10 Books Guaranteed to Help You Lead Better in 2020 and Beyond

Even if the only person you lead is yourself.

Kyle Chastain
Oct 9, 2020 · 8 min read
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Photo by Eliott Reyna on Unsplash

If you’d like to understand people better, influence others more, and stay more focused even in a difficult year, where should you start?

When you face challenging times, it’s a gift to be able to see things from a different perspective, think clearly about your challenges, remain cool under pressure, and grow in areas that are important to you.

Whether you’re leading a family or a board room, a tech startup, or a sports team, or if you’re a CEO or a teacher, there are at least one or two books on this list for you.

Here are 10 books — some new, some old, some well known, and some forgotten — that will help you lead better and stronger in 2020.

The Score Takes Care of Itself by Bill Walsh

Can I confess something? I’ve never been big into sports. Sure, I pull for local teams, but I can’t spit stats and I don’t belong to any fantasy leagues. That said, I appreciate outstanding leadership in whatever form it takes. Bill Walsh’s leadership of the San Francisco 49ers is nothing short of masterful. In just three years, he took the team from the worst in the league to a Super Bowl championship. He didn’t do it with flair or inspirational speeches, but by teaching them to implement what he calls his Standards of Performance — specific actions and attitudes to build performance across the entire organization. As a result, he established a dynasty.

I approached building the 49er organization with an agenda that didn’t include a timetable for a championship or even a winning season. Instead, I arrived with an urgent timetable for instilling an agenda of specific behavioral norms — actions and attitudes — that applied to every single person on our payroll. (P. 13)

Xenophon’s Cyrus the Great: The Arts of Leadership and War by Xenophon and Larry Hedrick

This book is a leadership classic that doesn’t get a lot of attention anymore. Xenophon, a soldier, and historian who lived in the 5th/4th century BCE wrote this book as a study of the leadership of Cyrus the Great. It’s a first-person account of Cyrus, a historical king who founded the Persian empire and is one of histories greatest conquerors. While most men in his position squashed enemies under their boot, Cyrus was known as a lenient and benevolent ruler. His achievements far outnumbered anyone else’s of his time, and Xenophon breaks down how he led others to achieve his dreams. He does this in a series of leadership principles that can be applied in many different ways. Originally called Cyropedia, this updated version by Larry Hedrick is written in modern language and easy to read. I will inspire you to go for your dreams and remind you to treat even your enemies well.

What really distinguished me was a clear and calculating — yet always benevolent — mind. I was the product of a strict warrior culture, and I learned early on to suppress my emotions and respond to danger with great composure. I was never the plaything of fear or greed. (p.1)

Play Bigger: How Pirates, Dreamers, and Innovators Create and Dominate Markets by Al Ramadan, Dave Peterson, et al.

Why do some companies and organizations compete year-to-year, while others break away from the pack and become icons in their own right? According to the authors of Play Bigger, it’s because they create entirely new market categories and become category kings. Think of companies like Uber, Ikea, Apple, or Salesforce — they weren’t content to compete in the game, so they invented an entirely new one. These companies created a new category in the market and dominated it. The authors’ research and insight will show you how to create and dominate a category no matter what type of organization you lead.

The most exciting companies create. They give us new ways of living, thinking, or doing business, many times solving a problem we didn’t know we had — or a problem we didn’t pay attention to because we never thought there was another way. (p.9)

The Obstacle is the Way by Ryan Holiday

I first read this book when I was trying to numerically grow and lead a team. As the subtitle says, it’s about the art of turning trials into triumph. Holiday bases this book on an ancient Greek philosophy called Stoicism. This philosophy focuses on “enduring pain or adversity with perseverance and resilience.” Stoicism is about controlling what you can control (your attitude, outlook, and perspective) in the face of adversity, and letting go of what you can’t control (opinions and outcomes). It focuses on turning obstacles into opportunities. Now if that doesn’t make you want to get off the couch and run through a wall I don’t know what will. This book offers practical direction for overcoming struggles.

Yet in our own lives, we aren’t content to deal with things as they happen. We have to dive endlessly into what everything “means,” whether something is “fair” or not, what’s “behind” this or that, and what everyone else is doing. Then we wonder why we don’t have the energy to actually deal with our problems. Or we get ourselves so worked up and intimidated because of the overthinking, that if we’d just gotten to work we’d probably be done already. (p.46)

Theodore Roosevelt on Leadership: Executive Lessons from the Bully Pulpit by James M. Strock

I’m a big fan of leadership biographies because they follow their subjects’ life and extrapolate actionable principles. This was one of the first I ever read and it covers two of my favorite subjects: history, and Theodore Roosevelt. This is a unique book because it looks at Roosevelt’s leadership as the chief executive of a country and breaks it down. As a leader who transformed America, he’s been admired and vilified by many for over a hundred years. He’s a fascinating character to read about and this is a great place to learn about his leadership.

