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Craig McCaskill

People, product and systems

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Thinking and Learning

A collection of 6 posts

August 24, 2025

The Bubble That Knows It's a Bubble

The four words that precede every crash: “This time is different.”

Technology and Future Thinking and Learning Systems and Scaling

June 11, 2025

Sensing and Sensemaking: The Hidden Skills of Product Management

Product management is built on a contradiction. We’re supposed to be data-driven, yet our most important decisions happen in the absence of clear data. We’re meant to be customer-focused, yet customers can’t tell us what they’ll want tomorrow. Navigating this...

Product and Strategy Thinking and Learning

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

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

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

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