From the lens of a Product Manager working in ML / Large Language Models...
The Alignment Problem
By Brian Christian
How do we tell the computer to do all the things we want it to do, all the things we don't want it to do, and all the things we didn't realize we want it to do or not do? How do we capture the rich implied and inferred nature of humanness? That's the Alignment Problem. The book dives into this broadly – but also gives an excellent non-technical survey of the evolution of machine learning.
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Understanding Comics: The Invisible Art
By Scott McCloud
This is magnitudes more than a dive into the perhaps easy to dismiss artform. This book is about storytelling and why great stories resonate. It's one of the best pieces of media, on media, period.
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An Elegant Puzzle: Systems of Engineering Management
By Will Larsen
When I my company was acquired by a very-big-Giant, my personal antibodies reacted negatively to the how the big G's way of thinking and doing – I was harmfully autoimmune. To some extent I had to accept things, to another extent I needed a different perspective. This book helped me transition and it's one I push on all of our leads. While we as PMs don't manage people directly we architect the whole system – and this book is an insightful (I buy it for all the team's leads) lens on how big teams where personal alignment and corporate alignment problems need to be negotiated.
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Exhalation Stories
By Ted Chiang (also recommend Stories of Your Life)
The author has an absolute magic way of taking a kernel of an idea and spinning not only a whole world, but a whole new way of looking at the world – all in the span of a short story. You can't get any closer to home than "The Lifecycle of Software Objects" where the protagonist rears an artificial intelligence from "pet" to a human-like mind.
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The Pragmatic Programmer
By David Thomas and Andrew Hunt
PMs need to get things done. Even if we don't code, we need to think deeply on how it's built to ensure it achieves our goals now, and what we project them to be in the future. As the title suggests, a pragmatic take on building code-driven systems.
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Design of Everyday Things
By Don Norman
The OG design-thinking before IDEO corporatized it.
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Principles
By Ray Dalio
"Principles are ways of successfully dealing with reality to get what you want out of life." This book influenced me to distill how we take action and prioritize and how we decide as a team. I'll admit some of the set up of the book irked me, but the distilled world view that form the Principles in the second half of the book generally resonates; the world works a certain way, find those patterns, use it to your advantage (and for good).
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The Visual Display of Quantitative Information
By Edward Tufte
You could jump into any of Tufte's books, on any page, and come away with new ways of looking/thinking/telling stories about data. ML problems are data problems – let's think well beyond raw dumps and tables.