Cover pages of the best leadership books for managers. Fooled by randomness, The power of habit, why we do what we do in life and business, Thinking, fast and slow.Books

Best Leadership Books: Essential Reading List For Future Leaders

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If you find yourself held back at work, this reading list of the best leadership books will set you free. They will teach you what it really takes to be an inspiring and effective leader. These top leadership books will show you surprising ways to dramatically improve your odds of being a successful at leading others in the workplace.

Those of us who are looking to improve our leadership abilities through books find ourselves caught in a cycle of frustration. We keep asking that elusive question: “What is the best leadership book that will finally help me?”

But most of the management books people recommend to us have almost no impact on our lives. After reading them, we still find ourselves stuck in the same place. With nothing to show for our efforts.

Leadership Books You Are Better Off Giving To Your Competitors

Many books that claim to improve your leadership skills don’t work. These authors describe a version of success that was mostly achieved through luck. But they ascribe it to talent and ability of the famous founders and CEOs of successful companies they talk about. Then they write a book on what they have imagined drove their success. And the rest of us fall for it.

Avoid leadership books based on the lives and methods of famous CEOs like Bill Gates and Steve Jobs. Also, books about the founders of companies like Google and Facebook. Instead, gift them to your competitors. Or people who are not nice to you.

And if you are wondering why, the first few leadership books listed here will answer this for you. But first, here are some bonus tips. Stay away from anything written by Simon Sinek. Or any leadership book that touts the “habits of successful people.”

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Top Books On Business Leadership, Management And Entrepreneurship You Should Read

If you are seriously asking the question: “How can I be a better leader?” Then, set yourself free with this reading list that captures the most effective and straight-forward leadership lessons you will find.

  1. Initially they will make you pause. They will make you say, “Really? I doubt that would work.”
  2. They won’t be based on someone’s story of success. The main leadership lessons, if applied, will be predictable of success at the onset. No backward fitting narratives of someone’s lucky run.
  3. They may not give you answers but will teach you how to ask the right questions. A real education comes more from being able to question things the right way than from knowing answers to random things.
  4. They will soon produce noticeable results for you. Once you understand and implement the concepts, you will get immediate results.

Books That Explain Why The Most Widely-Read Management Books Are A Waste

Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets (Incerto)

By Nassim Nicholas Taleb, Random House, New York, NY 2004.

By Nassim Nicholas Taleb - Fooled by Randomness: The Hidden Role of Chance in Life and in the Markets (2nd Revised edition)

“Fooled by Randomness” is one of the most eye-opening books you will read. It is the greatest and most profound leadership book out there. It shows how even intelligent people have fallen for false ideas on what drives success. Taleb shows how humans are probability-blind in most cases. They see patterns and causality where none exist.

The reason why leadership books, based on the abilities of a famous founder or CEO, fail for the rest of us is that it neglects to account for survivorship bias and luck. They don’t talk about the people who had the same skill set but failed to achieve the same enormous success. Luck or chance play a much bigger role in outcomes than differences in leadership skills between people.

Loserthink: How Untrained Brains Are Ruining America

By Scott Adams, Portfolio/Penguin, New York, NY 2019.

Loserthink: How Untrained Brains Are Ruining America

Our education system is geared more towards learning as much facts and concepts as possible. Few people are taught how to actually think and reason.

“Loserthink” is highly recommended for managers in the workplace and those looking to take on leadership roles. If we are willing to take stock of our own shortcomings in how we reason, we can start the process of breaking free. Only when our own internal thinking improves can we help others with their reasoning. You can read more from a book review on “Loserthink” here.

Outliers: The Story of Success

By Malcolm Gladwell, Little, Brown and Company, New York, NY 2008.

Outliers: The Story of Success

“Outliers” shows, through the examples of Bill Gates, Canadian professional ice hockey players and the Beatles, what factors helped them find success. These are conveniently left out by other writers. But they play the biggest role in their eventual success. And again, much of that is luck.

Thinking, Fast and Slow

By Daniel Kahneman, published by Farrar, Straus, and Giroux, New York, NY 2011.

Thinking, Fast and Slow

Daniel Kahneman won the Nobel Prize in Economics in 2002 and this book shows you why. Here, he summarizes his research that he did with his colleague, Amos Tversky. “Thinking, Fast and Slow,” will help you understand how people really think and make decisions.