The energies and talents [Roosevelt] possessed were not placed at birth in some natural harmony; they were through the passing years organized and directed by a sustained and splendid act of will. (p. 230)

Turning Pro by Steven Pressfield

You’re probably familiar with Steven Pressfield’s The War of Art, and Turning Pro is another book in that same series. In it, Pressfield describes the difference between two mindsets. The first mindset is that of an amateur — someone who goes through life directionless or only dabbling here and there in their purpose. The second is the mindset of a pro — someone who goes all-in and takes complete ownership of their life and desired pursuits. Amateurs never accomplish much of anything because they’re too caught up in the systems of their life and blame others for their condition. Pros have the best shot at achieving because they take responsibility for their life and refuse to blame others or play the victim. Pressfield answers the question of how do you go from An amateur to pro? You’ll want to this one again and again. Trust me.

“Turning pro is free, but it demands sacrifice. The passage is often accompanied by an interior odyssey whose trials are survived only at great cost, emotionally, psychologically, and spiritually. We pass through a membrane when we turn pro. It hurts. It’s messy and it’s scary. We tread in blood when we turn pro.” (P. 5)

Alexander the Great by Philip Freeman

By the age of 32, Alexander of Macedon established the greatest empire of the Ancient World. Crowned King at age 19, he toppled the Persian Empire founded by Cyrus the Great (see above), and spread his conquests as far as Egypt, Pakistan, and India. More than two thousand years after his death, he’s still considered one of the greatest generals in history. He spent most of his adult life away from his homeland on campaigns, and he spread Greek language and culture throughout the ancient world. He overcame impossible odds and faced down enemies with armies many times the size of his own. He was also brutal, a tyrant, and an egoist. You won’t want to emulate his methods of leadership, but his determination and resourcefulness are remarkable. This book isn’t a dry history but highly readable, and written in a way that accessible even for people who find history boring.

Favorite Quote:

As usual, the young king delighted in taking on the most difficult tasks. The expedition through the mountains took months of trudging over narrow trails and across raging streams. If there was an inaccessible fortress that refused to surrender to the Macedonians, Alexander took it, no matter how difficult. (p. 226)

The Four Obsessions of an Extraordinary Executive by Patrick Lencioni

Using stories for teaching is a powerful tool. and Patrick Lencioni uses a simple but powerful leadership fable in this book to teach about creating a healthy organization. It’s a story of corporate intrigue as a frustrated CEO attempts to uncover how his competition consistently beats him. What makes his competition so successful is that it’s an internally healthy company with its own unique culture built around central values. The second half of the book is dedicated to breaking down the story and showing his readers exactly what makes a healthy, thriving organization.

There is hope for us because we too can become extraordinary leaders if we only embrace the fact that success is not so much a function of intelligence or natural ability, but rather of commitment to the right disciplines.

Leadership in Turbulent Times by Doris Kearnes Goodwin

A book about presidential leadership during crisis periods? Yes, please. Highly respected historian Doris Kearnes Goodwin asks the age-old question: does the leader make the times or do the times make the leader? She draws on the lives of the four presidents she has studied most — Abraham Lincoln, Theodore Roosevelt, Franklin D. Roosevelt, and Lyndon B. Johnson. She looks at Lincoln’s leadership during the Civil War, TR’s leadership during the Coal Strike, FDR during his First Hundred Days in office in the heart of the Great Depression, and LBJ (whom she knew personally) during the Civil Rights Movement and the establishment of the Great Society. She explores their backgrounds and upbringings and examines how they each rose from obscurity to become the history-shaping leaders they were. She also provides tremendous insight into the transformational leadership, crisis leadership, turnaround leadership, and visionary leadership they embodied. There’s a ton of gold to be mined in these pages.

The fame [Lincoln, TR, FDR, and Johnson] craved, the recognition they sought, bears little resemblance to today’s cult of celebrity. For these leaders, the final measure of their achievements would be realized by their admittance to an enduring place in communal memory. (p. 343)

The Laws of Human Nature by Robert Greene

How would your life improve if you could better understand people? Imagine knowing why people act the way they do. If you could understand what motivates them, you could tap into that power and achieve extraordinary things in your family, relationships, and on the job. That’s what this book can do for you. Robert Green masterfully distills the wisdom of philosophy and psychology to give you 18 laws that will empower you to understand not only the people you lead but also yourself. It’s a hefty read at 624 pages, but there’s highlight-worthy content on almost every page.

We are subject to forces from deep within us that drive our behavior and that operate below the level of our awareness. We see the results — our thoughts, moods, and actions — but have little conscious access to what actually moves our emotions and compels us to behave in certain ways. (p. 3)

Now, if you’ll excuse me, I have some books I need to re-read.

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Kyle Chastain

Written by

My dreams are what get me up every day • Husband and dad 2x • I only share advice I’ve lived • Say hello: kyle@kylechastain.com

The Innovation

A place for a variety of stories from different backgrounds

Kyle Chastain

Written by

My dreams are what get me up every day • Husband and dad 2x • I only share advice I’ve lived • Say hello: kyle@kylechastain.com

The Innovation

A place for a variety of stories from different backgrounds

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