A new roof is one of the biggest checks you’ll write for your home. Up here, it’s also one of the most technical. A roof at 8,000 feet has to handle heavy snow loads, intense sun, big daily temperature swings, and wildfire risk, often all on the same house. The wrong product or a sloppy install doesn’t fail quietly. It fails in a way you notice in February.

I’ve been roofing in the Vail and Roaring Fork Valleys since 2010, first on crews and now as an owner. These are the questions I’d want my own family to ask any roofer, including us.

For each one, I’ll tell you why it matters in the mountains and what a good answer sounds like.

1. Have you installed this exact product before, and where can I see it? 
Not “have you done roofs like mine.” Have you installed this specific product, from this specific manufacturer, and how many times? Composite shake, composite slate, standing seam, and copper all have their own installation details, and experience with one doesn’t automatically transfer to another.

A good answer: real addresses of similar projects you can drive by, and names of owners you can call. We’re happy to share references, and in a small valley, you probably know someone whose roof we’ve done.

2. Are your installers your own employees or subcontractors? 
Plenty of companies use sub crews, and some do fine with it. But you should know who will actually be on your roof and who is responsible for their work.
At Umbrella, our crews are full-time employees, and we run our own sheet metal shop. That’s a big reason we take on the complex, custom roofs other companies pass on. The people who start your job are the same people who finish it, and they answer to us.

3. Will you tell me if I don’t actually need a new roof? 
This one tells you a lot about a contractor. Sometimes the honest answer is that you need a [roof repair], not a replacement. I’ve talked myself out of plenty of jobs that way. Sometimes it goes the other direction, and what looked like a small repair turns out to be a re-roof once we get up there.
A good answer: “Let me look first.” Nobody should quote you a replacement from the driveway.

4. How will the new roof behave differently from the one I have now?
This is the question most homeowners skip, and it’s the one that causes the most surprises. The biggest one we see: cedar shake holds snow because it absorbs water and the snowpack freezes to it. Synthetic shake, synthetic slate, and metal don’t absorb water, so snow slides. Owners who switch from cedar are often shocked the first winter when snow starts coming off a roof that never used to shed.

There are upsides to understand too. In my experience, composite roofs need less long-term maintenance, last a long time, and carry strong fire and impact ratings, which can help with insurance premiums and resale. Ask how the new roof will perform on fire rating, snow, weight, and maintenance compared with what you have now, so you know what you’re getting into.

5. Do I need snow retention, and who designs the layout? 
If you’re moving to a slick roof surface, the answer is almost always yes. The follow-up matters just as much: who decides where the snow guards go? A layout should be engineered for your roof’s pitch and your elevation’s snow load, not eyeballed. I wrote a whole post on how we lay out snow guards, and you can learn more about our snow retention systems.

6. Who pulls the permit, and will my roof need engineered drawings? 
Your contractor should handle permitting, and they should know the local rules cold. In Eagle and Pitkin counties, once a site’s ground snow load goes past the building code’s standard limit, the county requires structural drawings stamped by a Colorado-licensed engineer. A roofer who works here every day should be able to tell you early whether your home falls into that category, not halfway through the permit process.

If you’re in an HOA or a community with a design review board, ask about that too. Approvals can take time, and your roofer should know how to prepare a clean submittal.

7. Do you follow the manufacturer’s installation instructions? 
It sounds like a silly question. It isn’t. Manufacturer warranties generally depend on the product being installed to spec, and shortcuts on underlayment, fastening, flashing, and ventilation are exactly where roofs fail early. We’ve actually read the installation instructions for every product we install, and our crews are trained to them.

A good answer: specific details about how they install the product you’re considering, not “we’ve been doing this forever.”

8. What do the warranties actually cover? 
There are usually two: the manufacturer’s warranty on the material, and the contractor’s workmanship warranty on the installation. Ask for both in writing, and ask what happens if there’s a problem. Who do you call, and how fast do they come out?

It also helps to know how the manufacturer treats claims. We recommend products that are proven in our climate and backed by manufacturers who actually stand behind them.

9. Who is my point of contact from start to finish?
On a lot of projects, homeowners end up with a list of five people and no idea who to call for scheduling, a change order, or a warranty question. That’s frustrating and it’s avoidable.

A good answer: a named person who owns your project, with clear lines of communication through the project manager and superintendent from contract to cleanup, and a clear answer on who handles warranty calls after the crew is gone.

10. What maintenance will this roof need, and do you offer it?
Every roof needs some care, and mountain roofs need more than most. Gutters, valleys, flashing, and [heat cable] all deserve a look before winter and after spring melt. Knowing what your new roof needs, and having the option of professional maintenance, is one of the simplest ways to make it last.

11. How will you handle access, staging, and safety on my property?
Mountain job sites are rarely simple. Steep driveways, tight parking, homes you can only reach on foot, and neighbors a few feet away all change how a roof gets built. I’ve done a job where every bit of material went up 250 steps from the driveway. A good roofer has a plan for that before the first delivery.

Ask about safety, too. Our crews wear their safety gear at all times on the roof, and people who won’t follow the rules don’t last with us. That protects our crews, and it protects your property. Ask any contractor for a certificate of insurance and current license documentation for your town or county.

12. What will the project be like to live through? 
Here’s what I tell homeowners so there are no surprises:

• If you can, plan to be away during tear-off and dry-in. Those are the loudest, busiest days.
• If you’re staying, expect noise and activity from about 7:30 a.m. to 6:30 p.m., five to six days a week until the job is done.
• The site will look like a construction project while we’re working. It should be clean when we leave.
• Keep pets inside or leashed, or better yet, boarded away from home.
• Schedule new landscaping for after the roof is done.

Even careful crews can cause minor damage around a work area. Ask up front how that gets handled.

If your roof has storm damage, hire a roofer who has real experience working with insurance adjusters. Those projects need someone detailed and organized who will document the damage and make sure you get a like-for-like roof. You can also choose to upgrade to a better roof at that point. The insurance covers like-for-like, and you pay the difference.

Add a few questions for multi-unit and managed properties. Ask how the contractor phases work across buildings, how they communicate with owners and residents, how they keep walkways and parking safe during construction, and whether their bids are itemized so your board can compare them line by line. We work with a lot of HOA boards and property managers across both valleys, and we can walk you through how we handle each of these.

Answers that should make you pause

• A price or snow guard count quoted over the phone, before anyone has been on the roof.
• No local references, or only references from other markets.
• Pressure to sign the same day.
• A company that showed up after a storm and doesn’t have an office in the valley.
• Vague answers about who will actually be on your roof.
• Why local accountability matters

This is a small community. There aren’t thousands of roofers here, and I see the people I’ve roofed for at the grocery store, at church, and at the county fair. That keeps you honest. When you tell someone you’re going to do something, you do it.

It’s also why we give back where we work. Through our [1% Close to Home] program, we donate 1% of our gross revenue to the community, from surprise re-roofs for neighbors who couldn’t otherwise afford one to building and donating more than 1,000 bikes to local first and second graders across Eagle, Pitkin, and Garfield counties.

Watch: I talked about how we run Umbrella, from full-time crews to customer service, on RoofersCoffeeShop’s Roofer of the Month. 

Ready to ask us these questions?

We’d rather you ask all twelve than none. Call our Eagle office at 970.704.9130, or learn more about our roof replacement process. We’ll come look at your roof, answer every question straight, and tell you honestly whether you need a new roof at all.

As featured in 

AskARoofer, “Contractor Insights: Josh Yandle, Eagle, Colorado” (January 2024):
RoofersCoffeeShop, “Umbrella Roofing is the August R-Club Roofer of the Month!” (August 2024):