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Craig McCaskill

People, product and systems

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Communication and Influence

A collection of 6 posts

May 25, 2025

Old Code, New Voice: How Technical Debt Led to Better Storytelling

I’ve been writing again. After nearly four years of letting my website collect digital dust—publishing only a few posts while my day job consumed all my creative energy. I finally felt the itch to both write and fix the stagnant...

Product and Strategy Communication and Influence

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

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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