The 10 questions to ask any contractor before you sign

Hiring a contractor is a high-stakes decision and most homeowners do it once or twice in a lifetime. The contractor does it every day. That asymmetry is the whole problem — and these ten questions level it out.

1. Who's actually on my job?

Big company or small, you want to know whether the owner is showing up or whether it's a crew lead you've never met. Both can be fine — but you want to know.

2. Walk me through your insurance

Liability, workers' comp, and ideally an umbrella. Ask for a current certificate. If they hedge, stop the conversation.

3. What's your payment schedule?

Be wary of a request for most of the job up front. A reasonable schedule is a modest deposit to start, draws as the work hits milestones, and the last payment on punch-list completion. Ask what the deposit covers and get the whole schedule written into the contract.

4. Permits — yours or mine?

Ask who pulls the permit. It's usually the contractor, because their license is on the line. If they ask you to pull it, ask why.

5. Change order process?

Every contractor has change orders. Good ones write them up. The conversation should be: "Here's the new line item, here's the cost, please sign before we proceed."

6. Daily start time and clean-up

Sounds petty. Isn't. A crew that turns up when it said it would and leaves the site clean is a crew with discipline.

7. Subs — known or sourced?

If they sub out the electrical, plumbing, drywall — fine. Ask which subs they use. The answer should be names, not "the usual."

8. Lien waivers

You want a partial lien waiver from the GC and each major sub at every payment, and a final lien waiver from each at completion. Don't release the final payment without them.

9. Communication cadence

Weekly check-in? Daily? Slack? Email? Whatever it is, agree before kickoff.

10. References from a job that went sideways

Anyone can give you a happy reference. Ask for a job that had a problem and how it was resolved. The answer is the whole tell.