What to Ask a Contractor Before You Sign
Before you sign with a contractor, there's a conversation worth having that most clients never get around to. You've done the hard work of reading the bids, comparing the numbers, and checking references. You have someone in mind. But the bid tells you what the project will cost. It doesn't tell you much about the person you're about to spend the next several months working closely with. These questions will.
This post is part of our series on navigating the construction bidding process. Before you dive in: Why You Should Hire Your Interior Designer Before Your Contractor
The series:
1. How to Read and Compare Contractor Bids
2. Why Your Designer Should Set Your Renovation Allowances Before Contractors Bid
3. What to Ask a Contractor Before You Sign
4. Pre-Construction: What It Is and Why It Matter
Have you done projects like this before?
This sounds obvious but it's worth asking specifically. A contractor who is excellent at new construction may not have the same fluency with historic renovation. A contractor who regularly works on Back Bay brownstones understands the permitting process, the quirks of older construction, and the architectural commissions' expectations in a way that a general contractor without that experience doesn't. Ask for examples and photos. Ask to speak with a client from a comparable project.
Are you licensed and insured?
Ask for the contractor's license number and a certificate of insurance before you sign anything, and verify both independently. The certificate of insurance should list you as an additional insured for the duration of the project. This is standard practice. A contractor who is reluctant to provide either document is a contractor to walk away from.
Who will actually be on site every day?
There's often a gap between the contractor you meet during the bidding process and the people who show up on day one. Find out who is managing the day-to-day work, whether that's the contractor themselves, a dedicated project manager, or a site supervisor. Find out how often the contractor will be present in person. For a significant renovation, daily or near-daily site presence from someone with decision-making authority matters.
Who pulls the permits?
Ideally, the contractor should pull all permits for the project, not you. If a contractor asks the homeowner to pull permits, that's a significant red flag. It transfers liability to you and often signals that the contractor isn't properly licensed for the work. Confirm this is handled on their end before you sign. You should expect to pay for the permit fees, however.
How do you handle unforeseen conditions?
In an older home, something unexpected almost always turns up once walls open. The question isn't whether it will happen. It's how the contractor responds when it does. You want to hear a clear process: how they document the discovery, how they communicate it to you, how they price the additional work, and how they minimize the impact on the overall timeline. A vague answer here is worth paying attention to.
How do you handle change orders?
A change order is a formal amendment to the contract that adjusts scope, cost, or timeline. Ask the contractor to walk you through their change order process. How are additional costs calculated? What's the markup on materials and labor for out-of-scope work? How quickly are change orders documented and presented for approval? You want a contractor who treats change orders as a formal, transparent process, not an informal conversation followed by a surprise line item at the end of the project.
What does communication look like during the project?
Find out how the contractor prefers to communicate and whether that cadence works for you. Ask how they handle questions and decisions that come up during construction. A mismatch in communication style is a friction point that compounds over the course of a long project. Better to surface it now.
What is your current workload?
A good contractor is usually a busy one, but there's a difference between busy and overextended. Ask how many active projects they're managing right now and how yours would be prioritized among them. A contractor who hesitates or gives a vague answer is worth paying attention to. It's also one of the better ways to pressure-test whether the timeline they've projected is actually realistic.
What's your warranty policy?
Ask what the contractor's warranty covers, for how long, and how they handle callbacks after the project is complete. What happens if a tile cracks, a door won't hang correctly, or a plumbing issue traces back to the renovation? You want a clear answer before you need one. A contractor who is vague about post-completion support is a contractor who may be difficult to reach once the final payment clears.
What do you need from me to keep the project on schedule?
Contractors lose time when clients are slow to make decisions or unavailable to approve change orders. Asking this question upfront signals that you're a serious, engaged client and gives you a realistic picture of what the project will demand from you.
What most clients don't realize is that making a decision and making a decision on time are two different things. A homeowner might approve a tile selection two weeks before the installer arrives, which feels responsible. But if that tile has a six-week production lead time, the decision was already late before it was made. Lead times compound across a full renovation, and without someone actively tracking them, delays that feel sudden rarely are.
This is where having a designer on your team makes a significant difference. A contractor working without a designer has one place to go when a question comes up: you. Every material decision, every detail question, every field condition that needs a resolution lands in your inbox. For a client with a full life and a demanding schedule, that volume of communication is genuinely difficult to keep up with, let alone respond to with the timing construction requires.
A designer changes that dynamic entirely. They manage the decision timeline proactively, flagging what needs to be resolved and when before it becomes a construction delay. They serve as the primary point of contact for design-related questions, visiting the site regularly, fielding detail questions, and only bringing you into the conversation when a decision genuinely requires your input. The project moves faster, the contractor has the answers they need without waiting, and you stay informed without being overwhelmed.
Before You Sign: What to Look For in the Contract
Once the conversation goes well and you're ready to move forward, read the contract carefully before you sign. A few things to look for:
Scope of work should be written in detail, not summarized. Anything vague in the contract is a potential dispute later.
The payment schedule should be tied to specific milestones, not arbitrary dates. Avoid contracts that front-load payments heavily before meaningful work has been completed.
Change order language should require written approval from you before any additional work is performed. Verbal agreements mid-project are difficult to dispute after the fact.
A termination clause should exist for both parties, with clear terms for what happens to work completed and deposits paid if the relationship ends early.
Warranties and callbacks should be spelled out, including the duration and what's covered.
If anything in the contract contradicts what was discussed verbally, resolve it in writing before you sign. The contract is the document that governs the project. Make sure it reflects the project you agreed to.
The Conversation Tells You as Much as the Answers
Pay attention to how the contractor engages with these questions, not just what they say. A contractor who answers directly, offers specifics, and acknowledges complexity is showing you something important about how they operate. A contractor who is vague, defensive, or dismissive of questions you have every right to ask is showing you something important too.
By the time you sign, you should feel confident not just in the number but in the person. The contract defines the terms. The relationship determines whether the project actually goes well.
Nubuor Designs is an interior design studio based in Beacon Hill, Boston, working with homeowners across the country on renovations that deserve to be done right. If you're planning a project and want to make sure the process is set up correctly from the beginning, we'd love to hear more about you and your home.
