Choosing a painting contractor in 2020

When it comes to freshening up the exterior of your house its common knowledge that a new coat of paint provides the maximum bang for your buck. Not only does it protect your number one investment against the elements but it restores your curb appeal at a reasonable cost in terms of both time and money. The same holds true for your interior, you may want to update your homes look or just bring it back to a uniform appearance after years of dings, wear and tear, and fading. 

In both cases it’s not something you do every day. You will vacuum inside, cut the lawn outside, clean the gutters, etc. far more often than you will paint. Most homeowners may go a decade or more before painting their interior and five to ten years between exterior paint jobs. This leaves home owners in a position where they basically have two choices – do it yourself or hire a contractor to do it.

What if I am the painting contractor?

Generally speaking, most people won’t consider painting their own exterior simply because of the scale of the project, the height involved, the ladders, the wood repair that may be necessary, etc. The exterior can seem like too daunting a task. The same can be said for the interior though. When you watch DIY videos you are generally being instructed by a someone with a ton of experience telling you (with little to no experience) that its easy. Let’s assume though that you’re on the fence at this point.

You can certainly take a stab at either interior or exterior painting but you run a few risks. You run the risk of getting half way or all the way through only to realize that it didn’t come out anything like the DIY video and now it’s worse than before you started. Now you’re going to call a professional to “fix” it after you already spent money doing it yourself. Another risk is that you end up using cheap but readily available “homeowner” paint and tools and the result may not look uniform and it may not last. Another risk is not getting the prep work done correctly so you don’t notice things like mold, dry rot, leaking window frames, or other issues that turn your paint job into a band-aid. The last risk you subject yourself to is physical – what if you break something or hurt yourself in the process? 

If you choose the DIY route ask yourself if its partially because you don’t know what’s involved in engaging a professional painting contractor. You might be worried about cost, or their reputation, nobody wants to feel like they got taken, right? You may even have had a bad experience or know someone who did and that single example has led you down the DIY path. The best way to avoid this trap and keep your options open is to get informed about what to look for in a contractor and to be realistic about your own DIY capabilities. 

So, there is the fork in the road – DIY versus professional contractors – and it’s time to get educated. Let’s look at what you need to do to find a professional that’s right for your job, that matches your dollar budget and your time budget, and who can deliver in a way that protects your interests. We can then compare that to a DIY approach.

Let’s start with where to find a painting contractor – here is basically how it breaks down:

  1. You know a painter
  2. Your friends or family can recommend someone they know or someone they hired (likely only once)
  3. You can go online and find one

If you “know a guy” and you don’t want to DIY then you still have to make sure that they have the basics – insurance, workers comp, the right equipment and experience etc.

If you are getting a recommendation from someone who only has a single engagement with a painter, friend or family you would again want to check them out.

Lastly you can look online and sort through a selection of painters and check them out as well.

Notice that in all three cases you are going to want to “check them out” and checking them out starts online so you might as well start online yourself. Yeah, a recommendation from a family member is worth something, they wouldn’t steer you wrong, right? The thing is they aren’t paying, it’s not their house, their requirements, their comfort level etc. It’s yours.

So online you go, you search for house painters and when you get the results you will find:

  1. Google painter ads
  2. A map of the absolute nearest painters
  3. Lead generation services like Home Advisor and Angies List
  4. National franchise chains of painters like CertaPro
  5. Painting companies that are ranked by google based on a mix of where you are and where they are plus their reputation

1. Starting at the top, the ads you see are just that, people paying to get in front of you – fair enough right? 

2. The map of the nearest painters, this would be handy if it was a list of something like “nearest emergency room” where their proximity to you was somehow critical but it isn’t. If someone will come out to give you an estimate, they will come out to perform the work, nearest doesn’t mean anything.  Do you only use the absolute closest accountant?

3. Lead generation services like Angies List are next on the list. Contractors call them lead generation services but they call themselves contractor recommendation services. What’s the difference? Its who’s paying, that’s the difference. Contractors of every kind pay big money to get a lead that you supply and the lead is given to several of them to then slug it out for your business. Let’s say four of them pay $100 for your lead and one of them gets the job, now repeat the process and each contractor gets ¼ of the jobs they get a lead for. They basically pay $400 to finally land YOU as a customer. Now guess where the $400 bill ends up landing? You are either giving them a pay cut or they are, as a group raising their prices, and all so that you can see how many “stars” are next to their name and read their reviews. There isn’t anything wrong with this generally speaking, you want to see reviews and get piece of mind but there is a cost associated with that, I’m just offering full disclosure here. 

Other companies provide recommendation services for free, google has their own ratings and reviews free of charge. You can always just enter the name of a company in Google and see ratings and who provided them. Sometimes the reviews are provided by Yelp. Yelp sells a service to business owners and one of the services is “reputation management” that may include an ability to clean up the occasional bad review. 


The thing about any review system is that people are motivated to leave reviews for when they get excellent service and when they get terrible service. Very few people provide a review that says “they were okay”, It’s just human nature. In general, it’s better to read the reviews than just look at a star count because good review services allow for the contractor to respond to reviews. You may not be as impressed as the reviewer and you may be less critical than the reviewer, that’s where having a lot of reviews helps. The more reviews you read the more accurate a picture you get obviously.

4. National franchise companies have their pluses and minuses as well. They strive to offer a standardized service and vet who they accept as a franchisee but they are also in the lead generation business and they have franchise fees that must come out of the total cost you pay not to mention the cost paid by the contractor to acquire the franchise in the first place. Like all franchises the focus will be on providing a certain level of service using a certain level of materials that will appeal to the part of the market they are targeting. You may or may not be in that market (job too small, job too complicated, you want higher quality prep and paint etc.) and they are in the business of doing volume so again it’s your call.

