10 Essential Questions to Ask Before Starting Work With Your Contractor

Asking the right questions before any work begins can save you time, money, and frustration down the road. Here's a practical checklist of questions every Southwest Florida homeowner should ask their contractor.

1. Are You Properly Licensed for This Scope of Work?

Florida homeowners should verify that a contractor holds the appropriate license for the work being performed and confirm license status through the Florida Department of Business and Professional Regulation when applicable. Ask for proof of both general liability insurance and workers' compensation coverage, and verify the license independently rather than relying only on what the contractor tells you. Our general contracting and project management page explains how Joshua Scott Homes serves as the licensed Florida General Contractor and coordinates applicable permitting and qualified trade professionals as part of the project.

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. Timelines depend on scope, selections, inspections, and unforeseen conditions, so a realistic plan helps you prepare. 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?

Permit requirements depend on the scope of work and the local jurisdiction, so it's worth asking which permits your specific project may require. Your contractor should be familiar with the applicable local building codes and explain how permit applications are handled. Ask about the permit process, associated costs, and who is responsible for scheduling inspections. See our Sarasota home remodeling and Bradenton home remodeling pages for more on how local projects are planned.

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.