Top 10 Leadership Books Every Executive, Entrepreneur, and SMB Owner Should Read

by | November 17, 2020


Top 10 Leadership Books Every Executive, Entrepreneur, and SMB Owners Should Read

When it comes to creating a top ten list of any kind, it is apparent that hundreds of different choices, awards, opinions, accolades, and standards used to select the top ten are out there. Since our company is excited to find ways to support and simplify business owners’ working lives in numerous types of enterprises, it is our pleasure to offer this list of leadership-based books written with that same intent.

1. The Effective Executive, Peter F. Drucker

Mr. Drucker is known as “the creator and inventor of modern management.” Drucker died in 2005, after years of advising diverse giant companies, nonprofits, and government agencies. The author writes, in his concise manner, a book that is brilliant and straightforward. The subtitle of his work is “The Definitive Guide to Getting Things Done.” He clearly explains that the most influential management position is the executive. The most consequential practices in the business world are avoiding what is unproductive and completing what other people have overlooked. Imagination, intelligence, and knowledge are not the most critical elements for the making of a great leader, but the following practices are paramount:

  • Effective decision-making
  • Managing time
  • Setting the correct priorities
  • Knowing where and how to use strength for the best effect
  • Choosing what to contribute to the organization

2. Principles: Life and Work, Ray Dalio

Endorsed by such successful luminaries as Bill Gates, Tony Robbins, a Michael Bloomberg, Principles was written by one of the world’s most successful entrepreneurs and investors who, over the past forty years, has refined, developed, and used unconventional principles to create outstanding results. His postulates help hundreds of people and organizations achieve the goals they have set for themselves using Dalio’s ideas.

 Today, Dalio’s investment firm, Bridgewater Associates, has made more money for its clients than any other hedge fund in history.  And according to Fortune Magazine, Bridgewater is currently the fifth most important private company in the U.S. While he was at it, Dalio became one of Time magazine’s list of the 100 most influential people globally. The Bridgewater culture is exceptionally influential because, as Dalio shares:

It is an idea of meritocracy that strives to achieve meaningful work and meaningful relationships through radical transparency.

Principles offers an approach to decision-making that can apply to whatever you are seeking to achieve. Some call Dalio the “Steve Jobs of investing,” and others say he is “the philosopher king of the financial universe.”

3. Good to Great, Jim Collins

The single question discussed in Collins’ book is: how does a good company become a great company? Collins headed a five-year research project that compared companies that soared and companies that did not. One of his findings was that greatness is based on circumstances but seems more a matter of conscious choosing and discipline.

Collins’ concepts include:

  • Level 5 Leadership — Collins explains that Level 5 leadership consists of these personal characteristics: will, ferocious resolve, humility, the tendency to give credit where it is due, and assigning blame to themselves.
  • First Who — Get the right people for the positions you need.
  • Then What — Once the right people, then figure out what comes next.
  • The Hedgehog Concept – Isaiah Berlin wrote a famous essay, “The Hedgehog and the Fox.” Based on an ancient Greek parable, his thesis was that the fox knows many things, but the hedgehog knows one big thing.  Collins says those companies that went from good to great were hedgehogs by nature. They focused on one big thing. The fox companies tended to become diffused, scattered, and inconsistent.
  • The Flywheel — Collins explains that great things can happen by pushing a massive, giant flywheel. When you move intelligently and in a consistent direction, you will finally get a slow turn, but you continue to try,  get another turn, then 12 turns, then as much as 1,000 turns. The movement creates cumulative, consistent momentum, and many small actions make big things happen. This example supports the notion that consistency in a business brings dramatic results.

4. The 7 Habits of Highly Effective People, Stephen R. Covey

Covey’s #1 National Bestseller came out in 1989; however, the information it promotes is still relevant in our fast-changing, unpredictable new world. Stephen R. Covey explains his holistic, principle-centered, and integrated approach to solving professional and personal issues. Thirty million copies of this book have sold over 30 years, making it a classic that is still teaching and supporting individuals to this day.

Covey’s teachings highlight the habits that differentiate people who handle their lives in unique ways. Covey’s mission was to explain how readers can become better bosses or persons by aligning themselves with universal principles. Time recognized Covey as one of the magazine’s twenty-five most influential Americans. He was an internationally respected expert on leadership authority, family support, teacher, organizational consultant, and author.

