There's nothing wrong with a small operation. Some of the best work in any trade comes from a two-person crew with a truck and twenty years of experience. The difference that matters isn't company size — it's whether the person quoting your job runs it like a business.
These ten questions surface that quickly. Ask them at the estimate, before anyone is emotionally invested in the number.
How long have you been doing this specific kind of work?
Not how long they've been in business — how long they've done your job. A roofer who mostly does repairs is a different proposition on a full replacement. You're listening for specificity, not a number.
Who will actually be on my property?
Employees, long-time subs, or day labor found this week? All three can produce good work, but you want to know before you're deciding whether to leave the house. Ask whether the person quoting will be on site at all.
Who's my point of contact once work starts?
On many jobs the salesperson disappears after the deposit clears. Get a name and a number for the person who answers when something needs a decision at eight in the morning.
What's not included in this price?
The most useful question on the list. Every job has exclusions — disposal, permits, unexpected rot, restocking fees. A pro answers this fluently because they've been burned by it. A vague answer means you'll be discovering the exclusions one invoice at a time.
What happens if you open it up and find something worse?
You want a written change-order process: work stops, you get a documented price, you approve it before anyone continues. What you don't want is discovering a change after it's been done and billed.
What's the warranty — on labor, and on materials?
These are two separate things. Manufacturers warranty their product; the contractor warranties the installation. Most defects trace back to installation, so the labor warranty is the one worth pinning down in writing. Ask how long, and ask what voids it.
Are you pulling a permit for this?
If the answer is that it doesn't need one, ask them to explain why. Sometimes that's genuinely true. Sometimes it means they can't pull one, which is a much bigger problem than the permit fee.
What's your timeline, and what could push it?
Honest answers include weather, inspection scheduling, and material lead times. An answer with no contingencies in it usually means the schedule hasn't been thought about, and yours will be the job that slips when a bigger one appears.
How do you handle cleanup and debris?
Small question, disproportionately revealing. Contractors who have a real answer — dumpster on day one, daily sweep, magnet run for nails — tend to run organized jobs generally.
Can I see a job you finished about a year ago?
Anyone can show you work from last week. A year later, you find out whether the caulk lines held, whether the paint matched, and whether the homeowner is still happy. This is the question that separates a portfolio from a track record.
What you're really listening for
You're not grading the answers individually. You're listening for whether this person has thought about the parts of the job that aren't the fun part — the paperwork, the failure modes, the thing that goes wrong in week two.
Someone who has run a lot of jobs will answer most of these before you finish asking. Someone who hasn't will improvise, and you'll hear it.
One more signal worth weighing: how fast they got back to you in the first place. A contractor who takes four days to return a call about winning your job will not move faster once they already have your deposit.
And one question to ask yourself
Did they try to close you on the spot? Discounts that expire today, financing paperwork at the kitchen table, pressure to sign before you've compared anything — that's a sales process, not a trade. Good contractors are usually busy enough to let you think about it.