High Output Management by Andy Grove — A quick-to-read classic, HOM is a solid introduction to how a manager should measure processes, create goals, and evaluate outcomes — and introduces the concept of OKRs to the world.
Managing Humans by Michael Lopp — Michael Lopp is an engineering leader (currently at Slack) who writes under the pen name ‘Rands’ on his personal site. Many of his best essays on managing people (particularly engineers) are compiled in this book. Rands has provided me a series of mental models to help identify, grok, and respond to tough situations.
Antifragile by Nassim Taleb — Helps in understanding how highly interlinked and interdependent systems can underperform, particularly during periods of high variability. Nassim advocates for decentralized polities and systems which we can afford to let fail — and then learn from them.
The Visual Display of Quantitative Information by Edward Tufte — Tufte is the god-father of information display; reading Tufte offers a brilliant view into the earliest day of information design, and helps one understand the underlying fundamentals without getting distracted by pretty editing tools.
Imagined Communities by Benedict Anderson — By studying how the Industrial Revolution transformed France and created the nation-state, Benedict Anderson provides a powerful lens for understanding the impact of the internet on modern societies