Field guide
The roof inspection question set
Twenty questions that turn any contractor's inspection into evidence you can check. No roofing knowledge required: each one can be answered plainly by someone who actually examined your roof, and each one gets awkward for someone who did not.
The premise
An inspection should produce evidence, not a pitch
A roof inspection is a diagnostic. Its product is evidence: photographs tied to locations, condition notes, measurements, and a finding another professional could pick up and check. When the only product is a price and a place to sign, you did not get an inspection. You got a pitch with a ladder on the truck.
The twenty questions in this guide sort one from the other. They ask for nothing technical, only plain answers. A contractor who actually examined your roof can answer every one without flinching. A contractor who spent nine minutes on the shingles and forty at the kitchen table cannot.
Use every question here on K. Simon too. We publish this list knowing our own inspections have to survive it. That is the point: a recommendation built on evidence has nothing to fear from a sharp owner, whoever wrote it.
For what a documented inspection visit involves step by step, see the residential roof inspection page. The questions below work on any inspection, residential or commercial, whoever performs it.
Questions 1-4
About the inspection itself
You are not grading roofing technique. You are checking whether an examination actually happened, and whether its output is evidence you could hand to someone else.
What did you physically examine, and what could you not reach?
A thorough inspection covers the field (the broad surface of the roof), every penetration through it, the flashings where the roof meets walls, chimneys, and valleys, the drainage path, and the deck, from the attic where access exists. Anything skipped should be named as skipped, not silently left out of the report.
Can I see photos of every finding, tied to a location?
Dated photos tied to locations on the roof are the difference between evidence and a story. 'Your flashing is shot' is a claim. A photo of a specific flashing, marked with where it sits, is a finding you can hand to anyone else for a second opinion.
Did you look from inside: the attic or the underside of the deck?
Water travels before it shows. Stains on the underside of the deck, rusted fastener tips, damp or compressed insulation, and daylight where there should be none often say more than the surface does. On a home with an accessible attic, an inspection that never opened the hatch is incomplete.
How did you evaluate the drainage path?
Gutters and downspouts on a steep roof; drains, scuppers, and slope on a low-slope one. A large share of 'roof problems' are really drainage problems, and no surface repair fixes those. If the report says nothing about where the water goes, ask why.
Questions 5-8
About the finding
A real finding has four parts: a component, a location, a mechanism, and an extent. These questions pin down all four.
What specifically failed?
Not 'the roof is in bad shape.' A component, a location, and a mechanism: a cracked pipe boot on the south slope, an open seam at the parapet, step flashing buried behind stucco with no counterflashing. Vague findings produce vague scopes, and vague scopes are where money disappears.
How widespread is it?
One detail, one slope or section, or the whole roof? The honest answer sets the honest scope. A single failed boot does not open a replacement conversation, and shingles crumbling underfoot on every slope do not close one.
Is this condition active or cosmetic?
Some conditions are leaking today. Some will fail within a few seasons. Some are ugly and stable. A trustworthy report separates the three, because they carry different urgency and very different scopes, and it says plainly which one your roof has.
What is the evidence that it is active?
Moisture readings, wet insulation, fresh staining, water tracks in the attic. 'This will leak' is a prediction; 'this is wet, here is the reading' is a fact. Predictions can be honest, but you deserve to know which of the two you are being given.
Questions 9-12
About the recommendation
The gap between what failed and what is being proposed is where oversized scopes live. These questions measure that gap.
Why this scope instead of a smaller one?
Every recommendation should arrive with the road not taken. If replacement is proposed, what would a repair leave unsolved? If a repair is proposed, what is it deliberately not addressing? A contractor who cannot describe the alternative has not actually compared them.
What happens if I wait a season?
Sometimes the honest answer is 'probably nothing, watch it.' Sometimes it is 'the deck is absorbing water and every month adds scope.' Both answers are useful. Pressure to sign today is not an answer; it is a tactic, and it is the clearest possible signal to slow down.
What parts of the roof are sound?
An inspection that only finds problems is a sales document. A real condition report also records what is performing, because that is what a right-sized scope is built around: fix what failed, leave what works, and put both in writing.
