7 Secret Questions To Ask Roofing Contractors Over The Phone

This roofing contractor question checklist was last updated on October 27, 2022


If you’re looking to hire a roofing contractor (and if you’re anything like our friends and family), then I’m certain you want to do the job ONE time, right?

Carefully consider the questions to ask roofers before hiring a contractor because roofing isn’t a fun job to do twice. The entire process can quickly take up lots of your valuable time and hard-earned money if you don’t follow this roof estimate checklist.

7 Secret Questions To Ask Roofing Contractors Over The Phone

The cost of replacing your roof the wrong way is very high (more on this in a second). It’s one of the most expensive home remodeling projects you’ll ever take on! So with this being true I’m sure we can agree that as a homeowner you need to do everything in your power to make sure you hire an experienced contractor the very first time you replace your roof.

The most efficient way to do this is by doing your due diligence during the contractor research and roof estimate process. Consider the queries below a roof estimate checklist of sorts. Before you choose the roofer, make sure they pass each question in this checklist.

Our goal in writing this article is to make the research and estimate process much easier for you because consider the cost of replacing your roof the wrong way just one time.In this scenario, you’d be forced to re-roof your house again only a few years later because of avoidable mistakes made by the contractor you hired originally:

Save Money On Your New Roof By Pre-Screening Contractors

Big bucks only a few years later. Especially because the figures above don’t factor in the 3%+ yearly increase in roof prices or the cost of real damages that lead you need a second roof in the first place.

Again, the easiest way to avoid these headaches is to take time preparing for getting your first set of roofing estimates.

Sounds simple, but it’s one of the key steps most homeowners miss. They’re more concerned about how much the roof will cost- the estimate itself- than they are about whether or not the roofer will install your roofing system using industry best practice and manufacturer guidelines. This includes not only ridge vent installation, but also materials like synthetic underlayment and more. Depending on the shape of your roof, you may need a different type of roof ventilation system.

Roofing can get confusing, so we’ve put together this list of secret questions to ask roofing contractors over the phone in order to help you not only choose the right roofing company, but to help you save time along the way.

BTW: You may be wondering why this is a list of questions to ask over the phone, instead of in-person. We suggesting starting your roof replacement process this way because of the big mistake we see many Millennial and Generation X homeowners making time and time again as they prepare to re-roof their home. Feel free to use these questions for contractors when hiring a roof deck builder in Boston, Massachusetts, or any other location as well. Much like roofing, building a rooftop patio is a large project with many consequences of not doing it the right way.

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The big mistake many homeowners make while getting roofing estimates…

Nowadays, it’s easy to get a roofing contractor to your house. All you have to do is plug your name into a website and you’ll watch dozens of contractors compete for your business.

For most homeowners, this feels like a great thing…

Competition generally means a win for consumers, right?

We wish it was true, but unfortunately, this model doesn’t favor homeowners in the long run. In fact, getting lots of estimates makes choosing a credible, ethical roofer extremely difficult because with so many options, there’s far too much information involved in the decision-making process.

Taking a look at Yelp alone:

Calling Roofers In Boston

397 roofers in Boston, according to Yelp. And whether or not Yelp is trustworthy, the number of roofers in Boston is still extremely high compared to other parts of the country.

As a homeowner, it’s simply too much information to sift through…

Remembering important details like warranty length and installer certifications becomes impossible, and this is where most homeowners choose their roofer based how much the installation itself will cost.

How can you protect yourself from information overload?

When getting a new roof, we suggest a simple pre-screening of roofing contractors over the phone.

This will help you! And if you read until the end of this article, you’ll know exactly which questions to ask so you can best save time, money, and energy as you prepare to get your roof replaced.

Making sure you have the right roofers over for estimates comes down to 7 steps, which we’ve separated into two separate steps below.

Step #1 helps you determine whether or not a roofer is even credible,.

Step #2 helps pre-screen for ethics; because finding an ethical roofer is just as important as hiring an experienced one.

Let’s get started…

Checklist Step #1: Determine A Roofer’s Credibility With These 3 Simple Questions

The section in the roof estimate checklist has three questions that will save you time by pre-screening for credibility. Before you even consider a roofer’s price, you need to make sure they’re reputable and will do a good job on your project. This is beyond important in protecting yourself from getting a bad installation.

