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The Contractor Checklist: 7 Questions to Ask Any Roofer

The Contractor Checklist: 7 Questions to Ask Any Roofer

Ask these before you sign anything. For each one there's a good answer and a warning sign — knowing the difference is most of the job.

Print this or keep it open on your phone while you talk to them.

The seven questions, grouped by what they protect Questions 1 and 2 protect you legally, 3 and 4 protect the scope and price, 5 to 7 protect you after the work is done. BEFORE THEY START 1 · Insurance certificate 2 · Licence number If these two are wrong, nothing else matters. Ask them first. SCOPE & PRICE 3 · Who does the work 4 · Rotten decking price This is where surprise charges come from. Settle it in writing. AFTER IT'S DONE 5 · Warranty split 6 · Payment schedule 7 · Permit These decide what happens when something goes wrong.
Stage Questions Why this stage matters
Before they start 1. Insurance certificate · 2. Licence number If these are wrong, nothing else matters
Scope & price 3. Who does the work · 4. Rotten decking price Where surprise charges come from
After it's done 5. Warranty split · 6. Payment schedule · 7. Permit Decides what happens when something goes wrong

1. Can I see your certificate of insurance?

There are two policies that matter: general liability (damage to your property) and workers' compensation (injury to their crew on your property). Ask for both.

A good answer: they send the certificate without hesitation, the dates are current, and they're comfortable with you contacting the insurer to confirm it's active.

A warning sign: "we're fully insured" with no paperwork, a certificate that expired last year, or irritation that you asked. This is the single most important question on the list — ask it first, and don't let a good price talk you out of it.

What to check on a certificate of insurance Three things to verify: general liability coverage, workers compensation coverage, and that the policy dates are current. Three things to check on the certificate 1 General liability Covers damage to your house and property during the work. 2 Workers' compensation Covers their crew if someone is hurt on your roof. 3 Current dates An expired certificate is the same as no certificate.
Check What it covers If it's missing
General liability Damage to your house and property Damage becomes your problem
Workers' compensation Injury to their crew on your roof An injury claim can come back to you
Current policy dates That the cover is active today An expired certificate is no certificate

2. Are you licensed for this work here, and what's the number?

Roofing licence rules vary a lot — some states license contractors at state level, some at county or city level, and a few barely regulate it at all. So the useful question isn't "are you licensed" but "under what, and what's the number."

A good answer: a licence number offered without being chased, which you can then check against your state or county licensing lookup.

A warning sign: a number that doesn't match the business name on the estimate, or a licence belonging to someone who isn't actually on the job.

a man working on a roof with a power drill
Photo by Raze Solar / Unsplash

3. Will your own crew do the work, or subcontractors?

Neither answer is automatically wrong — plenty of good roofers use subs. What matters is that they tell you straight.

A good answer: a clear yes or no, plus who supervises on site and who your single point of contact is if something goes wrong at 4pm on a Friday.

A warning sign: vagueness. If they can't say who will physically be on your roof, the crew is likely being assembled per job.

4. What happens if you open the roof and find rotten decking?

This is the most common source of surprise charges in the whole trade. Nobody knows what's under the shingles until the tear-off starts, so the honest move is to price it before it happens.

A good answer: a specific price per sheet of plywood, written into the estimate up front, plus a commitment to show you the damage — photos at minimum — before replacing anything.

A warning sign: "we'll let you know if we find anything." That's an open cheque, signed by you, at the exact moment you have no leverage and half a roof.

5. What does the warranty actually cover?

There are two separate warranties and people constantly conflate them.

Manufacturer warranty versus workmanship warranty The manufacturer covers material defects. The contractor covers installation mistakes. Most early roof problems are installation, and that warranty disappears if the contractor goes out of business. MANUFACTURER Covers: defects in the shingles or membrane itself Backed by the material maker. Survives your contractor going out of business. WORKMANSHIP Covers: mistakes in how it was installed Backed by the contractor only. Disappears if they close down. Most roof problems in the first few years are installation, not materials So the workmanship warranty is the one protecting you day to day
Covers Who backs it Survives contractor closing?
Manufacturer warranty Defects in the materials themselves The shingle or membrane maker Yes
Workmanship warranty Mistakes in how it was installed The contractor No

A good answer: they separate the two without being prompted, give a term in years for each, and tell you plainly what voids them.

A warning sign: one blurred "25-year warranty" that turns out to be the manufacturer's material coverage only.

a woman sitting at a table looking at her cell phone
Photo by Vitaly Gariev / Unsplash

6. What's the payment schedule?

A reasonable payment schedule versus a warning sign A healthy schedule is a modest deposit with most of the money due on completion. A large up-front demand is the most reliable warning sign in roofing. Reasonable Deposit Progress payments Balance after you walk it Warning sign Most of the money demanded before materials arrive Balance A real contractor has supplier credit and does not need your cash to start.
Schedule What it looks like What it signals
Reasonable Modest deposit, progress payments tied to milestones, balance after you've walked the finished job They have supplier credit and stand behind the work
Warning sign Most of the money demanded before materials arrive The most reliable warning sign in roofing

A good answer: a modest deposit, progress payments tied to actual milestones, and a meaningful balance due only after the work passes inspection and you've walked it.

A warning sign: a demand for most of the money before materials arrive.

7. Who pulls the permit, and is it in the estimate?

A good answer: the contractor pulls it, and the fee appears as a visible line item rather than vanishing into a lump sum.

A warning sign: a suggestion that you skip the permit to save money, or that you pull it yourself as the homeowner. Both shift risk onto you — and an unpermitted roof can surface years later when you try to sell.

Before you sign

Get it in writing, itemized. A verbal quote isn't a quote. The estimate should show materials, labor, tear-off, disposal, permit, and the per-sheet decking price separately — if it's one number with no breakdown, ask for the breakdown before you ask for a discount.

And get more than one. Three written estimates is the standard advice for a reason: it's the only way to know whether the middle one is fair.

Want a number to judge those quotes against? The roof cost calculator gives you a range with every line itemized, so you can see where a quote is padded.

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