Writing · Learning · June 2025

A day back at Rotman: nine talks, three themes, one illegal sprinkle lawsuit

Reflections from the Lifelong Learning Conference, filtered through a product manager's brain.

A day back at Rotman for the Lifelong Learning Conference, and my main conclusion is that the faculty run on a different battery pack. My MBA batch onboarded virtually, and I've often suspected my virtual experience missed something. This day confirmed it. Nine speakers later, three themes emerged: leadership is being renegotiated, speaking up is a skill with preconditions, and AI is rearranging the furniture underneath all of it.

On leadership, renegotiated

Nouman Ashraf led our batch's onboarding years ago, and his energy stood out even through a screen; in person it's another level. The ideas that stuck: we need to move from being knowledge holders to experience creators. Leadership is facing a credibility crisis (so it's not just me being jaded). And growth isn't about owning your story — it's about owning your learning.

That first one lands differently in the AI era than it would have five years ago. When knowledge itself is a commodity you can summon in a chat window, "knowledge holder" stops being a viable identity for leaders, teachers, or (ahem) product managers. What can't be summoned is the designed experience: the workshop that surfaces what interviews couldn't, the demo that makes a skeptical stakeholder lean forward. I've built my whole research practice on that distinction without having the phrase for it. Now I have the phrase.

Ron Tite was another high-energy act with a serious core: the only thing worse than the Great Resignation is a great resignation of spirit. FOBO — fear of becoming obsolete — has replaced FOMO. His prescription: leadership needs to stop trying to squeeze more out of people; for organizations to grow, people need to grow into the roles the organization needs. A strong employee experience leads to a strong customer experience. Having spent years in contact centers watching exactly that causal chain play out (burned-out agents cannot deliver delightful support, no matter what the script says), I can confirm: this one isn't a platitude, it's mechanics.

On speaking up, with preconditions

Sumita Sah gave the talk I've thought about most since. That moment of tension when you feel the discomfort of resisting resistance — that's your power. She told the story of Jeffrey Wigand, who exposed wrongdoing at enormous personal cost, and offered two questions everyone should evaluate before speaking up: is it safe, and is it effective? Then she challenged us to rethink what being "good" means. Spoiler: it's not being compliant.

What I appreciated is that this wasn't a naive "always speak truth to power" pep talk. It was a framework, and frameworks respect reality. In my world the stakes are smaller than Wigand's but the structure is identical: telling a senior stakeholder their pet feature shouldn't ship, flagging that the metric everyone's celebrating is masking the real story. Safe and effective are the right two questions, and "effective" is the one PMs underweight. Speaking up in a way that changes the decision is a craft: timing, evidence, and knowing whether the room can hear it yet.

Geoffrey Leonardelli on negotiation paired well with this: a prospecting mindset brings curiosity and the ability to create value for everyone. You're not in a fight — the pie can get bigger before it's split. Focus on what you want to gain, and what your partner in the negotiation wants. Every difficult alignment conversation I've had at a bank is secretly this talk. The teams competing for placement in a product aren't enemies; they're negotiation partners who haven't been shown the bigger pie yet.

On AI rearranging the furniture

Jacqueline Carter brought the provocations: B2C is shifting toward AI2C, and even AI2AI, where agents talk to agents. Competition is moving from capital to data. The foundational skill is knowing which problem structures AI can solve well. Intern-level jobs are already being automated, and policymakers are overwhelmed by the speed of it. We're at a tipping point, and it's genuinely unclear which direction we go.

"Knowing which problem structures AI solves well" is the most compact definition of my job I've heard in a while. It's exactly the muscle that separates a shipped AI product from an expensive demo: not "can we use AI here?" but "is this a problem shape AI is actually good at, and what happens at the edges where it isn't?"

Sinead Bovell gave my favorite talk of the day. Think of AI as infrastructure: intelligence streaming may become as fundamental as electricity or the internet. And retire the sentence "AI will never do X" — along with its cousin, "people will never want Y."

People said they'd never get in a stranger's car or sleep in a stranger's house… and yet here we are.

As someone who watched an entire industry declare that customers would "never trust a chatbot with financial questions" roughly eighteen months before every bank raced to ship one, I felt that line in my bones.

And one movie about illegal sprinkles

Did not expect a film segment at a management conference, but "Get Baked" — a baker's journey from rock bottom to going viral after being sued for using illegal sprinkles in the UK (a real thing that really happened) — was hilarious, unexpected, and weirdly motivating. He also became a role model in the Q&A by cheerfully telling consultants to stay away from him. A moment.

Which was, in its own way, the most on-theme talk of the day: reinvention isn't a framework, it's a decision you keep making. The faculty battery pack helps, though.