Kahneman’s book will teach you most of the important cognitive biases humans have. This book is essentially the science behind how most of us think and make choices. As a leader, you have to know this if you want to better understand and develop your direct reports.

Best Leadership Books To Increase Your Odds Of Becoming a Successful Leader

Once you realize that extreme success comes mostly through luck, you can do things to position yourself to take advantage of any fortune when it comes your way. The books in this section will show you what to do and how those things will help you become a better leader.

How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life

By Scott Adams, Penguin, New York, NY 2013.

How to Fail at Almost Everything and Still Win Big: Kind of the Story of My Life

Our world has become too focused on developing highly specialized individuals. Being an expert at one thing will leave you vulnerable in our current time of disruptive innovations and technology. Instead, become moderately good at as many things as possible. Become a generalist is what this books is telling us.

Adams’ book, “How To Fail At Almost Everything,” will teach you how to develop a powerful talent stack. A group of talents that when combined together will make you stand out as a leader. And if you are an entrepreneur, this book is a must-read.

The Tipping Point: How Little Things Can Make a Big Difference

By Malcolm Gladwell, Little, Brown and Co., New York, NY 2000.

The Tipping Point: How Little Things Can Make a Big Difference

“The Tipping Point” will show you how to identify key people who you can collaborate with to spread your views and ideas. According to Gladwell, ideas spread like viruses.

They also benefit if they are more memorable and sticky. Certain psychological cues added to your proposals will draw people to them. These cues make people remember your ideas better and assign more importance to them.

Made to Stick: Why Some Ideas Survive and Others Die

By Chip Heath and Dan Heath, Random, New York, NY 2006.

Made to Stick: Why Some Ideas Survive and Others Die

“Made to Stick” also has great advice on what you can do to get better traction for your ideas. It is a supplement to Gladwell’s “Tipping Point,” and builds on similar concepts.

The Heath brothers provide an acronym “SUCCES,” to summarize their guide for getting ideas to stick:

  • Simple – no complicated explanations should be needed.
  • Unexpected – make sure some part of the idea gets attention through a surprise.
  • Concrete – should be easy to grasp and remember later.
  • Credible – develop trust for your idea by highlighting others who agree with it.
  • Emotional – people decide to accept or reject an idea based on how they feel about it. Elicit the right emotion with your idea by how you present it and what words you use to explain it. Tip: The book, “Pre-Suasion,” listed below will help you with this point.
  • Stories – use a story to narrate or explain part of the idea.

The Power of Habit: Why We Do What We Do in Life and Business

By Charles Duhigg, Random House, New York, NY 2012.

The Power of Habit: Why We Do What We Do in Life and Business

“The Power Of Habit” is a great book on business leadership. It will show you how to identify bad habits. And then, how to break them in yourself and people you manage. You will learn about the psychological and neurological basis for habits. Plus, the book details how some corporations have leveraged this information to sell and market consumer products.

Predictably Irrational: The Hidden Forces That Shape Our Decisions

By Dan Ariely, Revised and Expanded Edition, New York, NY 2009.

Predictably Irrational, Revised and Expanded Edition: The Hidden Forces That Shape Our Decisions

“Predictably Irrational” is a book that will teach you two key concepts. One, people make decisions not on a rational basis but through quirks and other social cues. Then two, and given that, you need to tweak your approach to getting people to do things. You cater to their unconscious and irrational decision-making process rather than arguing or reasoning with them.

Best Books To Develop Your Influencing And Persuasion Skills As A Leader

The most important skill for a leader or entrepreneur to have is the ability to influence and persuade all sorts of people. These leadership books on influence will show you easy ways to master this skill based on modern social psychology research.

Being influential, will increase the chances of you finding success. And it has never been easier to learn influence and persuasion. The books on influence below will show you how to get others to follow you.

Influence: The Psychology of Persuasion

By Robert B. Cialdini, Revised Edition, Collins Business Essentials, New York, NY 2007.

Influence: the Psychology of Persuasion

You should start with this bestselling book on influence by Robert Cialdini. It is the basis for understanding how influence and persuasion works. His premise is that our world is too information-rich. So people rely on shortcuts for decision-making instead of making rational choices. Cialdini explains these six principles of influence in his book and shows how you could use them in your own life.

