5 Questions to Ask Before Hiring a General Contractor

Choosing a general contractor is one of the highest-stakes decisions you’ll make on a renovation or build-out, and it’s usually made under time pressure, based on not much more than a bid and a gut feeling. A few sharp questions upfront can save you months of headaches and thousands of dollars later.

Whether you’re a homeowner planning a kitchen remodel or a property manager lining up a commercial build-out, here are the five questions that separate a smooth project from a stressful one.

Are You Licensed and Insured for This Specific Type of Work?

Every state and municipality has its own licensing rules, and “licensed” doesn’t always mean licensed for the scope you need. A contractor might be properly licensed for residential remodeling but not carry the commercial general liability coverage a build-out requires, or vice versa.

Ask to see the license number and certificate of insurance directly, not just a verbal assurance, and verify it against your state’s contractor licensing board. For commercial projects, also confirm workers’ compensation coverage, since the exposure is often higher with multiple trades on site.

Who Actually Manages the Day-to-Day Work?

The person who sells you the job isn’t always the person who runs it. Ask specifically who your point of contact will be once work starts, how often you’ll get updates, and whether that person is an employee or a subcontracted project manager.

This matters more for commercial clients than most expect. A property manager juggling tenant schedules, building access, and after-hours work needs a single, reliable point of contact, not a rotating cast of subs each answering a different question.

Can You Provide References From a Project Similar to Mine?

A contractor with beautiful kitchen photos in their portfolio isn’t necessarily the right fit for a multi-unit commercial renovation, and the reverse is just as true. Ask for two or three references from projects that match your scope and scale, then actually call them. Ask what went wrong, not just what went right; every project hits a snag, and how a contractor handled it tells you more than a spotless testimonial ever will.

What Does Your Payment Schedule Look Like, and What Triggers Each Draw?

A vague payment schedule is one of the most common sources of dispute on a renovation. Reputable contractors tie payments to clearly defined milestones, for example a deposit, a draw at rough-in, another at a defined completion percentage, and a final payment tied to a punch list being closed out.

Be wary of anyone asking for a large percentage upfront relative to the total project cost, or anyone who can’t explain what specific milestone triggers each payment.

How Do You Handle Change Orders and Unexpected Issues?

Almost every renovation uncovers something once walls or ceilings open up, whether it’s outdated wiring, water damage, or structural surprises. What separates a good contractor from a bad one isn’t whether they encounter this, it’s how they handle it. Ask how change orders are documented, priced, and approved before work continues, and get it in writing as part of your contract, not as a verbal understanding.

For commercial projects, also ask how they handle change orders that affect occupied space or tenant operations. A good contractor will have a clear process for minimizing disruption, not just a plan for billing more.

The Bottom Line

None of these questions are meant to put a contractor on the defensive; a contractor worth hiring will answer all five clearly and without hesitation. If you get vague answers, hedging, or pushback on providing references or insurance documentation, treat that as useful information in itself.

Ready to get started? Contact Raimo Renovations at info@raimorenovations.com or call/text (914) 361-5913.