The Best Leadership Books of 2019

The Best Leadership Books of 2019


I read a lot books. Some for my job, and some just because the topic interests me. Unfortunately, too many books aren’t worth the time I spend reading them. Sure I might walk away with 1 concept or idea, but overall a lot of books (from my experience) are better left on the shelf. At the same time, most of you don’t have a lot of free time that you can waste reading books that don’t add value.

That is why I wanted to start keeping a record of the few books that are actually worthwhile. You can be assured that any book that is recommended on Caveman in a Suit is something that will actually help you be a better person, leader, or family member. With that in mind, these are the best books from 2019.

Talking to Strangers: What We Should Know about the People We Don’t Know (Malcolm Gladwell)

Talking with Strangers is the book I wish everyone had read before the George Floyd. / Black Lives Matters protests began. The book is built around the story about Sandra Bland, an African American woman who was pulled over in a routine traffic stop in 2015 and committed suicide in a jail cell three days later. Through his book, Gladwell attempts to understand how two people (Sandra and the police officer) can be speaking the same language but completely misunderstanding each other.

Before this book, I felt like I was able to read people, and understand what they were thinking. And with my friends and family members, I am right in this belief. But this book showed me how much I (and everyone else) struggle when trying to understand someone I don’t know. We are in a moment where communication between people is even more critical than normal, so I hope you take the time and read “Talking with Strangers.”

Book Synopsis – How did Fidel Castro fool the CIA for a generation? Why did Neville Chamberlain think he could trust Adolf Hitler? Why are campus sexual assaults on the rise? Do television sitcoms teach us something about the way we relate to each other that isn’t true?

Something is very wrong, Gladwell argues, with the tools and strategies we use to make sense of people we don’t know. And because we don’t know how to talk to strangers, we are inviting conflict and misunderstanding in ways that have a profound effect on our lives and our world.

The Best Leadership Books of 2019


Range: Why Generalists Triumph in a Specialized World (David Epstein)

For the longest time, I believed in the 10,000 hour rule of building expertise. And most importantly, I believed that people at work should narrowly build that expertise. If you are a computer engineer, focus on building your field of expertise, and don’t waste time on unrelated skills like accounting. But as I wrote in my article inspired by Range, I can now admit that I was wrong.

Research shows that a team of siloed experts will actually perform worse than a team of cross functional generalists, without nearly the same depth of expertise. “Range” lays out its argument with study after study showing that people with broad knowledge do better than people with narrow expertise. I can honestly say this blew my mind, and changed how I look to develop myself and develop other people.

Book Synopsis – Plenty of experts argue that anyone who wants to develop a skill, play an instrument, or lead their field should start early, focus intensely, and rack up as many hours of deliberate practice as possible. If you dabble or delay, you’ll never catch up to the people who got a head start. But a closer look at research on the world’s top performers, from professional athletes to Nobel laureates, shows that early specialization is the exception, not the rule.    

David Epstein examined the world’s most successful athletes, artists, musicians, inventors, forecasters and scientists. He discovered that in most fields—especially those that are complex and unpredictable—generalists, not specialists, are primed to excel. Generalists often find their path late, and they juggle many interests rather than focusing on one. They’re also more creative, more agile, and able to make connections their more specialized peers can’t see.

Provocative, rigorous, and engrossing, Range makes a compelling case for actively cultivating inefficiency. Failing a test is the best way to learn. Frequent quitters end up with the most fulfilling careers. The most impactful inventors cross domains rather than deepening their knowledge in a single area. As experts silo themselves further while computers master more of the skills once reserved for highly focused humans, people who think broadly and embrace diverse experiences and perspectives will increasingly thrive.

The Best Leadership Books of 2019


Nine Lies About Work: A Freethinking Leader’s Guide to the Real World (Marcus Buckingham & Ashley Goodall)

If you have read a few of my Caveman in a Suit articles, then you probably already know that I love writing about biased decision making we have at work (the planning fallacy, the Lake Wobegone effect, biased hiring practices, etc…). Because it is such a passion for me, I am always on the lookout for new books that use science to destroy old ways of thinking about work. And to give Buckingham and Goodall credit, there were a few myths they busted that even surprised me.

This is a great book for Leaders and HR who are willing to be a little innovative, especially in the areas of company wide goal setting, engagement, talent management, and hiring. If you just want to do the same old things, then avoid this book, but don’t be surprised if you get the same old results. Take a chance, bust some of these common myths at your work.

Book Synopsis – Forget what you know about the world of work. You crave feedback. Your organization’s culture is the key to its success. Strategic planning is essential. Your competencies should be measured and your weaknesses shored up. Leadership is a thing.

These may sound like basic truths of our work lives today. But actually, they’re lies. As strengths guru and bestselling author Marcus Buckingham and Cisco Leadership and Team Intelligence head Ashley Goodall show in this provocative, inspiring book, there are some big lies–distortions, faulty assumptions, wrong thinking–that we encounter every time we show up for work. Nine lies, to be exact. They cause dysfunction and frustration, ultimately resulting in workplaces that are a pale shadow of what they could be.

