Why developing skilled workers is getting harder, and what contractors can do about it
A contractor told me not long ago that he had a full payroll, but hardly anyone who could run a job without him breathing down their neck. “All I’ve got is helpers,” he said, shaking his head.
People are finally talking about the trades again, which is excellent. But a fresh wave of eager greenhorns doesn’t get the actual work completed. There’s a reason we call them “skilled” trades.
We’ve been wringing our hands over the skills gap for years.
But there’s a teaching gap right alongside it. A time gap, too. And judging by how fiercely folks are poaching top talent from one another, there’s just a plain old retention gap.
We are ate up with gaps.
You already know what that looks like. You’re trying to get today’s work done while bringing along the people you’ll need for tomorrow. You’re answering questions, checking work, solving problems, and probably even running calls yourself because there aren’t enough experienced hands to handle everything.
Then, just when somebody tiptoes into proficiency, another contractor comes along waving a bigger paycheck.
So where do we start to close those gaps?
First, look closely at the crew you already have; they might be ready to do more than you’ve had the time to notice. Before assuming someone isn’t catching on quick enough, consider how you’re explaining the work.
Has He Seen the Movie?
Have you ever been telling somebody a story and realized that the perfect line to finish it comes from a movie?
Maybe you’re about to deliver the punchline: “I’m your huckleberry.”
But before you say it, you check: “Have you ever seen Tombstone?”
If they have, you fire away. They get the reference, and the joke lands.
If they haven’t, you pause. You know that if you drop the line anyway, it’s going to land flat. Because nobody wants to tell a joke that flops, you either explain the context beforehand or choose a different way to say it. We’re naturally careful about references in conversation because we hate the awkwardness of a failed punchline.
But then we get to the job site, get in a hurry, and leave out half the explanation, all while hoping the huckleberry will do the heavy lifting. It won’t.
You’ve spent years learning to recognize problems, anticipate what might go wrong, and make decisions that now seem almost automatic. You can walk up to a piece of equipment and instantly notice details a helper wouldn’t even think to look for. Then you give quick directions while he just stares back at you with a blank look.
It’s easy to assume he’s not paying attention or just needs more practice. But the real issue is that you delivered the punchline without checking if he ever saw the movie.

The Curse of Knowledge
There’s actually a name for this. Psychologists call it the curse of knowledge.
Once you know something well, it becomes surprisingly difficult to remember what it was like not to know it. You forget how many little pieces of information you had to collect before the whole thing made sense.
That can make teaching harder than it ought to be.
Experienced tradespeople have taught generations by demonstrating the work, but an apprentice who needs more than to be shown could still become your next great journeyman.
Before deciding somebody isn’t catching on, ask, “What are three practical ways to teach this skill?”
What about showing them the work, having the apprentice write down the steps, and coaching them through repeated practice?
Think about how much grace we give a dog we’re trying to train. We understand that the dog doesn’t speak English, so we pay attention to our tone, our timing, our body language, and whether we’re being consistent. If the dog doesn’t understand what we’re asking, we might try demonstrating it differently. Admittedly, there’s a fair amount of bribery involved.
We make similar adjustments when we’re speaking with someone whose first language isn’t English. We slow down, choose different words, gesture, or check to make sure we’re understanding each other. Or, God help us, we just start talking louder, as though English becomes easier to understand with more decibels.
But at least we recognize that there might be a communication barrier.
Put two people on a job site who both speak English, though, and suddenly we assume the explanation is obvious.
We leave out context constantly.
“Go check the subcooling and superheat on that unit.”
But, are you looking at a TXV or a fixed orifice? What kind of reading are you expecting based on today’s weather and indoor temperatures?
You know what those numbers mean because you’ve done this for years. Your apprentice might get a reading and have no idea whether it means the charge is right, airflow is blocked, or a part is failing. He doesn’t even know which questions to ask yet.
The apprentice might hook up the gauges and write down the numbers perfectly, yet still learn very little. He took the readings. You told him to take the readings. Everybody did what they were supposed to do.
Except nobody explained what he was supposed to be noticing.
