If you're staring at peeling paint, faded siding, or flaking trim, you're not alone. Omaha weather isn’t gentle, summers are hot and humid, winters can be brutal, and spring brings wind and rain that do a number on your home's exterior. You know your house needs attention, but trying to hire a painter can feel overwhelming. How do you know whom to trust? How do you separate the professionals from the crews that just slap on a coat of paint and disappear?
A lot is riding on this decision. A great exterior paint job can last you years and boost your home’s value, while a rushed or sloppy one might start peeling before the next Huskers season kicks off.
At Brush & Roll Painting, we’ve been painting homes in and around Omaha since 1996. We’ve seen just about everything—flaking trim that needed replacing and homes that needed far more prep than the homeowners realized. Through decades of experience, we’ve learned what homeowners wish they’d asked before hiring a painter—and the kinds of answers that tell you whether you’re hiring a reliable, quality-focused company or someone who just wants to get in and out.
This article is here to help. We’re not going to tell you who to hire, but we’ll arm you with the right questions to ask so you can confidently choose the right exterior painter for your home. By the end, you’ll understand what to listen for, what red flags to watch out for, and how to feel good about the painter you choose. Whether your home is in Elkhorn, Bellevue, or right in Midtown Omaha, this guide is built for you.
A well-done exterior paint job protects your home from the elements. It also reflects the care you put into your biggest investment. But too often, homeowners focus only on price and miss out on details that really determine the quality and longevity of the work. Asking the right questions can help you avoid headaches down the road and make sure you’re getting real value for your money.
Let’s walk through the questions you should ask—and what kinds of answers you should expect.
This one might sound like a no-brainer, but it’s one of the most overlooked. Painters should carry general liability insurance and workers' compensation. If someone falls off a ladder on your property, you don’t want to be the one footing the bill. Ask for proof—any reputable painter won’t mind showing it.
Not all exterior paints are created equal. Omaha’s freeze-thaw cycles and humid summers mean your home needs durable, high-performance paint. Not only should you ask what brand they like to use, ask about the specific product.
Even paint brands like Benjamin Moore and Sherwin Williams have a range of low to high quality paint options.
At Brush & Roll Painting, we like to use products by Benjamin Moore. Our favorite is their highest-end product, Aura.
Cheap paint may save a few bucks now, but it rarely holds up for more than 2-5 years.
Preparation is where most painting companies either shine or cut corners. You want to know how they plan to deal with peeling paint, dirt, mildew, or damaged wood. Will they scrape and sand? Do they power wash? Will they caulk gaps and prime exposed wood?
Here’s the bottom line: Proper prep is what makes paint last. A crew that skips these steps is setting you up for problems a year or two down the road.
Omaha homes—especially older ones—often have areas of soft or rotted wood hiding under flaking paint. Will the painter point out those issues? Can they repair or replace the boards? Or do they expect you to bring in someone else?
The best companies don’t just paint over problems. They catch them early and help you fix them before they become expensive repairs.
Ask them to walk you through their steps—from the initial quote to final cleanup. A clear, organized process is usually a sign of a well-run company. You want to know how they’ll schedule the work, how they handle weather delays, who will be on site, and how they’ll protect landscaping, windows, and walkways.
This is a good one to ask because some painters cut corners by using only one coat, even if two are needed. A quality exterior job almost always includes two full coats, especially if you’re changing colors or covering raw wood. Make sure this is spelled out in your estimate.
Look for a painter with a solid track record in your area. Ask for before-and-after photos or addresses of recent projects. It helps if they’ve worked on homes in your neighborhood or similar in age and style. If they’re proud of their work, they’ll be happy to share.
There’s nothing wrong with subcontractors, but you want to know who’s actually showing up at your house. Companies with their own in-house team tend to have more consistent results and tighter quality control. If they do use subs, ask how they’re selected, trained, and supervised.
Omaha weather doesn’t always cooperate. A good painter builds flexibility into the schedule and doesn’t rush work just to finish fast. Ask how they’ll keep you updated if storms roll in or the temperature suddenly drops.
Your estimate should be detailed. It should outline:
Be cautious if an estimate is vague or seems too good to be true. A low price that skips prep or only includes one coat can cost you more in the long run.
Ask how long the work is guaranteed and what’s covered. Paint failure caused by poor prep or rushed work usually shows up in the first few years. A strong warranty shows confidence in the job they’re doing. Don’t forget to ask if the warranty is in writing.
At Brush & Roll Painting, we offer options for a warranty based on the paint product you choose for your project. Each year of the warranty, we will make necessary touch-ups for up to an hour.
Ultra Spec 500 by Benjamin Moore - 2 Years
Regal Select by Benjamin Moore - 5 Years
Aura by Benjamin Moore - 9 Years
This is where you can learn about their values. Maybe they focus heavily on prep. Maybe they assign a project manager or crew lead to every job. Maybe they’ve served Omaha homeowners for decades and understand what homes here really need.
Their answer should give you confidence, not just in their skills, but in how they care about the work they do.
Choosing a painter isn’t just about price—it’s about trust. Your home is one of your biggest investments, and you want it to be protected with care, experience, and attention to detail. By asking these twelve questions, you’ll be better equipped to sort through the noise and find a painter who does it right the first time.
At Brush & Roll Painting, we believe homeowners should always feel informed and empowered when doing a painting project on their home, whether they hire us or not. Since 1996, we’ve helped homeowners across Omaha feel confident about their exterior painting projects by focusing on quality prep, top-grade materials, and clear communication every step of the way.
If you’re thinking about painting the outside of your home, we’re here to help guide you, no pressure, no pushy sales pitch. Just answers, experience, and honest guidance.
Click below to get a quote from Brush & Roll Painting.
If you’re not quite ready to schedule a quote but want to get a better sense of what exterior painting might cost for your home, our free pricing calculator is a great place to start. It’s quick, easy to use, and gives you a ballpark estimate based on your home’s size and details.
Whether you’re just curious or starting to plan your budget, the calculator can help you move forward with confidence. Give it a try and see what to expect for your home’s exterior painting project.