Hiring

Before You Hire: Questions to Ask a Roofer in Madison

By Madison Roof Repairs · September 10, 2026 · 7 min read

Madison has a lot of roofers. After a hailstorm it has three times as many, and most of the extras will be gone by Labor Day. Sorting the good local companies from the rest takes about twenty minutes and a handful of questions. Here are the questions to ask a roofer, with the answers you should hear.

"What Wisconsin credential do you hold, and who pulls the permit?"

Wisconsin has no roofing-specific license. Whoever pulls the building permit on a one- or two-family home generally needs a Wisconsin Dwelling Contractor credential — confirm with DSPS or your building department, and look any company up on the DSPS credential search. Check with the City of Madison Building Inspection (or your city or village) whether your job needs a permit, and ask the roofer who pulls it and whether it's in the price.

Any legitimate roofing company can tell you what it holds and who holds it. You can check it yourself on the DSPS credential lookup in a minute: search the business name and the person named, and check the expiry dates. A company that can't answer this question, or says "we don't need that for roofing," is telling you what you need to know.

"Send me your insurance certificates"

Two documents: general liability and workers' compensation. Ask for the certificates to come directly from the insurance agent, with your name as certificate holder, not as a photo of a piece of paper. A roofer whose crew member falls off your roof without workers' comp becomes a claim against your homeowners policy. This is the question that separates roofing contractors Madison homeowners regret from the ones they recommend. This guide follows the same rule when it passes on a request. Whoever you hire, ask to see their certificate of insurance before work starts.

"Where's your office?"

A local address you can drive to. A phone number with a 608 area code that someone answers. Trucks with a company name, not magnetic signs. None of this guarantees quality, but it guarantees someone to call in 2029 when the valley leaks.

"Will you go in my attic?"

A roofer who quotes a replacement from a satellite measurement and a walk around the yard hasn't seen the decking, the ventilation, the frost on the nail tips, or whether the ice-and-water shield from the last roof actually exists. The best roofers in Madison go into the attic on every estimate. If they won't, you'll find out what they missed on invoice day.

"What exactly is in the quote?"

Get it in writing, itemized. For a replacement, look for:

A quote missing three of these isn't cheaper. It's incomplete.

"What's the workmanship warranty, and who honors it?"

The manufacturer warrants the shingle. The roofer warrants the installation, which is where most leaks come from. Ask how many years, get it in writing, and ask what happens if the company closes. A storm chaser's ten-year workmanship warranty expires when the truck leaves the county.

"How do you handle my deductible?"

The only right answer is "you pay it." Be wary of any roofer who offers to cover, waive or rebate your deductible — Wisconsin restricts it and it can put your claim at risk. Ask your insurer, or check with DATCP or an attorney. Wisconsin also gives homeowners cancellation rights on some home-solicited and insurance-contingent roofing contracts; check the current rules with DATCP or an attorney before you sign. A roofer who raises this without being asked is one to keep.

"Can I see a job you did five years ago?"

Not a fresh one. Anyone can make a roof look good the week it's finished. Ask for a few addresses of roofs done years ago and drive past them. Look at the ridge line, the valleys, whether the flashing at the chimney is still tight.

Questions about the job itself

• "How long will it take, and what happens if the weather turns?" One to two days for most homes. Ask how the open deck gets protected if rain moves in.
• "Who will be on the roof, and who's in charge on site?" Know whether the company's own crew or a subcontractor does the work, and who to call during the job.
• "How will you protect the house and yard?" Tarps over plantings, plywood against the siding, and a magnet sweep for nails afterward.
• "How are payments staged?" A large deposit before materials arrive is a red flag; ask how payments are staged.
• "How long is this price good for?" Nobody should push you to sign at the kitchen table.

Questions about a repair

Not every call is a new roof. On a smaller job, ask:

• What exactly is causing the leak, in plain words?
• Will you replace the flashing or boot, or seal over it?
• Will the new shingles be hand-sealed if it's cold?
• How long is the work warrantied, in writing?
• What else did you see that I should plan for?

How to compare the answers

Write the answers down as you get them, one column per company. After two or three conversations the differences are obvious: one went into the attic and one didn't, one named a shingle line and one said "the good stuff," one gave you a written warranty term and one said "don't worry about it." The best answer isn't always the cheapest. It's the one you can check.

After you hire

Keep the signed contract, the certificate of insurance, the permit if there is one, and photos of the work in one folder. Ask for photos of any decking that was replaced. Walk the yard with the crew lead before the final payment, and look at the chimney, the valleys and the drip edge from the ground. Register the shingle warranty if the company doesn't do it for you, and note the date the job finished; that's when both warranty clocks start.

Questions about the company

• "Who will I talk to if something goes wrong in a year?" A name and a phone number, not a general inbox.
• "Can I call two homeowners you worked for in the last couple of years?" Ask them what went well and what they'd change.
• "Do you do this kind of roof regularly?" Steep century houses, low-slope porch roofs and big cut-up roofs each take practice; ask how often they do yours.
• "What happens if you find something unexpected?" Rotted decking, a hidden second layer, a cracked rafter. The answer should be that they stop, show you photos and price it before going on.

None of these should annoy a good company. If someone gets impatient with them at the kitchen table, that tells you how the job will go when a question comes up halfway through the tear-off.

The tells

Things that end the conversation:

• Knocked on your door the morning after a storm
• Wants a large deposit today, or "today-only" pricing
• Offers to waive the deductible
• Can't say what Wisconsin credential it holds, or won't produce insurance certificates
• Quotes from the driveway in ten minutes
• Can't say who pulls the permit, or tells you to pull it yourself

What the good ones sound like

A written scope after a roof-and-attic inspection, with photos. Prices in line with the cost page. A real address. A credential they'll name and you can look up. A willingness to say "this roof has three more winters" when it does. That's the whole test.

If you have storm damage, the hail and wind damage page covers the claim process, and the about page explains how this guide refers requests.