How to Choose the Right Roofing Contractor: 12 Essential Questions

Your roof is one of your home's most important investments. Choosing the right contractor can mean the difference between decades of protection and years of problems. Here are the essential questions to ask.
1. Are You Licensed and Insured?
This should be your first question. A legitimate contractor will have:
- General liability insurance
- Workers' compensation insurance
- All required state and local licenses
Ask to see proof. If they hesitate, walk away.
2. How Long Have You Been in Business?
Experience matters. While newer companies can be excellent, established contractors have proven track records and are more likely to honor warranties years from now.
3. Can You Provide Local References?
Ask for 5-10 recent references in your area. Actually call them. Ask about quality, communication, cleanup, and whether they'd hire the contractor again.
4. What's Included in Your Estimate?
A detailed estimate should specify:
- Materials (brand, type, color)
- Labor
- Tear-off and disposal
- Flashing and ventilation
- Cleanup
- Timeline
- Payment schedule
5. Do You Use Subcontractors?
There's nothing wrong with subcontractors, but you should know who'll actually be working on your roof and whether they're insured.
6. What Warranties Do You Offer?
Understand both material warranties (from the manufacturer) and workmanship warranties (from the contractor). Get everything in writing.
7. Will You Pull the Necessary Permits?
Professional contractors handle all required permits. If they suggest skipping permits to save money, that's a major red flag.
8. How Do You Handle Unexpected Issues?
Hidden damage is common in roofing. Ask how they handle unexpected repairs and who approves additional work.
9. What's Your Payment Schedule?
Beware of contractors demanding large upfront payments. A reasonable schedule is a small deposit, payment upon material delivery, and final payment upon completion and your satisfaction.
10. What Happens If I'm Not Satisfied?
A confident contractor will explain their process for addressing concerns and ensuring customer satisfaction.
11. How Do You Protect My Property?
Ask about their cleanup process, how they protect landscaping, and their policy on nails and debris removal.
12. Can You Help With Insurance Claims?
If you're filing an insurance claim, an experienced contractor can be invaluable in documenting damage and working with adjusters.
Red Flags to Watch For
- Knocking on doors after storms (storm chasers)
- Pressure to sign immediately
- Prices significantly lower than competitors
- Cash-only payments
- No physical address or local presence
- Unwillingness to provide references or proof of insurance
Trust Your Instincts
Beyond credentials and answers, trust your gut. Do they communicate clearly? Show up on time? Treat you with respect? These factors matter for a project that will last weeks.
At Holland Exteriors, we welcome these questions. We're proud of our 20+ years serving Milwaukee, our transparent process, and our commitment to quality. Learn more about our company or read our customer testimonials. Call (414) 340-3890 to schedule a free consultation.