What I ask in every first meeting with a contractor
I've interviewed a lot of contractors over 25 years. And I've learned that what you ask matters a lot less than how you listen to the answer.
Still, I have a set of questions I ask consistently. Not to catch anyone off guard — to understand who I'm dealing with.
"Walk me through how you staff a project like this." I want to know who's actually going to be on the job. Not the principal who won the work, but the superintendent and project manager who will live with it day to day. Their experience level, their communication style, and how many other projects they're running at the same time are things I need to know. A contractor is only as good as the team they assign.
"What's your subcontractor bench for the major trades?" Do they have long-term relationships with their subs, or are they bidding out every trade to the lowest price on every job? Strong relationships with subs mean better accountability when things get hard.
"Tell me about a project that went sideways — what happened and how did you handle it?" I'm not looking for perfection. I'm looking for honesty, ownership, and problem-solving. A contractor who blames everything on the owner or the architect tells me everything I need to know.
"How do you handle scope gaps in the drawings?" Every set of construction documents has gaps. The question is whether a contractor tries to fill those gaps professionally, or waits to find them during construction and charges change orders for each one. The answer to this question tells me their approach to the whole relationship.
"What do you need from the owner to run a successful project?" This one is underrated. Good contractors know what slows them down — slow decisions, unclear scope, delayed submittals approvals. The ones who articulate it clearly are the ones who've actually thought about collaboration.
"What does your reporting look like? How do you communicate problems?" I want to know how they'll talk to me when something goes wrong. Because something will go wrong. The only question is whether I hear about it early enough to fix it.
I'm not looking for contractors who give me perfect answers. I'm looking for ones who are self-aware, direct, and haven't prepared a pitch deck worth of spin.
Those are the ones who show up for you at 6am when the project needs it.
What's a question you wish you'd asked a contractor before you hired them?