Will your findings survive a second opinion?
The mark of an evidence-based recommendation is that it holds up under another set of eyes. A contractor confident in the finding hands you the photo record and welcomes the comparison. Reluctance to be checked tells you what the evidence would have.
When the recommendation is a fork in the road, the decision itself has its own guide: Repair, restore or replace? walks the inputs that separate a right-sized scope from a sales target.
Questions 13-17
About the contractor
The best scope in the world is worth little in the wrong hands. These questions establish who you are actually dealing with, and they are the ones a bad actor most wants you to skip.
What is your license for this state, and where do I verify it?
Contractor licensing runs state by state, sometimes city by city, so a license from somewhere else is not a license here. Ask for the number, then verify it with the issuing authority yourself. This matters most right after storms, when out-of-area crews follow the damage into town.
Can you send a certificate of insurance naming me?
Two coverages matter: general liability and workers' compensation. Ask for a certificate of insurance issued with you or the property named as certificate holder, sent from the insurer or agent, not a photocopy from the truck. If a worker is hurt on your property and the contractor is not covered, the exposure can land on you.
Who actually performs the work, and who supervises it?
The company selling the job and the crew installing the roof are not always the same people. Subcontracting is normal in roofing; hiding it is not. Ask who will be on the roof, who supervises them, and who answers for the workmanship after the trucks leave.
Will the full scope be in writing before I sign anything?
Materials by name, quantities, the details included (flashings, underlayment, ventilation), what is excluded, how hidden deck damage is priced if it turns up, and how change orders work. A one-line contract with one large number is not a scope. It is a blank check.
What is the payment schedule?
A large deposit demanded up front, in cash, or most of the price due before material arrives, is a reason to stop. Reasonable schedules tie payment to milestones: deposit, material delivery, completion. Keep the final payment in your hands until the closeout items below are delivered.
Questions 18-20
About the paperwork
Paper outlasts the crew. What exists in writing before and after the work decides what you can verify, and what you can enforce, years later.
Will this work be permitted, and who pulls the permit?
Most jurisdictions require a permit for roof replacement, and the permit brings an independent inspection with it. The contractor should pull it under their own license. When an owner is asked to pull the permit instead, responsibility for the work often shifts to the owner. Treat that request as a warning.
What does the manufacturer require for the warranty to hold?
Shingle and membrane manufacturers publish installation requirements: ventilation, fastener patterns, approved accessory products. An installation that ignores them can void the material warranty. Ask what your system requires and how the installation will meet it. Enhanced warranties often require registration too; ask who submits it, and get the confirmation.
What do I receive at closeout?
Completion photos of the details you cannot see from the ground, product records for what was actually installed, the permit sign-off, warranty documents with registration confirmation, and the workmanship warranty in writing with the process for claiming on it. Closeout is what you are left holding for the next decade. Treat it as part of the price.
The printable part
The full question set
All twenty in one place. Print this section, or keep it open on your phone during the walkthrough.
What did you physically examine, and what could you not reach?
Can I see photos of every finding, tied to locations on the roof?
Did you inspect from inside the attic or the underside of the deck?
How did you evaluate the drainage path?
What specifically failed, where, and by what mechanism?
How widespread is the problem?
Is this condition active or cosmetic?
What is the evidence that it is active?
Why this scope instead of a smaller one?
What happens if I wait a season?
What parts of the roof are sound?
Will your findings survive a second opinion?
What is your license for this state, and where do I verify it?
Can you send a certificate of insurance naming me?
Who actually performs the work, and who supervises it?
Will the full scope be in writing before I sign anything?
What is the payment schedule?
Will the work be permitted, and who pulls the permit?
What does the manufacturer require for the warranty to hold?
What do I receive at closeout?
Use it on the crew that knocks after a hailstorm (the storm restoration page covers that situation in depth), on the company your neighbor recommends, and on us. Then head back to the resource library for the decision framework and the detail atlas that pick up where these questions leave off.
Put it to work
Bring this list to our inspection.
Request an inspection and ask every question on this page. Photos tied to locations, a written scope, and a closeout record are the standard we expect to be measured against.