Painting is one of those projects where the gap between a good contractor and a bad one isn't always obvious from a quote alone. Two companies can hand you similar-looking numbers and very different experiences once work actually starts. After decades of working alongside — and occasionally cleaning up after — other contractors in this market, here are the seven questions worth asking before you sign anything.
1. Are you licensed and insured — and can you prove it?
This should be non-negotiable. A legitimate painting contractor in Florida carries general liability insurance and, depending on the scope of work, appropriate licensing. Don't just take a verbal "yes" — ask for a certificate of insurance and confirm it's current. If a contractor hesitates or can't produce documentation, that's a clear signal to keep looking. This protects you if something goes wrong on your property during the job.
2. Is the quote a fixed price or an estimate?
There's a real difference between a written, fixed-price quote and a loose estimate that can grow once work begins. Ask directly: "Is this the final price, or could it change?" A contractor who prices the job properly upfront — accounting for square footage, surface condition, and repairs — shouldn't need to revisit the number unless you change the scope yourself.
3. What does your prep process actually include?
Prep work is where paint jobs succeed or fail, and it's also where corners get cut most often. Ask specifically what's included: pressure washing, scraping and sanding, caulking, priming bare or repaired areas, and masking. If a contractor's answer is vague or skips straight to "we'll paint two coats," press for specifics.
4. Do you offer a warranty on the work?
A contractor confident in their process should be willing to stand behind it. Ask what's covered, for how long, and what would void it. This isn't about expecting problems — it's about knowing what happens if an issue does come up a year or two down the road.
5. Can I see reviews or talk to past customers?
Online reviews are a good starting point, but don't be afraid to ask for a couple of references from recent jobs similar in scope to yours — especially if you're considering a larger exterior or commercial project. A contractor with a long track record in the area should have no issue connecting you with past clients.
6. How clear is the timeline?
Ask when the project would start, roughly how many days it will take, and what could cause delays (weather is a real factor here in South Florida). A contractor who gives you a vague "we'll get to it soon" answer is harder to plan around than one who commits to a specific window.
7. What does the payment structure look like?
Be cautious of any contractor asking for full payment upfront before work begins — that's one of the more common red flags in this industry. A standard, reasonable structure is a deposit at the start of the project with the balance due upon satisfactory completion. Get the full payment terms in writing as part of your quote.
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None of these questions are meant to be adversarial — a contractor who's confident in their work will answer all seven without hesitation. If you'd like more background on how we handle scheduling, prep, and pricing specifically, our FAQ page covers many of these same topics in detail, and our About page has more on our history serving Palm Beach and Martin County homeowners since 1979. If your project also involves visible wall damage, it's worth reading about why drywall repair should happen before painting so you know to ask about it during your estimate.