People, product and systems
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.
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...
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.
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...
Something humbling happened last week: three hours of my life disappeared into a blank document with barely a paragraph to show for it.
Every company claims to be disciplined about prioritization; most roadmaps look like feature buffets with everything marked “high priority.” The space between strategic intention and daily execution is littered with good ideas that never shipped.