I never thought for a moment that I would end up in management. I was the introverted, hands on keyboard geek who got his start on the technical support side of the business. A few stars aligned (or collided ) that fundamentally altered my career trajectory. I occasionally make reference to being "tricked into management", so I thought I would tell the tale. I hope to tell it in a way that may help others who are unsure of where their technology careers may take them.


After a failed stint in university, I attended a private technical college and received a Computer/Network Technician diploma. Following my co-op placement, I ended up getting a term contract offer to move to North Bay, Ontario where I started my career on one of the provincial government's Technology Service Desk's. For me, this was an awesome first job and my aspirations at the time were to put one foot in front of the other and hopefully gain access to opportunities to do more senior technical roles.

Fast forward a few years, a few roles and a new city (St. Catharines, Ontario) and things were about to change more than I ever imagined. This point in the story gives me an opportunity to highlight a couple of key conditions that helped me make the leap:

  1. Finding my first mentor.
  2. My organization was about to embark on transformational change.

The Impact of a Mentor

I had no idea what I was actually capable of. I was bright and I worked hard but I had no sense of what my professional ceiling might be. It was at this point in my career where I encountered someone who saw more in me than I saw in myself. He challenged me. He advocated for me. He showed me that taking risks were okay. That failure was okay, assuming you learn from it.

If you want to move up in the technical stream or make the leap to the management stream, identifying a mentor is a must.

Transformational Change Means Chaos and Opportunity

Back in 2005, the Ontario Public Service launched the e-Ontario Infrastructure Consolidation Initiative. They decided to go after the duplication that existed in government with a specific focus on IT infrastructure and its associated service delivery. In doing so, they would take $100M/year out of the IT spend for the province. A massive undertaking.

They started by moving ~750 staff (including me) from various government departments into a central department with the mandate of delivering services to the rest of government. It was a crazy period because as unionized employees there were some choices to be made and if you had seniority you might have been in a position to "stay behind". Vacancies were also created because some who were eligible for retirement opted to push the eject button vs. deal with a change of this significance. This type of sweeping organizational change meant so many opportunities for those who were interested in contributing in new ways and at higher levels. When you can, you really need to ride the wave.

The Management Opportunity

When the e-Ontario initiative got started, I was in a senior technical role as the IT Security Lead for the Ministry of Transportation. This was the height of my technical powers and I had lots of buttons to push and boy did I love my work. As I rode the organizational change wave into the center of government, the first new opportunity presented to me was to play a leadership role in the research and development of a new online ordering portal for technology products and services. In of itself this was quite a learning opportunity as it was the first time I was asked to work on something that wouldn't go live until years in the future. It was a big change of pace.

... but then it started. My former mentor, who had also rode the wave of opportunity, was now responsible for leading the consolidation of the government's 9 legacy help and service desks into a single, enterprise service desk for government. He reached out and asked me if I'd like to join him as the Manager of the service desk location in St. Catharines, Ontario.

I said no. Because...

It had never occured to me before that moment that management would be for me. I was highly technical. I loved pushing buttons. No thanks.

Then a month later, he came back and asked me again. He told me I should trust him. That I'd be great at it.

I said no. I didn't want to manage people. I was a technologist!

Then a month later, he came back a final time and asked me again. He insisted that I trust him this time. It was a secondment after all. If I didn't like it, I could return to my current position. What was the risk, he said.

I did trust him. He always had my best interests at heart. I decided to take him up on the opportunity.

What happened next? I didn't sleep very well for the first month on the job because I was young and didn't have a frigging clue what I was doing. I was also managing a team of ~50 staff, most of which were older than I was at the time.

But you know what? He was right. I was meant for management and leadership. What followed has been a wonderful career leading great teams and significant change in several large organizations.

You don't always know what you're capable of. You might need someone to give you an encouraging shove in the back towards new opportunities and challenges. I did.

Kirk out.

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