Here’s what breaks when a contracting business grows past the size where one person can run it: the owner is still the head of sales, the operations manager, and the front office, except now there are ten crews instead of two. This is the same wall most contractor businesses get stuck at around 25 employees.
This piece covers what that breaking point looks like, why the fix feels wrong before it feels right, three moves that actually build a business that runs without you in the middle of it, and what’s waiting on the other side once you get there.
These insights come from Colin Nolan of Nolan Consulting Group, which has spent over fifteen years helping contractors build the systems their businesses outgrew.
The hourglass problem: when everything narrows down to one point
Every contracting business starts the same way. Someone is great at painting, or plumbing, or landscaping, and they start a company because they’re good at the work. For a while, it’s just them and a buddy, and that’s manageable.
Then the business grows, and the owner doesn’t. All of a sudden it’s them and ten employees, and every decision, every question, and every fire still runs through the same person. Nolan calls this the hourglass: everything in the business narrows down to one point, and that point is the owner.
You know you’re in it when a crew lead calls you from a job site because a permit question came up, and you’re the only one who can answer it. You know you’re in it when you can’t take a two-week vacation because nobody else knows how to handle what comes up while you’re gone. The company grew, but the way it runs hasn’t kept up with the system it’s outgrown.
Why working on the business feels wrong at first
The fix sounds simple: stop working in the business and start working on it. In practice, it’s uncomfortable. Contractors are used to measuring a good day by how much got done today, not by whether the business is set up to run without them in six months.
Nolan’s team pushes owners to focus on a three-year vision instead of this week’s schedule. That’s a real mindset shift, and it doesn’t pay off immediately. You may not have a more profitable year right away, but long term, it’s where the business needs to go.
There’s a second obstacle that shows up just as often: perfectionism. Some owners want every system fine-tuned before they’ll use it. Nolan’s answer to that is blunt. Good today is better than perfect tomorrow. You don’t need a finished employee handbook to start an HR policy, and you don’t need the ideal person trained on new software before you try it out. Systems change and adapt as the company grows. The point is to start.
Three moves that get you out of the hourglass
Getting out of the middle of every decision comes down to a short list of habits, not a personality overhaul.
- Know your numbers. Know your sweet-spot jobs and your average revenue per hour. Owners who say “I know we make money, but I don’t know what I’m doing right” can’t make informed decisions, and they can’t tell a crew lead what a good job actually looks like.
- Train for skill, not just attitude. Hiring for attitude and training for skill only works if the training program actually exists. That means weekly meetings, even when the instinct is “I don’t have time for meetings.” If the goal is maximizing profit, that mindset has to change.
- Communicate on purpose. Consistent communication about core values eliminates the side chatter that eats up a workday. Meetings exist so the team can commit work time to actual work, instead of talking about things that should have already gotten done.
None of these require the business to stop moving while they get built. They get layered in while the crew keeps working.
What’s waiting on the other side
The payoff isn’t just less stress for the owner. Growth creates real opportunities for the team: management roles that didn’t exist before, jobs people can actually build a career in, and a culture that’s worth sticking around for.
The clearest sign an owner has made it through is simple. You should be able to take a two-week vacation and trust that your team can handle whatever comes up while you’re gone. Nobody should still be needed to put out every fire. That only happens once systems are in place and people are trained to run them, which means the hourglass only breaks open once, on purpose, through the work described above.
