best in class 9 min read Updated 2026-03-18

    Best Questions to Ask Any Roofing Contractor Before Hiring Them

    Most homeowners don't know what to ask — and bad contractors count on that. Here are the 15 questions that separate trustworthy roofers from the ones who'll disappear.

    Key Takeaways

    • Ask: 'Who will actually be on my roof?' (employees or subcontractors?)
    • Ask: 'Can I see your certificate of insurance dated this month?'
    • Ask: 'Will you pull the permit, and can I see it?'
    • Ask: 'What does your workmanship warranty cover specifically?'
    • Ask: 'Can I see 5 local references from the last 6 months?'

    The 15 Questions Every Homeowner Must Ask

    Print this list. Ask every contractor the same questions. Their answers — and their reactions to being asked — will tell you everything you need to know:

    • 1. Are you licensed to do roofing in Kentucky? Can I see your license?
    • 2. Do you carry general liability and workers' compensation insurance? Can I see the certificate?
    • 3. Will you pull the building permit for this project?
    • 4. Who will actually be doing the work — your employees or subcontractors?
    • 5. Can you provide 5 references from Louisville projects completed in the last 6 months?
    • 6. What specific shingle product will you use? Brand and product line?
    • 7. Will you provide a fully itemized proposal with every material and cost listed?
    • 8. What does your workmanship warranty cover, and for how long?
    • 9. Are you a certified installer for the shingle manufacturer you use?
    • 10. Will ice-and-water shield be installed in valleys and at eaves?
    • 11. What type of underlayment will you use?
    • 12. Will drip edge be installed at eaves and rakes?
    • 13. How do you handle unexpected decking damage — is there an allowance?
    • 14. What's your cleanup process? Do you use a magnetic sweeper?
    • 15. Can I see your Google reviews and your physical business address?

    Red Flag Answers That Should Make You Walk Away

    Pay attention to how contractors respond. Red flags include:

    'We don't need a permit for this' — yes, you do. They're skipping it to save $150 and avoid inspection.

    'Don't worry about the insurance, we've got it covered' — ask to see it. If they won't show it, walk away.

    'We can start tomorrow' — in peak season, immediate availability often means they're not busy for a reason.

    'Just sign here and we'll figure out the details later' — never sign a contract without a detailed scope of work.

    'We'll beat any price' — price-matching isn't a quality indicator. Ask what they'll leave out to hit that lower number.

    Ready for an honest assessment?

    Get a online booking and transparent quote — no pressure, no gimmicks.

    Michael Nielsen

    Owner & Lead Estimator

    Mike founded Homestretch Roofing with a mission to bring radical transparency to an industry known for hidden fees. With 18+ years of roofing experience in Louisville, he personally reviews every estimate to ensure accuracy and fairness.

    Have questions about your roof?

    Schedule a online booking and get honest answers from our team — no sales pressure.