Most bad contractor experiences trace back to something that could've been asked, and answered, before any money changed hands. Here are five worth asking every time.
1. Are you insured, bonded, or warrantied for this kind of work?
Not every job needs all three, but you should know which ones apply and get a straight answer, not a shrug.
2. Who's actually doing the work?
Some contractors sub out parts of a job. That's not automatically a red flag, but you want to know who's showing up, and who's accountable if something's wrong afterward.
3. What's your estimated timeline, realistically?
Ask for a range, not a best case. A contractor who's upfront about delays being possible is usually more reliable than one who promises a perfect schedule.
4. How do you handle changes once work has started?
Almost every project has at least one thing that changes mid-way. Knowing how that gets priced and approved before it happens avoids an awkward conversation later.
5. Can I see recent work similar to mine?
Not a portfolio of their best-ever project from years ago, recent, comparable work. It's the closest thing to a preview of what your own job will actually look like.
Asking all five in one message might feel like a lot, but a contractor worth hiring will treat it as a normal, expected part of the conversation, not an inconvenience.