Dear CEO – The ROI Illusion – Are Digital & AI Transformations Really Delivering
Let's be honest: the hype around Digital and AI transformations has created a dangerous illusion. Everyone says it drives ROI through cost savings and efficiency, but are those promises actually being kept? For many, the answer...
Dear CEO – The Transformation Tightrope – Why Leadership is a Lonely Battle in the AI Age
Let’s be brutally honest: leadership is a tough gig. Now, layer on the relentless pressure of digital and AI transformation—the constant upheaval, the inevitable resistance—and suddenly, it's a lonely battleground. Pushing...
Dear CEO – The Digital Divide Is Now a Death Sentence for SMBs
The Digital Divide Is Now a Death Sentence for SMBs and almost all SMBs are on the wrong side of the divide. Since the release of ChatGPT (Generative AI), something seismic has happened. Productivity for large-cap companies has...
Dear CEO – Shohei Ohtani Didn’t Wing It — So Why Are You Winging Your AI Strategy
In high school, Shohei Ohtani didn’t just dream of the MLB — he engineered it. He wrote down his main goal and backed it with 8 sub-goals, each one tightly aligned to his ultimate MLB vision. That clarity, structure, and...
Dear CEO – Trust Falls – Rebuilding Employee Trust in the Age of AI Disruption
The headlines all scream "AI Job Losses," and your C-suite is likely paralyzed by fear. The erosion of trust isn't a leadership failure — it's a predictable consequence of relentless change and the looming specter of AI-driven...
Dear CEO – When Boomers Walk Out, Will AI Walk In
Canada is on the brink of an unprecedented labour shock. Canadian businesses face a mass exodus of experience, know-how, and productivity — and many don't even have a succession plan. 2.7 million Canadians aged 60–64 will retire...
Dear CEO – If AI Is Easy, Why Is Apple Struggling
AI is supposed to be the great equalizer — fast, scalable, transformative. So why is one of the world’s most valuable companies, with unmatched hardware dominance and billions in R&D, struggling to ship meaningful AI...
Dear CEO – Alignment First – The Generative AI Trap Most Executives Fall Into
Most teams jump straight to building generative AI projects, but that’s a recipe for wasted resources and missed opportunity. We want to play with the shiny object and this means it is just another technology project. The very...
Dear CEO – The Peril of the New Grad AI Strategy
This past summer we sat across from a C-suite executive who asked a question that stopped me in my tracks: "Should we just hire a new computer science grad and have them build us a bunch of AI agents?" Our reaction? A healthy...








