Top 4 Questions Before a Painting Estimate

There are four questions that tell you more about a potential contractor—and the job you’ll actually get.

Don’t Start With “How Much?”

Most homeowners start with: “Can I get an estimate?” That’s a fair question—but it’s not the most important one. Before you even talk about price, it helps to understand who you’re dealing with.

There are four questions we recommend you ask first—three for your contractor and one for yourself.

1. How Long Have You Been in Business?

Experience matters—but what matters more is how long the business itself has been operating.

Online reviews (testimonials, feedback, etc.) are uncensored and honest. There will likely be a balance between negative and positive. No reviews? Then you better ask lots of good questions.

Lots of painters will tell you they have 20+ years of experience. That’s great—but it’s not the same as running a company for 20 years. If someone started “Smith Painting” last year, that’s not the same as a 10-year-old business with a physical address and repeat clients.

Don’t confuse experience with longevity. Ask how long the business has been registered, how many years they’ve operated under that name, and whether you can verify it. It’s one of the easiest ways to separate seasoned pros from one-man startups.

2. Where Are Your Reviews?

Online reviews are transparent, permanent, and often more honest than hand-picked references.

References can be useful, but they’re often cherry-picked. No contractor hands out the phone number for a customer where the job didn’t go quite right. Online reviews—on Google, Yelp, Facebook, or Houzz—offer a broader and more balanced picture.

Look for consistent patterns, not perfection. If there are no reviews, that’s a red flag. A professional contractor should be able to point to a track record of public feedback.

A successful contractor will have a verifiable history of delighted customers and will have confident answers to those same questions.

We’ve collected many nice reviews over the years from happy homeowners—check them out if you're curious what others have said.

3. How (and When) Will You Deliver the Estimate?

The way a contractor handles an estimate tells you a lot about how they’ll handle your project.

Will they email you a detailed written estimate? Will they just tell you something on the spot? Will it be handwritten on a receipt pad?

Clear, professional estimates delivered in a timely way speak volumes. They reflect not just organization, but respect for your time and trust. If the estimate process is vague or slow, it’s fair to wonder what communication will be like once the work starts.

4. Do I Really Trust This Person in My Home?

Sometimes the most important question is the one only you can answer.

This is the gut check—the part of the process that isn’t about paperwork or credentials. Do you feel comfortable with the person in your home? Do they seem like someone who will do what they say?

Ask yourself

• Do I trust them to show up on time?
• Will they work full days?
• Can they complete the job safely?
• Will they treat my space with care?

If you’re unsure, listen to that feeling. You’re inviting someone into your home—choose someone who earns your trust.

Good Answers Reveal a Confident, Professional Contractor

A reliable painter will have clear, confident responses to each of these four questions.

You’re not grilling anyone—just gathering useful information. A trustworthy contractor won’t bristle at these questions. In fact, they’ll probably be glad you asked. It shows you care about quality and long-term value.

That’s why we’re proud to answer these questions—and why we encourage customers to ask them.

Avoid Relying on a Sample of One

Your neighbor’s good experience is a start—but it’s not a full picture.

Maybe your neighbor used someone they liked. That’s a great starting point—but it’s still just one data point. Don’t rely on a sample of one. Ask around, check reviews, and trust your own conversation with the contractor.

You can also check out our guide to the top 5 uninsured contractor questions to understand the risks when hiring based on reputation alone.

It’s Your House—Ask the Right Questions

Choosing a painter should be based on trust, clarity, and a track record—not just a low number.

There’s nothing wrong with asking about price. But if it’s the only question you ask, you could end up with more surprises than savings. These four questions are simple—but they reveal a lot.

For more perspective, you might enjoy why painters wear white or explore some interior projects we’ve completed recently.

Book a Quick Estimate

Curious about how we’d answer these questions? You can book an estimate online in just a few clicks. Appointments usually take less than 30 minutes, and we’ll give you clear answers with no pressure—just straight talk from a team that’s been around the block.