7 Questions to Ask Before You Sign With a Contractor

7 Questions to Ask Every Contractor Before You Sign Anything

The FTC received over 81,000 home improvement fraud reports in 2024 — and most of those homeowners thought they had done their homework. These seven questions target the decisions that generate the most expensive disputes: supervision, insurance, permits, payment leverage, references, warranty, and change orders. Ask all seven before you sign anything.

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Question 1: "Who will be on-site every day — you, a foreman, or a subcontractor?"

Why this question matters

Many homeowners hire based on a meeting with the business owner — and never see that person again once demolition starts. The actual work is handed to a foreman or subcontractor crew they have never met, with minimal supervision. When supervision gaps exist, material substitutions happen without your knowledge, inspections get skipped, and nobody owns the schedule. If you do not know who is in charge on-site, you have no one to call when things go wrong.

What a good answer sounds like

• The contractor names a specific foreman who will be present daily and offers to include that name in the contract
• The contractor explains which portions will be subcontracted and how those subs are vetted
• A communication cadence is described — daily check-ins or a project management system

What a red flag answer sounds like

• "We have great crews" without naming anyone specific
• Resistance to including a named supervisor in the contract
• The contractor confirms they will not visit the site until final walkthrough

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Question 2: "Can I see proof of your general liability and workers' comp insurance right now?"

Why this question matters

If a worker is injured on your property and the contractor lacks workers' compensation insurance, you can be held directly liable for their medical bills and lost wages. Your homeowner's policy does not cover this. General liability protects you from property damage the contractor causes. Asking for documentation in the meeting — not "before work starts" — separates contractors with active coverage from those who intend to get around to it. For a complete breakdown of each coverage type, see our guide to contractor insurance.

What a good answer sounds like

• A Certificate of Insurance produced on the spot or within 24 hours, showing at minimum $1 million per occurrence general liability and active workers' comp
• The contractor invites you to call the carrier directly to verify the policy is active

What a red flag answer sounds like

• "I'll send it before we start" — a delay, not confirmation
• "My agent is updating the certificate" — active policies have certificates ready immediately
• A certificate with expired dates or visible alterations

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Question 3: "Will you pull all required permits for this project, or am I expected to?"

Why this question matters

The contractor pulls the permit. When a licensed contractor applies, their license is on the line for code compliance. When you pull the permit as a homeowner, you become the legally responsible party for passing every inspection. Contractors who ask you to pull permits typically have a suspended license, outstanding violations, or no license at all. Unpermitted work causes failed home inspections at resale, retroactive permit fees at double or triple the original cost, and invalidated homeowner's insurance coverage for related damage.

What a good answer sounds like

• "We pull all permits — included in the cost, and you get copies of every inspection sign-off"
• The contractor names the specific permits required without being prompted

What a red flag answer sounds like

• "It's faster if you do it" or "It'll save you money" — both transfer the contractor's legal liability to you
• "This project doesn't need a permit" — for structural, electrical, plumbing, or HVAC work, verify independently with your municipality

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Question 4: "What is your payment schedule — and what milestones trigger each payment?"

Why this question matters

A milestone-based payment schedule is your primary leverage tool throughout the project. When payments are tied to dates instead of completion stages, you lose leverage the moment the check clears. More than half of homeowners encountered surprise expenses on home improvement projects in 2024, according to Angi — and change order disputes are far easier to negotiate when you still have a material payment outstanding. A contractor who resists milestone payments is removing the leverage that protects you if work stalls or materials get substituted. For more on payment structure and contract terms, see our guide on how to read your contract.

What a good answer sounds like

• 4–5 payments tied to verifiable completion events: demo complete, materials delivered, rough-in inspection passed, substantial completion, punch list resolved
• Upfront deposit of 15–20%; final payment of 5–10% held until punch list sign-off

What a red flag answer sounds like

• Request for 50% or more upfront before work begins
• A schedule based on calendar dates rather than completion stages
• Resistance to milestone triggers when you ask directly

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Question 5: "Do you have references from a similar project completed in the last 12 months?"

Why this question matters

A contractor who ran excellent projects in 2021 may have a completely different crew, different subcontractors, and a different financial condition today. References need to be recent and relevant. "Similar project" matters as much as "last 12 months" — a contractor with strong references for bathroom tile work may have no track record on structural additions. You are checking whether this contractor is doing good work right now, not whether they ever did.