The next time you give an instruction, try adding the reason behind it. Tell the apprentice what you’re looking for, why it matters, and what might happen if the problem goes unnoticed.
Here’s the important piece: Then ask him to tell you what he’s going to check and why.
That little exchange may take another minute, but it gives you a chance to discover whether you’re both watching the same movie.
What Lassie Knew About Communication
Remember Lassie?
That dog could communicate an entire emergency with a bark, a look, and a little determined back and forth.
Somehow, Timmy and his family eventually figured out that something was wrong.
But Lassie had a scriptwriter helping her out. The rest of us have to work a little harder.
There’s a useful lesson in the way we respond when communication isn’t straightforward. We watch. We listen. We look for clues. We try to figure out what the other party understands.
That same attention helps when you’re training employees.
An apprentice who stands quietly while you explain something may be listening carefully. He may also be completely lost and afraid to admit it.
Asking, “Got it?” isn’t much of a test.
Most people will say yes, especially when they’re standing beside somebody who has forgotten more about the trade than they may ever know.
Try asking different questions:
“What are you going to look for first?”
“Why do you think that happened?”
“What would you do if this didn’t fix it?”
Those questions tell you more than a nod. They also give the apprentice a chance to think through the work instead of memorizing the next instruction.
When the answer reveals a misunderstanding, you’ve found something useful to teach.
Try this on your next job: Before an apprentice begins a task, ask him to explain what he’s going to do, what could go wrong, and when he needs to stop and ask for help. Afterward, ask what he noticed and what he’d do differently next time.
It doesn’t require a classroom. It simply requires a conversation.
The Missing Middle: When Everybody Is a Helper
Better communication doesn’t magically create more hours in the day, which brings us to one of the hardest problems contractors face.
Many businesses have experienced master tradespeople and a growing number of helpers or apprentices. What they’re short on is the middle: enough capable, independent workers who can carry the production load and help bring newer employees along.
Journeymen have always played an essential role in teaching the trades. They still do. Apprentices learn from them on job sites every day.
But those journeymen are also responsible for getting the work done.
When there aren’t enough experienced workers, everybody gets stretched thinner.
I’ve spoken with owners of substantial contracting businesses who are still working in the field themselves, despite having employees, managers, and major commercial contracts.
They’re not out there because they haven’t figured out how to delegate. They’re out there because the work requires skills their businesses don’t yet have enough of.
Every hour they spend filling that gap is an hour they can’t spend developing somebody who might eventually fill it for them.
That’s the trap.
You need skilled employees to create more skilled employees. And because you don’t have enough employees capable on their own, the ones you do have are too busy to train anybody else. It’s a vicious cycle.
Hiring more helpers can actually make the situation worse in the short term. Every additional beginner needs instruction, supervision, and somebody to check the work.
More people on the payroll doesn’t always mean more work gets done.

Start With the Bottleneck, Not the Headcount
If this sounds familiar, resist the temptation to solve every training problem at once.
Instead, identify the work that keeps pulling you or your most experienced employees away from everything else.
Maybe you’re the only person who can diagnose a particular system. Maybe every estimate requires your personal inspection. Maybe your journeymen can handle installations but still need you for certain troubleshooting decisions.
Write down the five tasks or decisions that create the most interruptions.
Then ask:
- Which of these could another employee reasonably learn to handle?
- What knowledge or experience is that employee missing?
- Who could teach that particular skill?
- What would the employee need to demonstrate before working with less supervision?
You may discover that you don’t need another fully qualified technician to relieve some of the pressure. You need somebody who can competently handle a specific portion of the work.
Want a place to work through this? Download the Teaching Gap Workbook and map out your five bottlenecks, who could take them on, and what they’d need to show you first.
Doing that gives you something specific to teach, and then your employees can see what they’re working toward, too.
The next question is where the help you need is already hiding. In Part 2, we’ll look at the overlooked talent on your own payroll, how to tell whether training is actually worth paying for (yes, even the VR headset), and how to keep the people you develop from leaving for a bigger paycheck.
Your next great journeyman may be closer than you think.
