Short answer: finding questions to ask is easy. You can get a list of fifty in thirty seconds. The hard part is sitting across from someone confident and plausible and not knowing whether what they just told you was good.
So every question below comes with what a straight answer sounds like and what should make you pause. You will not ask all twenty, and you are not meant to. Pick the ones that fit your job, and if the conversation is short, there is a section near the end naming the five that matter most.
How to use these
Ask in person or on the phone, not by email. You are reading hesitation as much as content, and nobody hesitates in writing.
Ask the same questions of every contractor you are considering. Three different conversations with three different question sets tell you nothing comparable.
Write the answers down while you are talking rather than afterwards. You will think you remember. You will not, by the third conversation.
One thing worth knowing before you start: a good contractor has heard all of this before. Being asked reasonable questions is a normal part of winning work, and most will answer without blinking. Irritation at being asked is itself one of the answers you are collecting.
Part 1: Can they legally do this work?
1. Are you licensed for this type of work in this state, and what is the licence number?
Why it matters: licence requirements vary by state and by trade, and in states that require one, hiring an unlicensed contractor can leave you exposed rather than just them.
A good answer sounds like: the number, said from memory or pulled up on their phone, plus the classification it covers. Often with "feel free to look it up" attached, because they know you can and they would rather you did.
A red flag sounds like: "You don't need a licence for this sort of job" when your state says otherwise, or a number they will send on later and then do not.
2. Can your insurer send me a certificate of insurance with my name as the certificate holder?
Why it matters: a PDF the contractor emails you is a snapshot of one day. A certificate naming you as holder means the insurer tells you if the policy lapses mid-project.
A good answer sounds like: "Sure, I'll have my agent send it over this week." No pause at the certificate holder part, because anyone who works commercially does this routinely.
A red flag sounds like: offering to forward you their own copy instead, or treating the request as unusual or distrustful.
3. How long have you traded under this name?
Why it matters: a business trading under the same name for years has a local reputation it cannot afford to spend on your job.
A good answer sounds like: a straight number. If there was a previous name, they say so and explain why without being asked twice.
A red flag sounds like: vagueness, or a recent name change they would rather not discuss. The Illinois Attorney General's guidance suggests checking with your local village hall or township about past complaints against the companies you are considering, and a name change is exactly when that is worth doing.
4. Will you be pulling the permits?
Why it matters: this one is under-asked and it matters more than it sounds. Whoever pulls the permit takes on responsibility for code compliance.
A good answer sounds like: "Yes, that's on me and it's in the price."
A red flag sounds like: asking you to pull them yourself. Sometimes that is a legitimate cost-saving suggestion. Sometimes it is a contractor who cannot pull a permit in their own name, and it always shifts liability onto you. Ask why before agreeing.
Part 2: Do they understand your job?
5. Have you done a job like this in the last year?
Why it matters: experience in general is less useful than experience in this, recently.
A good answer sounds like: a specific recent job, with the parts that were similar and the parts that were not.
A red flag sounds like: "We do everything." A contractor who does everything equally well usually does nothing particularly well.
6. What did you notice when you looked round that I have not mentioned?
Why it matters: this is the best question in the article for separating people who have assessed your property from people who have glanced at it.
A good answer sounds like: something specific you had not thought about. A drain in the wrong place, old wiring behind a panel, a floor that is not level.
A red flag sounds like: generalities, or praise for your house. Someone who has genuinely looked has found something.
7. What is most likely to go wrong once you open it up?
Why it matters: every job has unknowns, and you want them named now rather than priced later.
A good answer sounds like: a named risk, roughly what it would cost, and how they would handle it.
A red flag sounds like: "Nothing, it's straightforward." That is either inexperience or a change order being held back for when you are committed.
8. Realistically, how long will this take?
Why it matters: optimistic timelines win jobs and then cost you.
A good answer sounds like: a range with the reasons attached. "Four to six weeks, depending on how long the inspection takes and whether the cabinets arrive on time."
A red flag sounds like: a single confident number that is noticeably shorter than everyone else's.
Part 3: The money
9. What is included in this price, and what is specifically excluded?
Why it matters: the second half of that question does the work. Most disputes come from something nobody mentioned.
A good answer sounds like: a clear answer on exclusions without having to think. Disposal, making good, permits, fixtures you are supplying yourself.
A red flag sounds like: "Everything's included," which is never true, or irritation at being asked to separate the two.
10. What deposit are you asking for, and what does it cover?
Why it matters: the FTC warns specifically about contractors who want everything up front or will only take cash, and notes that many states cap how much can be requested as a down payment.
A good answer sounds like: a modest figure with a reason attached, usually materials and scheduling.
