The Best Leadership Books of 2020 (so far…)

The Best Leadership Books of 2020

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 the first half of 2020

Upstream: The Quest to Solve Problems Before They Happen (Dan Heath)

I have been a big fan of Dan Heath (and his brother Chip) for almost a decade. Their books Made to Stick (on communication skills) and Switch (on change management) are some of my favorite books. So when I heard about Upstream, I had high expetations. And truth be told, it delivers.

I have read many books on problem solving, but this is the first one that focuses on problem prevention. And the truth is that very few teams or leaders have unique problems. Most people struggle with the same common issues we have seen time and time again. So instead of waiting to cure the disease, read Upstream, and invest in vaccinating yourself.

Synopsis – So often in life, we get stuck in a cycle of response. We put out fires. We deal with emergencies. We stay downstream, handling one problem after another, but we never make our way upstream to fix the systems that caused the problems. Cops chase robbers, doctors treat patients with chronic illnesses, and call-center reps address customer complaints. But many crimes, chronic illnesses, and customer complaints are preventable. So why do our efforts skew so heavily toward reaction rather than prevention?

Upstream probes the psychological forces that push us downstream—including “problem blindness,” which can leave us oblivious to serious problems in our midst. And Heath introduces us to the thinkers who have overcome these obstacles and scored massive victories by switching to an upstream mindset. One online travel website prevented twenty million customer service calls every year by making some simple tweaks to its booking system. A major urban school district cut its dropout rate in half after it figured out that it could predict which students would drop out—as early as the ninth grade. A European nation almost eliminated teenage alcohol and drug abuse by deliberately changing the nation’s culture. And one EMS system accelerated the emergency-response time of its ambulances by using data to predict where 911 calls would emerge—and forward-deploying its ambulances to stand by in those areas.

Upstream delivers practical solutions for preventing problems rather than reacting to them. How many problems in our lives and in society are we tolerating simply because we’ve forgotten that we can fix them?

The Best Leadership Books of 2020

The Future Is Faster Than You Think: How Converging Technologies Are Transforming Business, Industries, and Our Lives (Peter Diamandis & Steven Kotler) 

About 5 years ago, I was at a work conference and we had a speaker from Singularity University talk to us about how companies could exponentially grow. The fabled 10x growth of many of today’s “Unicorns”. Unfortunately, the audience was mainly a traditional shipping company, so a lot of the lessons could not be immediately applied, but I was hooked.

I began devouring all the books from Singularity, and that is how I came across Diamandis & Kotler’s first book Bold (which is another book I recommend). So I knew that I would be reading The Future is Faster.

Basically, the book is an engaging deep dive into how new technologies are giving innovators and entrepreneurs a platform for rapid growth. But it isn’t just stories about small startups that aren’t applicable to most of us working in large organizations. In my opinion, their pragmatic recommendations to the readers are the true value of the book.

Synopsis – Technology is accelerating far more quickly than anyone could have imagined. During the next decade, we will experience more upheaval and create more wealth than we have in the past hundred years. In this gripping and insightful roadmap to our near future, Diamandis and Kotler investigate how wave after wave of exponentially accelerating technologies will impact both our daily lives and society as a whole. What happens as AI, robotics, virtual reality, digital biology, and sensors crash into 3D printing, blockchain, and global gigabit networks? How will these convergences transform today’s legacy industries? What will happen to the way we raise our kids, govern our nations, and care for our planet?

Diamandis, a space-entrepreneur-turned-innovation-pioneer, and Kotler, bestselling author and peak performance expert, probe the science of technological convergence and how it will reinvent every part of our lives—transportation, retail, advertising, education, health, entertainment, food, and finance—taking humanity into uncharted territories and reimagining the world as we know it.

The Best Leadership Books of 2020

Do Nothing: How to Break Away from Overworking, Overdoing, and Underliving (Celeste Headlee)

There is no doubt that 2020 is going to be remembered as the year of Covid-19, and its transformative impact on our lives. For me, having to work from home (especially when the schools were closed), felt like a moment when I had to adapt or die. There was so much on my plate that I knew that I would burnout if I did not reprioritize some things at work and in my life.

That is when Celeste Headlee’s “Do Nothing” book came into my life. In the first part of the book she covers how historically our lives have become more and more filled with things to do. But then in the second part, she utilizes those historical lessons to provide some pragmatic approaches to reprioritizing your life. This is a must read for people feeling overwhelmed due to the Coronavirus (or just life in general).

Synopsis – Despite our constant search for new ways to optimize our bodies and minds for peak performance, human beings are working more instead of less, living harder not smarter, and becoming more lonely and anxious. We strive for the absolute best in every aspect of our lives, ignoring what we do well naturally and reaching for a bar that keeps rising higher and higher. Why do we measure our time in terms of efficiency instead of meaning? Why can’t we just take a break?
In Do Nothing, award-winning journalist Celeste Headlee illuminates a new path ahead, seeking to institute a global shift in our thinking so we can stop sabotaging our well-being, put work aside, and start living instead of doing. As it turns out, we’re searching for external solutions to an internal problem. We won’t find what we’re searching for in punishing diets, productivity apps, or the latest self-improvement schemes. Yet all is not lost—we just need to learn how to take time for ourselves, without agenda or profit, and redefine what is truly worthwhile.
Pulling together threads from history, neuroscience, social science, and even paleontology, Headlee examines long-held assumptions about time use, idleness, hard work, and even our ultimate goals. Her research reveals that the habits we cling to are doing us harm; they developed recently in human history, which means they are habits that can, and must, be broken. It’s time to reverse the trend that’s making us all sadder, sicker, and less productive, and return to a way of life that allows us to thrive.

The Best Leadership Books of 2020

Think Like a Rocket Scientist: Simple Strategies You Can Use to Make Giant Leaps in Work and Life (Ozan Varol)

I have to admit… I am a sucker for science books, especially when it comes to things like space, physics or technology. So, when I saw the title of this book, I already was interested. But when I saw that it was also recommended by Malcolm Gladwell, Satya Nadella, and Adam Grant I knew that there must be something more than just a catchy concept.

This book is all about thinking about how you think. That might sound like a weird concept for a book, but I found it refreshing. The first half of 2020 has felt like a steady stream of complex issues with no simple solutions (fight against structured racism, working from home, opening vs closing schools, teams shifting to virtual collaboration, etc…). “Think like a Rocket Scientist” is a great read for trying to tackle complex problem, and based on the year we are having I think this is a critical skill we all need to have.

Synopsis – Rocket science is often celebrated as the ultimate triumph of technology. But it’s not. Rather, it’s the apex of a certain thought process – a way to imagine the unimaginable and solve the unsolvable. It’s the same thought process that enabled Neil Armstrong to take his giant leap for mankind, that allows spacecraft to travel millions of miles through outer space and land on a precise spot, and that brings us closer to colonizing other planets. Fortunately, you don’t have to be a rocket scientist to think like one. 

In this accessible and practical book, Ozan Varol reveals nine simple strategies from rocket science that you can use to make your own giant leaps in work and life – whether it’s landing your dream job, accelerating your business, learning a new skill, or creating the next breakthrough product. Today, thinking like a rocket scientist is a necessity. We all encounter complex and unfamiliar problems in our lives. Those who can tackle these problems – without clear guidelines and with the clock ticking – enjoy an extraordinary advantage. 

The Best Leadership Books of 2020

More Book Recommendations from Caveman in a Suit

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