Hiring someone to work on your home means trusting a person you've just met. You can't remove the risk completely, but a handful of questions filters out most of the trouble before it starts.
1. Can I get that quote in writing?
The most useful question on the list. A written quote forces the details: what's included, what materials, what it costs. It also gives you both something to point at later. Verbal estimates are where the "I thought that was included" arguments come from.
What you want to hear: yes, without hesitation, and it turns up promptly.
2. What's not included in this price?
Better than asking what is included, because it brings the assumptions out. Does the price cover taking the old material away? 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, and a clear explanation of how surprises get handled. Usually that's "we stop, show you, and quote it before carrying on."
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. Anyone established expects this question and won't be offended by it.
What you want to hear: yes, and a willingness to show proof.
4. Have you done this particular job before?
"Handyman" covers a lot of ground. Someone excellent at drywall may never have set a fence post. Ask about the actual work you need and ask to see photos of similar jobs.
What you want to hear: specific examples, ideally with pictures. 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 want a realistic answer, not the most flattering one. Someone who says they can start tomorrow and finish in a day may be underestimating.
What you want to hear: a specific window, with anything it depends on named, like material lead times, weather or permits.
6. How do you handle payment?
For bigger jobs, a deposit up front and the balance on completion is normal. What should give you pause is a demand for the full amount before any work starts, or pressure towards cash only with no paperwork.
What you want to hear: a sensible structure, a receipt or invoice, and normal payment methods.
7. What happens if something isn't right?
Good work occasionally still has a problem. What matters is whether they come back. Ask directly what happens if something shows up in the first few weeks.
What you want to hear: a clear "I'll come back and fix it."
"Can I see a recent review, or speak to a past customer?" Anyone doing consistently good work has people happy to vouch for them, and they'll be glad you asked.
The short version
Written quote. Clear exclusions. Insured. Relevant experience. Realistic timeline. Sensible payment terms. Stands behind the work. Any professional will answer all seven easily, because those are just the normal terms of doing business properly.
