September 2026
You are about to spend real money on something you cannot see from the ground and will not be able to inspect afterward. These eight questions sort out who you are dealing with.
The paperwork questions
What is your license number, and can I see your certificate of insurance. Both should arrive without friction. Insurance matters to you specifically: if somebody is hurt on your property and the contractor is uninsured, that becomes your problem.
Ask whether the insurance covers workers compensation as well as liability, and check that the certificate is current rather than expired.
A contractor who treats these questions as an insult has told you something useful.
Ask who pulls the permit where one is required. The answer should be the contractor, and a request that you pull it as the homeowner is a signal worth pausing on.
The people questions
Who will actually be on my roof, and will they be your employees or a subcontracted crew. There is nothing inherently wrong with subcontracting, but you should know, and you should know who supervises.
Who do I call if something goes wrong in year two. Get a name.
Will the person I am talking to now be on site. With us the answer is yes, because Jonathan does the assessment and is on the job.
Ask what happens to your landscaping and how they protect it. The answer tells you how carefully the rest of the job will be run.
The money questions
Is this price fixed, and what would cause it to change. The honest answer usually involves decking: nobody knows what is under the shingles until they come off, so a per sheet price agreed in advance is the professional way to handle it.
What is the payment schedule. Some deposit on a large job is normal. Most of the money before materials arrive is not.
And what exactly is included: tear off and disposal, underlayment, flashing, drip edge, ridge vent, permits where required. A cheap quote is often cheap because something on that list is missing.
Ask for references from work done at least two years ago rather than last month, because that is the timeframe where quality actually shows.
The warranty question
What is covered, for how long, by whom, and what voids it. There are usually two warranties: the manufacturer's on materials, and the contractor's on workmanship. They are different and they fail differently.
A long manufacturer warranty means little if a workmanship error voids it, and a workmanship warranty means little from a company that will not exist.
Ask for it in writing. Every legitimate contractor expects that.
And notice whether they ask you questions. Somebody who never asks how long you plan to stay in the house is not solving your problem.
After you have chosen
Confirm the start date and what happens if weather moves it. Good contractors tell you before you have to ask.
Ask what you need to do to prepare: moving vehicles, taking pictures off walls on the top floor because tear off vibration knocks them loose, and planning around the noise if somebody works from home.
Agree how you will be reached during the job and who your point of contact is if the owner is not on site that day.
And at the end, walk it with them. Look at the cleanup, ask to see photographs of the work you cannot see from the ground, and get the warranty paperwork before the final payment rather than after.
Questions we get asked
How many quotes should I get?
Two or three is sensible. More than that tends to produce confusion rather than clarity.
Is the cheapest quote a bad sign?
Not automatically, but compare what is included line by line. Price differences usually come from scope, not generosity.
Should everything be in writing?
Yes. Scope, price, payment schedule, timeline and warranty.
What if they want full payment up front?
That is not normal for roofing work and it is worth walking away from.
Can I ask to see a job nearby?
Yes, and a local contractor can usually point you at something close. That is a real advantage of hiring local.
What to take from this
License and current insurance, produced without friction, are the baseline.
Find out who is physically on your roof and who supervises them.
A fixed price with a pre agreed per sheet decking rate is the professional answer.
Two warranties exist, materials and workmanship. Get both in writing.
Get it handled
Jonathan Stephenson answers the phone himself, walks the roof, and gives you a written number. Serving Germantown, TN and the Memphis metro.