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.

Why do so many homeowners skip these questions?

Because asking feels awkward, especially the money and insurance questions. Homeowners are used to hiring people they already trust, a plumber a neighbor used, an electrician from a coworker's recommendation, and the vetting stops there. A renovation is a bigger commitment than a single trade call, often tens of thousands of dollars and months of access to your home, and the contractor relationship deserves the same scrutiny you'd give a mortgage lender. A good contractor won't be offended by any of the ten questions above. If a question makes someone defensive rather than direct, that reaction is itself useful information.

What a written estimate should include

A verbal number is not an estimate, it's a guess with a dollar sign on it. A real written estimate breaks out labor and materials as separate line items, not a single bundled total. It lists the scope in enough detail that you could hand it to a different contractor and get a comparable bid: cabinet grade, counter material, tile allowance, appliance list, and any structural or plumbing changes named specifically. It states a payment schedule tied to milestones, not just a start date and a total. And it names who is responsible for permits. If a proposal is missing any of these, ask for the missing piece before signing, not after the deposit clears.

How many contractors should you actually get bids from?

Three is the number that gives you a real comparison without dragging the process out for months. One bid tells you nothing, you have no reference point for whether the number is fair. Two bids tell you there's a range, but you can't tell which one is the outlier. Three bids, especially if you ask all three the same ten questions, usually surface a pattern, two contractors land close together on price and scope, and the third is either a lowball missing something or a premium justified by real differences in crew, materials, or warranty. Get all three bids on the same written scope so you're comparing apples to apples, not comparing a detailed proposal against a napkin sketch.

What does a change order actually protect you from?

It protects you from a final invoice with line items you never agreed to. Renovation work regularly uncovers things nobody could see before demo, rot behind a wall, wiring that doesn't meet code, a subfloor that needs replacing instead of patching. None of that is a surprise to an experienced contractor, it's a normal part of opening up an older home. What separates a fair process from a bad one is whether you're told about it and given a price before the work happens, or whether it just shows up on the bill at the end. A written change order, signed by both sides before the extra work starts, is the single piece of paper that keeps a renovation from becoming a dispute.

Is the cheapest bid ever the right choice?

Sometimes, but only if it holds up against the same scope as the other bids. A lower number on an identical, detailed scope is a legitimate reason to choose a contractor. A lower number on a vague one-page proposal usually means something is missing, a smaller warranty, a payment structure weighted toward the contractor instead of you, subcontracted labor instead of a dedicated crew, or scope items priced as allowances that will change once work starts. The way to tell the difference is the same ten questions above, asked of the cheapest bidder specifically. If the answers are as solid as the higher bids, the savings are real. If they're vague, the number is probably incomplete.

What should be in the contract before you sign anything?

At minimum: the full scope of work in writing, the payment schedule tied to milestones, the start and estimated completion dates, who pulls permits, the warranty terms, and the change-order process. Verbal promises made during the sales walk-through, "we'll definitely have it done by the holidays," "don't worry about that fixture, we'll swap it," need to make it into the written contract or they don't exist once work starts. This isn't about distrust, it's about making sure everyone remembers the same agreement six weeks into the project when the original conversation is a memory instead of a document.

Why does the license lookup matter more than the contractor's word?

Because a license number you can verify independently removes the need to trust a claim at all, you're checking a public state record instead of taking someone's word for it. A contractor who's actually licensed has nothing to lose by handing over both numbers and encouraging you to look them up yourself, it takes two minutes on the state site and confirms exactly what they told you. A contractor who hesitates, changes the subject, or gives you a number that doesn't match what comes back in the lookup has just told you something important without saying a word. This is the single fastest of the ten checks to run, and it's worth doing before any of the others, since an unlicensed contractor makes every other answer moot.

What's the real risk if a contractor's crew isn't covered by workers comp?

If someone gets hurt on your property while working without workers compensation coverage, the injured worker's medical costs and lost wages can become your liability as the property owner, not just a headache for the contractor. This is one of the few items on this list where the downside isn't just a bad renovation, it's a direct financial and legal exposure to you personally. A Certificate of Insurance is the one document that actually proves coverage exists at the time of your project, a claim of being insured without a COI to back it up is not verification, it's a sales pitch.

Why does a specific payment schedule protect you more than a lower total price?

A contractor asking for a large upfront payment is asking you to fund the job before you've seen any work completed, which shifts nearly all the financial risk onto you if the project stalls, the contractor underperforms, or the relationship sours early. A milestone-based schedule, tying each payment to a completed stage of work, keeps the incentive aligned in both directions: you're not holding all the risk, and the contractor isn't working for free either. This matters more than the headline price in a lot of cases, because a slightly higher bid with a fair payment structure is a better deal than a lower bid that asks you to prepay half the job in cash.

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