A free roof estimate sounds simple enough: a contractor comes out, takes a look, and gives you a number. But for most homeowners, that interaction is also your single best opportunity to separate the trustworthy contractors from the ones you should walk away from.
Ask the right questions and you’ll walk away with a clear picture of what the job actually involves, what you’re paying for, and who you’re trusting with one of your home’s most critical systems. Ask the wrong questions (or none at all!) and you may not find out there’s a problem until it’s too late.
At Jasmor Roofing & Contracting, we’ve been doing free estimates across Concord, Loudon, Laconia, and Central New Hampshire for over 20 years. We welcome every question, and we think you should ask all of them. Here are the 12 we’d ask if we were in your shoes.
A. Questions About the Company
Before you even talk about your roof, you need to know who you’re dealing with. These questions protect you from unlicensed contractors and uninsured work — two of the most common sources of homeowner nightmare stories.
Question 1: Are you a registered business in NH, and do you carry General Liability insurance?
Why it matters: Unlike some states, New Hampshire does not require a state-level license for roofers. This makes checking their business registration and insurance certificates your only real line of defense. Without General Liability and Workers’ Compensation, you are personally liable for property damage or medical bills if a crew member falls off your roof.
What to listen for: A pro will proactively offer their Secretary of State registration and an insurance certificate. If they claim they “don’t need” insurance because of NH state law, or if they promise to “email it later” but never do, they are exposing you to massive financial risk.
Question 2: Do you carry workers’ compensation insurance?
Why it matters: General liability covers damage to your home. Workers’ comp is a separate policy that protects the crew working on your property. Without it, a worker injured on your roof could potentially file a claim against your homeowner’s insurance.
What to listen for: Ask specifically for workers’ comp — not just ‘insurance.’ Any contractor doing work in NH should have it.
Question 3: Are you a local company, and how long have you been in business in New Hampshire?
Why it matters: “Storm chaser” contractors — out-of-state crews that move into an area after bad weather — are a real issue in NH. They often offer low prices, do substandard work, and disappear before warranty claims come up.
What to listen for: Look for a contractor with a physical presence in New Hampshire, a verifiable track record, and reviews from local homeowners. Ask to see examples of completed work in your area.
B. Questions About the Estimate Itself
A roofing estimate should be detailed, transparent, and in writing. If it’s a single number on a napkin, that’s a red flag. Here’s what to dig into.
Question 4: Is this a written, itemized estimate?
Why it matters: Verbal estimates leave you with no protection if the scope of work changes or costs balloon. A written estimate should list the materials being used, the labor involved, any removal and disposal fees, and any additional work identified during the inspection.
What to listen for: A professional estimator will give you a formal document, not a ballpark. At Jasmor, our estimates are always in writing — no surprises.
Question 5: What materials are included, and what brand are you using?
Why it matters: Not all shingles are created equal. There’s a significant difference in quality, durability, and warranty coverage between standard contractor-grade shingles and products from manufacturers like Owens Corning. The materials specified in your estimate directly affect how long your roof will last.
What to listen for: Ask for the manufacturer name, product line, and color. If the estimate just says ‘architectural shingles’ without specifying a brand, ask why.
Question 6: What is and isn’t included in this price?
Why it matters: Some contractors give a low headline number but exclude things like ice and water shield, drip edge, underlayment, or plywood replacement — costs that can add up significantly. Make sure your estimate spells out exactly what’s covered.
What to listen for: Ask specifically: ‘If you find rotted decking or damaged plywood under my shingles, how is that handled?’ The answer tells you a lot about how the contractor operates.
Question 7: Will you pull the necessary permits?
Why it matters: Many NH municipalities require a permit for a full roof replacement. Some contractors skip this step to cut costs — but if work is done without a permit, it can create issues when you sell your home or file an insurance claim.
What to listen for: A reputable contractor will pull the permits as part of the job. If the answer is ‘that’s not usually necessary’ or ‘you can handle that,’ take note.
| JASMOR TIP: Get at Least Three Estimates |
| We encourage every homeowner to get multiple quotes before making a decision — including ours. A good estimate should be easy to compare apples-to-apples. If two estimates are dramatically different in price, ask both contractors to walk you through what’s different. The cheapest quote isn’t always the best value. |
C. Questions About the Inspection Process
A thorough roof inspection is the foundation of an accurate estimate. Here’s what to ask to make sure nothing gets missed.
