I love using AI to ask interesting questions. For example: What are the key points in hiring a good roofing contractor? While AI gives solid answers, it’s interesting that—as an experienced, state-licensed contractor of over 30 years—I can clearly see where AI has some blind spots.
So I asked AI a multi-phase question about this topic and filled in the blanks based on real-world experience. Below is what I consider a comprehensive contractor hiring checklist. While it leans toward roofing contractors, it applies broadly to most subcontractors (less so to general contractors).
I love using AI to ask interesting questions. For example: What are the key points in hiring a good roofing contractor? While AI gives solid answers, it’s interesting that—as an experienced, state-licensed contractor of over 30 years—I can clearly see where AI has some blind spots.
So I asked AI a multi-phase question about this topic and filled in the blanks based on real-world experience. Below is what I consider a comprehensive roofing contractor hiring checklist. While it leans toward roofing contractors, it applies broadly to most subcontractors (less so to general contractors).
✅ Roofing Contractor Hiring Checklist
- 📍Has a Physical Location – Top Priority
- Avoid any contractor that operates from a single-family home, PO box, strip mall, high-rise, or has no clear physical address. In 2025, this describes over 90% of candidates.
- Go to their office and meet them. If things go wrong mid-project and they disappear, having a physical address gives you legal recourse.
- Avoid contractors located more than 25 miles away (in the LA area). Many top Google search results are from companies far outside your area.
- ✔️License Check
- Verify their license number on the California CSLB site.
- Make sure their name and business details match.
- Confirm they’ve held the license for more than 5 years (ideally 20+). A new license may indicate inexperience—or someone who previously lost their license and re-registered under a different name.
- 💼Has Proven Workers’ Comp and Liability Insurance
- Workers’ comp is legally required in California if they have employees—and you should only hire companies with employees. Using subcontractors muddies legal accountability if something goes wrong.
- Is not listed as exempt from worker’s comp insurance due to “not having any employees.” This is just another way of saying they are subcontracting the work = don’t hire.
- Liability insurance is not required, but you should never hire someone without it.
- Ask for their ACCORD insurance certificate, which should list both coverages and the broker’s contact info.
- Ask to be listed as additional insured—this should be no problem.
- 📆Time in Business
- More experience = more reliability.
- A contractor with 10+ years in business is much more likely to deliver consistent, quality work.
- 📋Detailed Scope of Work – “A short contract is a bad contract”
- The contract should clearly outline the work, including brand names of materials/products.
- Expect a long, detailed contract. Mine are usually 12–14 pages, including:
- Terms and conditions
- Warranty info
- State-mandated documents (e.g. notice of cancellation, insurance disclosures)
- It may be tedious to read, but if you’re spending $20,000+, you want everything in writing.
- For small repairs, a shorter 1–2 page contract is normal.
- ⏱️Availability
- Be cautious of a contractor who’s available immediately.
- While slow seasons exist, most good contractors are booked out 2+ weeks, sometimes months during peak periods.
- Immediate availability can be a red flag—combine this with other factors when evaluating.
- 📞Check Referrals
- Ask for references and call at least one.
- Their willingness to share references is already a good sign.
- 👷Subcontracting
- Avoid roofing contractors who sub out the actual roof installation.
- It’s common and acceptable to subcontract roof tear-off or solar panel removal, but the contractor should:
- Disclose the subcontractors by name.
- Provide a written statement about their insurance coverage.
- 🌐Review Social Media Carefully
- Many businesses manipulate reviews—especially on Google. You may see:
- Hundreds of 5-star reviews in a very short time
- One-line reviews from users with no other review history
- These are often paid and fake
- Even the biggest companies struggle to get 200 real reviews in 3 months. Ignore the noise and look for:
- Balanced, thoughtful reviews
- A mix of good and bad (i.e. real) feedback
- A consistent rating above 4 stars
- Yelp has a more stringent filter process that does not let mass fake reviews flood in, don’t just check Google reviews.
- 🛠️How They Handle Problems
- Every contractor hits a bump eventually. What matters is how they respond.
- Look for contractors who reply to negative reviews reasonably and constructively.
- Keep in mind:
- Once a bad review is posted, even if the issue is fixed, it’s nearly impossible to remove.
- Responsiveness and fairness in handling issues is a strong indicator of accountability.
- A bad contractor won’t stay in business long. Longevity matters.