What a good answer sounds like

• Two to three references from comparable projects in the past year, with names and phone numbers
• References who describe specific experiences — timeline, crew behavior, how problems were handled — not just vague praise
• Openness to you visiting the completed project in person

What a red flag answer sounds like

• "Here are some great Google reviews" — reviews are not references
• Numbers that go to voicemail with no callback
• No references from any project in the last 12 months

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Question 6: "What does your workmanship warranty cover and for how long?"

Why this question matters

Manufacturer warranties cover defective materials. Workmanship warranties cover how those materials were installed — and that is entirely the contractor's responsibility. One year is the industry floor, not a sign of quality. Reputable contractors on major projects offer two to five years. A contractor who has no intention of returning to fix problems will offer vague terms upfront and be unreachable after the final payment. Warranty disputes are consistently among the most common home improvement complaints filed with Midwest state attorneys general.

What a good answer sounds like

• A stated warranty period (e.g., "two years on all labor") with a written claim process in the contract
• Clear explanation of what is covered (installation defects) and what is not (manufacturer defects, homeowner misuse)

What a red flag answer sounds like

• "We stand behind our work" without a defined period
• A warranty contingent on using their subcontractors for all future maintenance
• One-year warranty on a $40,000+ project from a contractor charging premium rates

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Question 7: "What is your process when you discover unexpected conditions mid-project?"

Why this question matters

Every remodel carries some risk of unexpected discovery — rotted subfloor under tile, knob-and-tube wiring in a wall, mold behind drywall. Change orders account for 10–15% of total project cost on average, and how a contractor handles surprises determines whether that extra cost is fair and documented or a verbal "we had to do more work" at final invoice. A contractor without a defined process will manage these moments in whatever way is most convenient for them.

What a good answer sounds like

• Stop work, photograph and document the condition, present a written change order with scope, cost, and schedule impact — before proceeding
• The contractor treats this as standard operating procedure and can point to the change order clause in the contract

What a red flag answer sounds like

• "We handle it and let you know at the end" — this is how surprise invoices get generated
• "It depends on how big the issue is" — no dollar threshold should substitute verbal for written authorization
• Treating the question as adversarial

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How to Document and Evaluate the Answers

Write the questions down and take notes during the meeting. After, email the contractor a brief summary of their answers to create a written record before the contract arrives. When the draft comes in, verify three things:

1. Named site supervisor appears by name
2. Payment milestones are tied to inspectable events, not calendar dates
3. Warranty terms are in writing with a defined period and claim process — verbal commitments are unenforceable

See our guide on how to read your contract for a full clause-by-clause review.

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What to Do If a Contractor Refuses to Answer

Refusal is informative. Three questions are automatic disqualifications:

• Question 2 (insurance): No documentation, no contract.
• Question 3 (permits): If they ask you to pull the permit, the conversation ends.
• Question 4 (payment schedule): More than 30% upfront with no milestone negotiation — walk away.

For the other four, follow up directly: "I'm asking because I want to start on the right foot." A contractor with nothing to hide engages. One who deflects or pressures you past the question is showing you how they handle problems mid-project.

See our list of contractor red flags for a full breakdown of predictive behaviors.

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Frequently Asked Questions

What is the most important question to ask a contractor before hiring?

Ask for proof of insurance in the meeting, not before work starts. No documentation means no contract. Uninsured contractors expose you to direct liability for any worker injured on your property.

Should I ask a contractor who will be on-site every day?

Yes. Get the name of the daily site supervisor and the direct contact number in writing. If the contractor cannot name that person, you have no point of contact when problems arise.

Who is responsible for pulling permits — me or my contractor?

Your contractor pulls all permits. If they ask you to pull the permit, the conversation ends. Doing so transfers legal code-compliance responsibility to you and typically signals a license problem on their end.

What is a fair payment schedule for a home improvement project?

15–20% at signing, milestone-based payments tied to inspectable events, and 5–10% held at punch list. Never more than 30% upfront.

How recent should a contractor reference be?

Within the last 12 months, from a project similar to yours in scope and cost. Older references reflect a different crew and business condition than what you are hiring today.

What does a contractor workmanship warranty typically cover?

Defects in installation, separate from manufacturer material warranties. One year is the minimum. Major projects warrant two to five years in writing, with a defined claim process.

What should a contractor say when unexpected conditions are discovered mid-project?

Stop work, document, and present a written change order before proceeding. Any contractor who handles surprises verbally and reconciles at final invoice cannot be held accountable.

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Start With Contractors Who Already Pass

These seven questions work best when the contractors you are interviewing are worth the conversation. Every contractor in the Above Board Pros network is programmatically verified against government licensing and insurance databases before receiving a single lead. Your questions become a final evaluation, not a first pass.

Read our complete contractor verification guide to see exactly what that process checks.