Though there are many questions you could ask, we recommend using these three during your phone screening:

Question #1: What is your legal business name?Ask Roofing Contractors Their Real Business Name

Getting a roofer’s legal business name is especially important nowadays because of how easy it is to falsely represent yourself online. A little detective work can go a long way in your pursuit of hiring the right contractor.

Answers you can accept:

  • The exact name they’re marketing themselves as
  • Our legal company name is X, but we’re ‘doing business as’ Y (as is the case with Roof Hub)
  • We market ourselves as ‘Roofing Company’, but our legal business name is Roofing Company LLC or Roofing Company Inc

Don’t accept answers that sound hesitant, or are unclear. This is the easiest way to guard against being scammed. When in doubt, ask for proof! No roofer should have trouble emailing you a copy of state licenses or proof of insurance (explained in question #2 below).

Using this information, you can search for their business in state and federal directories to ensure they even exist. If they don’t, then you may be dealing with a ‘fly by night’ contractor who’s out to either steal your deposit or install lower quality materials than you paid for.

For example, Roof Hub’s official company name is F&B Remodeling, LLC. We’re doing business as Roof Hub, which is perfectly legal and often encouraged for Limited Liability Companies. You can see that our LinkedIn company page matches the “doing business as” name.

Searching for us in the Massachusetts corporation search returns this:

Searching for Roofing Companies in State Databases

Question #2: What level of roofing insurance do you have?

Roofing insurance can get tricky as many states may require different levels of insurance depending on what type of contractor you are.

In Massachusetts roofing contractors are required to have at least $1,000,000 in general liability insurance in order to legally operate in the state. Rhode Island’s general liability requirements for remodeling contractors are half ($500,000)

To figure out what level of insurance is needed in your state, head over to Google, type in “[YOUR STATE] roofing insurance requirements,” then choose a result from your state’s official website. You’ll want a .gov website to be certain, not a .com or net. Using Massachusetts as an example, the site is “mass.gov.”

Answers you can accept:

    • An exact match, or an amount exceeding the minimum state requirements
    • A copy of the company’s liability policy sent via email after the phone call

Don’t accept answers that are indecisive, hesitant, or don’t match local, state, and/or federal requirements. Even if the company doesn’t have insurance, it’s easy to answer “yes, we have insurance.” Giving an exact amount is harder, which is why we recommend asking this way.

If a roofer is hesitant over the phone when you ask this question, it is a red flag, but they may not be lying. If so, you don’t need to rule them out right away. Just ask for them to email you a copy of their insurance liability policy.

Question #3: Who will be on the job site during my roofing installation?

Project Manager on Site for Roofing Installation

If you’re hiring a reputable roofing contractor, there’s a good chance they may have more than one roofing project going on in one day.

But if the company owner isn’t going to be on your property during the install, then who’s going to be around to ensure the project goes smoothly?

Don’t panic!

Many larger roofing companies have a “project manager” whose sole focus is to make sure your roof is being installed in accordance to both local laws and manufacturer guidelines.

So if the manager or owner of the company won’t be present during ‘install day,’ it’s important that an experienced project manager will be.

This is an easy question to ask any roofer over the phone.

Answers you can accept:

      • Owner of the roofing company
      • Manager of the company
      • Project manager trained by the organization

Don’t take this for an answer: “Our roofers are very experienced, so they don’t need supervision.” While it IS important to have experienced roofers on your crew, an efficient installation will only happen if there’s an industry expert in charge.

Roofing is complex, so if there’s “nobody running the show,” a small problem can easily turn your roofing project into one you read about in the newspaper.

The three questions (mentioned above) for establishing a roofer’s credibility don’t seem too hard-hitting, do they? That’s because they don’t need to be. Remember: these three questions are for pre-screening. And if you find a roofer that engages in one-off services that damage your roof (like painting asphalt roof shingles, which you should not do), then it is best to avoid this business.

The next four questions will help drill down to whether or not you should have the roofer out for the estimate…

After that, you’ll get prices. Then, it’s your right as a homeowner to compare all the facts and make a judgement call. But first, let’s tackle the next four questions you’ll need to ask roofers when you call for an estimate:

Checklist Step #2: Pre-Screen For Ethical Roofers Using These 4 Questions

The second section of the roof quote checklist is to pre-screen for ethical roofers.

