Hiring a roofer is one of the most significant financial decisions you’ll make as a homeowner. A new roof can cost anywhere from $20,000 to $60,000 or more — and the wrong contractor can turn that investment into a nightmare. The problem is, most homeowners don’t know how to choose a reputable roofer or even where to start.
That’s why we put together this questions-to-ask-a-roofing-contractor checklist. Before you sign any contract, there are five critical questions you need to ask every roofer you speak with. The answers — or the way they dodge the answers — will tell you everything you need to know.
If you’d like to download a free PDF with all the information you need on finding the right roofer, interviewing roofers, and choosing a roofer for your project, you can request it using the form on the bottom of our home page.
Question #1: Can You Provide Proof That You Have Insurance?
This seems like a basic question, but the details matter enormously here.
There are two types of insurance every roofing contractor must carry:
- General Liability Insurance — This protects you if anything on your property gets damaged during the project. Without it, you could be left paying out of pocket for any damage the crew causes.
- Workers’ Compensation Insurance — This is arguably even more important. If a worker is injured on your property and the contractor doesn’t carry workers’ comp, you as the homeowner could be held financially liable for their medical costs.
This isn’t a hypothetical. Shortly after starting Homestead Roofing, I attended a local roofing association meeting where this was the hot topic of conversation. A roofer in our city hired a subcontractor without workers’ comp insurance. One of the laborers fell off a roof — resulting in approximately $500,000 in medical costs. The homeowner was on the hook for it.
The Right Way to Verify Insurance
Don’t just take the roofer’s word for it. Don’t accept a paper copy handed to you. Don’t even accept an emailed copy directly from the contractor — those documents are too easy to counterfeit.
Here’s what you should do instead: Ask the roofer to have his insurance agent email you the certificates directly.
We almost learned this lesson the hard way ourselves. A subcontractor we were considering emailed us his insurance certificates directly. Something felt off, so I called the insurance agent listed on the certificate. The coverage had expired two years prior.
If a roofer says, “Don’t worry, we’re insured,” that’s not good enough. And if he offers you a liability waiver releasing you from responsibility if someone gets injured — don’t accept it. That document likely won’t hold up in court anyway.
The answer you want to hear: “Of course. I’ll have my insurance agent email you the certificates directly.”
Question #2: Are You a Licensed Roofing Contractor in My Area?
Not every state or municipality requires roofing contractors to be licensed — but if yours does and your roofer isn’t, that’s a serious red flag.
Here’s why it matters: Let’s say the job is complete and a city or county inspector comes out to review the work. If something fails inspection and your contractor isn’t licensed, the responsibility for bringing the roof up to code falls on you — the homeowner. You could end up in a costly dispute with very little legal recourse because you hired an unlicensed contractor.
How to Verify
Ask the roofer for his license number. Ask to see a copy of the license. Then, if you want to be thorough, contact your city, county, or jurisdiction authority to confirm the license is current and valid.
One more thing to watch for: if a roofer tells you that you need to pull the permit — not him — that’s a sign he isn’t licensed. A licensed contractor pulls his own permits. Walk away.
The answer you want to hear: “Yes, I’m licensed. Here’s my license number, and you can verify it online.”
Question #3: Can You Give Me Your Quote Without Seeing My Insurance Claim First?
This one might surprise you — and honestly, it tends to ruffle some feathers in the roofing industry. But it’s one of the most important questions on this list, especially if your roofing project involves an insurance claim.
Here’s what some roofers do: the moment they find out you’ve filed a claim, they ask to see your insurance claim document right away. On the surface, it might seem harmless. But there are real problems with handing that document over before you have a quote in hand.
Why This Is a Problem
You don’t know what work is actually being done. If a roofer hasn’t gone through the process of measuring your roof, creating his own scope of work, and putting together a formal quote, how do you know exactly what he’s agreeing to do?
You could end up overpaying. If the roofer’s actual cost would have come in lower than your insurance claim amount, you’d essentially be handing him extra money — money that should stay in your pocket or go toward other repairs.
You lose visibility into supplements. Supplements are additional line items added to an insurance claim when the original payout doesn’t cover everything. Legitimate supplements are sometimes necessary. But if a roofer is working off your claim document without giving you his own quote, how would you know whether the supplements he’s requesting are justified?
You could lose money meant for other repairs. This actually happened in our area. After a major hail storm, a roofer from out of state came in and told homeowners he’d do the roof for whatever the insurance claim amount was. The problem? Many of those claims included money for collateral damage — siding, windows, HVAC. The roofer collected the full claim amount, completed only the roof, and disappeared. Those homeowners were left without the funds to repair everything else.
