21 Questions to Ask Before Hiring Any Contractor (So You Don’t Get Burned)

Hiring a contractor can feel overwhelming, especially if you don’t do it often. You might need a repair done quickly, or you may be planning a larger project and don’t know where to start. Most people want the same thing: someone reliable who does good work, charges fairly, and doesn’t disappear halfway through the job.

Unfortunately, many homeowners learn the hard way that not all contractors operate the same way. Problems usually don’t start because someone asked too many questions. They start because important questions were never asked at all.

This guide walks through 21 questions that experienced homeowners and renters ask before hiring any contractor. These questions help you spot red flags early, avoid misunderstandings, and protect your time, money, and peace of mind — without turning the process into a confrontation.

Experience, Licensing & Legitimacy

1. Are You Licensed to Do This Type of Work?

Licensing requirements vary by location and trade, but a legitimate contractor should know whether a license is required and be able to explain their status clearly.

Asking this question isn’t about doubting someone’s skill. It’s about confirming they’re legally allowed to perform the work you’re hiring them for. If a contractor avoids the question or gives vague answers, that’s worth pausing on.

2. How Long Have You Been Doing This Kind of Work?

Experience matters, especially for specialized jobs. Someone may be new to running a business but still have years of hands-on experience — or the opposite.

Listen for specifics. Experienced contractors can explain what types of projects they handle most often and what challenges they commonly see.

3. Is This Work Something You Do Regularly?

Not all contractors specialize in the same types of jobs. Someone who mainly does new construction may not be the best fit for a small repair or remodel.

Hiring someone who regularly does your type of project reduces surprises and delays.

4. Can You Provide References From Recent Jobs?

References give you insight into what it’s like to work with the contractor, not just the final result.

Ask for recent references, not just long-ago success stories. A quick conversation can reveal how the contractor communicates, handles issues, and sticks to timelines.

5. Are You Insured, and What Does That Coverage Include?

Insurance protects both you and the contractor. Ask what type of insurance they carry and what it covers.

If a contractor doesn’t have insurance, you could be liable if something goes wrong on your property.

Scope, Pricing & Expectations

6. Can You Provide a Detailed Written Estimate?

A written estimate should clearly outline the scope of work, materials, labor, and total cost.

Vague estimates lead to misunderstandings. Clear estimates help both parties stay aligned and reduce disputes later.

7. What Exactly Is Included — and What Isn’t?

Many problems arise from assumptions. Ask what’s included in the price and what isn’t.

Clarifying details upfront prevents surprise charges and frustration during the project.

8. How Do You Handle Changes or Additional Work?

Projects often evolve. Ask how change orders are handled and approved.

A clear process protects both you and the contractor if something unexpected comes up.

9. What Is the Payment Schedule?

Understand when payments are due and what milestones trigger them. Be cautious of contractors who ask for large upfront payments.

A reasonable payment schedule usually aligns with progress, not promises.

10. Will You Provide a Written Contract?

A written contract protects both sides. It should reflect the estimate, timeline, payment terms, and scope of work.

If a contractor resists putting things in writing, that’s a red flag.

Timeline & Project Management

11. When Can You Start the Project?

Availability matters, especially if timing is important. Ask about start dates and how scheduling works.

Be wary of contractors who promise to start immediately without understanding the scope.

12. How Long Do You Expect the Project to Take?

No timeline is perfect, but experienced contractors can provide a reasonable estimate.

Ask how delays are handled and what factors could affect the schedule.

13. Who Will Be On-Site Each Day?

Clarify whether the person you’re speaking with will be doing the work or supervising others.

Knowing who will be present helps set expectations and communication channels.

14. Will You Be Working on Other Projects at the Same Time?

Many contractors juggle multiple jobs. That’s normal, but you should understand how it affects your timeline.

Ask how your project will be prioritized.

15. How Do You Handle Unexpected Issues?

Unexpected problems happen in construction and repairs. Ask how they’re typically handled.

Experienced contractors explain their approach calmly and transparently.

Communication & Professionalism

16. How Will We Communicate During the Project?

Clear communication prevents misunderstandings. Ask how updates will be shared and how often.

Knowing what to expect helps you stay informed without micromanaging.

17. Who Should I Contact If I Have Questions or Concerns?

Establishing a point of contact prevents confusion if issues arise.

This is especially important for larger projects with multiple workers.

18. How Do You Handle Problems or Complaints?

No project is perfect. Ask how concerns are addressed if something isn’t right.

The answer often reveals how the contractor values customer satisfaction.

Cleanup, Warranties & After the Job

19. How Will Cleanup Be Handled?

Cleanup expectations should be discussed upfront. Ask what’s included and what isn’t.

A professional contractor leaves the work area reasonably clean and safe.

20. Do You Offer Any Warranties or Guarantees?

Ask whether the work is guaranteed and for how long.

Understanding warranty terms helps you know what’s covered if issues arise later.

21. What Happens If I’m Not Satisfied With the Work?

This question may feel uncomfortable, but it’s important. A professional contractor should be willing to discuss how concerns are resolved.

Clear answers provide reassurance before you commit.

Quick Checklist: Contractor Questions to Ask

Use this checklist before hiring anyone.

• Licensing and insurance confirmed

• Relevant experience verified

• Written estimate provided

• Scope clearly defined

• Payment schedule agreed upon

• Timeline discussed

• Communication plan established

• Warranty explained

FAQ

Is it okay to ask contractors lots of questions?

Yes. Asking questions shows you care about the project and helps prevent misunderstandings.

Should I always get multiple estimates?

Getting more than one estimate helps you understand pricing and scope differences.

Are contracts really necessary for small jobs?

Even simple written agreements can prevent disputes.

What’s the biggest red flag when hiring a contractor?

Vague answers, pressure tactics, or resistance to written agreements.