Inspired by the posts A VP Product’s Reading List and A Startup Reading List, here I’ll share my personal favorite reading materials that have helped me think about leadership, management, people and technology.
As I wrote this list, I found that there were a few main themes that drove my interest in these works. These were:
- Management examples are everywhere. Any examples of groups of people working together have little bits of learning about human interaction, management, and leadership. The timelessness of management problems is empowering, helping you remember it’s expected, not bad luck, that management is hard.
- Learning about the world is important for leadership of a global company.
- The world is complicated. For every book I read that gives me more clarity and conviction, I find it healthy to find a book that gives me pause and forces me to reflect. I find the best leaders are mostly patient, never overreact, but are willing to make high conviction big bets when needed. Books that force me to challenge my world view, I believe, help me get towards this state of management.
In any case, I hope this list is useful - I love these books. Also, I’m always on the lookout for recommendations - let me know what I should read next!
Management
This is probably the best “ramp up to being a VP Engineering” book there is. It provides four main metrics to measure and modernize your engineering team:
- Lead time for changes
- Deployment frequency
- Mean time to restore
- Change failure rate
This is an old book that still applies decades later. There are two ideas that truly stood out for me:
- You must manage your time as an executive, or you will react yourself into mediocrity. This was recently echoed in a Yellowstone episode: “Here’s my best advice about this job. Good governors initiate action, and bad governors spend all their time reacting.”
- Leverage people’s strengths as much as possible, instead of focusing on trying to fix their weaknesses.
Biographies
Teddy Roosevelt was the definition of high output. Reading this book should give you at least a decade of If-Teddy-Can motivation.
Malcom X’s biography is one of the most page-turner books I’ve ever read (tied with In Cold Blood and Fight Club). Malcolm X’s life was defined by his ever-evolving worldview, executing each iteration with intense conviction; laudable traits for any leader.
Economics/Finance/Stocks
A Concise Guide To Macroeconomics
If you lead for long enough, eventually someone will ask you a question about inflation and how it impacts their compensation. Becoming reasonably versed in macroeconomics has been helpful in thinking about compensation systems that live in the real world. This book clearly concepts like monetary policy and inflation.
The Intelligent Investor was, for me, Investing 101.
I will say, however, as much as I’ve loved the Intelligent Investor, Martin Shkreli’s Intro To Investing series was even more useful for me. The videos are hands on teaching on how to do basic company valuations, how to think about future cash flows, and their impact on valuation.
If you’re a leader in tech, you want to know things like why your (growth) company valuation would go down if interest rates go up. These books/videos help you understand that, and how you can help drive business value, as a result.
The Economist is a great realtime drip of information on the economy and world events. Anyone who tells you that they read it all every week is a liar or a bore, but even skimming it regularly has given me much more awareness of the global environment we’re all operating in.
History
A History of Medieval Europe: From Constantine to Saint Louis
Paul Graham recommended this book on Twitter and I found it quite interesting. Any good history book that covers individual leaders reminds me that leadership across the past thousands of years is more similar than it is different. From Charlamagne to Phil Jackson to Lincoln, the core tasks of keeping people happy, managing the skills and egos and ambitions of the leaders that report to you, fending off external threats - it’s all the same.
I’m particularly always fond of reading about wild direct reports. I talk to people sometimes who say they have a strict no jerk policy. Well, General Patton was a bit of a jerk. Should Eisenhower have just fired him?
While we can’t see and learn from specific HR situations in other companies, history offers us endless examples of management decisions and outcomes.
Runner up: Lives Of The Caesars
Habit
This might be the best bathroom book of all time. Daily Rituals has very short descriptions of the working habits of great artists. Ideas that stuck with me:
- If you really want to do something, you can make time to do it. If Alice Munro could produce her life’s work in slivers of time between raising kids, so can you.
- Most great works are the outcome of many repetitive days of little progress.
The book on managing a TODO list.
Religion
The Bible
I found reading the Bible later in life an illuminating experience. Reading it cover to cover gave me a grounding in the foundation of Western culture that has helped me understand nearly everything better, from Shakespeare to the founding of America and more.
Humanity
Even if you’re not about to have a kid - maybe especially if you’re not having a kid - reading this economist’s takes on pregnancy decisions is both interesting and revelatory in terms of the things people go through during a pregnancy. If you manage parents and don’t have kids yourself, reading books like this - and Mom’s Oncall - can be a great way to empathize more deeply with the experience.
Studs Turkel went and asked a ton of people about their job. The resulting book is a fascinating insight into the ups, downs, banalities, and commonalities of the working world.
Evicted is a powerful book about how screwed up the system can be for lower income households. Not only is it a good empathy-builder for people out there in the world, it’s also a look into how laws and rules can go awry with local interests and bad actors.
The Alcoholics Anonymous Big Book is a look into the original vice of humankind. I found it illuminating in it’s timelessness.
Oliver Sach’s tales of the human brain’s function and dysfunction are a popular entry point to the wonder of cognitive science. Beyond the brain stuff, Sachs was a super cultured person, littering the pages with things like “at forty, it is said, a man has the face he deserves,” which sent me on a big fitness push.
Government
What is leadership if not forming a little government. This look into local governments - towns, villages, counties - and their operations was an eye-opener, both for how the world is working around me, but also for how similar some challenges are in local government and a growth SaaS company.
Strategy
This essay feels like reading math - so crisp and concise it’s like it was sitting in the universe all along. It provides a great primer for how to think about business strategy.
Ethics
Define Business Ethics. Well, maybe just define ethics. Peter Singer’s spicy take on ethics is a head scratcher, and I believe any good leader should be occasionally scratching their head about the ethical implications of all that they’re doing. The best thing this book did for me was halt any aggressively strong ethical opinions I had - the world is complicated and ethics are tricky, the best we can do is probably to be even, measured, effortful, and not a dirtbag.
Literature
I love literature. Great literature has helped me learn nuanced ideas about humans that transfer directly to being a thoughtful manager.
For example, when I read the following in The Brothers Karamazov, I immediately realized I needed to never again fall into the state of angry do-gooder:
The more I love humanity in general the less I love man in particular. In my dreams, I often make plans for the service of humanity, and perhaps I might actually face crucifixion if it were suddenly necessary. Yet I am incapable of living in the same room with anyone for two days together.
Here’s a collection of other literature that I’ve found insightful:
Drown - these short stories are imminently consumable, and, for me, eerily realistic/reminiscent.
The Magic Mountain - sometimes I think I’d like to retire, but then I imagine I’d end up like ole Hans Castorp, feeling weird, restless, and stuck.
Ulysses or Infinite Jest - I wouldn’t recommend both, but a lot of management is just about keeping going even when things are messy and you’re not sure what’s going on, which is what reading these is like.
Beauty: When the Other Dancer is the Self - I read this short story 15 years ago and still think about it.
My Struggle - insight into the Scandinavian brain, and you learn about Bergen which lets you seem more cultured when you talk about cities in Norway that aren’t Oslo.
To Kill A Mockingbird - I recently reread this and think it’s the purest example of the craft ever. It’s like reading the Unix manual.
The Solace Of Open Spaces - A recent favorite that is a palate cleanser after a day of tech work.