Talk to the Boss He Actually Worked For

The problem in one breath

You're about to hire a guy and all you've got to go on is what floats around town — somebody's cousin heard he walked off a job, somebody else swears he's the best hand in the county. Roofing's a small world and it runs on talk — half grudge, half gospel, and you can't tell which is which. So you hire on a rumor or you pass on a rumor. Both are guessing.

Why it happens

Checking references feels like paperwork you skip when you're short a man and the season's already on you. And the easy version — calling around behind his back to whoever you happen to know — feels like real diligence but isn't. Secondhand talk tells you more about the man doing the talking than the one you're hiring. The boss who runs him down might be the one who stiffed him on his last check. You're hearing a story with one whole side left out.

The play

Skip the gossip. Get the candidate to put you on the phone with the actual bosses he worked under — the ones YOU pick, not just the two buddies he'd offer up.

1. Get his real work history, not his reference list. Ask him to walk you through his last three or four roofing jobs — the company, the foreman or owner, roughly when, and why he left each one. You want the whole trail, including the job that ended bad. Now the names are yours to pick from, not the two he came in ready to hand you.
2. Pick who you call — and have HIM set it up. Out of that history, pick two that matter — three if you can get them — usually the most recent boss and the one he stayed with longest. Then tell him plain: "Have them expecting my call." A man with nothing to hide makes that happen inside a day, and the ducking is information too. One carve-out: if he's still working there, leave that boss alone until you're ready to hand him the job — take the next two down the list and make the current boss your last call.
3. Lead with the one must-ask question that gets a straight answer. Nobody bad-mouths a guy to a stranger on the phone, so don't ask "was he any good." Ask: "What job would you put him on tomorrow, and what job wouldn't you?" A boss will answer that one honest every time, because it lets him praise the man and warn you in the same breath. The "wouldn't" is where the truth is hiding.
4. Read a bad word as a data point, not a verdict. One boss running him down is one story — this trade is thick with grudges. Weigh it against the rest. The same warning from two or three bosses is the truth about the man. One sour boss out of three — especially the one he left over money — is just one man's side of a fight.
5. Read the guy who can't produce anybody. Here's the tell most owners miss. A man who's worked roofs ten years and can't put you on the phone with a single old boss willing to talk — that silence is worth chasing. Shops fold, bosses move, and plenty of good hands worked cash for outfits that don't exist anymore, so give him room to explain. But a man who can't put up one name out of a whole career, and can't say why, has told you something.

Do this this week

On your next serious candidate, before you talk money, get his last three jobs and the bosses' names. Pick two that matter — three if you can get them — and tell him to have them expecting your call. Then run each boss through the same five — the reference five below — leading with the must-ask: what job would you put him on, and what job wouldn't you? That's the whole check, and it beats every rumor in town.

The tool

The reference five — print them, keep them by the phone, and ask every boss the same five so you can line the answers up side by side:

FIVE QUESTIONS FOR HIS OLD BOSS  (ask all five, same order, every call)

  1. What job would you put him on tomorrow — and what job wouldn't you?
  2. Would you hire him back? (listen for the pause before the yes)
  3. When it got hard — bad weather, a long day, a screw-up — how'd he handle it?
  4. Did he show up, on time and ready, every day you needed him?
  5. Anything I ought to know that I haven't thought to ask you?

Same five, every boss. When two or three answer them the same way, that's the man you're really hiring.

If your crew is 1099

Same play, and if anything it matters more with a sub — you won't train him or watch him day to day, so what he's done on other roofs is most of what you'll ever get to know. Ask his past customers about the work and the terms: did he finish, did he stand behind a callback, did he bill you straight. You're checking his track record as a business, not whether he'd take coaching — a sub you pick on his history, you don't shape him into one. Hire the sub whose old customers would hand him the next roof themselves.