7 Questions to Ask Before You Hire a Contractor

Most renovation disasters were predictable at the first meeting — the signals were there before any contract was signed. These seven questions surface those signals early. Any contractor worth hiring will answer all seven without flinching; we certainly expect to.

1. Are you licensed with the City of Chicago — and can I verify it?

Chicago general contractors carry a city license with a number you can check. Ours is Class D License #TGC132820 — more about us here. If a contractor hesitates to give you a number, that's your answer.

2. Can I see a certificate of insurance, naming me?

General liability and workers' comp, with a COI issued to you for your project. Without it, an injury on your property can become your financial problem.

3. Will my estimate be line-item?

A lump-sum number hides everything: allowances, exclusions, and what happens when scope changes. A line-item quote shows cabinets, counters, labor, permits — each priced. It protects both sides.

4. Who pulls the permits?

The right answer is the contractor, under their license. A contractor who asks you to pull an owner's permit is moving the liability for their work onto your name.

5. How do payments work?

Milestone-based draws tied to completed phases are the standard: a deposit, progress payments after inspections or phase completions, final payment at walkthrough. Be cautious of anyone wanting half or more upfront.

6. Who is actually on my job site?

Is the crew in-house, regular subs, or whoever was available that week? You want a consistent team and a single point of contact — ask who that person is and how often you'll hear from them. (Our answer: weekly photo updates, same crew, direct line.)

7. Can I see a recent project or speak to a recent client?

Not a portfolio photo — a real, recent, local reference. The way a contractor's last client talks about communication and cleanup tells you more than any sales meeting.