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10 Questions to Ask Before You Hire a Contractor

The short list of questions that separates a professional operation from a truck with a magnet on the door.

6 min readUpdated June 18, 2026

Hiring a contractor is less about finding the lowest number and more about finding the company that will still answer the phone in eighteen months. Every professional in the Guild has already cleared license and insurance checks, but these questions help you choose between two good options.

1. Is your license active in Florida, and can you share the number? A license number should be offered without hesitation and can be verified in seconds. 2. Who carries the general liability and workers' compensation policy on my job? Ask for a certificate naming you, not a screenshot. 3. Are the crew members employees or subcontractors, and who supervises them on site?

4. What is the written scope of work? A one-line estimate is a red flag; a real proposal lists materials, brands, quantities and exclusions. 5. What is the payment schedule? In Florida, a modest deposit followed by progress payments tied to milestones is normal. Full payment up front is not. 6. What permits does this job require, and who pulls them?

7. What is your warranty on labor, and how does it differ from the manufacturer's warranty on materials? 8. How will you protect the rest of my home — floors, landscaping, pool cage — while you work? 9. Who is my single point of contact, and how quickly do you respond? 10. Can I see two recent jobs of the same type and size within ten miles of my home?

If a contractor answers all ten without friction, you are dealing with a company that has systems. That is what you are actually buying.

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