Canadian Tire put 47 leaders through the same five days of AI

Executive AI education usually fails in the same way. Each leader comes back with a different picture of what the technology is for, and the organisation spends the next year arguing about vocabulary. Canadian Tire Corporation tried to avoid that by putting its senior leadership team through the same five days together. The custom program at MIT Sloan Executive Education brought 47 participants, including president and CEO Greg Hicks, senior executives, functional leaders and several of the Dealers who own Canadian Tire stores.

Why leadership first

The company was already investing in AI across the business. What it lacked was alignment. "We knew we needed to get two things right: data readiness and people readiness," said Bob Hakeem, executive vice president and chief human resources officer. "The people readiness piece was really about leadership mindset." Christopher Gray, vice president of talent, performance and culture, said the brief was explicitly not technical skills or how to build agents, but the thinking and frameworks behind AI applied to real challenges the business faces. Hicks framed the stakes in one line: "AI isn't changing retail, it's becoming retail."

The faculty did fieldwork before the week began, from ethnography and interviews to store visits and competitive analysis, so the exercises reflected Canadian Tire's own context. Sessions covered responsible AI, customer trust, data readiness, experimentation, governance and organisational change.

What came back

Ilana Santone, senior vice president of business and AI transformation, said the program "raised our floor to a much more common level" and gave the team a shared language. Kevin Groh, senior vice president of corporate affairs and communications, said executives applied a questioning framework from the week to a longstanding business challenge as soon as they were back in the office. Chief merchant Micheline Davies named two takeaways: the need to shift to a culture of experimentation, and to think about AI and agents as members of the team. Keran McGuire, senior vice president of AI and technology platforms, put the case for doing it together: "There is no world in which we achieve this AI agenda through one team."

What this means for L&D

Two things stand out. The program was built around one company's strategy rather than a catalogue, and the people in the room included the operators who run the stores, not only head office. The open question is how that shared language travels to the next layer of managers, who have to turn a framework into a changed week of work. That cascade is where our AI Training programs start.

Sources:

• MIT Sloan Executive Education, 3 November 2026: Canadian Tire Builds Enterprise-Wide AI Leadership