The 15 Best Leadership Books Every Entrepreneur Must Read

What are the best leadership books available today? Read our expert guide with top recommendations and business insights to help you on your journey.

Over the past few years, I’ve read dozens of the best leadership books and listened to many audiobooks by entrepreneurs, CEOs, and business leaders. I like this genre because we can learn from an entrepreneur or leader in their field without meeting them.

If you want to start a business, you can pick up advice and strategies to help you grow it faster. And if you want to become well-known within your industry or improve your leadership skills, this genre offers practical advice. Some of the best leadership books also offer insightful stories, revealing how leaders built their companies or businesses up from nothing or overcame personal or professional setbacks. 

The best are usually autobiographies, albeit often ghostwritten, whereas others are biographies profiling these industry leaders. With all that in mind, here is a round-up of my recommended books on leadership. (Need to finish more books faster? Check out my guide to reading more often.)

Best Leadership Books Ranked

1. It’s Your Ship: Management Techniques from the Best Damn Ship in the Navy by Michael Abrashoff

In this leadership book, he talks about the crew’s problems when he took command and why it was regarded as one of the most unreliable ships in the US Navy. Abrashoff encouraged his crew to collaborate and to work hard toward a common goal. He was able to turn the performance of the ship around until it became recognized as one of the best and most reliable ships in the US Navy.

This leadership book is worth reading if you want to discover more about how to encourage your team to collaborate and work together as you become a good leader. It’s an interesting leadership book, too, in that it offers an insight into what real life is like in the Navy and on a ship. I was struck by sailors’ routine and structure, such as rigorous checklists and safety protocols.

“It taught me not to give up on people until I have exhausted every opportunity to train them and help them grow.”

Michael Abrashoff, It’s Your Ship: Management Techniques from the Best Damn Ship in the Navy

2. Principles: Life and Work by Ray Dalio

I listened to the audiobook, which Dalio narrates, and I also read it on Kindle. Dalio outlines his leadership principles for life and work. He talks about how he overcame obstacles to set up one of the biggest hedge funds in the United States, Bridgewater Capital. 

In the book’s first half, Dalio recounts some of his personal failures, such as incorrectly predicting what would happen to the US economy during the 1970s on live television. He also talks about how he set up Bridgewater Capital in his apartment and nearly went bankrupt.

Later in the book, the former investment officer applies his principles to personal problems. He writes about when a doctor wanted to perform life-altering surgery to combat a precancerous condition. Instead of immediately deciding to get the surgery, Dalio sought a second opinion and “triangulated” his doctors’ advice. He ended up not getting this surgery and recovered. This leadership book offers principles and strategies you can use for your business, setting goals, and knowing when to make decisions. It also covers topics like emotional intelligence. In fact, I wrote an article for Forbes about how you can use first, second, and third-order consequences to decide what to do and when.

“I learned that if you work hard and creatively, you can have just about anything you want, but not everything you want. Maturity is the ability to reject good alternatives in order to pursue even better ones.”

Ray Dalio, Principles

3. The 7 Habits of Highly Effective People by Stephen R. Covey

In this leadership book, the author presents 7 habits that will help you find success at work and in your personal life and become a high performer. 

These include: 

• Be proactive
• Begin with the end in mind
• Put first things first
• Think win-win
• Seek first to understand, then to be understood
• Synergize
• Sharpen the saw

I applied the “Put first things first” leadership advice by putting writing and creative work first each morning. I focus on other business tasks in the afternoon. I also write about the top 3 tasks I’ve to complete each day in advance. I also like the strategy, “Seek first to understand then to be understood.” I’ve got three kids, one of whom is a 14-year-old teenager. 

He often pushes boundaries and wants things that aren’t necessarily good for him. Sadly, Covey passed away after a bike accident back in 2012. Rather than being a disciplinarian. I try to understand where he’s coming from and how we can both come to an agreement.

“We see the world, not as it is, but as we are─or, as we are conditioned to see it.”

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

4. The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company by Bob Iger

In this book, Iger describes how he got started at ABC and became CEO of one of the biggest media companies in the world. He recounts his long career of more than 40 years at Disney (and the companies it acquired). Unlike authors of other business titles, Iger relies mostly on stories from his business life. He touches on his upbringing, marriage, and divorce but focuses more on the story of Disney over the past few decades.

Unlike Dalio, the author doesn’t offer principles or strategies most of us can apply. Instead, he tells the reader how he and Disney have approached business challenges over the years. Iger narrates the first and last chapters of the audiobook. I enjoyed hearing how and why Disney acquired companies like Marvel and Star Wars.

