10 Questions to Ask Before Hiring a Painting Contractor
Introduction
Hiring a painter isn’t just about finding someone with a brush. It’s about choosing a contractor who will respect your home, use quality materials, and deliver results that last. A fresh coat of paint has the power to completely transform your living space, boost curb appeal, and even increase resale value — but only if the job is done right.
Unfortunately, many homeowners rush into hiring the first painter who gives them a quote, only to end up with peeling paint, hidden fees, or weeks of frustration. The truth is, the painting industry is full of variation: some painters are seasoned professionals with decades of experience, while others are unlicensed, uninsured, and cutting corners.
So how do you separate the pros from the pretenders? It starts with asking the right questions.
Below are 10 essential questions every homeowner should ask before hiring a painting contractor in Ontario. These will not only help you find someone reliable but also protect your investment and ensure your project goes smoothly.
1. Are You Licensed and Insured?
This is the most important question on the list. A legitimate painting contractor should have the proper business license to operate in Ontario and carry both liability insurance and workers’ compensation coverage.
Why it matters: If an uninsured painter damages your property or gets injured on your job site, you could be held financially responsible. Insurance protects both you and the contractor.
Pro tip: Don’t just take their word for it — ask for proof of insurance. A professional painter will be happy to provide documentation.
2. How Long Have You Been in Business?
Experience matters in painting. While every business has to start somewhere, painters who have been in business for several years have usually honed their skills, built a reputation, and learned how to handle unexpected challenges.
Why it matters: Painting isn’t just about applying color. It requires knowledge of surfaces, primers, prep work, finishes, and how different products perform in Canadian weather.
Pro tip: A contractor with at least 5–10 years of experience will generally have the systems, staff, and processes in place to complete your job efficiently and professionally.
3. Can You Provide Recent References?
A trustworthy painting contractor should have no problem connecting you with past clients who can vouch for their work. References allow you to verify not just the quality of the paint job, but also the contractor’s professionalism, punctuality, and communication.
Why it matters: Online reviews can be helpful, but nothing beats speaking directly to another homeowner who has hired the same painter.
Pro tip: Ask for references from projects similar to yours (e.g., exterior homes, interior trim, or deck staining) so you know they have relevant experience.
4. What Prep Work Is Included in Your Estimate?
Prep work is where the difference between a “cheap painter” and a professional painter becomes obvious. High-quality results come from proper preparation, not just the final coat of paint.
Typical prep work should include:
Patching holes and cracks
Sanding rough areas
Caulking gaps around trim and windows
Cleaning surfaces before painting
Applying primer where necessary
Why it matters: Without prep, even the best paint will peel, bubble, or fail within months.
Pro tip: Always get a written estimate that clearly outlines what prep work is included so there are no surprises later.
5. What Brand and Grade of Paint Do You Use?
Not all paints are created equal. Premium brands like Benjamin Moore and Sherwin-Williams offer higher durability, richer colors, and better coverage compared to bargain paints.
Why it matters: Using cheap paint may save a few dollars upfront but will cost more in the long run when the finish wears quickly or requires extra coats.
Pro tip: Ask if the contractor is open to using a specific brand if you have a preference. A professional should be comfortable explaining the pros and cons of different paints for your project.
6. Do You Offer a Warranty on Your Work?
Professional painters should stand behind their workmanship. A typical warranty may cover 1–3 years against issues like peeling, blistering, or flaking that result from poor application (not normal wear and tear).
Why it matters: A warranty shows that the contractor is confident in their work and willing to fix problems if they arise.
Pro tip: Make sure the warranty is in writing and clearly states what is covered and for how long.
7. How Do You Protect Furniture and Flooring?
A quality painter doesn’t just care about walls — they also take steps to protect your belongings. This includes covering furniture with plastic, laying down drop cloths, and taping off edges for clean lines.
Why it matters: A beautiful paint job isn’t worth much if your floors, trim, or furniture are ruined in the process.
Pro tip: Walk through your space with the contractor before the project begins to confirm how they’ll handle protection and cleanup.
8. What’s Your Payment Schedule?
Be cautious of contractors who demand full payment upfront. A standard payment structure might include:
A deposit (often 10–30%) before work begins.
Progress payments for large projects.
Final payment upon completion and inspection.
Why it matters: A clear payment schedule protects both parties. It ensures the painter has cash flow to start, while you retain leverage until the job is done to your satisfaction.
Pro tip: Never pay the full amount before work begins.
9. Who Will Be Doing the Work (Employees vs. Subcontractors)?
Some painting companies employ their own crews, while others hire subcontractors. Neither is necessarily bad, but you should know who will be in your home.
Employees: Usually trained to the company’s standards, more consistent quality.
Subcontractors: May vary in skill and reliability unless carefully managed.
Why it matters: You want to ensure the people on-site are qualified, background-checked, and insured.
Pro tip: Ask if the owner or project manager will personally supervise the job.
10. How Long Will the Job Take?
Time is money — for both you and the contractor. A professional painter should be able to give you a reasonable timeline based on the project’s size and complexity.
Why it matters: Clear timelines help you plan around the work, especially if you need to move furniture, schedule other contractors, or take time off work.
Pro tip: Ask what happens if the job runs behind schedule. Will they bring in extra crew? Do they have a policy for delays?
Why These Questions Matter
Each of these questions ensures accountability, professionalism, and transparency. Too often, homeowners hire based on the lowest bid, only to discover that the job includes no prep work, cheap paint, or uninsured workers. By asking these 10 questions upfront, you protect your home, your wallet, and your peace of mind.
Painting is more than just color on a wall. It’s an investment in your home’s beauty, comfort, and value. And like any investment, it pays to do your research.
Final Thoughts & Next Steps
When you’re ready to paint your home — whether it’s refreshing your living room, tackling a full exterior repaint, or staining your deck — make sure you hire a contractor who checks all the right boxes.
At Painters Near Me, we encourage every homeowner to ask these questions. We’re licensed, insured, and proud to use top-quality paints. Our team provides detailed estimates, protects your home like it’s our own, and guarantees workmanship you can trust.
👉 Ready to transform your home? Contact us today for a free, no-obligation quote. Let us show you what professional painting should look like.