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Craig McCaskill

@craigmccaskill

Building enterprise products at ServiceNow as part of the AI Platform. Tracking what works, what scales, and what's left after the tourists leave. AI pragmatist, systems thinker. Opinions my own.

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30.11.2024
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Latest posts by Craig McCaskill @craigmccaskill

Most organizational dysfunction isn't caused by bad people. It's caused by rational people responding to badly designed games.

New post: The Games Your Organization is Actually Playing

08.03.2026 23:20 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

New post: The Case for Being Wrong Faster. On intellectual honesty as a competitive advantage, and why the system is designed to stay wrong longer than the market will wait. The winners are the ones that learn the fastest.

08.03.2026 22:22 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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 even...

When Seeing Is No Longer Believing craigmccaskill.com/when-seeing-...

26.01.2026 04:47 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0

Thanks Jim!

30.08.2025 23:43 πŸ‘ 0 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
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 pers...

Netflix used to help you discover films. Spotify was a music lover's sanctuary. Now they're engagement traps optimizing for the wrong metrics. Why do all our favorite platforms get worse over time? New post on the predictable lifecycle of digital products:
craigmccaskill.com/the-great-en...

26.08.2025 04:30 πŸ‘ 1 πŸ” 0 πŸ’¬ 0 πŸ“Œ 0
The Bubble That Knows It’s a Bubble The four words that precede every crash: β€œThis time is different.”

In 2002, you could buy Amazon for $6. Netflix traded at $3 in 2008. The best investments emerge from bubble wreckage, not bubble peaks. What will be the AI equivalent? New post on why the crash creates the opportunity: craigmccaskill.com/ai-bubble-history

26.08.2025 01:30 πŸ‘ 8 πŸ” 2 πŸ’¬ 1 πŸ“Œ 0