Leading IT at scale

Right now I am the IT Director for the Winnipeg School Division, and honestly, it is the most rewarding work I have done in my career. Our team supports close to 40,000 users, and when I say users I mean students, teachers, and the people who keep a school division running every single day. That is not an abstraction. Those are real people who need technology to work, and who deserve a team that actually shows up for them.

We are in the middle of a significant modernization effort right now. Networks, devices, software, student information systems, collaboration platforms. A lot is moving at once. And through all of it, what I keep coming back to is the same thing I have always believed: the technology is important, but how we deliver it is what people actually remember. That is the heartbeat of everything our team is trying to build.

Technology matters. How we deliver it matters more.

33 years behind the bench

Long before I had a title in IT, I was coaching hockey. For 33 years I worked with players at different ages, skill levels, and stages of their lives. It taught me more about leadership than any course or framework I have encountered before or since.

You cannot fake it on the bench. Players know when you are not present. They know when you are not being straight with them. They know the difference between a coach who is managing them and one who actually cares about their development. That same truth holds in every leadership context I have ever been in.

Coaching taught me that empathy is not softness. It is how you reach people. It taught me that accountability only works when it is paired with genuine trust. And it taught me that how you deliver a message matters as much as the message itself. Those ideas run through everything I have written.

Why I started AI, Eh?

When AI started moving fast, I noticed a gap. There was plenty of content for people who already work in tech, and plenty of breathless headlines for everyone else. What was missing was something honest and practical, written for regular Canadians who just wanted to know if any of this was actually useful to them.

So I started AI, Eh? A free newsletter in plain English, with Canadian context, that treats readers like adults. I recommend Claude, ChatGPT, and Gemini equally because I do not have a stake in any of them. I read and reply to every message personally. That part matters to me.

The book

I started writing LinkedIn articles about leadership a while back. I was processing things I had lived through and trying to make sense of them in writing. People kept reading. Eventually I had enough material that pulling it together into a book felt like the right next step. I took it on as a personal challenge, with no particular expectation of what would come of it.

The Human Side of Leadership is not a management textbook. It does not offer a framework or a five-step system. It is a collection of honest reflections on what leadership actually looks like when you are in the middle of it, shaped by decades of experience in IT, education, and coaching. The themes that come up most often are the ones that kept coming up in my own work: trust, empathy, humility, accountability, and the weight that words carry when you are in a position of influence.

I wrote it from somewhere on the path, not from the top of the mountain. I am still climbing. If that sounds familiar, it is probably for you.

The eBook and print edition are both live on Amazon now.

Speaking and consulting

I am occasionally available for speaking engagements and consulting on topics I actually know something about: IT leadership, AI literacy for non-technical audiences, and leading with empathy, humility, and accountability. If you are looking for someone who will speak from real experience rather than a slide deck full of frameworks, get in touch.

Outside the office

I spend time behind a camera too. Landscape photography, mostly. Mountains, lakes, the changing seasons. The kind of thing that gets you up before sunrise and out somewhere quiet, which suits me fine.