The Bubble That Knows It's a Bubble
The four words that precede every crash: “This time is different.”
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:
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...
The Innovator's Dilemma: Why Good Companies Fail at the Very Thing They Do Best
Your product is crushing it. Customer satisfaction scores are through the roof. Your biggest clients are renewing multi-year contracts. The board is thrilled with your margins. And yet, somewhere in a garage or a dorm room, someone is building the...
How to Think About AI
New tools don’t just change what we can do, they change who wins. The printing press didn’t eliminate scribes overnight, but it made literate societies dramatically more powerful than illiterate ones.
Old Code, New Voice: How Technical Debt Led to Better Storytelling
I’ve been writing again. After nearly four years of letting my website collect digital dust—publishing only a few posts while my day job consumed all my creative energy. I finally felt the itch to both write and fix the stagnant...