By the time most disputes reach me, the answer was available at the very beginning — it just was never asked for. Choosing a contractor is the single most consequential decision in a project, and it is usually made on the basis of a price and a good first impression. Here are five questions that reveal far more than either.
1. “Can I see the schedule, not just the start date?”
Anyone can name a start date. A real schedule shows the sequence — when trades arrive, what they depend on, and where the critical path runs. A contractor who can’t produce one hasn’t planned the job; they’re going to plan it on your time.
2. “How do you handle change orders?”
The answer should be specific and in writing: how changes are priced, who approves them, and when. “We’ll work it out as we go” is the most expensive sentence in construction.
3. “Who, exactly, is on site every day?”
The person who sells the job is rarely the person who runs it. Ask who your day-to-day point of contact will be, how many other jobs they’re carrying, and how often the principal actually visits.
4. “What does your bid exclude?”
Every bid has exclusions; cheap bids simply hide them. Reading what a bid leaves out tells you more about the final cost than the number on the cover page. This is where an owner’s representative earns their keep.
5. “Can I speak with a client from a job that went sideways?”
Anyone can supply a happy reference. The more useful question is how a contractor behaves when a project hits trouble — because every project eventually does. The willingness to answer this question honestly is itself the answer.
You don’t have to ask these alone. Part of representing an owner is sitting in these conversations with you, hearing what’s said, and noticing what isn’t.