Guide · 7 min read · Updated August 14, 2026
12 questions to ask a painting contractor (and the answers to listen for)
We wrote this knowing it will occasionally be used against us. That is fine — a customer who asks these questions is a customer who understands what they are buying, and those jobs go better for everyone.
The twelve questions
How much surface preparation is in this price?
Listen for: specifics. “Scrape and feather-sand all loose and failing paint, spot-prime all bare wood, caulk trim-to-siding joints.” Worry about: “full prep” with no detail. Prep is 60–80% of the labour and it is where quotes diverge.
How many coats, and is that written down?
Listen for: two finish coats over prepared surfaces, plus primer where needed, stated on the proposal. Worry about: “one coat should be fine” without a reason. Sometimes it genuinely is — over a sound, same-color surface. Make them say why.
What exact product are you using?
Listen for: a named line and sheen — “Benjamin Moore Aura Exterior, low lustre.” Worry about: “premium paint” or “contractor grade.” Contractor-grade product on a repaint is a false economy that shows in three years.
Can I see your certificate of insurance — general liability and workers compensation?
Listen for: yes, from the agent, within a day. Worry about: hesitation, or a liability certificate offered when you asked about workers comp.
What is your HIC registration number?
Listen for: a number, immediately, offered without defensiveness. Check it yourself → Ours is 177081.
My house was built before 1978. How does that change this job?
Listen for: an accurate description of lead-safe requirements and a line item for it. Worry about: “it’s fine, we don’t worry about that.” Why this matters →
Who will actually be on my property, and who is my point of contact?
Listen for: a named project manager with a direct number, and whether the crew is employed or subcontracted. Worry about: “we’ll see who’s available.”
What is the warranty, in years, and what does it actually cover?
Listen for: a written warranty naming what is covered — peeling, blistering, cracking from workmanship — and what is not. Worry about: a verbal “we stand behind our work.” Ours, in full →
What are the start and completion dates?
Listen for: real dates on the contract, which Massachusetts law requires, with a weather-permitting clause for exterior work. Worry about: “sometime in the spring.”
What happens if you find rot once you start?
Listen for: we stop, photograph it, and issue a written change order with a price before doing the work. Worry about: a vague allowance, or a promise that there will not be any.
How do you protect my landscaping, floors and furniture?
Listen for: a written protocol. Breathable covers on beds, plants pre-wet and rinsed, nothing stored on lawns, floors papered and taped, daily set-up and take-down. Worry about: “we’re careful.”
How does the job end?
Listen for: a scheduled walk-through, a written punch list, the punch list completed, then final payment. Worry about: anything that has you paying in full before the last items are done. This is the most common failure point in the entire trade — including for the best-regarded companies in this area. How we handle it →
One more, for the estimate appointment itself
Ask how long the price is good for. A contractor who needs an answer today, or who produces a discount that expires when they leave your kitchen, is managing you rather than quoting you. A real estimate holds for weeks and is still there after you have compared it.