10 Questions to Ask Any Contractor Before You Sign

We get hired and not hired. Sometimes we're not the right fit and we say so, but more often we get hired because the homeowner asked good questions of three or four contractors and we were the only one with straight answers. Here are the questions we'd want you to ask us, and what to listen for in the answer.

1. Are you licensed in Massachusetts? Show me both numbers.

There are two licenses that matter in MA. Construction Supervisor License (CSL) for any structural work, and Home Improvement Contractor (HIC) registration for residential remodeling. They're separate. A contractor should be able to recite both numbers from memory, and you should be able to look them up on the MA state license lookup.

Walk away if: They get evasive, only mention "I'm licensed" without numbers, or claim a handyman registration is enough for a kitchen remodel.

2. Are you insured? What carrier and what limits?

Minimum: $1M general liability, $2M is better, plus workers compensation on every employee, check this if more than one person is on site. Ask for the COI (Certificate of Insurance) before signing.

Walk away if: They only have GL but no workers comp, or they say "my guys are sub-1099s". That means you are liable if one of them gets hurt on your property.

3. Who's actually doing the work, your crew or subs?

This isn't bad either way, but the answer should be specific. "I have a 4-person full-time crew plus licensed electrical and plumbing partners" is a real answer. "I'll see who's available" is not.

Walk away if: The person you're talking to won't be on site, and they can't tell you exactly who will be.

4. What's your written warranty?

A real workmanship warranty is a year minimum. Some contractors offer two. The warranty should be written into the contract, not promised verbally.

Walk away if: "Manufacturer warranty only". That means they won't stand behind their own labor.

5. How do you handle change orders?

The right answer: "Written change orders signed before any extra work happens." Wrong answers include "we'll figure it out at the end" or "we never have change orders."

Walk away if: They don't have a change-order template or process. This is the #1 reason renovations end up over budget, verbal scope creep that gets billed on the final invoice.

6. What's the payment schedule?

Reasonable: deposit at signing (10–20%), progress payments at milestones, hold-back of 5–10% until punch list is complete and signed off.

Walk away if: They want 50% upfront, especially in cash, or if they ask for full payment before substantial completion.

7. Will you pull permits, or am I expected to?

The contractor should pull permits. If they ask you to, that's often a sign they're not licensed in your jurisdiction.

Walk away if: "We don't need permits for that" on work that clearly does need permits (electrical, plumbing, structural). MA permit requirements are clear and avoidable only by working unsafely.

8. What happens if you find rot or asbestos behind the walls?

The right answer: "We document with photos, give you a written quote for the additional work, and you sign before we proceed." For asbestos: "We stop and call in a licensed abatement contractor, that's not our scope."

Walk away if: "We just deal with it". That means it'll appear on your final bill, twice the price, and you'll have no recourse.

9. Can you give me three references from projects similar to mine?

Not just any references, ones with comparable scope. A contractor who's done a hundred kitchens but never a basement should tell you that, not pretend the kitchen-references apply to your basement.

Walk away if: They can't produce three references inside the first 48 hours, or the references are all over a year old.

10. What's your project management like? How will I hear from you?

The right answer is specific: "Glenn runs every project. You'll hear from him by text most days. Weekly progress reports on Friday with photos." Or whatever their actual system is.

Walk away if: It's vague, or there's a project manager between you and the people doing the work, and you can't get the project manager on the phone.

How we'd answer these for our own company

1. MA HIC: pending registration display. MA CSL: Glenn, unrestricted.
2. Insurance: $2M GL through a regional carrier, workers comp on every employee.
3. Crew: Glenn + 4–6 full-time, plus licensed electrical and plumbing partners we've worked with for years.
4. Warranty: written one-year workmanship warranty plus manufacturer warranties pass through.
5. Change orders: written and signed before any extra work. We won't proceed without your sign-off.
6. Payment: 15% at signing, progress payments at milestones, 10% hold-back until punch list sign-off.
7. Permits: we pull every one and meet the inspector on site.
8. Surprises: documented with photos, written change order, your sign-off.
9. References: ask Glenn, he'll text you three names by the next morning.
10. Communication: Glenn runs every project. Texts daily, weekly progress reports.

If those answers fit how you want to work, tell us about your project. Glenn does walk-throughs the same week.