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10 Essential Questions to Ask Before Starting Work With Your Contractor

March 10, 2026 Joshua Scott Homes 8 min read

Embarking on a home renovation or construction project is a significant decision. Before any work begins, asking the right questions can save you time, money, and headaches down the road. Here's your essential checklist of questions every Southwest Florida homeowner should ask their contractor.

1. Are You Licensed and Insured?

This is non-negotiable. In Florida, contractors must hold a state license for jobs over $2,500. Ask for proof of both general liability insurance and workers' compensation coverage. This protects you from liability if someone gets injured on your property or if damage occurs during construction.

2. Can You Provide Local References?

Request at least three local references from projects completed in the last year. Ask references about their experience, whether the project stayed on budget and on schedule, and how the contractor handled any issues that arose. Consider visiting a completed project in person if possible.

3. What Is the Project Timeline?

Get a detailed timeline including start and completion dates. Ask about potential delays due to weather (especially important in Florida's rainy season), material availability, or permit processing. A realistic timeline helps you plan and sets clear expectations for everyone involved.

4. Who Will Be Working on My Project?

Will the contractor use employees or subcontractors? If subcontractors are involved, ask about their qualifications and how they'll be supervised. You want to know exactly who will be on your property and who you should direct questions to.

5. What Permits Are Required?

Sarasota and Manatee counties have specific permit requirements. Your contractor should be familiar with local building codes and handle permit applications. Ask about the permit process, associated costs, and who is responsible for scheduling inspections.

6. What Is Included in the Written Estimate?

Get a detailed, itemized estimate that clearly outlines what is and isn't included. This should cover materials, labor, site preparation, cleanup, and any potential additional costs. Be wary of vague estimates or contractors who are reluctant to provide written documentation.

7. How Do You Handle Changes or Unexpected Issues?

Every project encounters unexpected situations. Ask about the process for handling change orders and how additional costs will be communicated and approved. A good contractor will document all changes in writing before proceeding.

8. What Warranty or Guarantee Do You Provide?

Ask about warranties on both materials and workmanship. Understand what's covered, for how long, and what steps to take if an issue arises after completion. Get warranty information in writing as part of your contract.

9. How Do You Communicate Progress Updates?

Establish communication expectations upfront. Will you receive regular updates? How quickly can you expect responses to questions? Who is your main point of contact? Clear communication prevents misunderstandings throughout the project.

10. What Is Your Payment Schedule?

Be cautious of contractors who demand full payment upfront. A typical payment schedule might include an initial deposit (usually 10-20%), progress payments tied to milestones, and a final payment upon completion. Never pay more than what's been completed in work or materials.

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