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Craig McCaskill

People, product and systems

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Systems and Scaling

A collection of 3 posts

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

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

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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