I recently wrote about what I’d say to an artist who hates AI. That post surprised me. Not because of the response – but because of where my mind went after I hit publish. I kept thinking about culture. Specifically, I kept thinking about a place I worked at over twenty years ago, during my second year at Wilfrid Laurier University, that had one of the best workplace cultures I’ve ever experienced. And I started wondering whether the real conversation about AI – the one most companies are missing – has nothing to do with AI at all. But this article isn’t really about AI. It’s about amazing leadership.
That place was the Laurier Athletics Department. A couple of leaders there (PB, RW – you know who you are) saw something in a 19-year-old computer nerd and cleared the path for me to build websites for a university athletic program. I had no business being there. I was a student. I was wildly underqualified. But that was the point: the culture they built didn’t treat us like students. It handed us adult work and expected us to grow into it. It was fantastic.
And we did. We ran events. We built tools. We worked weekends. We were working late on nights that had no deadline.
“We”… was a handful of passionate, crazy, amazing students.
And here’s the thing I didn’t fully appreciate until twenty years later: we loved it. We weren’t grinding under duress.
Let me give you a small example. It’s more for me (and those that know), than for you.
There was a “hot seat”. An office chair wrapped in red ribbon. Wish I had a photo of it. If you’d gone on a date over the weekend, or had some major event in your university life, you sat in it and answered questions. You got interrogated.
I hated it. (I don’t think I ever sat in it due to a date – read above – I am/was a nerd.) It was awesome. We laughed. We showed up. We cared about each other. We produced.
The leadership didn’t manufacture that. They modelled it. Culture flows downhill from people who mean it.
A summer before that, at 18, I worked for the Ontario Rangers program through the Ministry of Natural Resources. Boys camp, June through August, all physical labour: sawing branches so trees could be logged, tearing down beaver dams clogging up river systems, canoeing through Algonquin Park for weeks at a time, cleaning outhouses along portage routes. None of it was glamorous. Most of it was miserable – on paper.
But we smiled. We genuinely smiled. All of us (… um… except … that guy). Because the people leading us weren’t there because they had to be – they wanted to be.
Two completely different environments. Same invisible ingredient.
Here’s where I’m going with this.
Most conversations about AI inside organizations start with the wrong question. They start with: What tools should we use? or What processes should we automate? or What SOPs do we need?
Those questions aren’t wrong. But they’re downstream of a question almost no one is asking: Does this organization have a culture that can actually absorb AI?
You can install the best agent stack money can buy. You can build custom LLMs trained on your business. You can map every workflow, automate every report, and run the most sophisticated AI-driven operation in your industry. And it will fail if the culture underneath it can’t hold it.
Because AI isn’t a tool you bolt onto an organization. It’s a shift in how people think about their work – a shift in how all of us need to think. It’s a shift in how your team knows what they own, what they delegate, what they’re responsible for creating versus what they’re responsible for directing. That requires a culture that trusts people to make decisions, tolerates experimentation, and doesn’t punish the question “could AI do this better than me?”
That’s an AI culture. Not a chatbot. Not a workflow. A culture.
I didn’t fully understand what I’d been given at the Laurier Athletics Department or the Ontario Rangers until years later. I just showed up, did hard things, and somehow loved it. It took running my own organizations for 20 years to realize: I had been the recipient of something rare – leaders who knew exactly what they were building, not just the work product, but the environment people would do it in.
That’s what I’m trying to pass forward with these four things. They’re not a framework I invented. They’re what I experienced, translated into something you can start building tomorrow – through an AI lens.
The biggest enemy of AI adoption isn’t resistance – it’s embarrassment. When people feel dumb for asking basic questions about AI, they go quiet and go through the motions. Create explicit permission to not know, to try things, to ask the beginner question out loud. In the cultures I described above, nobody got made fun of for not knowing something. They got helped.
Sit with your team and ask: What’s something you do every single day that you don’t like doing? Not what’s hard – what’s tedious, repetitive, soul-draining. That’s the AI conversation. The answer to that question almost always points to a workflow AI can improve, and it puts the person in control of the change rather than on the receiving end of it. That’s a culture move, not a technology move.
Every culture shift needs an early adopter who runs visible experiments. Find the person in your organization who is most curious about AI and give them a mandate – not a side project, a real mandate – to try things. Let them report back. Let them teach. That one person changes the permission structure for everyone else.
AI cultures move. The Laurier Athletics Department worked because we had enough trust and clarity to make decisions without a meeting for every one. AI tools are the same: they’re only as powerful as the decision-making culture that uses them. If your team needs approval for every step, AI just makes the bottleneck faster. The goal is an organization where people are empowered to act on what AI surfaces.
None of this is new. The Laurier Athletics Department didn’t have AI. The Ontario Rangers program didn’t have AI. But they had the thing that makes AI work: a culture where people showed up fully, felt empowered – and then made decisions, did hard things, and trusted each other.
I was lucky to experience that before I ever had to build it. Very lucky. Very very lucky. Not everyone gets that head start. But the good news is – it’s buildable. Before the tools, before the workflows, before the agents: ask whether your culture is ready to hold all of it.
Make your team lucky too.