Ethics are a slippery slope because everyone views them differently. What’s “okay to do” in one homeowner’s eyes is the worst thing in the world from another homeowner’s point of view. For example; some Massachusetts homeowners have chosen Roof Hub because we have a project manager on-site during the install. This 100% guarantees there won’t be any drinking or smoking by roofers on the property. Other homeowners however, could care less…

We’ve had homeowners try tossing our roofers beer from the ground while they were in the middle of an install!

Regardless of whether or not you want to drink with our crew, we assume you DO want to choose a roofer who acts ethically.

Formal definition of “roofing ethics” aside:

At the end of the day, you want to choose a contractor who has YOUR best interests at heart!

Here are four questions you can ask any roofer over the phone as a “pre-screen” for whether or not they’re operating ethically. Please keep in mind that these questions are a big more hard-hitting than the three above. This is by design. Ask each question exactly how it’s written below and you’ll uncover more than enough information to make sure you’re having the best contractors possible to your home for a written estimate.

Question #4: Can you leave the roof estimate in my mailbox?

Don't Let Contractors Drop Off Your Estimate In The Mailbox

If a roofer agrees to leaving your estimate in the mailbox or agrees to just “drop it off,” then it may be a good idea to sprint in the opposite direction! Sounds counter-intuitive, here’s why:

Most roofers get away with dropping estimates off because it’s what homeowners want! Most homeowners like you and I are using this method to gather a bunch of estimates so we can compare, contrast, and choose the best deal. Makes senses, but this plan unfortunately backfires because in the long run.

Getting a just price on a piece of paper does YOU a disservice because you lost the opportunity to ask any questions about the company, product, or installation practices. And as we’ve discussed above, you NEED this information in order to make an informed decision when before hiring a roofing contractor or local roofer.

Leaving an estimate in your mailbox is a terrifying proposition for the roofing company too because they may not even be able to complete the job! We’ll explain why in question #7…

Answers you can accept:

  • No, because we may need to ask you questions.
  • No, because you’ll need to choose which materials you prefer so the estimate is accurate.
  • No, because depending on what we find outside we may need to inspect your attic.

Don’t accept answers that allow a roofing contractor just to drop off an estimate in your mailbox because the price they leave may increase when materials change, or if more work needs to be done than was originally expected.

Experienced local roofers know better than to just drop off an estimate… So if you ask a roofer to “leave it in the mailbox” and they agree, then turn the page and dial up another contractor. It’s a warning sign you just can’t ignore. Your home’s health depends on it!

Question #5: What is your roofing price per square foot?

Roof Cost Factors Explained

Like the question above, this question helps uncover unethical, inexperienced, or lazy roofers who are just trying to get your business regardless of the cost.

Asking this question over the phone will save you time by protecting against contractors who “race to the bottom” based on price alone. These unethical business practices help contractors win jobs in the short term, but ultimately set the roofing business up for failure. In these cases, unexpected costs can ruin profit. And if the contractor fails to make a profit, then it’s ultimately YOU who pays because they won’t be around long enough to honor a warranty.

Roof pricing is complex, especially in the Boston area where Roof Hub is located.

Lots of factors that go into how much your roof will cost, including:

And many more…

Important: if many factors go into determining the price of a new roof, then shouldn’t you choose a roofer who’s able to both explain each factor? Don’t you want a roofing company to holistically determine your roof’s health before putting a price tag on it’s replacement?

We think so… Which is why we factor in all of the above when determining how much new roofs cost in Massachusetts.

Answers you can accept include ones that take many factors into consideration. You’ll want a roofer who prices your roof from a holistic point of view because it shows they’re acting ethically and are pricing the job from an experienced point of view.

Don’t accept answers that consider just one factor. You don’t want to hire a roofer who only prices your roof based on it’s pitch, how many layers it has, or even how big it is (size). This is a recipe for disaster because it not only allows lots of room for error, but leaves you as a homeowner open for surprises on install day, when you’re most vulnerable.

When speaking with roofers over the phone, make sure the roofer is speaking from a holistic point of view and knows that there are a variety of factors that determine how much your roof costs. If they have a one-track mind, it means they won’t be prepared if there are any setbacks during the installation.

Question #6: Can you do a layover instead of a full roof replacement?

