CEOs:

Part 1 of this series is a phrase book of programmer-speak.
Part 2 is the meaning of “done” and how to know when you’ll get there. There’s another Bill Gates story here as well.
Part 3 is about features that kill projects.
Part 4 is about super debuggers.

Programmers
Managing Non-Technical CEOs
Managing Technical CEOs

The Managing the Technical CEO is some very fine writing.