My Favorite Leadership Reads
An unconventional list
What leadership books should I read?
This is one of the most common questions I get. My response might be surprising. You won’t find the most popular books on this list. I don’t read a ton of leadership books these days. It’s not that I hate classic books on this topic. I was lucky enough to interview Liz Wiseman about Multipliers, one of my favorites. Turn the Ship Around by L. David Marquet is an interesting peek into military leadership. An insightful book is Sheree Atcheson’s Demanding More, written about in this edition.
Outside of the few gems like these, it’s a sea of sameness. I’m interested in busting myths and seeing leadership through a new lens. Given this, it’s probably not surprising that I look to other fields for inspiration. These are unexpected choices but as insightful as the classic tomes often recommended.
The Psychology of Money
This book by Morgan Housel is not about leadership. It made the list because it’s packed with psychology principles that relate to the work of leaders. For example, the rule of compounding inspired this edition.
Like investing, small incremental shifts can make a big difference in leadership. For instance, leaders are influential in creating an environment of psychological safety. These conditions engender trust, a sense of belonging, and creativity. The best teams swim in it. Psychological safety builds through actions like listening to feedback, holding confidential information sacred, and how we respond to mistakes. That’s the rule of compounding at work in leadership. The very best leaders live by this rule.
This post was the inspiration though I recommend reading the book.
Transitions: Making Sense of Life’s Changes
I discovered this classic by William Bridges during a class on organizational behavior. It’s the one I’ve recommended more than any other. Leaders are knee-deep change all the time. It’s easy to focus on the physical logistics of change like titles, reporting structures, projects, and timelines. These aspects are essential, but they don’t count for human reactions to change. Transitions articulates the emotional journey of change. Understanding that how shifts cause emotional responses helps leaders navigate it more smoothly. Understanding reactions to change can mean the difference between a smooth transition and one that leads to a loss of trust.
The follow-up book, Managing Transitions translates these principles to organizational change. This handy guide is also highly recommended.
The Boys in the Boat
Despite glowing recommendations, I put off reading this book for a year. I decided to read one chapter before I finally returned it to the library. It gripped me, not letting go until the last page.
With its emphasis on the unit over extraordinary individuals, I find rowing fascinating. Team sports like rowing where alignment is crucial offer ample glimpses into the mechanisms of group dynamics. Like rowing coaches, leaders need to get everyone moving in the same direction. They experiment with configurations, have to resolve conflicts, and work with different styles. These threads are interwoven throughout this book. The resilience and quirky style of Joe Rantz offers insights for leaders too.
You won’t regret putting The Boys in the Boat on your reading list.
Frankenstein
Growing up I avoided anything horror-related — it terrified me. I got through high school and college without having to read Frankenstein, only to have it picked as a book club selection. Committed to the other members, I read carefully, ready to flick past gory scenes. I discovered a rich and thoughtful book that was more science fiction than horror.
What struck me was Victor’s desire to do something great. His ambition helped him push beyond boundaries; it was also his undoing. Founders are often driven to create something disruptive. They ride the edge between the triumph of innovation and potential destruction — be that financial, reputation, or mental well-being. We can become single-minded in our pursuit of achieving a feat deemed impossible. When creating something new, how do we know when to persist and when we've lost our perspective? How do we know when the cost is too high?
Though tempting, skip the cliff notes and read the book.
Deep Survival
I have a penchant for stories about people exploring the wilderness. Environments where the stakes are high offer fascinating insights. My very favorite of this genre is Deep Survival by Laurence Gonzales. He examines the psychology behind why some survive extreme situations while others flounder. The book explores how we make decisions and how to manage our emotions under pressure. Both are relevant for those leading organizations.
One section examines how people respond when they're lost. Becoming a new leader isn't more of the same, it's a divergent path requiring new mental models. The terrain might look familiar but the landmarks are very different.
“Admitting that you are lost is difficult because having no mental map, being no place, is like having no self…Being lost, then, is not a location; it is a transformation. It is a failure of the mind….like it or not, you must make a new mental map of where you are.”
The blend of stories and neuroscience makes Deep Survival invaluable.
Looking to discover new books in this genre?
I host Lead Dev’s monthly Bookmarked series where I've been lucky to interview Liz Wiseman, Marty Cagan, Nadia Egbhal and more. I hope you’ll join us.
What are your favorite books about leadership? Hit reply or respond below.
Until next time, be well.