“True authority and true leadership come from knowing who you are and not pretending to be anything else.”

Bog Iger, The Ride of a Lifetime: Lessons Learned from 15 Years as CEO of the Walt Disney Company

5. The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers by Ben Horowitz

In this book, he recounts his story of founding, managing, and selling technology companies. He also offers practical advice for founders, entrepreneurs, and anyone who wants to learn about management and leadership. If you’re a creative entrepreneur, not all of the strategies Horowitz provides apply to your potential roadmap. 

He writes this more for technology companies and those who want to build the next Google or Facebook (or at least get acquired by them). He’s also an author who takes no prisoners and doesn’t apologize for his abrasive style. You’ll learn leadership lessons like how to promote or demote a friend, hire someone from somebody else’s company, become a founder CEO, and when to sell your business.

I particularly enjoyed the chapter about having the right people in the right seats. This is helpful even if you’re running a small business. Speaking from experience, I know contractors can let you down, and hiring is always expensive. The book also offers some nuggets on decision-making and company culture.

“Life is struggle.’ I believe that within that quote lies the most important lesson in entrepreneurship: Embrace the struggle.” 

Ben Horowitz, The Hard Thing About Hard Things: Building a Business When There Are No Easy Answers

6. Great by Choice: Uncertainty, Chaos, and Luck—Why Some Thrive Despite Them All by Jim Collins and Morten T. Hansen

In his follow-up bestseller, Great by Choice, Jim Collins and co-author Morten T. Hansen profile companies that have succeeded and lasted over the years and the traits of leaders within these companies. The must-read book is based on hundreds of hours of research meetings. The authors conducted many third-party interviews to profile the companies featured in this book. It took them approximately nine years to write this book, and they explored why some companies like Apple and Microsoft became great by choice while other companies like Circuit City fell by the wayside.

The key takeaway from this book is that the best leaders of companies don’t necessarily take many risks or aren’t more visionary than their competitors. They’re more disciplined, empirical, and paranoid about what could go wrong. I also liked the way the authors worked interesting concepts or metaphors into what could be a dry book. For example, “The 20 Mile March” explains how leaders will help their companies work over the long term rather than a sprint toward the finish line of a short-term objective. 

“Far more difficult than implementing change is figuring out what works, understanding why it works, grasping when to change, and knowing when not to.”

Jim Collins, Great by Choice

7. The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win by Jocko Willink and Leif Babin‎

This book juxtaposes Willink and Babin’s experiences while training a SEAL team and fighting in Iraq with their experiences in the boardroom and counseling leaders of companies in trouble. The key premise is that leaders are often faced with hard choices they must reconcile, and it’s their job to find the balance between them. High-performance entrepreneurs and CEOs accept these leadership challenges and move on rather than complain.

The authors apply lessons from war to business, which makes for some intriguing insights. Get the audiobook because Willink narrates some of it.

“There is no growth in the comfort zone.“

Jocko Willink and Leif Babin, The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win

8. #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness by Gary Vaynerchuk

Personally, I’ve always found his particular take on leadership and entrepreneurship brash yet entertaining. In this book, he explains how entrepreneurs and successful leaders, particularly those setting up online businesses, can find success online and capture their audience’s attention. It provides practical strategies that work right now on social media and gets into his awe-inspiring work ethic. Vaynerchuk was criticized for glorifying insane work hours or “hustle.” He’s veered away from this line of thinking since writing the book.

This leadership book is a compilation of advice the author has given through talks, interviews, podcasts, and episodes, all of which were edited for this book. It’s a book you can dip in and out of rather than something you’d read like a novel.

“Bet on your strengths. It’s an underrated business strategy in a world where so many people are obsessed with fixing their weaknesses they give short shrift to the skills they were born with.”

Gary Vaynerchuk, #AskGaryVee: One Entrepreneur’s Take on Leadership, Social Media, and Self-Awareness

9. How to Win Friends and Influence People by Dale Carnegie

It was first published in 1936 and has been a best-seller. I listened to it a few years ago on Audible and Kindle and still return to it occasionally. This business book contains useful insights and leadership lessons about motivating others, encouraging people to like you, and the skills of a good listener.

“When dealing with people, remember you are not dealing with creatures of logic, but with creatures bristling with prejudice and motivated by pride and vanity.”

Dale Carnegie, How to Win Friends and Influence People

10. To Sell Is Human By Daniel Pink

You can use lessons from Pink’s books for leadership and personal development. And they’re useful for entrepreneurs and those in a more traditional company. Unlike other authors of other business books, Pink is informative and entertaining at the same time. 