What to Do Instead
Simply ask the roofer to provide his quote before you show him your insurance claim document. If he pushes back and says, “That’s not how it’s done,” consider that a significant red flag and find a different contractor.
The answer you want to hear: “Absolutely. I’ll write up my quote, and then we can sit down and compare it with your insurance claim.”
Question #4: If Something Unexpected Comes Up During the Project, How Will It Affect the Price — and Will You Put That in Writing?
Roofing projects have a way of revealing surprises once the work begins. Rotted decking that wasn’t visible during the inspection. Multiple layers of old shingles or underlayment that weren’t apparent from the outside. These things happen, and a professional roofer knows that.
The question isn’t whether surprises might come up — it’s how your contractor handles them when they do.
Why This Matters
Without a clear process for handling unexpected costs, you could reach the end of your project and receive a bill that’s hundreds or even thousands of dollars more than you agreed to. And at that point, the work is already done.
We recently worked with a homeowner who had been speaking with another roofer. That roofer assumed all of the roof decking needed to be replaced — without tearing off a single shingle or inspecting the decking — and wanted the homeowner to agree to an additional $14,000 upfront. That’s not how a professional operates.
What Good Looks Like
A trustworthy roofer will have a clear, documented process for handling change orders. If something unexpected is discovered mid-project, he should:
- Stop work on that area
- Take photos and/or video of the issue
- Contact you before proceeding
- Explain what needs to be done and what it will cost
- Put the change in writing with a change order that you sign
That last step is critical. A signed change order protects both you and the contractor. It confirms that you understand the additional scope of work and have agreed to the price before it’s done.
The answer you want to hear: “If we find something unexpected, we’ll document it with photos, call you before we do anything, explain the cost, and put it in a written change order for you to sign.”
Question #5: Will You Show Me Photos or Videos of My Roof to Demonstrate Why It Needs the Work You’re Recommending?
Think about it — how many homeowners actually get up on their own roof to inspect it? Most of us have no idea what our roof looks like up close. That means we’re largely dependent on what a roofer tells us.
So how do you know he’s telling the truth?
Every roofer carries a smartphone. There is no legitimate reason a contractor can’t show you photo or video evidence of the damage he’s claiming exists on your roof. If he can’t — or won’t — that’s a problem.
Why This Protects You
Without visual evidence, you’re being asked to spend thousands of dollars — or file an insurance claim that could affect your rates — based entirely on someone’s word. That’s not acceptable.
If a roofer can’t show you demonstrable proof of damage, get a second opinion from another contractor before making any decisions.
The answer you want to hear: “Of course. I can show you right now on my phone, or I can text or email them to you. Which would you prefer?”
So, How Can I Find a Reliable Roofing Contractor in My Area?
That’s the question every homeowner eventually asks — and the honest answer is that the best contractors are rarely the ones knocking on your door after a storm or running the flashiest ads. The most reliable roofers are found through referrals from people you trust, through repeat business from homeowners who’ve used them before, and increasingly, through educational content that lets you evaluate a contractor’s knowledge and integrity before you ever pick up the phone.
Whichever way you find a roofer, these five questions give you a reliable framework for separating the professionals from the ones you should avoid.
Don’t Be Afraid to Ask
Reading through these five questions, you might be thinking: “I don’t want to come across as difficult or hard to work with.”
Here’s the reality: every professional, reputable roofing contractor will expect you to ask questions like these. And he’ll have confident, clear answers for all of them.
This is your home. It’s one of your largest financial assets. You have every right — and every reason — to protect it by asking the hard questions before you hand over your trust and your money.
If a roofer gets defensive, dodges your questions, or can’t give you straight answers, that tells you everything you need to know. Move on.
The Bottom Line
Here’s a quick reference summary of the five questions and the answers you’re looking for:
| Question | Green Flag Answer |
|---|---|
| Can you prove you have insurance? | “Yes — my agent will email you the certificates directly.” |
| Are you licensed in my area? | “Yes — here’s my license number. You can verify it online.” |
| Can you quote me without seeing my claim? | “Absolutely — I’ll write my quote first, then we’ll compare.” |
| How do you handle unexpected costs? | “We document it, call you, and put it in a written change order.” |
| Can you show me photos of the damage? | “Of course — right now, or I can text/email them to you.” |
At Homestead Roofing, we believe an educated homeowner makes the best client. If you’re looking for a trusted roofing contractor in Colorado Springs or the surrounding El Paso County area and have questions about your roof — whether you think you need a repair, a replacement, or just want a second opinion — we’re happy to have an honest conversation. No pressure, no sales tactics. Just straight answers.
Serving El Paso County, Elbert County, Teller County, and surrounding areas.