“Twenty-five years after it first appeared, the wisdom of The 7 Habits is more relevant than ever. On an individual level, people are burning out, and on a collective level, we are burning up the planet. So Dr. Covey’s emphasis on self-renewal and his understanding that leadership and creativity require us to tap into our physical, mental, and spiritual resources are exactly what we need now.” — Arianna Huffington

5. The Case for Servant Leadership, Kent Keith

Dr. Kent M. Keith, CEO of the Greenleaf Centre for Servant Leadership — Asia, argues that servant leadership is practical, ethical, and meaningful. Service, Keith says, is universally essential, defines servant leadership, and describes some servant leaders’ essential practices. Keith adds that servant leadership is a philosophy and set of rules that enrich the lives of individuals, builds more outstanding organizations, and, in the end, creates a more just and caring world.

“This is my thesis: caring for persons, the more able and the less able serving each other, is the rock upon which a good society is built. Whereas, until recently, caring was largely person to person; now most of it is mediated through institutions – often large, complex, powerful, impersonal; not always competent; sometimes corrupt. If a better society is to be built, one that is more just and more loving, one that provides greater creative opportunity for its people, then the most open course is to raise both the capacity to serve and the very performance as servant of existing major institutions by new regenerative forces operating within them.” — Robert Greenleaf of the Greenleaf Centre for Servant Leadership

6. Leaders Eat Last, Simon Sinek

Some may not know that biology is responsible for whether a person is a leader or a follower. Simon Sinek contrasts modern societies with those from thousands of years ago to define real leadership qualities and what makes a leader worth following. Sinek says he wanted his book for those who want their work and themselves to matter. He also wants to inspire all his readers to feel the same.

In almost all cases, senior Marines take their place at the back of the dining line. Most junior Marines take their place at the front of the line. The Marine Corps general explained that great leaders sacrifice their comfort, even their survival, for the good of those in their care.

7. Meditations of Marcus Aurelius, translated by George Long

Meditations, written almost two thousand years ago, remains significantly relevant for leaders and those who search for a meaningful life. Marcus Aurelius, emperor of Rome (A.D. 161-180), and philosopher shares a list of spiritual exercises filled with guidance on human behavior and ethical reflection. Reconciling the demands of leadership with a concern for personal integrity makes this book one for the ages.

8. Thinking, Fast and Slow, Daniel Kahneman

Kahneman, who won the Nobel Prize in Economics, examines the two major ways the human mind works. He calls them System 1 (fast, intuitive, emotional) and System 2 (slow, logical, deliberate). He writes that the way human beings interplay between these two systems shapes our judgments and decisions. The author says that fast thinking is not always wrong and, often, is necessary. Intuitive thinking is helpful, as well, until we begin to make wrong decisions incessantly.

Reviewers agree that Kahneman’s book is not meant to be read fast.  It is meant to be savored.

9. The Advantage: Why Organizational Health Trumps Everything Else in Business, Patrick M. Lencioni

New York Times best-selling author, Patrick Lencioni, shares that the difference between successful companies and mediocre companies is not based on what the company knows or how smart they are as a collective. A business’s success is really based on how healthy it is. The author believes that there is a unique advantage provided by organizational health. The definition f a healthy business, according to Lencioni, is a business that is:

  • Whole, consistent, and complete
  • Unified in its management, operations, and culture
  • Outperforming their counterparts
  • Free of politics and confusion
  • Able to provide an environment where star performers never want to leave
  • Maximizes human potential and aligns the company around a common set of principles

10. 5 Levels of Leadership, John C. Maxwell

This internationally recognized leadership expert, John C. Maxwell, has sold more than 19 million books. His writings and company have trained more than 5 million leaders across the globe. Maxwell’s 5 Levels of Leadership include:

  • Position — People follow because they do not have a choice.
  • Permission — People follow because they choose to follow.
  • Production — Employees follow you because of what you, as a leader, have done to improve the organization.
  • People Development — People follow you because of what you have done for them.
  • Pinnacle — People follow because they see who you are and what you represent.

Leadership and Reading

Reading to learn more about the job you do is always a terrific idea and can be helpful in ways you might never imagine. If you want to stay ahead of the curve, reading will support you. The world’s most successful individuals read from four to five books a month. The personal and professional benefits of reading are a vital ingredient to your success. Develop and expand your thinking. Read a book.