Contractors: How to Train Your Crew Leaders

Hi there, Greg here from DYB Coach.

Today I wanted to talk to you about some leadership training for your field staff and your team leaders.

I’m sure you guys have received the phone calls where your guys need materials asap and then you have to go all over the place to get them.

A simple solution is to make an Excel document and list out each day of the week.

Make sure that there is enough space for each day for your crew leaders to write a plan.

At the end of the day, or at the beginning of the day, whichever you decide, you are going to call them up and ask them several questions:

1. “How far did you guys make it today?” –Did they have a goal that was set already and you are tracking the day before, did they achieve that goal, if not, why?

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2. “What products did you use?” –do they need anything the following day, do you need to get an order in?

3. “Are you guys going to be able to finish tomorrow?” –Ask them this if they are coming to the finish line on a project. When they say yes, ask, “What needs to happen so that you guys can achieve that goal?”

This way, you are setting it in their mind the day before, they know what the goal is, they can communicate that with the guys or the girls that are working with them, and that’s how you start to culture leadership thinking and planning.

Please leave a comment on what you’re going to implement today!

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About the Author

As many of you know, my journey has been one of grit, grace, and transformation. At 19, I was a high school dropout, single father, and struggling paint contractor in Michigan. I later moved to Florida, where I faced both personal and professional hardships. With nothing left to lose, I turned to prayer—and was blessed with a relentless hunger to learn. I devoured books, attended seminars, and discovered better ways to streamline and grow my business—even through the Great Recession (and yes, I did hit the wife lottery along the way!). In 2014, I published How To Double Your Business and later sold the painting business, launching a new chapter: coaching others to grow their businesses. For the past 10 years, I’ve dedicated myself to helping business owners scale through the DYB System, while also drawing from frameworks like EOS, Scaling Up, and The Four Disciplines of Execution. Yet something was still missing—something more adaptive, integrated, and complete. Then I found Pinnacle. After months of research and interviews with other Guides, I joined Pinnacle. Their tools and strategies have exceeded every expectation. Now, as a Pinnacle Business Guide, I help leadership teams implement a custom-tailored operating system that draws from the best in the industry—but flexes with your unique business. It’s a dynamic, proven approach to achieve clarity, momentum, and lasting growth. I’m no longer taking on any more 1:1 coaching clients… Instead, I now specialize in working with visionary business owners who are ready to get their leadership teams aligned—around a clear vision, a focused strategy, and an actionable execution plan. With the tools and process I now have as a Pinnacle Business Guide, I help turn alignment into momentum, and momentum into results. If your business is growing—but your leadership team isn’t fully rowing in the same direction—let’s talk.