When someone is getting ready to build something whether its a project, a home, an office, a restaurant; The decision to hire a general contractor often feels like a leap of faith. Most clients aren’t experts in construction. They don’t know the questions to ask, or they assume the contractor will just “handle it.” Sometimes that works out. But sometimes, that lack of clarity leads to delays, budget surprises, and stress that no one saw coming.
Klasik Construction in Chicago aims to position itself not just as a builder, but as a guide — someone clients can trust before, during, and after a project. And I can tell you this: the smartest clients are the ones who ask the best questions early. Not “How much will this cost?” Although yes, that’s important, the deeper questions that reveal how your contractor thinks, how they solve problems, and how they communicate when things go sideways (because eventually, something always does) is what's going to tell you the most about how the project ahead is going to go.
If you’re planning to build, and you’re about to sign with a contractor, here’s what I’ve learned are the most revealing things you can ask.
This might be the single most telling question you can ask. Good builders know that the success of a project starts long before the first nail. If your contractor talks about timelines, permits, value engineering, material sourcing, and collaborative planning? That’s a green flag. If they skip right to demo and framing, that’s not someone thinking strategically. As you can see in the customer journey here in figure 1.1, we have a comprehensive overview of what it will be like for you from the beginning to the end.
A lot of people assume that the contractor they meet with will be the one managing the build. That’s rarely the case. Ask who’s in charge day-to-day. How many other projects are they managing at the same time? What’s their communication style? Do you get updates weekly? Daily? Through email or text?
If you want a smooth project, you need to know the people who will be running it — not just selling it.
No one loves talking about change orders, but they happen. What you want to hear is a clear process: who initiates them, how they’re documented, how costs are communicated. Vague answers here are a bad sign.
A good contractor will walk you through how they protect you from scope creep and keep surprises under control.
Ask for real examples. Every contractor will tell you they stay on schedule — but how do they actually deal with a materials delay or a rainy month? The best ones don’t pretend these problems won’t happen. They show you how they plan for them.
You’re not just checking references. You’re gauging their willingness to be transparent. If they hesitate, or say they’ll “circle back,” that’s something to take seriously. If they hand over names without a second thought, that’s a sign of confidence.
The goal of these questions isn’t to interrogate your contractor — it’s to understand whether you’re entering a partnership or a transaction. At Klasik, we try to make that distinction really clear. We don’t want to just build. We want to solve problems, eliminate stress, and create an experience that makes clients want to work with us again.
If you’re reading this because you’re about to start a project, take your time. Ask these questions. And trust your instincts. The right contractor won’t just answer — they’ll welcome the conversation.
Author: Austin Woo - Digital Strategist at Rococo Creative
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