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Contractor Interview Guide · Westchester NY

10 Questions to Ask Before Hiring a Contractor in Westchester

By Cristian Poblete, Licensed Contractor WC-34542-H21 · Ossining, NY · Updated June 2026

The best contractors welcome these questions. If a contractor gets defensive or evasive, that tells you something important before you spend any money.

1. What's Your Westchester Home Improvement License Number?

Every licensed contractor knows this number. If they hesitate or can't provide it, stop there and verify before proceeding.

2. Can You Provide Current Certificates of Insurance?

You need current general liability AND workers' compensation certificates. Ask them to email the certificates directly from their insurance agent — this prevents forgeries.

3. Will You Pull the Permits?

The permit is the contractor's responsibility in Westchester. Any contractor who suggests you pull your own permit (to "save money") is transferring both responsibility and liability to you.

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4. Who Will Actually Be Doing the Work?

Some contractors are primarily salespeople who subcontract all the work. Know who will be on your property and whether they're employees of the licensed contractor or independent subs (whose insurance you should also verify).

5. Can You Provide References from Similar Projects in the Last Year?

Ask for references from projects similar to yours, completed recently. Call them. Ask if the work passed inspection and if they'd hire the contractor again.

6. What's the Payment Schedule?

A fair schedule: 10-30% deposit, milestone payments during the project, 10-15% final payment upon completion and your satisfaction.

7. How Do You Handle Change Orders?

The answer should be: in writing, signed by both parties, with the cost specified before work begins. Verbal change order agreements lead to disputes.

8. What's the Realistic Timeline?

Get a written start date and estimated completion date. Understand that permit approval times add 2-5 weeks to any permitted project.

9. What's Included in "Cleanup"?

Debris disposal in Westchester costs real money. Make sure your contract specifies what gets removed and by whom. A clean site every day is a sign of a professional operation.

10. What Warranty Do You Provide on Labor?

One year on labor is standard in Westchester. Some contractors offer more. Get it in writing.

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