's Picture

Craig McCaskill

People, product and systems

  • Home
  • About
  • Search
  • Contact Me

Thinking and Learning

A collection of 7 posts

January 25, 2026

When Seeing Is No Longer Believing

Imagine you watch a video. Multiple angles, timestamped, from bystanders with phones. You see what happens. A confrontation. A shooting. The sequence of events is clear.

Technology and Future Thinking and Learning

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

Page 1 of 2 Older Posts
Page 1 of 2 Older Posts

Craig McCaskill © 2026. Powered by Jekyll.

Back to top