Summer doesn’t build a crew. It grades one. By the time the work stacks up in July, whatever habits your people carried into the season are the habits you’re stuck with, and the schedule leaves no room to fix them.
TL;DR: The slow season is when you train, cross-train, fix broken habits, and decide who leads next year. Contractors who treat winter as dead time show up to the busy season with the same problems they had last year, then blame the schedule for a problem the calendar didn't create.
Most contractors have this backwards. They spend the winter cutting costs and waiting for the phone to ring, then spend the summer wondering why the same three problems keep showing up on the same jobs. The building happens in the months nobody is watching.
Summer reveals your crew, winter builds it
Busy season is a test. Nobody learns much during a test. When volume is high, every hour of instruction costs production hours, and production is what the whole company runs on, so teaching gets cut first. The foreman who’d normally walk a new guy through a detail is handling the schedule, the weather, a late delivery, and an inspector, all before lunch.
So the new hire learns by watching whoever is standing closest. Sometimes that’s your best installer. Sometimes it’s the guy with six shortcuts and a bad attitude. You don’t get to choose, because you’re not there.
The crew you see in July is a report card on decisions you made in January. Callbacks, punch lists, safety near-misses, the two guys who can’t cover for each other. All of it traces back to time you either invested or skipped months earlier. Grading the crew in the summer is fair. Expecting to fix them in the summer isn’t.
The slow season removes that tax. Nobody is losing billable production while a second-year guy takes three tries to get a detail right. That’s the whole point. Winter is the only stretch of the year when a mistake costs almost nothing, which makes it the only stretch when you can afford to let people make some.
Training that sticks looks like the work
Training that happens once, in a conference room, with a slide deck, doesn’t survive contact with a roof. People remember what their hands did. If the training doesn’t look like the work, it won’t show up in the work.
OSHA’s guidance on education and training says peer-to-peer training, on-the-job training, and worksite demonstrations can convey hazard controls and promote good work practices. Worth reading directly if you’re building a safety program this winter (OSHA, Education and Training).
OSHA’s worker participation guidance goes further on who should be involved. It says workers should participate in training coworkers, defining safe practices, and improving safety programs (OSHA 3886, Worker Participation). That is guidance about safety programs specifically, not a claim about craft quality or production speed.
The same structure works for craft training, and that part is opinion rather than anything OSHA says. Build the detail in the shop. Build it wrong on purpose, then have the crew find what’s wrong with it and fix it. Set up a mock-up wall and let people run flashing, fasteners, and terminations on it until the sequence is boring. Boring is the goal. Boring is what holds up when it’s 94 degrees and the crew is behind.
Keep the sessions short and frequent. An hour a week for three months beats a full day in February that everyone forgets by April. And let your best installers teach. The person who can explain why a detail matters is worth more to you than the person who can only do it fast.
Cross-train before you need it
Look at your crew and count how many tasks have exactly one person who can do them. One guy runs the brake. One guy does layout. One guy is the only one the customer likes talking to. Every one of those is a single point of failure sitting on your schedule.
In July those points fail at the worst possible moment. Somebody quits, somebody gets hurt, somebody takes the vacation they earned, and suddenly four people are standing around because the one who knew how to start the work is gone. Everybody calls that a labor shortage. It’s a training gap you chose not to close.
Winter is when you can afford the slower hand. Rotate the assignments. Put the layout guy on the brake and the brake guy on layout, and accept that the first few runs will be ugly. Ugly in January is cheap. Ugly in July is a change order.
Write it down while you do it. A skills matrix isn’t complicated: names down the left side, tasks across the top, and three levels in each box for cannot do it, can do it with help, can teach it. Fill it in honestly and post it where the crew can see it. Two things happen. You can see instantly where your depth is thin, and your people can see exactly what they need to learn to move up. That second part matters more than most owners expect.
Winter is when you pick next year’s leaders
Promoting a foreman in June is a panic decision. You end up with whoever is standing there when a crew needs a head, and you hand them a title with no runway and no coaching. Then you spend the rest of the season managing the consequences.
The right time to name a foreman is before you need the seat filled. Winter gives you months to run low-stakes tests. Have a candidate run the toolbox talk. Have another do the material takeoff on a job you already priced, then compare their numbers to yours. Let one lead the shop mock-up. Put someone in charge of truck and inventory readiness for the whole slow season.