But there are those who can get past the lies and discover what’s real. These freethinking leaders recognize the power and beauty of our individual uniqueness. They know that emergent patterns are more valuable than received wisdom and that evidence is more powerful than dogma.

With engaging stories and incisive analysis, the authors reveal the essential truths that such freethinking leaders will recognize immediately: that it is the strength and cohesiveness of your team, not your company’s culture, that matter most; that we should focus less on top-down planning and more on giving our people reliable, real-time intelligence; that rather than trying to align people’s goals we should strive to align people’s sense of purpose and meaning; that people don’t want constant feedback, they want helpful attention.

This is the real world of work, as it is and as it should be. Nine Lies About Work reveals the few core truths that will help you show just how good you are to those who truly rely on you.

The Best Leadership Books of 2019


Stillness is the Key (Ryan Holiday)

I am a big fan of Stoicism as a philosophy to live by, and every 5 years or so I will reread the 2 classic Stoic books “Meditations” by Marcus Aurelius and “The Art of Living” by Epictetus. What I love about the Stoic philosophy is that it really pushes you to consider what is in your control, and to not get hung up on what is outside your control.

For me Stoicism is the path of focus and discipline, so when 2020 brought about its tumultuous changes, I felt like I needed a Stoicism boost. In “Stillness is the Key”, Holiday blends some of the best parts of Stoicism with Buddhism, historical leaders, and even some cultural icons (I loved the stories about Fred Rodgers). If you are feeling stressed or if you just want to become more focused in your life, then this is the book for you.

Book Synopsis – All great leaders, thinkers, artists, athletes, and visionaries share one indelible quality. It enables them to conquer their tempers. To avoid distraction and discover great insights. To achieve happiness and do the right thing. Ryan Holiday calls it stillness–to be steady while the world spins around you.

In this book, he outlines a path for achieving this ancient, but urgently necessary way of living. Drawing on a wide range of history’s greatest thinkers, from Confucius to Seneca, Marcus Aurelius to Thich Nhat Hanh, John Stuart Mill to Nietzsche, he argues that stillness is not mere inactivity, but the doorway to self-mastery, discipline, and focus.

Holiday also examines figures who exemplified the power of stillness: baseball player Sadaharu Oh, whose study of Zen made him the greatest home run hitter of all time; Winston Churchill, who in balancing his busy public life with time spent laying bricks and painting at his Chartwell estate managed to save the world from annihilation in the process; Fred Rogers, who taught generations of children to see what was invisible to the eye; Anne Frank, whose journaling and love of nature guided her through unimaginable adversity.

More than ever, people are overwhelmed. They face obstacles and egos and competition. Stillness Is the Key offers a simple but inspiring antidote to the stress of 24/7 news and social media. The stillness that we all seek is the path to meaning, contentment, and excellence in a world that needs more of it than ever.

The Best Leadership Books of 2019


The Infinite Game: How Great Businesses Achieve Long-lasting Success (Simon Sinek)

If you haven’t seen any of Simon Sinek’s TED Talks, then you are missing out. For a while, I thought he was all polish and little substance, but then I came across his book “Leaders Eat Last”. “Leaders Eat Last” is a great read and focuses on the power of servant leadership. I heartily recommend to all leaders.

In “The Infinite Game” Sinek looks at how we set goals for ourselves (both individually and as an organization). A lot of people focus their goals on easily definable achievements (i.e. a promotion, a raise, hitting Q3 sales targets…), but those rewards provide little fulfillment to our lives. In a couple weeks we are back to chasing the next set of targets.

Sinek challenges us to approach our goals in a completely different way. Instead of trying to win a series of short term contests, focus on a long term cause that can make your world a better place. Imagine what you and your team could accomplish if you stopped worrying about the next quarter…

Book Synopsis – How do we win a game that has no end? Finite games, like football or chess, have known players, fixed rules and a clear endpoint. The winners and losers are easily identified. Infinite games, games with no finish line, like business or politics, or life itself, have players who come and go. The rules of an infinite game are changeable while infinite games have no defined endpoint. There are no winners or losers—only ahead and behind. The question is, how do we play to succeed in the game we’re in?

In this revelatory new book, Simon Sinek offers a framework for leading with an infinite mindset. On one hand, none of us can resist the fleeting thrills of a promotion earned or a tournament won, yet these rewards fade quickly. In pursuit of a Just Cause, we will commit to a vision of a future world so appealing that we will build it week after week, month after month, year after year. Although we do not know the exact form this world will take, working toward it gives our work and our life meaning.

Leaders who embrace an infinite mindset build stronger, more innovative, more inspiring organizations. Ultimately, they are the ones who lead us into the future.

The Best Leadership Books of 2019


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