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Craig McCaskill

People, product and systems

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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

July 30, 2023

Truth in a Post-Truth World, Revisiting Frankfurt's On Bullshit

Last week, philosopher Harry G. Frankfurt passed away. As a young adult, his essay “On Bullshit” completely changed how I thought about truth and lies, especially given a personal history with family who had a tenuous relationship with the truth....

Books and Ideas Thinking and Learning

June 24, 2014

What makes them click?

Here are the slides for the lightning talk I gave at Conversion Conf 2014, aimed as an introduction to psychology in design, why it matters and what drives us to make decisions.

Leadership and Culture Product and Strategy Communication and Influence

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