What is your license number? In California, any job over five hundred dollars in labor and materials requires a licensed contractor. A licensed painter answers this instantly, because the number is on the truck and the estimate. You can check it yourself on the CSLB website in about thirty seconds. Ours is 1118205.
Are you insured, and can I see the certificate? Liability insurance protects your property. Workers' compensation protects you from being on the hook if someone is hurt on a ladder at your house. Both should be produced on request without any friction.
What does your prep include? This is the question that separates bids. Ask specifically about pressure washing, crack patching, caulking, and spot priming. If those words do not appear in the written estimate as line items, assume they are not in the price.
How many coats, and is the second coat on every elevation? Some bids quote two coats on the front of the house and one on the sides, which is how a job comes in cheap and fails on the sun-facing walls first. Get the number of coats per surface in writing.
What happens if you find dry rot? The right answer is that they probe for it during the estimate and quote the replacement up front. The wrong answer is that they will let you know if they find something, which usually means a change order on day three.
Who is actually on my property? Some companies sell the job and subcontract the work. That can be fine, but you deserve to know who will be in your yard, whether they are employees, and who is accountable for the workmanship.
What is the warranty, and is it written? A verbal promise to come back is worth nothing eighteen months later. Ask for the workmanship warranty in writing, read what it excludes, and keep it with your estimate.
A contractor who answers all seven quickly and in writing is usually organized on the job site too. One who gets vague on the fourth question is telling you something useful, and it is better to learn it now than in year two.