Most homeowners hire the wrong fence or deck contractor for the same reason: they ask the wrong question first. They ask “how much?” before they ask anything else, and by the time they figure out the rest, the cheap guy is gone and the deck is rotting.

I’ve been in this trade thirty-plus years. I’m not going to tell you to “always get three quotes” and call it advice. You already know that. What I’m going to tell you is the stuff the cheap guy doesn’t want you asking, because the answers to these five questions will tell you in about ten minutes whether he’s a pro or a problem.

1. Are the guys doing the work your employees, or are they subs?

This is where most homeowners get tripped up. They assume the guy they signed the contract with is the same guy swinging the hammer in their backyard. He’s not. A lot of fence and deck outfits sub out the labor.

That matters for one reason: insurance and accountability don’t automatically flow through. If “Bob’s Fence Co.” has a liability policy but Bob hired a two-man crew off Craigslist, those two guys aren’t necessarily covered under Bob’s policy. And if something goes wrong — bad install, damaged sprinkler line, kid trips over a pile of post sleeves — Bob can point at the subs, and the subs can disappear.

If they use subs, that’s not automatically a deal-breaker. Plenty of legit outfits run that way. But you need it in writing that the subs are covered under the contractor’s policy, and you need the contractor on the hook for the work — not the subs.

2. Can I see your worker’s comp certificate? Not just liability — worker’s comp.

People hear “fully insured” and stop asking questions. Don’t.

General liability covers property damage. If a guy puts a post hole through your gas line, that’s liability. Worker’s comp is the other one — it covers what happens when somebody gets hurt on your property while working on your job. Broken ankle off your deck framing, nail gun through a hand, hit in the head by a falling 4x4. That’s worker’s comp.

Here’s why this matters: if the contractor doesn’t carry worker’s comp and somebody gets hurt at your house, you’re the deep pocket. Your homeowner’s policy gets dragged in. I’ve watched it happen. A homeowner ended up writing a check because a sub fell off a ladder and the contractor had zero comp coverage. The contractor was a ghost two months later. The injury was real, and the bill stayed real.

Ask to see the certificate. Don’t take a verbal “oh yeah, we got that.” Get the actual cert, and confirm it’s active. Most pros have it on their phone and will send it before you finish asking.

3. Give me four references — two from the last six months, two from over a year ago.

Everybody asks for references. That’s why everybody hands over the same three names — neighbors, a cousin’s friend, and the one job they nailed last spring.

The trick is the timing. You want two recent references — within the last six months — so you can see how they finish a job, how they handle final cleanup, how they communicate at the end. And you want two old references, ideally a year or more out. Because anybody can build a deck that looks good on day one. The real question is whether it looks good after a full Pennsylvania winter, a hot summer, and a couple of freeze-thaws.

A guy I worked with in Roxborough got called back to a deck three years after the fact. The boards were cupping like potato chips because the previous contractor used green PT lumber, slapped it down wet, and never spaced it right. Looked great in the listing photos. Looked like a roller coaster two years later. The old references would’ve caught that — the recent ones never would.

If a contractor can’t produce two older references, ask why. Maybe he’s brand new, in which case price that risk in. Maybe he’s just selective. Or maybe his older work doesn’t hold up and he knows it.

4. When can you start, when will you finish, and how often will I hear from you?

If a fence or deck contractor tells you he can start tomorrow in the middle of building season, something is wrong. Good guys are booked three to eight weeks out, sometimes longer. Empty calendar in May or June means other people already said no.

Get a start date and an end date in writing. Not “early summer.” Not “in a few weeks.” Actual dates. And get a clause about what happens if it runs past the end date — most pros are fine with that, because they plan their schedules around it.

Then ask the question almost nobody asks: how often will I hear from you? Daily check-in? Weekly call? Text every morning before the crew shows? Pin this down. Half the complaints I’ve heard about contractors aren’t about the work — they’re about radio silence. Guy disappears for six days, homeowner panics, calls fifteen times, contractor shows up annoyed. All of it avoidable if you set the expectation up front.

5. What’s the payment schedule, and what happens if you hit rock or need a permit?

Here are the numbers to memorize:

  • Maximum 50% deposit. Anyone asking for 75% or 100% up front is either broke, scamming you, or about to be. Walk.
  • Balance on completion. Not “when we finish the framing.” On completion. Final walk, punch list done, then check.
  • Every add-on in writing before they do it. Rock drilling. Permit fees. Engineered footings. Concrete upgrade. Stair changes. If it’s not in the original contract and they discover it mid-job, they tell you, you sign a written change order, then they do it. No verbal “yeah we hit some rock, that’s another $1,200.” That’s how people get robbed.

Rock is the big one around here. Plenty of Philly-area properties have shale or bedrock closer to the surface than you’d think, and post holes turn into a different kind of job real fast. A pro will tell you up front: “If we hit rock at depth, here’s the per-hole charge for drilling.” A guy who waves it off and says “we’ll figure it out” is telling you he plans to figure it out on your wallet.

Bonus: Who’s locating your property corners?

This one catches people every time. Your fence goes on the property line. Great. Where exactly is the property line?

If your contractor says “we’ll pull it off the plat” or “we’ll measure from the house” — be careful. A plat map and a house measurement are not the same as a legal survey. If you put a fence three inches over the line, your neighbor can legally make you tear it out. I’ve seen that fight go ugly more than once.

A proper survey from a licensed surveyor runs $600 to $1,000 in most of the Philly metro depending on lot size and how marked-up the property is already. Some contractors will help you locate existing pins. Some won’t touch it. Either way, you need to know before signing who’s responsible for locating the corners, and what the plan is if the pins are missing.

One last thing: reviews and “get it in writing”

Online reviews are a starting line, not a finish line. Anybody can buy a five-star Google profile. Anybody can pay a service to bury bad ones. Use the reviews to build a short list, then do the actual work — call the references, see the certs, walk a job site if you can.

And get everything in writing. Start date. End date. Payment schedule. Scope. Materials. Brand of lumber. Stain or no stain. Disposal of old fence. Who handles the permit. Property corner plan. All of it. Verbal promises evaporate the second something goes wrong, and the contract is the only thing that decides who pays for it.

You don’t need to be a hardass. You just need to be the homeowner who clearly knows what to ask. Once a contractor sees that, the games stop — and the pros actually respect it. The problems? They go quote somebody else’s house. Which is exactly what you wanted.