Two Layers on Roof is Dangerous

Another quick test to determine whether or not you’re dealing with an ethical, reputable roofing service is to ask for a “layover.” This is a trick question, so it’s important that you ask exactly how it’s written above.

What is a roofing layover?

A roofing layover is when the roofer nails new shingles directly over your existing shingles instead of first taking them off. Laying one layer directly over the other.

Important: If the roofing contractor answers “Yes, we can do a layover instead of a full roof replacement!” then it may be a sign that they’re just out to make a buck because this practice can be detrimental to your roof’s health.

Why is a “roofing layover” bad for your roof?

Think about why you’re looking to replace your roof in the first place…

Most likely, it’s because there’s something wrong! And if this is the case, then why cover it up? Covering up your existing problems with a roof layover won’t protect your for long, if at all, and in many cases will do more damage than good in the short term.

If your roof has signs of water damage like moss or lichen, then avoiding a layover is even more important. Adding a layer of shingles on top of a roof that already has water damage will encourage the moss or lichen to fester, spread, and break down both the old and new layer of shingles. Definitely not a good use of your remodeling budget…

On top of the issues festering, a layover takes away your ability to really know what’s going on on your roof because you can no longer see the damage.

Do you know how heavy shingles are?

HEAVY! Like, really heavy…

Strong architectural shingles from well-known manufacturers like GAF and Tamko can weigh up to 350 pounds per square!

This 350 lb. number quickly starts to compound up on your roof because a square of roofing is equal to 100 square feet. If your roof is an average size of 1800 square feet, then ONE layer of shingles weighs at least 6,000 pounds… and that’s just the second layer!

If you’re living in Massachusetts, take a step back from this article and really think about two, or even three layers of shingles on your roof combined with snowfall during one of our average February months.

Layover on roof plus snow is dangerous

Answers you can accept, especially if you’re living in New England, should only include a “no” when you ask for a layover.

Don’t accept answers that allow for any type of layover because although you’ll save money in the short-term, the long term downsides (including exponentially increasing your chance of a cave-in) are far greater.

Please note: any roofer could do a layover on your roof, but it doesn’t mean they SHOULD. Especially in cold climates like Massachusetts, an ethical roofer will advise you to strip the shingles first so your roof isn’t at greater risk of collapse during heavy snowfall. They’ll be able to explain exactly why a layover is bad, too. All you should have to do is pick up the phone and ask!

Question #7: Does the roof estimator really need to come inside my house?

Let Roofers Inside Your Attic for Small Attic Inspections

It’s common to think of a roofer and picture a truck with ladders stacked high, barreling down the highway. But as technology improves, many roofing companies are moving in a different direction…

Gone are the days of speeding around to drop off a bunch of estimates before heading home after a long day of roofing. Nowadays, many reputable local roofers have an expert team dedicated to performing small-scale inspections and estimates for homeowners all day long. As a result, what really goes into a roofing estimate has drastically changed over the last few years! And it’s changed for the benefit of YOU, the homeowner!

Why a roofer needs to come inside your home…

Roofers should come inside your home for an estimate so they can inspect the attic space, especially if there are signs of water damage (moss, lichen, etc) on the exterior of the roof. Not doing so can result in thousands and thousands of dollars in surprise charges on install day…

We know this because our team of expert roofers has given thousands of small-scale roof inspections over the last 10 years. However, not all roofing companies are experienced inspecting attic spaces. A precaution you can take before even getting a roofing estimate is to hire a professional attic inspection service like Tiger Home Inspection.

Professional attic inspection companies will give you an unbiased opinion on what’s going on up there and how it affects your home. Though this option does add costs to your roofing project that will need to be paid for , for many homeowners it is worth the peace of mind if the roofing company your choosing did not conduct at least a small scale attic inspection.

But what if you don’t have an attic space?

If you don’t have an attic space, letting a qualified roofer inside your home is that much more important! A trained roofing eye can quickly spot small cracks and stains along your interior walls or on your ceilings. These are tell-tale signs of a leak and such a discovery MUST be taken seriously.

Answers you can accept include only those that require the estimator to come inside your home. If the roofing service your speaking with over the phone does not make this a priority, then only hire them if they require you hire a professional attic inspection before they complete the job.