Then watch how they handle it, not just whether they finish. Does this person explain the task, or take it over and do it themselves because that’s faster? Do they say “I don’t know” out loud, or guess and cover? Do the other guys ask them questions when you’re not in the room? Your best set of hands is not automatically your best leader, and a lot of companies lose a great installer and gain a bad foreman in the same afternoon.
Tell the candidates they’re being considered. Some owners keep it quiet to avoid disappointing anyone. That’s backwards too. People rise to a stated expectation, and the ones who aren’t ready usually tell you so themselves once they see what the job actually involves.
How to keep good people through a slow winter
You can’t train a crew you lost in December. Retention through the slow season comes down to two things, and neither one is a speech.
The first is honesty about hours. Tell people what the winter looks like as early as you know it. What weeks are light, what work is available, when the calls pick back up, what you can and can’t guarantee. Silence is what pushes a good installer to answer another contractor’s ad. A guy who knows February will be thin can plan for it. A guy who finds out in February starts looking.
The second is giving the winter a purpose. Shop fabrication, service calls, repairs, warehouse work, equipment maintenance, and site inspections are all real work that doesn’t stop when the weather turns. Pay for certification and training time the same way you pay for production time, because it is production, just deferred. Ask each person what they want to be able to do by spring, then build part of the winter plan around those answers.
People stay where they’re getting better at something. A winter that makes someone more valuable is a reason to come back in March. A winter of silence and no hours is a reason to be somewhere else.
What to run this winter
Here’s the short version, in the order I’d do it.
- Write down last season’s five most expensive mistakes. Not vague problems, actual jobs with actual costs. Those five items are your training curriculum. You don’t have to guess what to work on.
- Build the skills matrix. Names, tasks, three levels. Post it. Circle every task with only one qualified name next to it.
- Pick three details to train hands-on. Shop mock-ups, short sessions, your best installers teaching. Run them until the sequence is boring.
- Put safety training on the calendar with real dates. Not “sometime this winter.” Dates, times, who is running each one. Start with OSHA’s education and training guidance if you don’t have a program yet.
- Name two or three foreman candidates and give each one a winter assignment. Real ownership of something small, then a real conversation about how it went.
- Have a straight conversation with every crew member about winter hours. One at a time, not as a group announcement.
- Decide who isn’t coming back. If someone was a problem all summer, winter is when you deal with it. Carry that decision into spring and you’ll end up making it in the middle of a busy week, badly.
None of that requires a budget you don’t have. It requires deciding that the slow season is work, not a gap between work.
The takeaway
Winter is the one stretch of the year when you can work on the crew instead of through it. Every hour you put into training, cross-training, and leadership development in January is an hour you don’t have to spend firefighting in July, and every hour you skip comes back with interest.
Your July crew is already being built. The only question is whether you’re the one building it.
About Khary Penebaker
Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.
Common questions
How should roofing contractors use the slow season?
Treat it as build time, not dead time. Start by writing down the five most expensive mistakes from last season, because those become your training list. Then build a skills matrix, run short hands-on sessions in the shop, rotate people through tasks they don't normally handle, and give foreman candidates real assignments. A mistake in the slow season costs almost nothing, and that is exactly why it's the right time to let people make some.
What training actually sticks with field crews?
Training that looks like the work. People remember what their hands did, not what they watched on a slide. Build mock-ups in the shop, run the actual detail, and repeat it until the sequence is boring. On safety specifically, OSHA's guidance says peer-to-peer training, on-the-job training, and worksite demonstrations can convey hazard controls and promote good work practices. Short and frequent beats one long session in February that everyone forgets by April.
How do you keep good crew members through a slow winter?
Honesty about hours and a reason to come back. Tell people early what the winter looks like: which weeks are light, what work is available, when calls pick back up. Silence is what sends a good installer to another contractor's ad. Then give the winter a purpose with shop fabrication, service calls, repairs, and paid certification time. People stay where they're getting better at something.
When is the right time to promote a foreman?
Before you need the seat filled. Promoting in June is a panic decision, because you end up with whoever is available rather than whoever is ready. Use the slow season to run low-stakes tests: have candidates lead a toolbox talk, run a takeoff you already priced, or own the shop mock-up. Watch whether they explain the work or take it over, and whether the crew asks them questions when you're not in the room. Your best set of hands is not automatically your best leader.