Most bad contractor experiences were predictable at the estimate. The warning signs were there; the homeowner just did not know which questions to ask. These are the twelve that matter, and what a good answer sounds like.
Credentials and coverage
1. Are you registered with the State of Connecticut, and what is your registration number?
Connecticut requires home improvement contractors to register with the Department of Consumer Protection. A professional will give you the number without hesitating. You can verify it yourself through the state's license lookup — do that, do not just accept the number.
2. Can I see a current certificate of insurance?
You want two coverages: general liability and workers' compensation. Liability covers damage to your property. Workers' comp matters more than people realize — if an uninsured worker is injured on your property, you can end up exposed. Ask for the certificate to be sent directly from their insurance agent, which is the version that cannot be edited.
3. Who is actually doing the work — employees or subcontractors?
Either is fine. Not knowing is not. If subs are involved, ask whether they carry their own insurance and who supervises them day to day.
Scope and money
4. What exactly is included, and what is explicitly not?
The exclusions matter as much as the inclusions. Disposal, permits, cleanup, restoring landscaping, painting after drywall work — these are the common gaps that become change orders.
5. What is your payment schedule?
A reasonable deposit tied to material orders, progress payments tied to milestones, and a final payment on completion. A large up-front payment is the single biggest red flag in this industry. Never pay for the whole job before it starts.
6. How do you handle change orders?
You want: in writing, priced, and signed before the work happens. "We'll settle up at the end" is how a budget doubles.
7. What happens if you open it up and find something unexpected?
Rot, old wiring, asbestos, a surprise under the floor. A good contractor has a clear process and often a contingency allowance. Someone who says "that won't happen" has either not done many of these or is not being straight with you.
Permits and process
8. Does this job need a permit, and who pulls it?
Most structural, electrical, plumbing, and HVAC work does. The contractor should pull it. If a contractor suggests skipping the permit or asks you to pull it yourself as the homeowner, walk away. Unpermitted work causes problems at resale, can void insurance coverage, and shifts liability onto you.
9. What is the schedule, and what could move it?
Start date, rough duration, and the honest dependencies — material lead times, inspections, weather. Precision here is a good sign; vagueness is not.
10. Will there be a dedicated point of contact?
One name, one number, and how quickly they typically respond. On a job of any size this determines whether the experience is pleasant or maddening.
After the work
11. What is your workmanship warranty?
Materials carry a manufacturer warranty. Workmanship is the contractor's own promise and it is the one that matters when something leaks. Ask for the length and get it in writing.
12. Can I have three references from jobs like mine in the last year?
Recent and similar. Then actually call them, and ask the question that produces honest answers: "What was the hardest part of the job, and how did they handle it?" Everyone says the work was fine. This asks about the friction.
Three answers that should end the conversation
- "I need a large deposit today to hold your spot." Urgency plus money up front is the oldest pattern there is.
- "We can skip the permit and save you money." They are offering to transfer risk to you and calling it a discount.
- "This price is only good if you sign right now." Real pricing survives a night's sleep.
Get the contract right
Connecticut has specific requirements for home improvement contracts, and generally they must be in writing and signed. At minimum yours should name both parties, describe the scope in detail, state the total price and payment schedule, give start and completion dates, and spell out the warranty. Certain contracts also carry cancellation rights.
Read it before you sign. If a contractor is impatient about you reading the contract, that tells you what working with them will be like.
This is general information, not legal advice. For a large project or a dispute, talk to an attorney.
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