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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.
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.
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.
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.
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.
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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