Question 8: Will you actually go up on the roof, or is this a ground-level inspection?
Why it matters: Some contractors do drive-by estimates or assess your roof with binoculars from the street. While that might give a general sense of condition, it misses critical details — damaged flashing, soft spots in the decking, failing pipe boots, or compromised ridge vents.
What to listen for: A legitimate inspection involves someone physically on the roof. At Jasmor, we use EagleView satellite measurement technology to verify dimensions and flag potential issues — but we also go up every time.
Question 9: Are you checking the flashing, gutters, soffit, fascia, and ventilation — or just the shingles?
Why it matters: A roof is a system, not just shingles. Flashing failures around chimneys, skylights, and valleys are among the most common causes of leaks. Poor attic ventilation can cut your roof’s lifespan nearly in half. If the inspector only looks at the shingles, you may be missing the real problems.
What to listen for: A comprehensive inspection should cover every component. Ask what the inspector will specifically be looking at, and get it in writing if the scope includes more than just the shingles.
Question 10: What’s the condition of my decking and underlayment?
Why it matters: The shingles are the visible layer, but your roof deck (the plywood underneath) and underlayment are what protect your home from water intrusion if a shingle is damaged or displaced. If either is compromised, shingles alone won’t keep you dry.
What to listen for: A good contractor will look at or inquire about the condition of these layers during the inspection, especially on older roofs.
D. Questions About Warranty and Timeline
Question 11: What warranties come with this job, and who backs them?
Why it matters: There are typically two types of warranties: the manufacturer’s material warranty (covering defects in the shingles themselves) and the contractor’s workmanship warranty (covering installation errors). Both matter. A shingle that fails due to poor installation may not be covered under the manufacturer warranty if the work wasn’t done by a certified contractor.
What to listen for: Ask specifically: ‘Are you a certified installer for this manufacturer?’ Owens Corning Platinum Preferred Contractors — like Jasmor — are trained and credentialed to offer enhanced warranty coverage, including labor.
Question 12: What’s the timeline, and what happens if there are weather delays?
Why it matters: Most standard residential roof replacements in New Hampshire take one to two days. But weather — especially in spring and fall — can push timelines. You deserve to know what the realistic schedule looks like and how the contractor handles unexpected delays or mid-job rain.
What to listen for: Ask: ‘If you start my roof and can’t finish due to weather, how will you protect my home overnight?’ The answer reveals how seriously they take job-site management.
Red Flags to Watch Out for During an Estimate
Beyond the questions above, here are some patterns that should give you pause, regardless of how good the price looks:
- Pressure to sign the same day. A reputable contractor doesn’t need to rush you. High-pressure tactics are a classic sign of a contractor who knows they won’t hold up to comparison.
- Cash-only payment or large upfront deposits. Standard practice is a deposit at signing and the balance on completion. Asking for the full amount upfront — especially in cash — is a serious warning sign.
- No physical address or local references. If you can’t verify where the company is based or find reviews from NH homeowners, be cautious.
- An estimate that seems dramatically lower than the others. Significant price gaps usually mean something is being cut — materials quality, proper underlayment, permits, or crew experience. Ask them to explain the difference line by line.
- Reluctance to provide proof of insurance. This should be non-negotiable. No documentation = no job.
The Bottom Line: A Good Contractor Welcomes Your Questions
A contractor that gets defensive, evasive, or impatient when you ask these questions, that tells you everything you need to know. The best contractors — the ones who take pride in their work and stand behind it — want an informed homeowner. It makes the whole job go more smoothly.
At Jasmor Roofing & Contracting, every estimate starts with a real conversation. We’ll walk you through exactly what we found during the inspection, what we recommend, what it costs, and why — no pressure, no jargon, no shortcuts.
If you already had your inspection and want to know what to expect on the day itself, check out our companion guide: What to Expect on Roof Installation Day [INTERNAL LINK: /blog/what-to-expect-on-roof-installation-day/].
| Ready for a No-Pressure Roof Estimate? |
| We’re an Owens Corning Platinum Preferred Contractor with an A+ BBB rating and 20+ years of experience serving Concord, Loudon, Laconia, and all of Central New Hampshire. |
| Call (603) 961-0335 or request your free estimate online → https://jasmorprop.com/contact |