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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
26 May, 2026
Systems and Scaling
26 May
Systems and Scaling

Introducing Posthorn: the missing layer in self-hosted email →

Five apps, five copies of the same Resend integration, five different ideas about what to do when a send fails. The missing layer between self-hosted apps and the provider you already picked.
19 Apr, 2026
Featured
Technology and Future
19 Apr
Technology and Future
Featured

Toothpaste Back in Tubes: On opportunity cost, art, and what stays human →

The AI debate keeps leaving out the part that matters most: what gets made with the time it gives back. On opportunity cost, art, and what stays human.
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.
25 Jan, 2026
Technology and Future
25 Jan
Technology and Future

When Seeing Is No Longer Believing →

We spent years worrying about deepfakes. Then we watched authentic video get contradicted by official statements, with media treating both as valid perspectives.
24 Aug, 2025
Featured
Technology and Future
24 Aug
Technology and Future
Featured

The Bubble That Knows It's a Bubble →

Railway Mania, dot-com, AI. Technology bubbles follow a pattern older than any of them. What's different this time is that everyone knows the script.
11 Jun, 2025
Featured
Product and Strategy
11 Jun
Product and Strategy
Featured

Sensing and Sensemaking: The Hidden Skills of Product Management →

The best product managers develop two underappreciated capabilities that turn ambiguous signals into strategic clarity: sensing what others miss and making sense of what it means.
01 Jun, 2025
Product and Strategy
01 Jun
Product and Strategy

The Innovator's Dilemma: Why Good Companies Fail at the Very Thing They Do Best →

Good management kills great companies. Here's how product managers can see disruption coming and actually do something about it.
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.
25 May, 2025
Product and Strategy
25 May
Product and Strategy

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

After four years of neglecting my website, I dove into modernizing my Jekyll setup. What started as a simple tag page implementation turned into rethinking how I present my ideas online.
24 May, 2025
Featured
Thinking and Learning
24 May
Thinking and Learning
Featured

Writing is still thinking →

A blank page doesn't lie about what you actually know. In a world of AI shortcuts, writing is still the best way to really think.
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.
25 May, 2024
Featured
Technology and Future
25 May
Technology and Future
Featured

Playing Favorites - How AI Shapes Our Knowledge Without Us Noticing →

We're building a world where AI increasingly decides what information we see. These systems have a built-in bias toward the average, and it's narrowing what we collectively know.
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.
23 Aug, 2023
Featured
Product and Strategy
23 Aug
Product and Strategy
Featured

The Great Enshittification - How Product Evolution Becomes Product Regression →

Platforms enshittify. The predictable pattern by which products get worse for users while their metrics keep climbing, and why the marginal user is usually to blame.
30 Jul, 2023
Books and Ideas
30 Jul
Books and Ideas

Truth in a Post-Truth World, Revisiting Frankfurt's On Bullshit →

Revisiting Harry G. Frankfurt's 'On Bullshit' in a world where attention matters more than accuracy, and bullshit is louder than both.
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.
20 Apr, 2014
Books and Ideas
20 Apr
Books and Ideas

The Elements of User Experience →

A 2014 reading of Jesse James Garrett's foundational framework for designing user experience, and what still holds up.
06 Aug, 2013
Product and Strategy
06 Aug
Product and Strategy

Mental Models →

A 2013 note on mental models and the ways we borrow, misuse, and forget them when designing for people.
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Craig McCaskill © 2026