Before You Hire a Contractor: 8 Questions Worth Asking

A home improvement project is a major investment. Whether you are remodeling a kitchen or building an addition, knowing the right questions to ask a contractor helps you compare professionals and protect your property.

Asking the right questions helps you compare professionals more effectively and understand how they’ll manage the project before work begins.

This is not about assuming every contractor is a problem. Most homeowners don’t hire professionals often enough to have a standard process. Before you sign a contract or hand over a deposit, a checklist of essential questions to ask a contractor can clarify expectations.

Before you sign a contract or hand over a deposit, start with these eight questions.

1. Are You Properly Licensed or Registered for This Work?

Core questions to ask a contractor should always start with credentials. Requirements vary by project type and location.

Ask which licenses, registrations, or credentials apply to the ongoing work, and verify them through the appropriate state or local resources whenever possible.

Do not rely only on a logo on a truck or a statement that someone has “been doing this for years.”

Experience matters, but required credentials matter too.

If a contractor claims you need no license or registration, verify that requirement independently if you feel unsure.

2. What Kind of Contractor Insurance and Workers’ Compensation Do You Carry?

Ask the contractor about applicable business insurance and workers’ compensation.

Do not simply ask, “Are you insured?” and stop there.

Ask for documentation and review it.

Contractors’ insurance needs vary by business and work, but homeowners should know who is working on the property and whether the contractor has appropriate insurance.

If you have questions about how a major renovation affects your homeowners insurance, contact your insurance agent before the project begins.

3. Will You Use Subcontractors for My Home Renovation Contractor Project?

The person who gives you the estimate may not be the person completing every part of the job.

Many contractors appropriately use subcontractors for electrical, plumbing, roofing, specialty work, or other portions of a project.

Ask:

• What work will be subcontracted?
• Who selects the subcontractors?
• How are they qualified?
• Who supervises their work?
• Who is responsible for paying them?

• Knowing who will actually be on your property helps avoid surprises.

4. Can I Speak With Recent Customers and Check Contractor References?

References can provide useful context.

Ask for customers with projects similar to yours, preferably completed recently.

When speaking with a reference, ask about more than whether the finished project looked good.

Ask:

• Was communication consistent?
• Did the project stay reasonably close to the expected schedule?
• How did they handle unexpected changes?
• Did they keep the worksite orderly?
• Would they hire the contractor again?
• Online reviews can also help, but direct conversations may reveal details star ratings miss.

5. What Exactly Is Included in the Estimate?

A price without detail is hard to compare. When comparing bids, one of the most critical questions to ask a contractor is whether they itemize materials and labor.

Ask for a written estimate or proposal that clearly describes the work.

Depending on the project, it may address:

• Materials.
• Labor.
• Demolition.
• Disposal.
• Fixtures or finishes.
• Permit costs.
• Cleanup.
• Subcontracted work.
• Items the homeowner must provide.

• If one estimate is much lower than the others, compare the scope before assuming it is the better deal.

• The contractors may not be pricing the same work.

6. Who Is Responsible for Permits?

Permit requirements depend on the project and municipality.

Ask whether you need permits and who will obtain them.

Be cautious if someone tells you to skip a required permit to save time or money.

Permits and inspections exist for a reason, and unpermitted work can create issues later when selling, refinancing, or completing additional renovations.

If you’re unsure about the requirements, check with your local building department.

7. How Will Changes Be Handled?

Even with careful home improvement planning, home projects do not always go exactly as planned.

A wall may reveal hidden damage. A material may become unavailable. You may decide to upgrade something once the project is underway.

Ask how changes to the original scope will be documented and priced.

A good process should help both the homeowner and contractor understand what changed, how much it costs, and whether it affects the schedule.

Avoid relying on a series of informal verbal agreements that people remember differently later.

8. What Is the Payment Schedule?

Understand when each payment is due and what it covers.

Watch out for any pressure to pay the entire project cost before the contractor finishes substantial work.

Payment practices vary by project, but you should outline the schedule clearly in writing.

Know the deposit the contractor requires, when progress payments occur, and which milestones you must approve before the final payment.

Keep copies of payments and receipts.

Common Mistakes When Hiring a Contractor

The first mistake is choosing solely on price.

Cost matters, but so do scope, experience, communication, and professionalism.

Another mistake is starting work on a handshake for a significant project.

A written agreement helps define expectations.

Homeowners also sometimes fail to discuss the project with their insurance agent. Major renovations can change the property and may create insurance considerations during or after construction.

Finally, don’t wait until the work is complete to save documentation.

Keep contracts, permits, receipts, change orders, and photographs as the project progresses.

Tell Your Insurance Agent About Major Improvements

A new roof, finished basement, addition, garage, or major interior renovation can change your home.

Contact your insurance professional before or during a significant project and again when major improvements are complete.

Explain what you are doing.

Keep records of the work and update your home inventory when appropriate.

Your agent can review your homeowners insurance and discuss whether changes are needed.

Keep the Relationship Professional

Build good contractor relationships with clear expectations.

Know how you will communicate.

Ask who your primary contact is.

Agree on work hours and property access.

Discuss where materials will be stored and how the site will be left at the end of each day.

If you work from home, tell the contractor about meetings or other access concerns.

Small details can make a long project much easier for everyone.

Do Your Homework Before Work Begins

Hiring a contractor should not feel like an interrogation. Taking time to understand who you are hiring starts with asking the right questions to ask a contractor before work begins.

Professional contractors expect customers to ask reasonable questions about their businesses and projects.

Take time to understand who you are hiring, what work is included, and how the project will be handled.

Safety Northeast Insurance works with homeowners in Massachusetts. Reviewing these questions to ask a contractor alongside your insurance agent helps ensure your property stays protected during major updates. If you are planning a major home improvement, contact our team to review your homeowners insurance and discuss changes to your property.

A quick conversation before construction begins can help make sure your insurance professional understands what is happening at your home.

FAQs

What should I ask a contractor before hiring them?

Ask about licensing or registration, insurance, subcontractors, references, written estimates, permits, project changes, and payment terms.

Should a contractor provide proof of insurance?

Ask contractors about applicable insurance and request documentation. Requirements and needs vary by type of work and business.

Should I tell my insurance agent about a renovation?

It’s worth discussing significant renovations with your insurance professional, ideally before work begins and again when major improvements are complete.

Who should obtain building permits?

That depends on the project and local requirements. Clarify responsibility in advance and verify requirements with the local building department.

Is the lowest contractor estimate always the best choice?

No. Compare the scope, materials, experience, schedule, and terms as well as the price.

Related Reading

How to Hire a Home Contractor: The Complete New England Homeowner’s Checklist