5. Lastly, we get to the contractors that are listed and ranked by google, these results are presented as a mix of proximity, reputation and how long (and how well) the contractor has been established. If you use Google’s recommendations and feedback combined with Google’s results to create a short list of contractors, you may be doing yourself a favor. You are then able to contact them and make it clear that you found them without an ad or a service and that, up to this point, your conversation with them is based on your online research and not them having paid out money to find you.

Now you are armed with a list of painting contractors – what’s next?

Call them and tell them about your project. Tell them you are trying to find the right contractor, let them know the size of the project, the details you have and your time frame.  They will want to arrange a time to give you an estimate. They will want to meet with you and take you through what they do, and let you know what it will cost. You will usually get an estimate. A quote is better than an estimate however, with an estimate you aren’t certain to be looking at the final cost, a quote is a final cost.

Before you arrange an estimate ask these questions: 

Are they licensed as contractors? 

That should be question number one because it’s the law. You need a Home Improvement Contractor’s license to paint houses as a business, it has to be a current license as well. You can ask a contractor for their HIC license number and they should be happy to give it to you, it should be on their website, it should be valid! In Connecticut for example you can look them up at:

Do they have proof of insurance? 

How much insurance do they have? What does it cover? Generally, they will have a large policy that will more than cover any accidental damage that might occur no matter how unlikely it is to occur. Overall the odds of issues like insurance becoming a big deal are tiny, nobody wants an accident, house damage or an injury, right?

Do they have workers Compensation insurance? 

If one of their workers falls off a ladder are you completely protected, are they?  With both insurance and workers comp it’s the kind of thing every decent contractor has but you still need to ask.

At this point you should be having a conversation about your project and also finding a time to meet for an estimate. With Custom Colonial Painting we offer a phone App you can download so that you can take pictures and get a quote for most jobs without having to meet in person. This is great for people who are very busy but some people prefer a face to face meeting. 

The estimate

During the estimate you want to ask each contractor what materials (paint and primer etc.) they use and what their process is as well as what they recommend. As simple as painting a room may sound it’s not always going to be an apples-to-apples comparison between contractors. For exterior painting this is even more important. Its critical for your exterior because the paint is doing double duty, it has to seal and protect your house from the environment and also make the place look nice. The process and the materials are what you are buying, make sure you know what they are rather than assume it’s all the same and the hunt is just for the lowest price.

When you get the final estimates or quotes it’s important to note how long the paint job should last because a cheap job that lasts 5 years will cost more than a job that is 20% more expensive but will last for 10 years. 

Be very specific about what you want done and make sure it’s all included in writing so that both you and the contractor have a clear understanding and a point of reference. Also make sure to ask about the timing of the job, when can they start and will they work straight through. Companies that are just a two-man crew may be at your house for a couple of days then go to another job as they try to maximize their time at your expense. If you don’t mind, that’s fine, but if you do, you need to make it clear you want a start-to-finish job without interruption.

At Custom Colonial Painting we have a dozen or more crews painting during peak painting weather so if any job needs additional help to make a hard date (like a backyard wedding) we have the ability to bring more painters to the job. That’s a kind of insurance not every contractor can offer so ask about it. The only thing that ever really causes delay is the weather and we are expert at working around the rain and making sure it doesn’t affect the final result.

Ask for references

If you have read reviews online, seen testimonials on their website and still want to actually speak to a former customer feel free to ask for references. Any decent contractor should be ready to provide them.

See a contract

You have to understand that there may be limits like the weather, rot that goes undiscovered until your house gets power washed, and other issues that are completely unforeseeable. See how they are addressed and understand that if you were painting your exterior as a DIY project you could be rained out or surprised as well. 

Ask about the process

You may have to move things around, the contractor may do that for you. They normally move furniture etc. but you may want to take delicate items off the wall etc. Ask about all the prep leading up to the actual painting. Believe it or not usually the majority of the work is in the prep. Ask about the process end-to-end. Ask about being left with some touch-up paint, ask about drying times etc. A good contractor will tell you all of this as they go along even if you forget to ask and they will also leave your house just the way they found it in terms of clean-up. 


The last thing you should consider when looking at a contractor is payment options. Beyond just paying by check or credit card etc. ask if they offer financing and what the terms are. Custom Colonial Painting works with a finance company that can very rapidly and easily provide you with a finance option for those that qualify. Why would you finance? If you are about to sell the house you might want to and then use the proceeds from the sale to pay off the loan. Painting a house makes it sell quicker, it’s a well-known fact any realtor will tell you. The other benefit is that you might have the money to paint three rooms in your house but it might make sense to paint an entire floor or the whole interior in one go. Considering that there will be some amount of disruption to your routine you may want to get it all over and done with in one project. The added benefit at that point is the entire interior paint job is that same age and will last the same amount of time.


By the time you get to this point you may have decided against DIY simply because you have to calculate your own cost in time, paint, prep, learning, equipment etc. You also will have nobody to blame and no recourse if the job doesn’t meet your own standards. You won’t be giving yourself a one star review and you might have to find a place to store your newly purchased ladder BUT if you want a challenge and are trying to get the absolute most bang for your buck, come what may, you can always do it yourself.

We hope you found this to be an honest look at your painting options and how to find a painting contractor. If you live in Connecticut and would like a no-cost quote please feel free to stop at our contact page at Custom Colonial Painting and thank you for stopping in.