Ask the Contractor These 5 Questions Before You Sign Anything

Ask the contractor these 5 questions before you sign anything. I've been on both sides of that table for 38 years, and I can tell you that the questions you don't ask are what cost you money. Most homeowners are too polite or too nervous to push back. Don't be. You're paying for a job, not a favor.

A fair bid isn't just the price. It's the details behind it. If you ask the contractor the right things upfront, you'll know whether you're getting a pro or a guy who'll leave you with a half-finished job. Let me walk you through the five questions I wish every homeowner would ask.

1. Who's actually going to be on my job site every day?

This is the first thing I'd ask the contractor. A lot of outfits sell you their best guy in the estimate, then put a green apprentice on the actual work. I've seen it happen. When I ran my crew, I made sure the foreman I promised showed up. But not every company does that.

Ask the contractor to name the person who will be there every day, and how much experience that person has. If they dodge the question, that's a red flag. You want a dedicated lead who answers to you, not a different face every morning. I've fixed enough jobs where the homeowner assumed the lead carpenter was the one they met. Ask me how I know.

2. How do you handle change orders?

Every renovation has surprises. You open a wall and find rotten studs or old knob-and-tube wiring. Ask the contractor how they price changes mid-job. Do they give you a written quote before starting the extra work? Or do they just bill you at the end?

A good contractor will tell you: “We stop, I give you a price, you approve it, then we proceed.” Anyone who says “don't worry, we'll work it out later” is setting you up for a fight. I learned that the hard way on my own kitchen. The original plan was $22,000. Change orders pushed it to $31,000 because I didn't pin down the process first.

3. What's not included in this bid?

The number on the estimate never covers everything. That's why you need to ask the contractor for a list of exclusions. Is permit fees in there? Dumpster rental? Moving the fridge so we can install flooring? I've seen bids that look cheap because they left out the electrical rough-in.

Get it in writing. Ask the contractor to show you exactly what's excluded. If they say “oh, that's standard,” tell them you want it itemized. Standard in my book means written down. I used to hand clients a sheet titled “What This Price Does Not Include.” It saved us both from arguments later.

4. How do you handle payment?

Never pay the full amount up front. I don't care how good the references are. Ask the contractor for a payment schedule tied to specific milestones. For example: 20% at signing, 30% when framing is done, 30% at drywall, 15% for finish work, and 5% upon final walk-through. That last holdback is your leverage.

If they want 50% upfront, walk. I've seen too many people lose their deposit to a guy who took off to another state. Legitimate contractors expect progress payments. It keeps both sides honest. And never pay cash – use a check or credit card so there's a trail.

5. Can I talk to your last three customers?

References are the obvious one, but ask the contractor for recent clients – jobs finished within the last six months. Even better if you can visit those jobs in person. I always gave my past clients' contact info and told them to call. If the contractor hesitates or gives you only one name, that's a warning.

When you call, ask specific questions: Did the crew show up on time? Were there surprise costs? Would you hire them again? Listen to hesitation. I once had a guy tell me “well, they finished eventually.” That's not a recommendation.

Ask the Contractor Yourself – Don't Let Your Spouse or Friend Do It

I know it's uncomfortable to grill someone who's selling you a service. But you're the one paying. If you don't feel comfortable asking these questions, bring a friend who will. I've seen couples where one person does all the talking and the other just nods. That's a mistake. Both of you need to hear the answers.

Ask the contractor directly. Look them in the eye. If they get defensive, that tells you everything. A pro won't flinch at these questions. They've heard them before. They'll respect you for asking.

Of course, I've screwed up plenty of jobs too. That's why I'm telling you this. The job I regret most is the one where I didn't ask the contractor myself – I assumed. Don't assume. Ask. It'll save you thousands and a lot of headaches.

6. What If the Job Runs Over Schedule?

Timing is money, but most contracts don't protect you if the project drags on. Ask the contractor for a realistic timeline and what happens if they miss it. A pro will give you a written schedule with key milestones. If they say “roughly six weeks,” push for specifics. “Roughly” is not a schedule.

Ask the contractor if they will include a clause that reduces the final payment if the job runs late due to their fault. Some contractors will offer a discount of a certain percentage per week of delay. That keeps them motivated. And ask how they handle delays from suppliers or weather. You want to know who bears the risk. I always built in a buffer, but I also communicated delays early. A good contractor does the same.