The questions worth asking a contractor before you hire

The person quoting is frequently not the person building. Ask who the lead on site will be, whether the crew is employed or subcontracted, and who you call when something is wrong on a Tuesday. There is nothing wrong with subcontracted labour — most trades work that way — but a contractor who cannot tell you who is turning up is a contractor without a schedule.

This is the single most useful question you can ask, and the answers vary enormously. A good contractor has a process: they stop, document it, price it, and get your written approval before continuing. A vague answer here predicts exactly how the mid-project conversation will go, and mid-project is the worst possible time to discover you have different expectations about who decides and who pays.

On any project opening a wall in an older house, some allowance should be in the bid. A contractor who has priced zero contingency is either inexperienced or planning to bill it as a change order. Ask what it covers and what falls outside it.

The answer should be the contractor, under their own licence. If they ask you to pull it as an owner-builder, they are shifting liability onto you — you become responsible for the work meeting code, and your recourse narrows considerably if something goes wrong. It is occasionally legitimate on very small jobs. On anything substantial it is a warning.

Money should track completed and inspected milestones, not calendar dates. A deposit to secure the slot and order materials, payments at defined stages, and a meaningful final payment held until the punch list is genuinely done. Be wary of a large up-front deposit relative to the total, or any schedule where you have paid most of the contract before most of the work exists.

Recent references are curated and everyone has three happy customers from last month. A client from two years ago tells you what the work looks like after a winter, whether the contractor came back when something needed attention, and whether the relationship survived the final invoice. That is the reference worth chasing.

Asking what is included gets you the sales pitch. Asking what is excluded gets you the truth: disposal, permits, painting after drywall repair, moving furniture, reconnecting appliances. Exclusions are where two bids that look similar turn out to be thousands apart.

Every project ends with small unfinished items. What matters is whether there is a process — a walkthrough, a written list, an agreed timeframe — or whether it depends on you chasing. This is where the largest share of homeowner frustration lives, and it is entirely predictable from how the question is answered.

After the conversation, ask whether they answered the question you asked or the question they wanted to answer. Contractors who deflect during a sales conversation, when they are trying hardest to win you, do not become more direct once they have your deposit.

'Fully insured' is a phrase, not a fact. Ask for a certificate of insurance naming the current policy period, and check two things: general liability, which covers damage to your property, and workers' compensation, which matters if someone is injured on your job. The workers' compensation question is the one people skip and the one with the largest downside. If an uninsured worker is hurt on your property, the exposure can land on your homeowner's policy — or on you.

Most contractors subcontract at least some trades, and there is nothing wrong with that. What matters is whether they have long-standing relationships or find someone new each job. Ask who does their electrical and plumbing, how long they have worked together, and who is responsible if a subcontractor's work fails. A contractor who names the same people repeatedly is running a stable operation. One who is vague is assembling a crew per project, which shows up as scheduling problems later.

Every timeline rests on assumptions, and the useful question is which ones. Does it assume permits are issued within a normal window? Does it include inspection scheduling? Does it assume materials arrive on the quoted lead time? A contractor who can articulate what would push the date has thought about it. One who gives a confident single number without qualification is either extremely experienced or has not planned it at all, and those two look identical in a first conversation.

This is the most revealing question on the list, and it is uncomfortable to ask. Everyone who has built anything has had a job go sideways — a discovery, a supplier failure, a subcontractor who let them down. What you are listening for is whether they take responsibility for the parts that were theirs, and whether the resolution sounds like a process or a fight. Someone who claims nothing has ever gone wrong is either new or not being straight with you.

Good projects have obligations flowing both ways. Ask what decisions they will need from you and by when, whether they need clear access at particular times, and what would delay them if you did not provide it. A contractor who answers this specifically has run organised projects. It also gives you a genuinely useful list — most homeowner-caused delays are selection decisions made two weeks after they were needed.

Rather than asking for references, ask for the contact details of the last three clients in sequence, whoever they were. Curated references are all happy. The last three in order include whichever one was difficult. If a contractor is comfortable with that, it tells you a great deal before you have called anyone. If they steer you toward a selected list instead, that is information too.

Ask for the exact legal business name and Oregon CCB number, then compare them with the state record, proposal, contract, permit applicant and payment instructions. Oregon CCB consumer tools show active status, bond, insurance information and available history. If a salesperson, trade name or lead service differs from the contracting business, ask each party's role. The company signing the contract, supervising the project and receiving payment should not remain ambiguous.

Oregon BCD directs owners to project-specific building and specialty-trade permit resources. Ask which approvals apply, who prepares documents, who obtains each permit, who schedules inspections and what final evidence you receive. A contractor who says no permit is needed should identify the reviewing jurisdiction and scope behind that answer. Keep approved plans and inspection records with the contract.