20 Questions to Ask a Roofing Contractor Before You Sign

Every roofing bid sounds confident in the driveway. The gap between a contractor who can back that confidence up and one who is guessing shows up in the answers to specific questions, not in the pitch. Below are twenty questions, grouped into seven themes, that a homeowner can ask any bidder before signing anything. For each one we describe what a good answer sounds like and what a dodge sounds like, because the shape of a non-answer is often more useful than the words in it. Print this list, bring it to every estimate, and ask the same questions of every contractor so the answers are actually comparable. Once you have them, our quote comparison guide shows you how to line the written bids up side by side.

01 / THE SHORT ANSWERWhy the questions matter more than the quote

A roofing quote is a promise on paper, and the questions below are how you test whether the person making the promise can actually keep it. A full asphalt replacement in Macomb County runs $9,000 to $18,000 installed, with most homes landing $12,000 to $16,000, and within that range two contractors can hand you nearly identical numbers while one is licensed, insured, and staffed with a supervised crew, and the other is a truck, a phone number, and a hope. The dollar figure will not tell you which is which. The questions will.

The twenty questions below are grouped by theme on purpose: credentials, crew, scope, timeline, cleanup and payment, and warranty. Work through a section at a time with every bidder, and use the same wording each visit, ideally at the same appointment where you are also collecting the written quote itself. A contractor who welcomes the whole list is telling you something. A contractor who gets impatient with it is telling you something too, usually the more important of the two. None of this requires confrontation; the tone that works best is closer to a homeowner doing due diligence on a five-figure purchase than an interrogation, because that is exactly what it is.

02 / CREDENTIALSCredentials and insurance: questions 1 to 3

These three come first because everything else depends on them. If the answers here are weak, the rest of the interview is academic.

1. Are you licensed to do roofing work in Michigan, and can I see the number?

A good answer gives a license number on the spot, or a card with it printed, and does not flinch at being asked to verify it. A dodge is "we don't need one for this" or "my supervisor has it," both of which shift the liability onto you if something goes wrong. Our guide on how to verify a roofing license walks through checking the number yourself.

2. Can you send me a certificate of general liability and workers compensation insurance?

A good answer is a yes, followed by an actual certificate emailed with your name as the certificate holder, not a photo of someone else's policy. A dodge is "we're covered, don't worry about it" with nothing in writing. Without workers compensation, an injury on your roof can become your homeowner's insurance problem.

3. Do you pull the permit, and under whose name?

A good answer names the municipality's permitting process and confirms the permit is pulled under the company's license before work starts. A dodge is "we don't usually bother with the permit for a reroof" or offering to let you pull it yourself as the homeowner. Skipping the permit skips the inspection that catches mistakes while they are still fixable.

03 / THE CREWCrew and supervision: questions 4 to 6

The person who sold you the job is rarely the person on your roof. These questions find out who actually is.

4. Is the crew your employees or a subcontractor?

A good answer is direct, either way, and comes with follow-up detail about who supervises. A dodge is vague deflection, because subcontracting is common and not automatically a problem, but not knowing who is on your roof is. Our guide on subcontractors versus in-house crews covers why this distinction matters and what to ask next.

5. Who is the on-site supervisor, and will they be there the whole job?

A good answer names a specific person, gives you a way to reach them, and confirms supervision for the duration, not a drive-by check. A dodge is "the crew knows what they're doing" with no named point of contact, which leaves you with no one to call when a question comes up mid-tear-off.

6. What is the crew's workers compensation coverage, separate from the company's?

A good answer confirms the crew, whether employees or a sub, carries its own coverage and can produce it. A dodge folds this question back into question 2 without actually answering it, which matters because a general liability certificate does not always mean every worker physically on the roof is covered under workers compensation.

04 / THE SCOPEScope and materials: questions 7 to 10

This is where quotes quietly diverge the most, and where a vague answer costs you the most money later.

7. Is this a full tear-off, and what happens to the old shingles?

A good answer confirms a full strip to the deck and names the disposal method, dumpster or trailer. A dodge suggests an overlay to save money without you asking for one, which hides the deck condition and shortens the life of the new roof.

8. What shingle line, by manufacturer and name, are you quoting?

A good answer names the specific product, not just "architectural shingle," so you can compare wind rating and warranty apples to apples. A dodge says "a good 30-year shingle" with no name attached.

9. What is your per-sheet price if you find rotten decking?

A good answer states a specific dollar figure per sheet, in writing, before tear-off starts, and offers to photograph any sheets they replace so you can see exactly what was swapped. A dodge says "we'll figure that out if it comes up," which turns a routine discovery into a mid-job negotiation with your roof half open.

10. How much ice barrier goes down, and where?

A good answer describes the eave coverage in feet and confirms it meets Michigan's climate zone requirement. A dodge says "we always put down what's needed" without a number, which is the same non-answer dressed up as confidence.

