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Craig McCaskill

People, product and systems

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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

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

December 13, 2024

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

You ship feature after feature, your development team works overtime, your backlog is always full—yet customer satisfaction remains flat and business metrics barely budge. Sound familiar? You’re not alone. Most product organizations have fallen into what Melissa Perri calls “the...

Product and Strategy Leadership and Culture

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

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