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Craig McCaskill
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Everything

Books and Ideas

4 posts

Communication and Influence

6 posts

Leadership and Culture

8 posts

Product and Strategy

10 posts

Systems and Scaling

5 posts

Technology and Future

6 posts

Thinking and Learning

10 posts
08 Mar, 2026
Featured
Leadership and Culture
08 Mar
Leadership and Culture
Featured

The Games Your Organization is Actually Playing →

Most organizational dysfunction comes from rational people responding to badly designed games. Before you blame the players, check the rules.
22 Feb, 2026
Featured
Leadership and Culture
22 Feb
Leadership and Culture
Featured

The Case for Being Wrong Faster →

Most organizations punish people for changing their minds. The ones that win are the ones that learn fastest.
29 May, 2025
Featured
Technology and Future
29 May
Technology and Future
Featured

How to Think About AI →

Jensen Huang is right about AI's real impact on jobs, but most people are missing his deeper point about competitive advantage.
24 Feb, 2025
Featured
Leadership and Culture
24 Feb
Leadership and Culture
Featured

The Science of Saying No - Frameworks and Execution →

The practical mechanics of prioritization: framework selection, implementation tactics, and the sustainability habits that let systems survive under pressure.
17 Feb, 2025
Featured
Leadership and Culture
17 Feb
Leadership and Culture
Featured

The Art of Saying No (Or At Least, Not Yet) →

The math of product is simple but brutal: too many demands, not enough resources. A case for saying no to the good so you can say yes to the great.
13 Dec, 2024
Product and Strategy
13 Dec
Product and Strategy

Escaping the Build Trap: How Effective Product Management Creates Real Value →

Product teams trapped in endless feature delivery cycles can break free by shifting focus from outputs to outcomes. A reading of Melissa Perri.
02 Jan, 2024
Product and Strategy
02 Jan
Product and Strategy

Beyond Metrics - Why OKRs often miss the human element of work →

OKR rituals produce green metrics and unhappy teams. Why measurement captures what's easy rather than what matters, and how to tell the difference.
24 Jun, 2014
Leadership and Culture
24 Jun
Leadership and Culture

What makes them click? →

A 2014 review of Susan Weinschenk's behavior-design classic: what makes users click, and what it means for the products we build.
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Craig McCaskill © 2026