Hiring someone to work on your home takes a certain amount of trust, usually extended to a person you just met. You can't eliminate the risk entirely, but a handful of questions filters out most of the trouble before it starts.
1. "Can I get that quote in writing?"
This is the single most useful question on the list. A written quote forces specifics — what's included, what materials, what it costs — and it gives you both something to point at later. Verbal estimates are where "I thought that was included" arguments come from.
What you want to hear: Yes, without hesitation, and it arrives promptly.
2. "What's not included in this price?"
Better than asking what is included, because it surfaces the assumptions. Does the price cover hauling away the old material? Permits, if the job needs one? What happens if they open up a wall and find rot?
What you want to hear: A straight answer about exclusions and a clear explanation of how surprises get handled — usually "we stop, show you, and quote it before continuing."
3. "Are you insured?"
If someone gets hurt on your property or something gets damaged, insurance is what stands between you and a bad situation. Any established pro expects this question and won't be offended by it.
What you want to hear: Yes, plus a willingness to show proof. Hesitation or deflection here is a real signal.
4. "Have you done this specific job before?"
"Handyman" covers enormous ground. Someone excellent at drywall may have never set a fence post. Ask about the actual work you need, and ask to see photos of comparable jobs.
What you want to hear: Specific examples, ideally with pictures — and honesty when something is outside their wheelhouse. Being told "that's not my strength, but I know who to call" is a good sign, not a bad one.
5. "When can you start, and how long will it take?"
You're looking for a realistic answer, not the most flattering one. Someone who says they can start tomorrow and finish in a day may be underestimating — or may not have much work, which is its own signal.
What you want to hear: A specific window, with any dependencies named (material lead times, weather, permits).
6. "How do you handle payment?"
Standard practice for larger jobs is a deposit up front and the balance on completion. What should give you pause is a demand for the full amount before any work begins, or pressure toward cash-only with no paperwork.
What you want to hear: A reasonable structure, a receipt or invoice, and normal payment methods.
7. "What happens if something isn't right?"
Good work occasionally still has an issue. What matters is whether they come back. Ask directly what their policy is if a problem shows up in the first few weeks.
What you want to hear: A clear, unhesitating "I'll come back and fix it." That answer tells you a lot about how they see their reputation.
The short version
Written quote. Clear exclusions. Insured. Relevant experience. Realistic timeline. Sane payment terms. Stands behind the work. A pro will answer all seven easily — those are just the normal terms of doing business well.
