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Craig McCaskill

People, product and systems

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Leadership and Culture

A collection of 6 posts

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

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

January 2, 2024

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

In the quest for clarity and alignment, modern organizations increasingly embrace structured goal-setting frameworks like OKRs (Objectives and Key Results). But beneath the surface of these seemingly rational systems lies a deeper question: Are we measuring what truly matters, or...

Product and Strategy Leadership and Culture Communication and Influence

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