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K M. Kerr
K M. Kerr

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Your Contractor Hopes You Never Ask These 3 Questions

The woman on the phone was crying. Not the quiet kind — the kind where she had to stop mid-sentence three times.

She'd handed a contractor $18,500. He gutted her kitchen, framed one wall, then vanished. Phone disconnected. Website gone. The "company" was a Gmail address and a cell phone.

She called me because a neighbor had used Kerr's Painting & Renovations three years earlier and still had my number. She wanted to know if I could finish what someone else started.

I could. But what I really wanted to do was go back in time and hand her three questions before she wrote that check.

I've been painting and renovating in the Bahamas since 1992. I've walked into the aftermath of this exact situation more times than I can count. And here's what I know: bad contractors don't hide. They reveal themselves. You just have to know where to look.

Here's what nobody in the trade will tell you about hiring a contractor.

The Three Questions

1. "Can I see your last three jobs — in person?"

Not photos. Not a Facebook gallery. Not a "portfolio" on their phone.

Photos lie. I've seen contractors show pictures of work they didn't do. I've seen them photograph the one good corner and crop out the mess. I've seen them use stock images.

Ask to visit. If they hesitate — even for a second — that's your first red flag. A contractor who does good work has clients who will open their doors. A contractor who doesn't will suddenly have "privacy concerns."

What you're looking for when you get there: look at the corners. Look at the trim lines. Look at the floor protection. When I walk onto a job site, the first thing I put down is a proper canvas drop cloth — 9x12, heavy cotton, the kind that actually stops paint from bleeding through to a $4,000 floor. Not plastic sheeting. Not old bedsheets. A real painter uses real drop cloths because they've learned the hard way what happens when they don't.

2. "What tape are you using?"

This sounds small. It's not.

Walk out to their truck. Look at what's in the bed. If you see cheap blue painter's tape — the kind that's $3 a roll at the discount bin — they're cutting corners before they've opened a can.

The difference between cheap tape and FrogTape Multi-Surface is the difference between a line you have to fix with a razor blade and a line that looks like it was cut with a laser. I learned this the expensive way. I spent years touching up bleed-through because I was saving $4 a roll. Then I did the math: I was spending 20 minutes per room fixing tape lines. At my rate, that $4 "savings" was costing me $15 in labor every single time.

A contractor who uses cheap tape is telling you something about every decision they make. They'll save $4 here, $10 there — and you'll pay for it in the finish.

3. "Do you own your sprayer, or are you renting it?"

If they're spraying cabinets, trim, or exterior — and they're renting the sprayer from Home Depot — they don't do this enough to own the equipment.

A Graco Magnum X5 in the truck bed means something. It means this person sprays regularly. It means they've put enough hours through the gun to know how to dial in the pressure, how to thin the paint correctly, how to avoid orange peel and runs. You can't learn that on a rental.

I've watched homeowners pay premium prices for a "professional spray finish" and get a textured mess because the guy was learning on their walls. The rental receipt was still in his pocket.


What the uninformed homeowner does: They ask about price first. They compare three quotes and pick the middle one. They never look in the truck, never ask to see work in person, never question the materials. Then they wonder why the trim lines look like a child drew them and there's paint on the hardwood.

What the smart homeowner does now: They interview the contractor. They ask the three questions. They watch the face when they ask them. A good contractor lights up — they want to talk about their work. A bad one gets defensive or vague. That difference is worth more than any online review. It's worth the entire cost of the job.


You didn't hire a contractor to gamble with your home. You hired them because you want it done right — once. These three questions won't catch every bad actor, but they'll catch most of them. And the ones they don't catch? They'll make nervous. And nervous contractors fix their mistakes faster.

I've spent 34 years watching what separates the pros from the pretenders. It's never the price. It's never the sales pitch. It's what's in the truck and what's under the drop cloth.


Get The Homeowner's Price Protection Guide — free.
I put 34 years of job-site experience into this. No opt-in walls, no courses to buy — just the guide.
👉 Get it here

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