From Apprentice to CEO: Toby McCosker on Learning Every Role

You Don’t Lead What You Don’t Understand

When I started in construction, I didn’t know where it would lead. I just wanted to learn the trade. Get my hands dirty. Prove myself. What I didn’t realise was that those early days swinging tools would become the foundation for how I lead today.

Because real leadership doesn’t start in the boardroom—it starts on site, when no one’s watching. I’m Toby McCosker, and every role I’ve worked—from apprentice to CEO—taught me something no textbook ever could.

The Apprentice Years: Grit, Humility, and Hustle

My first lessons weren’t about profit margins or contracts—they were about showing up. On time. Every day. Ready to work. I learnt how to listen, how to take feedback, how to carry gear without complaining.

You learn quickly who’s there to teach and who’s there to test you. And you take it all—because that’s how you earn your place.

Those early years taught me the value of patience and persistence. They gave me a work ethic I still carry today. Because before I could lead people, I had to learn how to follow properly.

Climbing Up the Ladder (Without Skipping Rungs)

I didn’t wake up one day in a leadership role. I built my way into it—brick by brick, mistake by mistake. I worked as a foreman, site supervisor, project manager. Each role showed me a different part of the business puzzle. And each came with new pressure, new responsibilities, and new lessons.

I remember thinking the hardest job was being on the tools. Then I had to manage a dozen guys. Then a budget. Then clients. Then the whole company. And suddenly, the tools felt like the easy part.

But because I’d done the work—I could speak the language. When I talk to trades, they know I’ve walked their path. When I meet with clients, they know I understand more than just spreadsheets.

CEO Isn't Just a Title—It’s a Responsibility

Being a CEO isn’t about power—it’s about service. I don’t sit in an office barking orders. I get out there. I solve problems. I guide the team. I take the heat when things go wrong.

That’s what real leadership is: absorbing pressure so your people can perform.

And the only reason I can do that well is because I know what it’s like at every level. I know what it’s like to be the last one on site. The one redoing the concrete pour. The one double-checking invoices after hours.

That perspective? You can’t fake it. You earn it.

What I Tell Young Builders Now

You want to run a business? Learn the business from the ground up. Don’t rush the process. Every role you play teaches you something critical.

Don’t just aim for the top. Aim for depth. Know your trade, know your team, know the problems before they become disasters. That’s how you build trust. That’s how you scale sustainably.

I’m Toby McCosker, and the only reason I can run what I run today is because I never skipped the hard parts.

Conclusion: Leadership Is Earned One Role at a Time

You can’t shortcut credibility. You can’t buy experience. And you definitely can’t fake understanding. The best leaders in this industry are the ones who’ve lived it at every level.

From apprentice to CEO, every role shaped me. Every mistake taught me. Every win humbled me.

And now, when I walk into a room—whether it’s a boardroom or a muddy job site—I bring every lesson with me.

More from Toby McCosker

Lessons from the Frontline: Leading Through Adversity
How pressure shaped leadership beyond the job site.

Reputation vs. Reality: What the Media Got Wrong
Why headlines don’t always tell the full story.

Tobias (Toby) McCosker is the founder of Built By Toby. After two decades in construction and business, he now shares raw lessons from the frontline.
Explore more at BuiltByToby.com.au