Roof System & Inspection
1. Ask Them to Explain Your Roof's Ventilation System
Ask
“Can you explain how you determined whether my current attic ventilation is adequate for this roof?”
Why ask?
Ventilation is one of the most misunderstood parts of residential roofing.
A contractor should not simply point at a few vents and say the house is ventilated.
The homeowner should understand whether the contractor actually evaluated how air enters the attic, how it exits, whether the system is balanced, and whether anything about the proposed roof could affect that system.
What measurements or observations did you use to reach that conclusion?
That question forces the conversation beyond generalities.
2. Ask What Happens Where Two Roof Planes Meet
Ask
“How are you planning to build the valleys on my roof?”
Why ask?
Valleys carry significant amounts of water and are frequent trouble spots when roofing systems are poorly designed or installed.
There are multiple ways a roofing contractor may approach a valley depending on the roof, materials, manufacturer, and system being installed.
The important part is whether the contractor can explain what method is being used on your house and why.
Do not simply accept: “We've always done it this way.”
Ask: “Why is that method appropriate for this particular roof?”
3. Ask About Every Roof-to-Wall Intersection
Ask
“Can you show me every location where this roof intersects a wall and explain how each one will be handled?”
Why ask?
Homeowners tend to focus on the large open areas covered with shingles.
Some of the most technically important areas of a roof are the transitions.
A qualified contractor should notice them during the inspection.
The homeowner should know whether these details were actually identified before the proposal was written.
Flashing & Roof Transitions
4. Ask About Existing Flashing
Ask
“Which pieces of existing flashing are you planning to replace, and which—if any—are you planning to reuse?”
Why ask?
“New roof” does not automatically tell you what happens to every flashing component already on the house.
That distinction should be understood before the roof is removed.
Then ask: “Is that spelled out in my written scope of work?”
If an important installation detail is only a verbal promise, that is worth noticing.
5. Ask What Happens Around the Chimney
If the house has a chimney, ask:
Ask
“Walk me through exactly how you plan to handle the roofing system around this chimney.”
Why ask?
A chimney creates several transitions and water-management considerations.
Rather than telling the contractor what method to use, let them explain their own process.
The depth of the explanation can tell you quite a bit about how technically involved the person actually is.
6. Ask About Pipe Penetrations
Ask
“How many roof penetrations did you identify, and what is your plan for each one?”
Why ask?
Plumbing vents and other penetrations can become leak points.
This question also tests something very basic:
Did the contractor actually inspect the roof carefully enough to identify them?
Underlayment & Water Management
11. Ask Them to Explain the Underlayment Plan
Ask
“What underlayment system are you specifying for my roof, and where will each type be installed?”
Why ask?
The material beneath the visible roof covering is part of the roofing system.
You are not asking because you need to memorize product specifications.
You are asking to see whether the contractor can clearly explain what is going underneath your finished roof.
12. Ask Specifically About Ice Protection
Ask
“Based on this house and Northern Wisconsin conditions, where are you planning additional ice and water protection?”
Why ask?
Cold-weather roofing creates considerations that homeowners in warmer climates may rarely encounter.
The contractor should be thinking about your roof as a Northwoods roof—not simply applying a generic roofing scope used everywhere.
13. Ask About Eaves
Ask
“What are you doing differently at the eaves compared with the main field of the roof?”
Why ask?
The edge of the roofing system is not just another row of shingles.
This question tests whether the contractor thinks in terms of an entire roofing assembly rather than simply replacing the visible surface.
14. Ask About Rakes and Drip Edge
Ask
“What is your plan at the eaves and rake edges, and how will the edge-metal details integrate with the rest of the system?”
Why ask?
Small perimeter details can have an outsized effect on water management and finished appearance.
A contractor should be able to explain how these details fit together.
15. Ask About Fastener Placement
Ask
“What determines where and how your installers fasten the roofing material?”
Why ask?
Fasteners disappear beneath the completed roof.
The homeowner cannot easily evaluate them afterward.
That makes installation training and quality control especially important.
Do not tell the contractor where the fasteners belong.
Let the contractor demonstrate that they understand the system they are selling.
16. Ask Whether Installation Changes With Roof Pitch
Ask
“Does anything about your installation change because of the pitch of my roof?”
Why ask?
A contractor should not treat every roof geometry identically.
The homeowner does not need to know the technical thresholds.
The point is to discover whether the contractor does.
17. Ask About Very Low-Slope Areas
If any section looks noticeably flatter than the rest, ask:
Ask
“Is this section appropriate for the same roofing material as the steeper portions of the house?”
Why ask?
This is an excellent technical question because it forces the contractor to evaluate the roof section rather than simply price square footage.