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“Influence” will maximize your leadership, influencing and persuasion skills at work 10-fold. And it is an engaging and fast-paced read.

The One Sentence Persuasion Course – 27 Words to Make the World Do Your Bidding

By Blair Warren, eBook 2012.

The One Sentence Persuasion Course - 27 Words to Make the World Do Your Bidding

As far as simplified and feel-good methods of influence go, this is the best book for positive ways to influence and persuade people.

If you are short on time (and money), you should read the original 2005 version of this wonder from Blair Warren. It will change your life. He made the original free to download and you can find it by clicking here.

I have used techniques from this course in the introduction of this article. You should go up and re-read that part now. If the technique worked on you, that is your filter for recognizing a master influencer move. It is simple, and truly a gem. This book will improve your influencing and persuasion skills by about 50%.

The Enigma of Reason

By Hugo Mercier and Dan Sperber, Harvard University Press, Cambridge, MA 2017.

The Enigma of Reason

The Enigma of Reason provides a key insight into why it is futile to influence people by reasoning with them. Reasoning with others makes them argue with you and resist. You will almost never influence and persuade others with reasoning. You can learn more on this topic and what to do instead here.

Pre-Suasion: A Revolutionary Way to Influence and Persuade

By Robert B. Cialdini, Simon & Schuster, New York, NY 2016.

Pre-Suasion: A Revolutionary Way to Influence and Persuade

Pre-Suasion is another of Cialdini’s must-read books on influence. Here, he shows how to get people in a state where they will be more receptive to your future requests. It is filled with great examples and makes for an interesting read. A review on the book and some quick tips on how to pre-suade is available here.

How to Win Friends & Influence People

By Dale Carnegie, 80th Anniversary Ed., Simon & Schuster, New York, NY 2009.

How to Win Friends & Influence People

Dale Carnegie’s book is the quintessential favorite and a must-read if you want to learn ways to influence people and put it in practice. It is regularly cited as one of the best books on influence and persuasion. It shows you how to influence people in a positive and uplifting manner. And if you ask the million dollar question: What books should leaders read? The cover of this book provides the truthful answer — This could be the only book you need to lead you to success.

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Win Bigly: Persuasion in a World Where Facts Don’t Matter

By Scott Adams, Penguin, New York, NY 2017.

Win Bigly: Persuasion in a World Where Facts Don't Matter

Top Business Management Books To Develop Your Negotiation Skills

Trump: The Art of the Deal

By Donald J. Trump and Tony Schwart, Random House, New York, NY 1987.

Trump: The Art of the Deal

Before he became president, Trump’s book was the definitive guide to negotiation and making deals. And it still is. Just because you may not like him as a president, is no reason to think his advice here should be ignored.

His book will teach you how an entrepreneur needs to think and behave when getting what you want. Professors in business schools who have never spent a day in real world of entrepreneurship, don’t get this. And cannot, therefore, teach it.

Win Your Case: How to Present, Persuade, and Prevail–Every Place, Every Time

By Gerry Spence, St. Martin’s Press, New York, NY 2005.

Win Your Case
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Bonus Books On Leadership And Management

What Every Body Is Saying: An Ex-FBI Agent’s Guide to Speed-Reading People

By Joe Navarro and Marvin Karlins, HarperCollins, New York, NY 2008.

What Every Body Is Saying: An Ex-FBI Agent's Guide to Speed-Reading People

The Upside of Irrationality: The Unexpected Benefits of Defying Logic at Work and at Home

By Dan Ariely, HarperCollins, New York, NY 2015.

The Upside of Irrationality: The Unexpected Benefits of Defying Logic

Shaun Mendonsa, PhD is an influencing expert and pharmaceutical development leader. He writes on the topics of influence and persuasion, and develops next generation drugs in human pharma by advising international pharmaceutical CROs and CMOs.


Keywords

Best leadership books; Best management books; What is the best leadership book?; Books to improve your leadership skills and abilities; What books should leaders read?; Reading list for entrepreneurs and future leaders; Entrepreneurship books; How can I be a better leader?; Career development; Leadership development; Talent management

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