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Ep 35: How To Evolve From “Boss” To “Coach” – James Dale

How to tackle the very common scenario of moving a skilled employee into a management role
What happens to contractors that don’t see themselves as a coach in their business
How to work with someone when they have low skill but high commitment
The coaching style most contractors skip when their employees are doing OK that holds back big opportunities for growth
How NOT to lead employees that have high competency and high commitment
What to do when you are too busy to properly coach each employee that reports to you

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Listen to Episode 35

Read a Summary of Episode 35

Let’s be honest: no matter how passionate you are as a contracting leader, at some stage you’ll want to earn more money and free up more personal time to enjoy that hard-earned cash.

The way to achieve this: Develop leaders within your workforce who can drive your company forward – you need empowered leaders that execute well without you, rather than worker bees who need babysitting.

This is why coaching will ALWAYS be more effective than bossing.

In today’s episode of Contractor Evolution we’re joined by James Dale, director of training and development at Breakthrough Academy (BTA) who is here to help you move from boss to coach.

James will examine the development levels staff members undergo in order to become leaders – and the steps you can take to help them with that transition.

Let’s Start With . . . A Common Mistake Leaders Make In Developing People

James has heard the same story many times in various trades: a crew member who shows great proficiency on the job site is pegged as a potential leader by their boss – and made foreman to oversee a new crew that will expand the business.

At first they’re excited, super-motivated to succeed. But several months later they’re ready to quit, or at least yearning to return exclusively to the on-site work they were so good at and loved.

What went wrong? This person didn’t receive proper support from their boss. They were out of their element and left fumbling in the dark. The assumption that you can toss a talented worker into a higher role and expect the cream to rise to the top is just wrong, and can be very damaging.

How To Avoid This Painful Scenario: USE THESE 3 DEVELOPMENT LEVELS!

There are 3 Development Levels that a staff member will go through after taking on a new role, and you, the leader, will need to lead those transitions appropriately:

“Your ability to lead and develop others is probably one of the biggest things you can work on. And the one with the biggest ROI.”


This is for the employee with the ‘Right Stuff’ who is given a new role and has low competence for the new work they are given, but high commitment. This person is excited and is like, “Hey I have a new title; I’m driving the truck, I have a wage increase,” James says. “They really want to prove themselves, even though it’s their first time doing these tasks.”

What coaching style is needed: A directive style of leadership. “Give them very clear directions on how to do things. It could be checklists, ‘this is step one, this is step two’ – very explicit instructions. Their motivation is high, so they’ll be open and wanting to do a good job,” James says. This will really motivate them.

Potential pitfalls to avoid: Don’t run the risk of overwhelming your golden boy/girl with a rush of information. “Give them clear direction in different aspects of the role: the agenda and the steps,” James says. Easy does it.


This is for your up-and-comer who has gained some competence thanks to your diligence, and their commitment remains strong – they have had some wins and some losses, and the risk now is that without further coaching, their progress could easily unravel.

What coaching style is needed: A coaching/supportive leadership style. Shift gears subtly from being completely directive to slightly more collaborative – afterall, your fledgling leader does have some experience under their belt. “Ask questions,” James says. “‘How do you think we should do this? How’d that go last time? How can we do better next time?’ It’s more like partnering in that you’re involving them more in the process, making him think and become more resourceful.” At this stage, and with your support, they might even come up with better solutions to issues than you! Help them become more resourceful.

The potential pitfalls to avoid: This is a stage many contractors skip to far too quickly. They still need support. It’s like teaching someone to ride a bike: the training wheels are gone, but they still need someone to catch them if they fall.


This is for your leader in the making who is now highly competent and highly committed. They’ve been in their new role for some time now and enjoyed more wins than losses.

What coaching style is needed: A delegative leadership style. “You’re basically letting them make the calls,” James says. “They’re the ones responsible now and you’ve kind of stepped back. You’ve turned over responsibility to them. It’s almost like, ‘Here’s the project, let me know when you’re done.’”

The potential pitfalls to avoid: Continuing to use a directive approach at this stage will just piss them off. In other words, you’ve created a new leader: let him lead (not leave)!

But hang on . . .you’re super-busy, and all this sounds so time-consuming!

We get it. All of the above takes a lot of time and patience: you’ve got a company to run and fires to put out; surely someone with talent can figure things out for himself with minimal hand-holding?

James commiserates, but he points out that if you choose that route, your chances of having a revolving door of failed potential leaders intensifies. “Your ability to lead and develop others is probably one of the biggest things you can work on,” he says. And the one with the biggest ROI.

And if it takes 2-5 years, just remember, you’ve still got a long career ahead of you. “The point is, would you rather have 40 semi skilled people or 25 who are really dialed in?” James says.

So, if you’re starting to dream about the day you’ll have more spare time and the money with which to enjoy it, have a listen to this episode of Contractor Evolution – we guarantee you’ll feel motivated to hone your coaching skills!

For the free resources we talk about in this episode, head this way [LINK].

Benji Carlson

Benji Carlson

As the son of two proven entrepreneurs, Benji’s spirit for self-starting business runs deep. Since he was a young teen, Benji has been starting and running profitable small businesses; most recently culminating in a highly successful 4-year career as a franchisee with College Pro Painters. Benji’s enormous heart and passion for people is what drove him to produce over $1,000,000 in revenue while taking the highest quality care of his employees and customers. He was consistently acknowledged for having the most productive staff in the company, while leading more junior franchisees to fulfill their potential. Benji’s uncanny ability to find the right people and put them in the right place make him a natural fit for Breakthrough Academy’s Assessment Team.

Upon finishing up his career with College Pro, Benji set out on the ultimate victory lap: a nine-month transcontinental motorcycle trip from Canada to Peru.

Benji lives in beautiful Kelowna BC. During the summer you’ll usually find him on two wheels: either bombing down a trail on his mountain bike or cruising the pavement on his motorcycle. When the snow falls, he escapes to the mountains for steep and deep powder.

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Welcome to Contractor Evolution, a show created for high-performing contractors that are focused on scaling up, working less and increasing profitability.

While a lot of other shows focus on early stage growth challenges, we focus on real life scenarios faced by contractors that are scaling at a rapid rate, and how they keep everything dialed in without losing sight of work/life balance.

If you’re ready to evolve from a contractor into a better business owner, you’re in the right place.

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