Most painting bids arrive in the same range. The difference shows up 2–3 years in, when one finish still looks fresh and another has peeled at the trim. Asking the right questions up front separates the two.
1. Are you licensed and insured in Massachusetts?
Every reputable painter carries general liability and workers' comp. Ask for the certificate of insurance — and check that it's current. Unlicensed crews are a problem waiting to happen.
2. Walk me through your prep process
A good painter can describe prep in detail: wash, scrape, sand, caulk, prime. If the answer is short or vague, the prep will be too.
3. Which paint lines do you specify?
Premium lines (Benjamin Moore Aura/Regal, Sherwin-Williams Emerald/Duration) are the baseline for work that lasts. Contractor-grade paint is fine for rentals and quick flips — not for the home you plan to live in.
4. Who actually does the work?
In-house crews you've met are better than revolving subcontractors. Ask if the team on your estimate is the team on your job.
5. What's your workmanship guarantee?
Two years on exterior workmanship is standard for premium painters. Interior guarantees are usually 1 year. Get it in writing.
6. Can I see a recent local project?
Not photos — an actual home. Painters who've worked in your zip code will have one nearby. Drive by and look at the trim lines.
7. How do you handle the unexpected?
Rot discovered mid-prep, a color that looks wrong once on the wall, a weather delay — the answer tells you how communication will go under pressure.
If a painter answers all seven cleanly, they're probably the right hire. If any answer feels hand-wavy, keep looking.