Ask the last contractor question
"Has anyone else worked on this?" is the most informative question in the walkthrough, and almost nobody asks it.
A customer who says the last contractor was slow but fine, and shows you what got finished, is telling you a normal story. A customer who describes three previous contractors as thieves, incompetents, and liars is telling you what they will say about you.
Listen for whether they ever describe their own role in what went wrong. People who can say "we changed our mind halfway and it cost us" are people you can work with.
Watch how they treat the paperwork
Pressure to start before the contract is signed is the clearest single predictor of a payment fight. So is a request to skip the permit, work off the books, or split the invoice into a smaller documented amount plus cash.
Those requests are not just risk to your license and insurance. They tell you this customer intends to keep the relationship undocumented, which is exactly the condition under which unpaid extras thrive.
A customer who reads the contract carefully and asks hard questions about it is the opposite signal. That is a good sign, even when it slows you down.
Find out who actually decides
If one spouse is walking you through and the other has not been mentioned, ask directly who signs and who approves changes. Jobs with a hidden second decision maker generate reversals mid-project, and reversals are unpaid work.
Same for property managers, adult children handling a parent's house, HOA boards, and landlords with an absent owner. Get the approving party named in the contract, and get change-order authority named with them.
Notice what they compare
A customer collecting three bids and asking each of you about scope differences is doing normal diligence. A customer whose only question is the number — and who mentions a much lower quote from someone unnamed — is shopping price and will keep shopping price after you start.
Price shoppers are not automatically bad customers. They become bad customers when the low bid they wanted meets the real cost of the work, and they look for the difference in your change orders and your final invoice.
Read the timeline expectations
Unrealistic urgency with no reason behind it is a flag; so is urgency attached to an event you cannot control, like a wedding or a closing date, without any acknowledgment of what happens if inspection slips.
Ask what happens if the work runs a week long. The answer tells you whether you are about to be blamed for the county's inspection backlog.
Trust the site itself
The property talks. Uncontrolled dogs nobody mentions, no parking within a block, blocked access to the work area, hoarded rooms, active leaks the owner describes as normal, and prior work that was clearly done badly and cheaply all change the real cost of the job.
None of those are disqualifying on their own. All of them belong in the price and in the contract, in writing, before you start — because unmentioned site conditions are the extras that never get approved.
Check the address before you price it
Your read on a customer is one data point from one conversation. Other crews have already been to that address, and some of them wrote it down.
Search the address on Union Break before you send the quote. If nothing is there, file your own report when the job is done. The system only works because crews keep feeding it.
The short version
- Ask who worked on the property before, and listen for how they describe it.
- Pressure to start before signing, skip permits, or pay cash predicts payment fights.
- Name the decision maker and the change-order approver in the contract.
- Price-only shoppers keep shopping price after the work starts.
- Probe timeline expectations and who absorbs a delay.
- Put dogs, access, parking, and existing conditions in the price and in writing.
- Search the address before quoting, and file a report after the job.