exactly what it is. You’re deciding whether to give someone access to your home and tens of thousands of dollars. You’re entitled to ask.

For each section: the questions, how to phrase them, what a solid answer sounds like, and what should make you stop.

Section 1 of 6

Business Legitimacy and Credentials

These questions confirm you’re dealing with a properly structured business – not someone operating in cash with no documentation and no accountability.

Ask

  1. Are you registered for HST?
  2. Do you carry liability insurance, and can you send me a certificate?
  3. Are you registered with the WSIB, or do your workers carry their own coverage?

How to phrase it

“Before we get into project details – can you confirm you’re HST registered? And I’ll need a copy of your liability insurance certificate and your WSIB clearance letter before we finalize anything. Is that something you can provide?”

What a solid answer sounds like

They confirm HST registration without hesitation, offer to send insurance and WSIB documents promptly, and treat the request as routine – because for a legitimate contractor, it is.

What to watch for

  • HST avoidance: “We can work something out.” A legitimate contractor should be able to provide HST registration details through the CRA. Skipping it means no proper paper trail – and that trail matters if anything goes wrong.
  • Coverage below $2M. Smart Renovations carries $5M liability. Always ask for the certificate, not just a verbal confirmation.
  • WSIB confusion: “My guys are independent so it doesn’t apply.” Ask for a valid WSIB clearance letter and verify it at wsib.ca. Any contractor who hesitates is worth questioning further.
Section 2 of 6

Experience and Track Record

You want evidence – not just assurance – that they’ve successfully completed work like yours.

Ask

  1. Have you done projects similar to mine in size and complexity?
  2. Can you share two or three references from recent comparable projects?
  3. Do you have photos of completed work I can look at?

How to phrase it

“I’d like to see examples of work similar to what I’m planning. Do you have photos of recent projects? And would you be able to share a couple of references – ideally from projects in the last year or two at a similar scale?”

What a solid answer sounds like

Photos are readily available. References are offered without pushback. The contractor can describe past projects specifically – scope, challenges, what went well.

What to watch for

  • References who “prefer privacy” – a contractor with a strong track record has clients who are happy to talk.
  • Portfolio photos inconsistent with your project scope.
  • Evasiveness about timelines on past projects.

When you call the references, ask specifically

  • Did the project finish within the agreed timeline? If not, by how much?
  • Was the final cost close to the original quote?
  • How did the contractor communicate during the project – did you have to chase them?
  • Would you hire them again without hesitation?

That last question matters most. Listen for any pause before the answer.

Section 3 of 6

How They Run a Project Day-to-Day

This section reveals what working with them actually looks like – and filters out contractors who are strong at selling but poor at executing.

Ask

  1. Will you be on-site personally, or will a foreman or crew lead manage the job?
  2. Who is my single point of contact during the project?
  3. How do you handle changes to the original scope – do you have a written change order process?
  4. How often will you update me on progress, and through what channel?
  5. What’s your realistic timeline for a project like mine, and what factors could push it?

How to phrase it

“Can you walk me through how you manage a project day-to-day? I want to understand who I’m talking to on-site, how I’ll get updates, and what happens if something comes up that changes the scope or the cost.”

What a solid answer sounds like

They name a specific person who leads the job on-site. They explain their communication rhythm (daily texts, weekly progress calls – something concrete). They mention change orders naturally: any scope change is documented in writing and approved before work proceeds.

What to watch for

  • “My guys know what they’re doing” without naming who’s on-site – vague supervision is how accountability gaps form.
  • Verbal change order processes. A homeowner agrees verbally to add a kitchen island; the contractor bills $8,000 at the end with no written record. This is one of the most consistent sources of renovation disputes in the GTA.
  • Unrealistically tight timelines. At Smart Renovations, a kitchen typically runs six to ten weeks on-site plus two to five weeks for design, permits, and materials. Three weeks is not efficient – it’s optimistic.

Section 4 of 6

The Quote Structure

Before you can compare quotes fairly, you need to understand what’s actually in them. These questions reveal whether a contractor builds quotes with transparency or leaves room for surprises later.

Ask

  1. Will the quote be itemised – labour and materials broken out separately?
  2. Does it cover all trades, or are some excluded?
  3. How do you handle allowances for materials like tile or fixtures?
  4. What’s explicitly excluded from this quote that I should budget for separately?

How to phrase it

“When you send the quote, will it show the breakdown of labour and materials? And can you flag anything that’s excluded so I know what to budget for on top of the quoted number?”

