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Craig McCaskill

People, product and systems

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February 17, 2025

The Art of Saying No (Or At Least, Not Yet)

The math of product is simple but brutal: too many demands, not enough resources. Your backlog isn’t just full—it’s a graveyard of good intentions. When every feature is called “critical,” nothing actually gets built well. This isn’t about managing tasks...

Leadership and Culture Systems and Scaling 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

May 25, 2024

Playing Favorites - How AI Shapes Our Knowledge Without Us Noticing

AI is making us all smarter in exactly the same way, and that might be the problem. What happens when the most accessible knowledge becomes the most uniform? As AI increasingly curates what information we see, are we trading the...

Technology and Future Thinking and Learning

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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