The questions worth asking a contractor before you hire

Nearly every guide to hiring a contractor gives you the same questions: are you licensed, are you insured, can I see references. They are worth asking and they filter almost nobody, because any contractor who has been in business a year answers all three fluently. The questions below are the ones where good and bad answers actually look different.

Who is actually on site, and who runs the job?

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.

What happens when you find something unexpected?

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.

What is your allowance for concealed conditions?

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.

Who pulls the permit?

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.

How is the payment schedule structured?

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.

Can I talk to a client from two years ago?

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.

What is not included in this price?

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.

How do you handle the punch list?

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.

The one to ask yourself

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.