Articles written by guest contributors

Weston Zimmerman

If you could go back to day 1 as a contractor
By Weston Zimmerman

I just got back from spending 2 days on the road doing a podcast tour with contractor customers of mine. One of the questions I ask on the podcast is, “If you could go back to day 1 as a contractor and do one thing differently, what would that be?”

Now, I’m sitting out on my back patio, a cup of coffee beside me, and reflecting on the conversations I had with these customers and friends, and that’s what I want to share with you this morning.

Before I got into it, each of the contractors I had on as guests had already successfully overcome the “surviving” phase of business and are effectively “thriving”.

But how? What struck me was the commonalities in their responses when I asked each of them what they’d do differently if they could go back to day 1 as a contractor.

There were 2 main themes in their answers:
  • I’d focus on the numbers right away and fix my pricing.
  • I’d focus less on “doing the work” and focus more on building systems and processes.

Fixing your pricing
It’s not who works the hardest that wins. And unfortunately, when cashflow is tight, we’re working harder and making less, the default response is “I’ll just work harder.” We all did this on day 1 as a contractor:

Put in more hours. Get back out in the field. Do estimates at night instead of during the work day. I want it done right, so I’ll just do it myself.

We focus on working harder when we should be asking “How is it possible to be producing more work than ever, have happy clients, have more top-line revenue than ever, but have even less cash in the bank?”

How is that possible!?

Well, if you are losing 5% on $5,000 jobs, losing 5% on $50,000 jobs hurts even worse. And by the time you are hurting in cash flow, you are months downstream from the source of the problem. The source is, “My math on my quotes is wrong, and it’s costing me money.”

And every single guest I interviewed this week said the same thing: “If I could go back to day 1 as a contractor, I’d focus on fixing my pricing first.” That means finding out what it costs your business to do that job. Not guessing. Using cold hard emotionless math.

You do that by building a budget. You can do it with our free budgeting tool on

Building systems and processes
The other thing that every single guest I interviewed said they’d do if they could go back to day 1 is they’d focus less on “doing” the work, and focus more on building the systems and processes that “do” the work.

This means educating employees, setting them up for success with the proper process, the proper training, the proper equipment, and defining the “definition of done.” What defines each task or job as “done?”

The definition of a system and process is that: Someone else, not you, can do the task properly by following the predefined process.

Systems and processes are the keys to the entrepreneurial prison. Without them, you are a prisoner to your own business. Only you can do the task. With them, your employees are empowered, gain autonomy, and will surprise you with their capability.

Without them, you are the bottleneck in your own business. Good employees won’t stand for that. They’ll leave. Good employees want autonomy, pride in their job well done, and feel like they can produce value without needing babysitting.

An owner with no systems and processes has no choice but to either do the task themselves or babysit the employees doing it.

Don’t get caught in the “Tell, check, next” loop. (Tell your employees what to do, check their work, and tell them what to do next.) The tell, check, next style of leadership will create a total bottleneck in your business.

Rather, focus on the outcome. Define and agree on the outcome, then step back and let them figure out the best way to produce that outcome. That, my friends, will produce leadership in your team and freedom for you.

Dig in further
To listen in to these conversations, check out The Cost of Doing Business podcast at

I’d like to hear your perspective on what you would do differently if you could go back to day 1 as a contractor?” My contact info is below.

For help with your company, email, follow on IG at @synkedup, call (814) 383-1901 or visit Weston Zimmerman is CEO & co-founder of SynkedUP project management software and app. SynkedUP helps contractors know and track their numbers, estimate and job-cost jobs, and manage their jobs efficiently. Check out his podcast "The Cost of Doing Business."

Digital Edition
June/July 2024