7 Questions Homeowners Forget To Ask Before Hiring A Roofing Contractor

Most homeowners only think hard about their roof when something is already wrong. Water is dripping into the attic, shingles are missing after a storm, or an inspector flagged something during a home sale.

That urgency is exactly when people tend to make rushed hiring decisions, and rushed decisions are how homeowners end up with a contractor who disappears halfway through the job or leaves behind a warranty that's worth less than the paper it's printed on. In Chicago, where weather swings hard between brutal winters and humid summers, a roof gets tested constantly, and the contractor doing the work matters just as much as the materials they're using.

In this article, we share seven questions you need to ask before hiring a roofing contractor.

No. 1

Are You Licensed and Insured for This Specific Type of Work?

This sounds basic, but it's worth asking directly rather than assuming. Licensing requirements vary by state and city, and insurance coverage can have gaps that only show up after something goes wrong. A contractor should be able to provide proof of both general liability insurance and workers' compensation coverage without hesitation.

If a contractor can't produce documentation quickly, that's a real red flag. Homeowners are financially responsible for injuries on their property if a contractor's crew isn't properly covered, which turns a roofing decision into a much bigger liability question than most people realize going in.

No. 2

How Long Have You Been in Business Under This Name?

Some roofing companies dissolve and reopen under a new name after accumulating bad reviews or unresolved complaints, which makes this question more important than it sounds. A company that's been operating under the same name for years has a track record that can be verified through reviews, the Better Business Bureau, and local permit records.

When looking for a top rated roofing contractor Chicago, one of the foremost things to check is how long they've actually been operating under that name. Some companies have only been in business for a few years. That doesn't automatically disqualify them, but companies that have been around for decades, such as Lakeland Exteriors & Roofing, tend to be the ones with a track record homeowners can actually verify through years of accumulated reviews. That history usually means you're dealing with long-time professionals who know the industry inside and out, along with every material they might come across on the job.

No. 3

What Warranty Comes With the Materials, and What Comes With the Labor?

These are two separate things, and a lot of homeowners assume one warranty covers everything. Material warranties come from the manufacturer and typically cover defects in the shingles or membrane itself. Workmanship warranties come from the contractor and cover installation errors, which are actually the more common cause of early roof failure.

Asking for both warranties in writing, including their length and what voids them, prevents a painful surprise later. A roof that fails because of poor installation isn't covered by a material warranty alone, and homeowners who didn't ask this question upfront often discover that gap only when they're already dealing with a leak.

No. 4

Will You Provide a Written, Itemized Estimate?

A verbal estimate or a vague one-line quote leaves too much room for scope changes and unexpected costs once the work starts. A written, itemized estimate should break down materials, labor, disposal, permits, and any other costs separately, which makes it much easier to compare against other quotes and catch anything that seems off.

Contractors who resist putting details in writing, or who only offer a single bottom-line number, are harder to hold accountable if the final invoice doesn't match what was discussed. This is one of the easiest questions to ask and one of the most revealing in terms of how a contractor actually operates.

No. 5

Who Handles Permits, and Is That Included in the Price?

Roofing work often requires a permit, and pulling that permit is the contractor's job, not the homeowner's. Permits exist so an inspector can catch installation problems early, before they turn into bigger structural issues down the road.

A contractor who suggests skipping the permit to save money or speed up the timeline is cutting a corner that protects them, not the homeowner. Unpermitted roofing work can also complicate insurance claims and future home sales, so this is worth asking about directly and getting a clear answer before anything starts.

No. 6

What Happens If You Find Additional Damage Once the Roof Is Opened Up?

Hidden damage, rotted decking, mold problems, or structural issues sometimes only become visible once the old roofing material is removed. A reputable contractor will explain how they handle this situation before the project starts, including how they communicate the issue, what documentation they'll provide, and how pricing changes if additional work is genuinely necessary.

Contractors who can't clearly explain this process, or who seem evasive about it, are more likely to either ignore real problems to keep costs down or pad the bill with unnecessary add-ons once the job is underway. Getting this answer upfront sets clear expectations before any surprises happen.

No. 7

Can You Provide References From Recent, Similar Projects?

Online reviews are useful, but a contractor willing to connect you directly with recent customers, ideally for similar roof types and project sizes, gives a more complete picture. A quick phone call to a past client can reveal details that never make it into a five-star review, like how communication was handled or whether the timeline held up.

This step takes a little extra time, but it's one of the most reliable ways to verify that a contractor's reputation matches the actual experience of working with them.

Takeaways

The questions that get skipped are usually the ones that matter most once something goes wrong. Asking about licensing, warranty terms, written estimates, permits, hidden damage protocols, and references upfront takes maybe twenty extra minutes during the hiring process, but it's the difference between a roofing project that goes smoothly and one that turns into a months-long headache. 

A contractor who answers these questions clearly and without hesitation is already showing you something important about how they do business.

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