Getting roofing estimates? Here’s how to choose the right contractor

AAR Expert John Kenney says a good roofing contractor helps you understand your options, respects your property and stands behind their work. 

Getting multiple roofing quotes is a smart move. It gives you perspective, helps you understand the market and protects you from overpaying. But comparing bids isn’t as simple as lining up the bottom numbers. Two proposals can look similar on the surface and deliver very different results once the work begins. Knowing what to look for and what questions to ask can help you choose the right contractor, not just the lowest price. 

Start with the materials being proposed. Roofing products vary widely in quality, performance and lifespan, even within the same category. One contractor may price a basic shingle or membrane, while another may include a higher-grade system with better wind ratings or more extended warranties. Ask for the exact manufacturer, product line and warranty coverage listed in writing. If the quote is vague, that’s a red flag. Clear material descriptions protect you from substitutions later and help you understand what you’re actually buying. 

Labor is the next significant difference between quotes, and it’s one that many owners overlook. Roofing is skilled work, and experience matters. A lower price often reflects lower labor costs, which may mean less training, fewer safety controls or rushed installation. Ask whether the contractor uses in-house crews or subcontractors, how long their crews have been working together and what kind of supervision is provided. Quality labor doesn’t always cost the most, but it’s rarely the cheapest. 

Timeline is another area where quotes can differ significantly. Some contractors may promise a fast start and quick completion, while others build in more realistic scheduling. Ask when the work will begin, how long it’s expected to take and what could cause delays. Weather, material availability and unexpected deck repairs can all impact timelines. A contractor who talks openly about these factors is usually more reliable than one who promises everything will go perfectly. 

Measurements are also worth paying attention to, especially with today’s technology. Some contractors measure roofs by hand, others use aerial measurement tools or digital modeling. Both methods can be accurate when done correctly, but the key is consistency and verification. Ask how the measurements were taken and whether they were checked. Accurate measurements affect material quantities, waste and cost. Sloppy measurements often lead to change orders later, which can quickly erase any initial savings. 

When reviewing quotes, look closely at what’s included and what isn’t. Tear-off, disposal, underlayment, flashing, ventilation upgrades and permit fees should all be clearly spelled out. If one bid is significantly lower, there’s usually a reason. It may exclude items others have included, or it may assume conditions that don’t exist. Don’t be afraid to ask contractors to walk you through their proposal line by line. 

Communication style matters more than most owners realize. Pay attention to how each contractor explains their scope, answers questions and responds to concerns. Roofing projects can uncover surprises once work begins, and you want a contractor who communicates clearly and professionally when that happens. The way a contractor handles the quote process often reflects how they’ll handle the job itself. 

Finally, remember that value isn’t just about cost, it’s about confidence. A good roofing contractor helps you understand your options, respects your property and stands behind their work. When comparing quotes, trust your instincts as much as the numbers. The right choice is usually the contractor who provides clarity, not confusion and solutions, not pressure. 

A roof protects everything beneath it. Taking the time to compare quotes properly helps ensure you’re making a decision that holds up long after the paperwork is signed.