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Craig McCaskill

People, product and systems

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June 1, 2025

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...

Product and Strategy Books and Ideas

May 29, 2025

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.

Technology and Future Leadership and Culture

May 25, 2025

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...

Product and Strategy Communication and Influence

May 24, 2025

Writing is still thinking

Something humbling happened last week: three hours of my life disappeared into a blank document with barely a paragraph to show for it.

Thinking and Learning Communication and Influence Books and Ideas

February 24, 2025

The Science of Saying No - Frameworks and Execution

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.

Leadership and Culture Systems and Scaling Communication and Influence

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