To Sell Is Human has a strong focus on sales, but it also shows how you can sell through leading people, making it a great addition to your leadership library. I interviewed Daniel Pink a while ago for the Become a Writer Today podcast.

“Human beings have an innate inner drive to be autonomous, self-determined, and connected to one another. And when that drive is liberated, people achieve more and live richer lives.”

Daniel Pink, To Sell Is Human

11. Leaders Eat Last by Simon Sinek

When you think of a leader, you probably think of someone taking charge and going forth to head their team members. In Leaders Eat Last, Simon Sinek argues that leaders lead by following and serving. I found it fascinating how he pointed out the need to serve people to lead them well. When it comes to self-help books for leaders, their unique approach makes it well worth reading.

Sinek’s no newbie to the world of leadership books. He’s also the author of Start with Why and Together Is Better, two must-reads for business leaders. If you don’t already have a collection of Sinek books on your bookshelf, start with one of these titles.k

“The true price of leadership is the willingness to place the needs of others above your own. Great leaders truly care about those they are privileged to lead and understand that the true cost of the leadership privilege comes at the expense of self-interest.”

Simon Sinek, Leaders Eat Last

12. The 21 Irrefutable Laws of Leadership by John C. Maxwell

If you’re like me, you want a surefire way to get people to trust and follow you as you grow your business. The 21 Irrefutable Laws of Leadership by John C. Maxwell promises You need to follow these unwritten rules to inspire others and encourage them to follow as you lead. 

Through the pages of this volume, Maxwell explores how leaders can use the principles of Influence, Empowerment, Intuition, Respect, and Legacy to build effective teams and hone in on the well-being of the people under them. I was impressed with how thorough this book was. It is about everything you need to know about becoming an effective leader.

“Great leaders always seem to embody two seemingly disparate qualities. They are both highly visionary and highly practical.”

John C. Maxwell, The 21 Irrefutable Laws of Leadership

13. Drive: The Surprising Truth About What Motivates Us by Daniel H. Pink

Another Daniel Pink book makes its way to this list of the best leadership books, and for good reason. Pink has proven that he’s skilled and knowledgeable in this field due ts own success in business. As you read this book, you’ll be surprised that it’s not money that motivates you and the people around you. Instead, it’s an inborn need to direct our lives and use creativity to build or direct new things.

That’s not something you will learn in business school, but it is something you’ll learn in the pages of Drive: The Surprising Truth About What Motivates Us. Once you understand and embrace what motivates people, you’ll be well-positioned to encourage them to push toward success.

“Greatness and nearsightedness are incompatible. Meaningful achievement depends on lifting one’s sights and pushing toward the horizon.”

Daniel Pink, Drive: The Surprising Truth About What Motivates Us

14. Dare to Lead by Brene Brown

As a number-one New York Times bestselling author, Brene Brown is no stranger to those who want to learn to embrace their personal leadership styles. Dare to Lead is one of her most popular works. It explores Brown’s personal belief that everyone can train themselves to be courageous. It then applies that idea to the workforce.

What I love about this book is that it provides actionable steps to become a more effective leader. If you put into practice the steps outlined in this book, you will find that people naturally follow you. You’ll also find that you can embrace and unleash your courageous side, even if courage doesn’t come naturally to you.

“One of the most important findings of my career is that courage can be taught, developed and measured. Courage is a collection of four skill sets supported by twenty-eight behaviors. All it requires is a commitment to doing bold work, having tough conversations and showing up with our whole hearts.”

Brene Brown, Dare to Lead

15. The Five Dysfunctions of a Team by Patrick Lencioni

No leader is perfect. Those who are leading change today were once making leadership mistakes. If you want to avoid making those same mistakes, then grab a copy of The Five Dysfunctions of a Team by Patrick Lencioni. This book is written as a fable of leadership, as it follows a young CEO through her pathway to becoming a trusted, effective leader.

This is the perfect book to round out our list because it teaches you how to avoid the mistakes others have made. If you’re going to be an effective leader, you need a team that’s not dysfunctional. You can create just that with a little bit of help from Lencioni.

“Great teams do not hold back with one another. They are unafraid to air their dirty laundry. They admit their mistakes, their weaknesses, and their concerns without fear of reprisal.”

Patrick Lencioni, The Five Dysfunctions of a Team

Apply Lessons From the Best Leadership Books Today

After spending hours reading these books and many others, I realized it’s possible to spend a lifetime consuming without acting. If you want to become a better leader, putting the advice into practice is far better. Much like the self-help genre, get a relevant book, read it and act because that’s what great leaders do.

Looking for more? Check out our writing style guide for business!