1. Can You Provide a Certificate of Insurance?
This is the first and most important question. Any legitimate painting contractor operating in Ontario carries general liability insurance — typically $2 million minimum — and, if they have employees, WSIB (Workplace Safety and Insurance Board) coverage. These protect you if something goes wrong: paint spilled on expensive hardwood, a ladder through a window, a worker injured on your property.
Ask for the certificate of insurance before you sign anything. A legitimate contractor will send it the same day without any hesitation. If they make excuses — "my broker is getting it to me," "I'm in the process of renewing" — walk away. Operating without insurance is a serious risk for you as the homeowner, and it often signals a broader lack of professionalism.
2. Who Will Actually Be Doing the Work?
This one surprises people but it matters enormously. Some "painting companies" are actually brokers — they quote the job, take the margin, and then subcontract the actual work to whoever they can find that week. The person who quoted you, walked your home, and made all the commitments has nothing to do with the people who show up.
Ask directly: will you be on-site? Is this your crew or subcontractors? At Cornerstone, I'm personally on-site or closely overseeing every job. The people doing the work are painters I know and have worked with for years. That continuity and accountability matters for quality.
3. What Paint Brand and Product Will You Use?
The difference between a $35-per-litre contractor-grade paint and a $70-per-litre premium paint like Benjamin Moore Aura is significant in terms of coverage, durability, and washability. Ask specifically what brand, product line, and sheen they plan to use. A good answer is specific: "Benjamin Moore Regal Select, eggshell finish on walls, semi-gloss on trim." A vague answer like "good quality paint" or "professional grade" is not an answer — push for specifics.
For exterior work, this is even more critical given Toronto's climate. Ask whether the exterior paint is elastomeric-modified and what its temperature application range is.
4. How Many Coats Are Included?
One coat of paint is not a paint job. It's a tint. Two full coats, properly applied with appropriate dry time between them, is the minimum standard for professional work. On new drywall, going from a dark colour to white, or on surfaces that need priming, three applications (prime plus two coats) is correct.
If a quote doesn't specify the number of coats, or if the answer is "one coat should be enough," that's a problem. Make sure the written quote states explicitly: two coats of finish paint minimum.
5. Is There a Written Scope of Work?
A verbal agreement is not a contract. Any professional contractor will provide a written quote that specifies exactly what's included: which rooms, what surfaces (walls only? walls and trim? ceilings?), the paint brand and product, the number of coats, what prep is included, and what's excluded. If someone gives you a number verbally and asks you to trust them on the rest, that's how you end up arguing about whether the closets were in scope at the end of the job.
A written scope also protects the contractor — it sets clear expectations on both sides. Any painter worth hiring will have one.
6. What Is Your Payment Schedule?
A reasonable payment schedule for a residential painting job in Toronto: a deposit of 25–35% at contract signing, a progress payment at mid-point for larger jobs, and the balance upon satisfactory completion. If a contractor asks for full payment upfront, that's a red flag. You lose all leverage once the money is gone and the work is still in progress.
Conversely, a contractor who asks for zero deposit is also unusual — it can signal they're desperate for work or don't have the working capital to purchase materials in advance. The standard deposit range above is the professional norm in this market.
7. What Is Your Warranty?
Reputable painting contractors stand behind their work. A standard workmanship warranty covers peeling, bubbling, or adhesion failures that result from the application itself — not from normal wear and tear or damage. The length varies: one year is common, two years is better for interior, and some contractors offer longer on specific product lines.
Ask: if there's a problem with the paint within the warranty period, what's the process? A confident professional has a clear answer. Someone who hedges — "well, it depends on why it happened" — may be setting up to deny any warranty claim after the fact.
8. Can You Provide References From Recent Jobs in My Neighbourhood?
References matter, but they need to be recent and relevant. A testimonial from 2019 doesn't tell you much about a contractor's current work quality, crew, or responsiveness. Ask for references from jobs completed in the past 12–18 months, ideally in your area of the GTA.
When you call the reference, ask two things beyond the basic "were you happy": did they stick to the timeline, and would you hire them again without hesitation? The second question separates genuinely satisfied clients from politely diplomatic ones. Most people will be honest if you ask directly.
We're happy to provide recent references from jobs across Toronto, Richmond Hill, Vaughan, and the broader GTA. If you'd like to discuss your project and ask any of the questions above, give me a call at 437-242-3829 or use the contact form.