05 / THE CALENDARTimeline and weather plan: questions 11 to 13

Roofing is outdoor work in a state with real winters, so the schedule questions are not small talk.

11. How many days will the job take, and what happens if weather stops it midway?

A good answer gives a realistic range and describes how the crew protects an open roof if rain moves in, tarping and dry-in procedure included. A dodge promises a firm one-day timeline for a job the estimator has not actually measured. Our guide on whether a roof can be replaced in one day explains when that promise is realistic and when it is a red flag.

12. When on the schedule would my job actually start?

A good answer gives a real window and is candid if the season is booked out. A dodge is "we can start tomorrow" from a company that just knocked on your door, which is a classic sign of a crew chasing storm work rather than running a real backlog, not building a real one.

13. What is the plan if you open the roof and find a bigger problem than expected?

A good answer walks through documentation with photos and a signed change order before the extra work proceeds, whether that is rotten decking, hidden storm damage, or a ventilation gap. A dodge is "we'll just take care of it," which sounds reassuring and leaves you with no paper trail for what changed or why.

06 / THE MONEYCleanup and payment terms: questions 14 to 17

This section covers what the property looks like when the crew leaves, and how the money actually moves. Both are where a shaky operation shows its hand.

14. How do you protect my landscaping, siding, and gutters during tear-off?

A good answer describes tarps over shrubs and AC units, plywood or ladder pads to protect siding contact points, and gutter guards during tear-off. A dodge shrugs off the question as though damage is simply the cost of a new roof.

15. How do you handle nail cleanup, and do you use a magnetic sweep?

A good answer confirms a magnetic roller sweep of the lawn and driveway is standard, not an upsell. A dodge says the crew "cleans up as they go" with no mention of a magnet, which is how loose roofing nails end up in a lawnmower tire or a bare foot weeks later.

16. What is the payment schedule, and is any of it due before work starts?

A good answer describes a modest deposit at signing, at most, with the balance due on completion after a walkthrough. A dodge asks for the full amount up front or insists on cash only. Our guide on roofing deposits and payment schedules covers what is customary and what is a warning sign.

17. If I finance the job, who is the lender and what happens if I am not approved?

A good answer names an actual financing partner and explains that approval and terms depend on the lender and your credit profile, never a guaranteed rate. A dodge promises a specific monthly payment before you have applied for anything. As an illustration only, a $13,500 project financed over 10 years at 9.9% APR works out to about $178 a month, subject to approval; that is not an offer of credit.

07 / AFTER THE SALEWarranty and service after: questions 18 to 20

The install day answers are easy to check. These last three only get tested years later, which is exactly why they belong in the interview now, before there is a signature on anything.

18. What manufacturer warranty comes with this shingle, and is it standard or an enhanced system warranty?

A good answer names the coverage in years and explains whether it requires a full accessory system from one manufacturer to qualify for the enhanced version. A dodge says "lifetime warranty" with no further detail, which our guide on what a lifetime shingle warranty really means unpacks in full.

19. What is your workmanship warranty, in years, and is it in writing?

A good answer states a specific term and puts it in the written contract, separate from the manufacturer's material coverage. A dodge says "we stand behind our work" with nothing in the paperwork to enforce it. Our full breakdown in roof warranties explained covers how the two warranties differ and what each really covers.

20. Who do I call if something goes wrong in year three, and how fast do you respond?

A good answer gives you a real phone number and a sense of typical response time for a warranty callback, and is candid that a callback inspection usually comes before any repair work is scheduled so the cause gets confirmed first. A dodge is silence on this question entirely, because a contractor who has not thought about year three is not planning to still be reachable in year three.

THEME	QUESTIONS	WHAT TO LISTEN FOR
Credentials	1 to 3License, insurance, permit	A number, a certificate, a named process, not reassurance
Crew	4 to 6Employees, supervisor, sub coverage	A named person and a real phone number
Scope	7 to 10Tear-off, shingle, decking, ice barrier	Specific products and figures, not categories
Timeline	11 to 13Duration, start date, surprises	A range and a documented change-order process
Cleanup and money	14 to 17Protection, sweep, deposit, financing	Modest deposit, magnet sweep, a real lender
Warranty	18 to 20Material, workmanship, callbacks	Years, in writing, a number to call later

The best answer to any of these twenty questions is specific and boring. It is the vague, reassuring ones that deserve a second look.

Once you have run this list past two or three bidders, the comparison usually sorts itself, because the contractor who answers every question in specifics is very often the same one whose written quote holds up under the checklist in our quote comparison guide. If you are still assembling your shortlist, our step-by-step playbook on how to hire a roof replacement contractor walks the whole hiring path from first search to signed contract, and this list of twenty questions is the tool you bring to every stop along the way. If our answers are the ones you are comparing against, our roof replacement service page lays out our own process and pricing so you can hold us to the same standard.