The Games Your Organization is Actually Playing
Or: before you blame the players, check the rules.
Hello, I'm Craig McCaskill. I build products guided by a simple belief: technology should feel inevitable, not imposed. I focus on creating experiences that enhance human capability rather than demanding adaptation.
I write about books and ideas that change how I see the world, stakeholder alignment and building consensus, building teams that deliver meaningful outcomes, product strategy and what makes technology feel inevitable, how organizations grow and adapt, artificial intelligence and our digital future, and critical thinking and lessons learned along the way.
Latest thoughts:
The Case for Being Wrong Faster
Or: intellectual honesty is your competitive advantage.
When Seeing Is No Longer Believing
Imagine you watch a video. Multiple angles, timestamped, from bystanders with phones. You see what happens. A confrontation. A shooting. The sequence of events is clear.
The Bubble That Knows It's a Bubble
The four words that precede every crash: “This time is different.”
Sensing and Sensemaking: The Hidden Skills of Product Management
Product management is built on a contradiction. We’re supposed to be data-driven, yet our most important decisions happen in the absence of clear data. We’re meant to be customer-focused, yet customers can’t tell us what they’ll want tomorrow. Navigating this...