Follow with: “What determines your answer?”
18. Ask About Roof Transitions
Ask
“Are there any areas on my roof where pitch, geometry, or material transitions require special detailing?”
Why ask?
Complicated roofs frequently fail at transitions rather than in the middle of a large, simple roof plane.
You want to know whether those areas were identified before installation.
Roof Features & Drainage
19. Ask About Skylights
If the home has skylights, ask:
Ask
“What exactly are you planning to do with each existing skylight during the roof replacement?”
Why ask?
Homeowners sometimes assume a skylight is simply worked around.
The contractor should explain how it fits into the roofing project and whether its age or condition affects the recommendation.
20. Ask About Dormers
Ask
“What additional flashing and water-management details does this dormer create?”
Why ask?
Dormers create intersections that deserve deliberate attention.
This is another opportunity to see whether the estimator actually studied the roof instead of producing a generic square-foot price.
21. Ask About Sidewalls and Headwalls Separately
Ask
“Are the sidewall and headwall conditions on this house handled differently?”
Why ask?
That question is intentionally technical.
You are testing whether the contractor understands that different roof-to-wall conditions may require different details.
Let the contractor explain the difference.
22. Ask About Kick-Out Details
Ask
“Are there locations where roof runoff meets siding or a wall termination that require special water-diversion detailing?”
Why ask?
This question makes the contractor examine the interaction between the roof and the exterior wall system.
A technically experienced contractor should understand why you are asking.
23. Ask About Gutters Before the Roof Starts
Ask
“Do my existing gutters affect any part of your roofing installation plan?”
Why ask?
Roof edges, drainage, fascia, drip edge, and gutters interact.
The contractor should know whether existing conditions create any complications before work begins.
24. Ask What They Do When They Find Rotten Fascia
Ask
“If deterioration is discovered at the roof edge after tear-off, what happens next?”
Why ask?
Again, this exposes the contractor's process for hidden conditions.
Good roofing is partly about installation and partly about what happens when the job stops going exactly according to plan.
Ventilation & Attic Conditions
25. Ask About Intake Ventilation Before Adding Ridge Vent
Ask
“Before recommending additional exhaust ventilation, did you verify how this attic receives intake air?”
Why ask?
This is intentionally a difficult question.
The goal is not for the homeowner to debate ventilation calculations.
The goal is to see whether the contractor considers the system as a whole before recommending individual components.
26. Ask Whether Different Attic Sections Are Actually Connected
Ask
“Is this house one continuous attic ventilation space, or are there separate sections that need to be evaluated independently?”
Why ask?
Complicated houses may not have one simple attic cavity.
That can matter when evaluating how the roof and attic function together.
27. Ask About Cathedral Ceilings
If applicable, ask:
Ask
“How does the cathedral-ceiling portion of this home change your ventilation or roofing approach?”
Why ask?
Not every roof has a large, accessible open attic underneath it.
Different construction conditions may require different thinking.
28. Ask About Ice Dams Before Asking About Shingles
Ask
“If this house has experienced ice dams, what would you investigate before assuming the shingles are the cause?”
Why ask?
This question reveals whether the contractor understands that symptoms visible on the roof can sometimes involve conditions elsewhere in the building system.
A contractor should investigate before simply selling.
Repair vs. Replacement
29. Ask Whether the Existing Roof Failed or Simply Reached the End of Its Life
Ask
“What specifically tells you this roof needs replacement rather than repair?”
Why ask?
A replacement is a major purchase.
A homeowner deserves more than:
“It's old.”
Ask the contractor to identify the conditions driving the recommendation.
30. Ask Them to Identify the Failure Points
Ask
“Can you physically show me the areas of this roof that concern you most?”
Why ask?
The contractor should be able to connect the recommendation to real observations on your home.
Photographs are especially useful on roofs homeowners cannot safely inspect themselves.
31. Ask What They Would Repair If You Were Not Replacing the Roof
Ask
“If I decided not to replace this roof this year, what areas would you address first?”
Why ask?
This is an excellent way to understand how the contractor prioritizes actual roofing risk.
It can also reveal whether they have thought about the house beyond simply producing a replacement proposal.
32. Ask About Material Compatibility
Ask
“Are all of the components in the roofing system you're proposing designed to work together?”
Why ask?
A roof is made from multiple products.
The homeowner should know whether the contractor has intentionally selected a system or simply assembled whichever materials were convenient.
33. Ask About Manufacturer Requirements Without Giving Them the Answer
Ask
“Which parts of your installation are specifically dictated by the manufacturer's instructions for the product you're proposing?”
Why ask?
A contractor selling a particular roofing system should know the installation requirements of that system.
You should not have to teach them.
