For CIOs · Reading list
A reading list for CIOs
Three versions of the same problem, each with a couple of essays to start from. The technology is rarely what breaks — the breakage is almost always cultural. Find the one that sounds like your org. For the short version and how to work with Steve, start on the For CIOs page.
If you're skeptical
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2024
The Death of the Junior Developer
What AI coding tools do to the bottom rung of the career ladder.
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2023
Cheating Is All You Need
The early, emphatic case that coding assistants were a step change, not a toy.
If you're going too fast
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2026
Vibe Maintainer
Maintenance is the new bottleneck.
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2025
The AI Vampire
Cost-versus-value at scale.
If you've been piloting for a year
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2012
Notes from the Mystery Machine Bus
The conservative/liberal axis of engineering culture — central to thinking about why pilots stall.
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2011
Stevey's Google Platforms Rant
Why most internal initiatives fail to compound into a platform.
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2006
Good Agile, Bad Agile
The case against process-for-its-own-sake, from inside Google's early engineering culture.