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Craig McCaskill

People, product and systems

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Product and Strategy

A collection of 8 posts

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 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

December 13, 2024

Escaping the Build Trap: How Effective Product Management Creates Real Value

You ship feature after feature, your development team works overtime, your backlog is always full—yet customer satisfaction remains flat and business metrics barely budge. Sound familiar? You’re not alone. Most product organizations have fallen into what Melissa Perri calls “the...

Product and Strategy Leadership and Culture

January 2, 2024

Beyond Metrics - Why OKRs often miss the human element of work

In the quest for clarity and alignment, modern organizations increasingly embrace structured goal-setting frameworks like OKRs (Objectives and Key Results). But beneath the surface of these seemingly rational systems lies a deeper question: Are we measuring what truly matters, or...

Product and Strategy Leadership and Culture Communication and Influence

August 23, 2023

The Great Enshittification - How Product Evolution Becomes Product Regression

In 2012, Netflix was a meticulously organized catalog that helped you discover films and shows across genres, decades, and continents. In 2015, Spotify was a music lover’s sanctuary that put your personal library and thoughtful exploration front and center. Fast...

Product and Strategy Technology and Future Systems and Scaling

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