's Picture

Craig McCaskill

People, product and systems

  • Home
  • About
  • Search
  • Contact Me

Leadership and Culture

A collection of 8 posts

March 8, 2026

The Games Your Organization is Actually Playing

Or: before you blame the players, check the rules.

Leadership and Culture Thinking and Learning

February 22, 2026

The Case for Being Wrong Faster

Or: intellectual honesty is your competitive advantage.

Leadership and Culture Thinking and Learning

May 29, 2025

How to Think About AI

New tools don’t just change what we can do, they change who wins. The printing press didn’t eliminate scribes overnight, but it made literate societies dramatically more powerful than illiterate ones.

Technology and Future Leadership and Culture

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

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

Craig McCaskill © 2026. Powered by Jekyll.

Back to top