Don’t accept answers that only consider exterior roof damage like curling shingles or moss. In many cases, roofing systems that look okay from the outside are riddled with interior damage that is far more important to your home’s health than interior damage ever would be.

Replacing a roof is a big project but one that will protect your home forever. If you’re considering a repair instead, we’ve included some questions below to ask about roofing repairs.

Roof Repair Questions To Consider Asking

Many homeowners don’t know if they need to fully replace their roof or do a simple repair. When you compare the price of each, roof replacements will always be more expensive and a roof repair definitely run you less money in the short term. But before opting for the cheaper route, it’s important to know why leaks happen and what to ask a contractor about repair options vs. replacement options.

Roof leaking during a rain storm

Water is pouring into your house and suddenly your home’s roof is your top priority! Roofing companies are always extra busy after a few days of heavy rain because that’s when homeowners start to notice their roof is leaking. If your roof starts leaking during heavy rains, then it’s likely due to an issue that has been festering for quite some time. Make sure you vet the repair service well before shelling out hundreds of dollars to fix an issue that could pop up again after a few more rain storms.

Questions to ask about your leaking roof before agreeing to a repair

These questions will help you make an informed decision about your roof before hiring a roof repair service. After the repair company inspects your roof, ask them:

Repair Question #1: How long do you think the leak been occurring?

Acceptable answer: From the looks of the ceiling stains, it’s been leaking for at least a few months.

Unacceptable answer: I’m not sure, it could have been happening for years.

Repair Question #2: What is causing the leak?

Acceptable answer: The shingles are curling and there are gaps around the chimney flashing.

Unacceptable answer: You know, I think it’s probably just old age, all roofs leak eventually.

Repair Question #3: Is the leak isolated to one area or does it span across multiple sections of my roof?

Acceptable answer: The leak is isolated to the direct chimney region and is cause by water pooling in that area and because you’re lacking a chimney cricket.

Unacceptable answer: I really do not know, it could be leaking in multiple places.

Repair Question #4: While you were up there, did you notice any missing shingles?

Acceptable answer: I saw quite a few shingles missing near the west side’s eaves and a couple at the ridge line towards your neighbor with the blue two-story victorian home.

Unacceptable answer: No, I didn’t really look for that. That’s not what you called me for.

Repair Question #5: Are my gutters full of asphalt granules and clogging the downspouts?

Acceptable answer: Yes, they are. I recommend you have them cleaned out as soon as possible.

Unacceptable answer: No, I didn’t really look at the gutters.

Repair Question #6: What should be done to fix the leak?

Acceptable answer: We can repair the leak by installing new flashing and sealing the gaps around the chimney, but it will be a temporary solution. It may get you through a few seasons, but you will need to replace the roof soon.

Unacceptable answer: I’m not sure, you might need to replace the whole roof.

Should I repair or replace my roof?

Repairs are temporary and if you choose the right roofer, a full replacement can last almost forever. Any reputable roof replacement company that’s been in business long enough to see their roofs go through a few winters will tell you that you should opt for a replacement over a repair. Instead of repairing the roof a few times then doing a replacement anyway, you bite the bullet and just get it over with. This way, you won’t need to worry about leaks and repair problems for as long as you live in the house.

Some roofing companies offer repair services but we choose not to because we cannot back the work with a warranty. At Roof Hub, we only engage in projects that we can stand behind. And whether you choose us or another company, make sure that’s their motto too.

Interrogating contractors isn’t rude, you’re protecting your home

Asking hard questions about any home remodeling project isn’t rude, so don’t feel nervous thinking you’re being rude. Being diligent about your project is the best way to protect your biggest investment– your house.

And as you can see, these 7 questions (plus 6 repair-oriented questions) are far from a complete list. They should be used simply as a guide and in combination with your gut feeling of a given roofer’s ethics and credibility. If a situation doesn’t quite feel right or you think a roofer is “trying to pull a fast one” on you, then we always suggest playing it safe and choosing someone else.

Choosing who replaces your roof is one of the most important decisions you’ll ever make for your home. A roof installed poorly will cause more headaches than you can imagine, often years down the road when the contractor is out of business.

And now that you’ve chosen contractors to come give you an estimate, you’ll need to be prepared for the next step in the roofing process; call a few and get started! Let us know if you have any questions, or would like to have us out for an estimate! Our phone number is (857) 237-7648.

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