A red flag sounds like: the full amount, cash only, or a deposit that seems to have no relationship to what they need to buy.
11. How are progress payments tied to the work?
Why it matters: payments on a calendar can leave you fully paid up on work that has not happened.
A good answer sounds like: milestones. "A third when the rough-in passes inspection, a third at drywall, the rest on completion."
A red flag sounds like: dates. "The 1st and the 15th" tells you nothing about progress.
12. How do change orders work?
Why it matters: this is where budgets go, and the process matters more than the price.
A good answer sounds like: written, priced and signed before the work happens, every time, even for small things. Wisconsin's consumer protection guidance is blunt about not relying on oral agreements, and change orders are where that usually breaks down.
A red flag sounds like: "We'll sort it out at the end," which means you will find out what it cost when you can no longer say no.
13. Will you give me a sworn statement of everyone owed money before I pay anything?
Why it matters: this is the most useful question on the page and almost nobody asks it. The Illinois Attorney General's guidance recommends requiring the contractor to provide a sworn statement listing everyone furnishing materials and labour and the amounts owed to each, before any payments are made.
It tells you who could place a lien on your house before you have paid anyone, rather than after.
A good answer sounds like: yes, without needing it explained.
A red flag sounds like: not knowing what you mean. From a contractor running subcontractors, that is itself an answer.
The same guidance also suggests an independent escrow agent, such as a bank or title company, releasing payments only as work is completed and subcontractors are paid. On a large job, worth raising.
Part 4: Who is actually doing the work?
14. Who will be on site day to day?
Why it matters: the person who sold you the job is often not the person who turns up.
A good answer sounds like: a name, a role, and how often the person you are talking to will be there themselves.
A red flag sounds like: "My guys will handle it," with no names and no site supervision described.
15. Will you use subcontractors, and can I verify their insurance too?
Why it matters: an uninsured sub on your property is your problem, not your contractor's. Illinois guidance recommends meeting them and verifying their licences and insurance.
A good answer sounds like: which trades are subbed, who they are, how long they have worked together, and no resistance to you checking.
A red flag sounds like: reluctance, or subs who change job to job with no established relationship.
16. Have you paid your subcontractors on time on your recent jobs?
Why it matters: this aims directly at what creates lien risk. A contractor who does not pay their subs leaves you exposed even when you have paid in full.
A good answer sounds like: a direct yes, usually with mild amusement, and often an offer to show you lien waivers from a recent job.
A red flag sounds like: defensiveness, or an explanation involving a client who did not pay them. That may be entirely true and it is also the circumstance in which suppliers come looking for your house.
17. How many other jobs will you be running at the same time as mine?
Why it matters: overcommitment is the most common reason good contractors deliver badly.
A good answer sounds like: an honest number, and how they will sequence yours around them.
A red flag sounds like: "Just yours." It is rarely true, and it is usually what someone says when they want the job.
Part 5: After the work is done
18. What is the warranty on labour, and what does it exclude?
Why it matters: materials are usually covered by the manufacturer. Labour is covered by the contractor, or by nobody.
A good answer sounds like: a stated period, in writing, with the exclusions named plainly.
A red flag sounds like: "We stand behind our work," with nothing written down.
19. Who handles cleanup and disposal, and is it in the price?
Why it matters: small, boring, and a surprisingly common source of extra charges.
A good answer sounds like: it is included, with skip hire or disposal specified.
A red flag sounds like: a pause, which usually means it is about to become an extra.
20. Can I speak to two customers from the last year with similar jobs?
Why it matters: recency and similarity matter far more than the number of references.
A good answer sounds like: names offered without hesitation, recent, and comparable in scope.
A red flag sounds like: references from several years ago, or jobs noticeably smaller than yours. Ask those references what went wrong and how it was handled, since nobody supplies a reference who will say "they were terrible."
If you only ask five
You will not get through twenty in a first conversation, and you do not need to. These five carry the most weight.
The certificate of insurance question, because it is the only one that protects you from a six-figure accident.
The permit question, because the answer decides who is responsible for code compliance.
The deposit question, because it is the clearest early signal of how a contractor runs their business.
The sworn statement question, because it is the one that stops a supplier you have never met from attaching a claim to your house.
The recent references question, because everything else is what they say about themselves.
The thing you are actually testing
You are not testing whether a contractor knows the answers. Most do.
You are testing whether they answer plainly, whether they volunteer the inconvenient parts, and whether being asked bothers them. That is a much better predictor of how the next three months go than anything on their website.
Once you have had the conversation and found someone you like, the paperwork side matters just as much. Our guide to vetting a contractor before hiring covers the verification steps and includes a printable checklist you can take to the site visit.
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