34. Ask What Could Void or Limit a Warranty
Ask
“What installation mistakes or conditions could affect the warranty on the roofing system you're proposing?”
Why ask?
It is easy to advertise a warranty.
Understanding the conditions behind the warranty is more meaningful.
Quality Control & Supervision
35. Ask Who Checks the Work Before It Is Covered Up
Ask
“Which installation details are inspected before the next layer of roofing hides them?”
Why ask?
Many of the most important parts of a roof become invisible as construction progresses.
Quality control needs to occur while those details can still be observed.
36. Ask Who Has Authority to Stop the Crew
Ask
“Who on my project has the authority to stop installation if something isn't being done correctly?”
Why ask?
Every professional production system needs accountability.
This question tells you whether there is meaningful supervision or whether the project simply moves forward until completion.
37. Ask Who Makes Technical Decisions on Installation Day
Ask
“If an unexpected condition is discovered after tear-off, who makes the technical decision about how it is handled?”
Why ask?
The person who sold the project may not be the person running it.
Homeowners should know where technical authority actually sits.
38. Ask How Installation Quality Is Documented
Ask
“What parts of the installation do you document before they become hidden?”
Why ask?
Documentation creates accountability.
It also demonstrates that the contractor has thought about quality control as a process rather than simply relying on memory.
Metal Roofing & Northern Wisconsin Conditions
39. Ask About Snow Loads and Roof Geometry
Ask
“Are there any characteristics of this roof that make snow accumulation or snow movement especially important?”
Why ask?
Northern Wisconsin roofs experience conditions that contractors in other markets may rarely think about.
Roof shape, adjoining roof sections, entrances, walkways, decks, and mechanical equipment can all make snow behavior worth discussing.
40. Ask About Metal Roofing Differently
If considering metal roofing, ask:
Ask
“What details on this particular house make metal roofing more complicated than simply replacing shingles with metal panels?”
Why ask?
Metal roofing is its own system.
The contractor should be able to discuss the house itself—not merely repeat general benefits of metal roofing.
41. Ask About Expansion and Movement
For metal roofing, ask:
Ask
“How does the system you're proposing account for movement of the roofing material over time?”
Why ask?
This is the kind of question that quickly separates basic product sales knowledge from deeper installation knowledge.
Again, let the contractor supply the explanation.
42. Ask About Snow Retention on Metal Roofs
Ask
“Are there areas around this home where snow leaving a metal roof could create a safety or property concern?”
Why ask?
Changing roofing materials can change how snow behaves.
A contractor familiar with Northwoods conditions should be considering more than appearance.
43. Ask How the Contractor Handles Extremely Cold Installation Conditions
Ask
“At what point do weather conditions cause you to change, postpone, or modify your installation process?”
Why ask?
Weather affects construction.
You are looking for evidence that production deadlines do not override technical judgment.
Project & Weather Management
44. Ask What Happens if Weather Changes Mid-Project
Ask
“What is your procedure if unexpected weather arrives after the existing roof has been removed?”
Why ask?
Every roofing contractor eventually encounters changing weather.
The quality of the contingency plan matters.
45. Ask About Property Protection Technically
Ask
“Before tear-off begins, what areas of this property have you identified as particularly vulnerable to roofing debris or equipment?”
Why ask?
Property protection should be planned around the actual house.
Landscaping, siding, windows, decks, driveways, air-conditioning equipment, lakefront features, and other areas may require attention.
The Most Important Technical Question May Be the Simplest
After asking several of these questions, ask one more:
Ask:
Why?
- Why that material?
- Why that ventilation approach?
- Why that valley?
- Why that flashing detail?
- Why replacement instead of repair?
- Why that underlayment?
- Why that installation method?
- Why is this roof different from the last house you worked on?
A homeowner does not need to know every answer beforehand.
That is the point.
You are hiring the roofing contractor because they are supposed to know the answers.
The purpose of technical questions is not to trick anyone.
It is to determine whether the contractor can look at your specific house, identify its conditions, and explain the reasoning behind the proposed roofing system.
A polished presentation can tell you that someone knows how to sell roofing.
Technical questions help determine whether they actually know roofing.
A Final Thought From Roof Masters
At Roof Masters, we encourage homeowners to ask detailed questions.
You should understand what is being done to your home and why.
And when you ask a technical question, you should not receive a vague response, a rehearsed sales line, or an attempt to change the subject.
Ask the difficult questions.
Let the contractor provide the answers.
You may be surprised how much you learn about the company before a single shingle ever comes off your roof.
Ask Roof Masters the Difficult Questions
Planning a roof replacement in Northern Wisconsin? Bring us your questions. We believe homeowners should understand what is being recommended and why.
Request an Estimate