What a solid answer sounds like

The quote will be itemised. They explain allowances clearly – for example, “we include a $3,500 tile allowance; anything above that is a change order before we order.” They list exclusions proactively: permits, structural engineering, appliances.

What to watch for

  • A single lump-sum with no breakdown on a $30,000+ project.
  • A $500 tile allowance for a full bathroom – that’s not a budget, it’s a placeholder for a future change order conversation.
  • A quote 30-40% below others with no explanation. In my experience, that’s a scope that’s been quietly cut, not a deal.
Section 5 of 6

The Contract

You’re not asking them to explain every clause. You’re establishing whether they use proper written contracts at all and whether they’ll walk you through theirs before you sign.

Ask

  1. Do you use a written contract on every project?
  2. Does it cover scope of work, timeline, payment schedule, change order process, and warranty?
  3. Are you willing to walk me through the contract before I sign?

How to phrase it

“I want everything in writing before any work starts. Do you use a standard written contract, and can you walk me through it – specifically the scope, payment milestones, and how changes are handled?”

What a solid answer sounds like

Yes on all three counts, delivered without hesitation. A contractor who stands behind their work isn’t afraid of a contract – they want one too.

What to watch for

  • “We usually keep it simple.” A one-page contract for a $50,000 renovation is not simple – it’s underspecified. A professional contractor should always provide a written contract covering scope, timeline, payments, and change orders. Vague protects them, not you.
  • Scope described as “kitchen renovation” rather than “remove existing cabinets, install new upper and lower cabinets per approved design, supply and install quartz countertop.” Vague scope is the setup for every “that wasn’t included” conversation.
Section 6 of 6

Deposits and Payment Structure

You don’t need to negotiate the full payment schedule in the first meeting – but you do need to understand their general approach before you commit.

Ask

  1. What deposit do you require upfront, and what percentage of the total is that?
  2. Are the remaining payments tied to specific milestones?
  3. Do you provide written receipts for all payments?

How to phrase it

“Can you walk me through how payments are typically structured? I want to understand the deposit and whether remaining payments are tied to completed stages of work.”

What a solid answer sounds like

A reasonable upfront deposit – in the GTA, 10-15% is typical and fair for most projects – with subsequent payments tied to visible milestones: demolition, rough-in approval, cabinet installation, substantial completion. Receipts confirmed for every payment.

What to watch for

  • Deposit requests above 25-30% before any work begins. A deposit covers mobilization and materials – not the contractor’s general overhead. 50% or more upfront is a significant risk signal.
  • Payments tied to dates rather than milestones. “Pay by the 15th” gives you no leverage if work isn’t progressing.
  • Cash-only with no receipts. Without documentation you have no paper trail for warranty claims, disputes, or follow-up conversations about what was paid and when.

Watch out

If You Feel Pressured to Sign on the Spot

It happens regularly. “I have another client interested in this slot.” “This price is only valid until Friday.” “Spring is booking up fast.”

Sometimes this is true. Often it’s a closing tactic. Either way, here’s the appropriate response: thank them for their time, and tell them you need a few days to review.

A quote that expires while you’re doing your due diligence can usually be extended if the contractor wants the work. A contractor who refuses to give you 48-72 hours to review before signing has told you something important about how they’ll handle reasonable requests once you’re mid-project and committed.

Your Quick-Reference Checklist

Print this out or save it before your first contractor call.

Credentials

  • HST registered?
  • Liability insurance certificate (request a copy)?
  • WSIB clearance letter (verify at wsib.ca)?

Experience

  • Similar project examples available?
  • References from recent comparable projects?
  • Called the references and asked the right questions?

Project Management

  • Named person on-site daily?
  • Single point of contact identified?
  • Written change order process confirmed?
  • Communication frequency and method explained?
  • Realistic timeline with stated variables?

The Quote

  • Itemised (labour + materials separate)?
  • All trades included or exclusions listed?
  • Allowances explained clearly?
  • Exclusions explicitly identified?

The Contract

  • Written contract on every project?
  • Covers scope, dates, payment schedule, change orders, and warranty?
  • Willing to walk through it before signing?

Payments

  • Deposit percentage confirmed and reasonable?
  • Remaining payments tied to milestones?
  • Receipts issued for all payments?

Once you’ve worked through these questions with your shortlisted contractors, you’ll have a clear read on who’s operating transparently and who isn’t. The next step is verifying the credentials they’ve described – WSIB, insurance, HST – with actual documentation.

Book a Free Consultation

Share: