My leadership journey started in Cutco sales, where early success shaped both my strengths and my flaws. I was one of the top performers in the Prairies, even ranking in the top three across Canada during summer sales. While this built my confidence, it also inflated my ego in ways that would later need correction.
One particular memory stands out from those Cutco days. A new sales rep came in during our fast start program and was absolutely crushing it in their first three days. When they came in one Sunday, tired but successful, instead of offering the praise they deserved, I challenged them with 'Do you think winners would go home right now? Or would they make five more calls?' They quit the next day, despite holding sales records. It was my first lesson in failed leadership - though it would take years for that lesson to truly sink in.
My next humbling experience came during my travels to Southeast Asia. Coming from a small town of 5,000 people, stepping into Kuala Lumpur with its 7.5 million population was mind-bending. It showed me just how vast the world really was beyond my limited perspective. Yet, even this experience didn't completely transform my approach.
After returning, I bounced through various sales roles - car sales for three months, insurance sales for six months. In insurance, my cockiness remained intact. When my boss backed me into a corner threatening termination, I simply walked across the building to a pre-arranged interview and landed a new job. Still no real humility there.
The property management and passenger elevator industries followed, introducing me to big business operations. While these experiences started chipping away at my 'take no prisoners' attitude, the real transformation didn't happen until I became a division manager at Best Version Media.
Despite being consistently ranked in the top five performers across 40 North American divisions, my leadership approach was problematic. I was a steamroller - focused purely on logic and performance metrics, showing little regard for people's feelings or individual needs. This ultimately led to what I jokingly call getting 'side-moted' to Director of Productivity for Canada.
This career shift became my biggest wake-up call. Through honest feedback from colleagues, I finally understood how my interactions were actually harming team members rather than helping them. I had to pivot from being a pure logic-driven dictator to understanding the emotional intelligence required for true leadership.
Today, my leadership philosophy centers around education and allowing people to learn through their own experiences. I compare it to my parenting style - letting people do dangerous things safely. The hardest part? Sitting back when I see my team about to make a mistake, knowing they're often just minutes away from solving the problem themselves.
This approach builds stronger leaders because it lets people own their growth journey. It's about recognizing that different people need different types of support, sometimes a push, sometimes praise, and sometimes just the space to figure things out on their own.
Looking back at that early Cutco rep who quit, I now understand that what they needed wasn't a challenge - they needed recognition and encouragement. Sometimes the best leadership isn't about pushing harder, but about knowing when to step back and let people shine in their own way.