Some of My Favorite Books on Leadership

Open Book

I have always been a bookworm, and I have tried to use my hobby to improve my skills and abilities at whatever I was facing at the time or interested in for the future.

Over the years I have read a lot of books on leadership, both general and technical. I thought I would share what some of my all-time favorites are. These are the top ones based on mainly two criteria: a) it made enough impact that I remember its explicit influence on my behavior or skills and b) I valued it enough I have recommended it to others in the past. It’s also a pretty good sign if I remember the author’s name years later.

Below are some of my favorites. I would love to hear from you what some of yours are.

General Leadership

Crucial Conversations by Kerry Patterson, Joseph Grenny, Ron McMillan, and Al Switzler - This one is easier to understand than implement but valuable. I think this probably helped me at least try to be a better person, not just more successful.

The Seven Habits of Highly Effective People by Stephen R. Covey - This book is so famous several of the habits turned into clichés so widespread that they are often ridiculed, but I think it was only that popular because it was on point. Look past the negative connotations others have piled on “synergize” and “win-win” and read the original content from Covey.

How to Win Friends and Influence People by Dale Carnegie - This book arguably founded the genre of self-help books, which I don’t always view in a favorable light. However, Carnegie gave effective, timeless advice about influencing and working with people. This book is applicable now, and probably always will be. It still sells 250,000 copies a year even though it was first published in 1936 according to Wikipedia.

Old school technical leadership classics

The Mythical Man-Month - by Frederick Brooks Jr. - This one should need no introduction. As much as technology, software, hardware, and tools used by developers have changed since this was written, the mistakes described in this book are still repeated by managers and leaders well-meaning or otherwise. Every time we call a person a resource or headcount, I think of this book, and try to remind myself that people and situations are all unique.

Peopleware: Productive Projects and Teams by Tom DeMarco and Tim Lister - I wish people designing, planning, funding, or making other decisions about workplaces ever read this book. As far as I can tell, few have. I have spent years of my life unable to accomplish anything without hiding and wearing headphones trying to ignore the visual distractions of people walking past where I was sitting to try and concentrate.

Writing Solid Code and Debugging the Development Process both by Steve Maguire - I read these while at my first job, which was actually as the lead dev/engineering manager, whatever you call it when you own half the company and it has 7 people in it. I’m not sure how applicable the examples are to most developers anymore (I think they were all in C which is all I was using then), but these books improved my ability to write maintainable code, test and debug software effectively, and introduced me to defensive programming.

High Output Management by Andy Grove - This is an influential book by the former CEO of Intel. It is very no-nonsense. Andy’s backstory is also pretty inspiring in terms of bootstrapping yourself from humble beginnings.

Other Technical Leadership Books

Clean Agile: Back to Basics by Robert C. Martin -My favorite book on Agile, maybe because I’m a minimalist and natural skeptic, by one of the signatories of the agile manifesto.

The Lean Startup by Eric Ries - This is the core book of lean. Again, appeals to the minimalist in me. Success is often about the right trade-offs, focus, and prioritization. This also emphasizes measuring the success, qualitatively and quantitatively, viewing our efforts from the lens of experiments, and how to get to that feedback and data sooner.

Books On Skills Related to Leadership

On Writing Well by William Zinsser - This is my favorite book about writing more effectively. I am naturally verbose, and any skills I have at brevity largely came from this book.

The Checklist Manifesto by Atul Gawande - I read this one while I was working as an SRE. It’s quite interesting, though I think the pragmatic lessons could be summarized more concisely without the stories and data that make them interesting and compelling.

Related to Focus and Well Being

Walden by Henry David Thoreau - this was one of the first non-fiction books that really resonated with me. I first read it for summer reading for high school, and I have reread parts of it many times over the years.

Atomic Habits by James Clear - I read this one recently after reading The Power of Habit by Charles Duhigg quite a while back. I wish I had gotten around to it sooner because it has a much more practical focus than the latter.


The Obstacle is the Way - by Ryan Holiday is one of my all-time favorite books. It was basically my gateway drug to stoicism.

Ryan Holiday’s book lead me to read Courage Under Fire: Testing Epictetus's Doctrines in a Laboratory of Human Behavior by James Stockdale which will, for most of you, put your current challenges in sharp perspective compared to being the highest-ranking American POA in the Hanoi Hilton at the time.

Those books on stoicism both pointed me to The Enchiridion By Epictetus which I highly recommend for practical philosophy. I found this easier to read than Meditations by Marcus Aurelius, but the latter is great for content as well just more verbose. I recommend checking out some of the quotes from meditations.

What I’m Reading Currently

I am usually reading at least two books concurrently. One that requires focus due to the nature of its content or is not available as an ebook or audiobook plus a second book that I can read or listen to while in line or when I have a short block of time or I’m taking a break.

Right now I’m reading Essentialism because I had a paper copy laying around I had not made it to reading yet, plus Leadership is Language. I quite like both of these so far.

By Richard Anton

Sep 10, 2021