What Questions Should You Ask a Contractor Before Hiring?

Most homeowners interview contractors by asking about price and timeline. Those are reasonable questions. But they''re also the two things a contractor can most easily say whatever you want to hear. Price can be scoped down until it sounds competitive. Timeline can be estimated optimistically and adjusted later. If you want to evaluate a contractor accurately before you sign anything, you need to ask questions that are harder to fake.

Ask to see their license and insurance certificate. In Chicago, general contractors working on projects that require permits must be licensed with the City of Chicago. Ask for their license number and verify it at the city''s business licensing portal. Ask for a certificate of general liability insurance — $1M per occurrence is the minimum, $2M or higher is better for larger projects — and ask that you be named as an additional insured on the certificate. A legitimate contractor will provide this without hesitation. One who stalls, says the paperwork is being renewed, or pivots to talking about their reputation instead of producing documents is telling you something.

Ask how they handle change orders. Scope changes during a renovation are common — demolition reveals problems, clients change their minds, materials get discontinued. The question isn''t whether there will be changes; it''s whether those changes are documented in writing before work proceeds. Ask: "If something changes mid-project, how does that get handled?" The right answer is a written change order that describes the work, cost, and schedule impact, signed by both parties before anything changes. The wrong answer is "we''ll just figure it out" or "we track it and settle up at the end."

Ask who will be on site every day. On a lot of renovation projects, the person you met in the sales process is not the person running your job. Ask: "Who is the project manager and who is the field lead? Can I meet them before we start?" A named PM who owns the schedule and a field lead who knows your project day to day is the operational structure that makes a renovation run well. A GC who runs multiple jobs simultaneously and visits each one once a week is a different thing.

Ask for references from similar projects — and actually call them. Ask for two or three references from projects in the last two years that are similar in scope and budget to yours. When you call, ask three questions: Did they finish on budget? Did they finish on schedule? Would you hire them again? The first two questions have yes or no answers and are hard to spin. The third question tells you everything the first two don''t.

Ask how they communicate during the project. This sounds soft but it''s operationally important. Find out: how often will you get progress updates, in what format, from whom? Weekly photo updates from the PM are a reasonable baseline. Ask what the process is if you have a question or concern mid-project. What''s the response time expectation? Who is your single point of contact? The contractors who are hardest to reach during the sales process are usually harder to reach during construction.

Ask what''s included in the warranty. Most legitimate contractors offer a one-year workmanship warranty on their work. Ask what it covers, what the process is to make a warranty claim, and whether it''s in writing in the contract. Ask separately about manufacturer warranties on materials — cabinets, tile, windows — which are separate from the contractor''s workmanship warranty and handled differently.

Ask about the payment schedule. A standard payment schedule is structured around project milestones: a deposit at contract signing (typically 10–20% of the total), payments tied to completion of rough work, completion of finishes, and a final payment at punch list completion. Be skeptical of any contractor who asks for more than 30–40% of the total before work begins, or who wants to be paid in cash. Both are patterns associated with contractors who don''t intend to finish the job.

Ask about permit responsibility. Who pulls the permits — the contractor or the owner? On any project in Chicago that touches plumbing, electrical, structural, or HVAC, permits are required. The contractor should pull them, because the permit ties the work to their license and makes them responsible for passing inspections. An owner pulling their own permits on a contracted project is unusual and worth asking about. A contractor who suggests skipping permits to save money is offering to do unlicensed work — which is your liability if something goes wrong.

One thing worth noting: a contractor who can answer all of these questions directly, without deflecting, without getting defensive, and without a sales pitch — that''s who you''re looking for. The questions aren''t a gotcha. They''re a baseline. Any experienced, legitimate contractor has given these answers hundreds of times.