Best Startup Books on Leadership
Many of the books on leadership below have been read by countless successful entrepreneurs on their path to becoming better leaders of their own teams. They each have unique wisdom and advice that should help you discover the tools within yourself to become your own successful entrepreneur.
Also Recommended: Check out our list of the best startup books.
1. ‘The Hard Thing About Hard Things’ by Ben Horowitz
In “The Hard Thing About Hard Things,” Horowitz draws on his own experiences as a founder, CEO, and investor in Silicon Valley to provide readers with insights and advice on how to build and run a successful business. Humorous and honest, Horowitz doesn't shy away from the hardships of running a business which sets this book apart from others that paint a prettier picture. You'll get advice on firing friends, cultivating a CEO mentality, and poaching competitors.
2. ‘How to Win Friends & Influence People’ by Dale Carnegie
One of the most well-known and read books on leadership, Carnegie's book, “How to Win Friends & Influence People,” has sold over 30 million copies since it was first published in 1936. It remains relevant today as it teaches the basics of human relations and how to communicate with people effectively. You'll learn how to make friends easily, avoid arguments, and be more persuasive. There are countless entrepreneurs who have used this book to redefine relationships with their employees.
3. ‘Startup CEO’ by Matt Blumberg
Startups face an entirely different set of leadership responsibilities compared to those entrepreneurs who take their business slowly. In “Startup CEO,” Matt Blumberg walks you through the process of building and running a startup from the perspective of a CEO. He covers topics such as fundraising, product development, and recruiting employees. You'll get an inside look at what it's like to be in the shoes of a startup CEO and learn how to handle some of the unique challenges.
4. ‘On Becoming a Leader’ by Warren G. Bennis
There aren't many authors on this list who can be considered by many to be a pioneer in leadership studies which is what makes Bennis' book so special. “On Becoming a Leader” has been called one of the most definitive works on leadership and continues to inspire entrepreneurs today. Bennis explores what it means to be a leader, how leaders emerge, and what effective leadership looks like. If you're looking for a more theoretical approach to leadership, then this is the book for you.
5. ‘Good to Great’ by Jim Collins
Jim Collins turns the narrative of what it means to have a successful company in the long term in “Good to Great.” Collins believes that any company, good, bad, or great can achieve long-term success using the right tools. He takes readers through a detailed case study of how 28 different companies made the transition from good to great. You'll understand what separates the good from the great and learn key management strategies and practice like the level 5 leaders he writes about.
Looking for more book recommendations? We asked startup founders to share their favorite books on entrepreneurship, and here's what they said.
6. ‘The 7 Habits of Highly Effective People’ by Stephen R. Covey
When “The 7 Habits of Highly Effective People” was released in 1989, it quickly became a bestseller and has since sold over 25 million copies. The book was so popular because it proposed a new way of thinking about time management and personal effectiveness. Covey's insights are just as relevant today as they were 30 years ago and continue to help entrepreneurs be more efficient with their time. You'll learn how to better prioritize your time, set goals, and delegate tasks to your team members.
7. ‘The 21 Indispensable Qualities of a Leader’ by John C. Maxwell
In a follow-up to his “The 21 Indispensable Qualities of a Leader,” John C. Maxwell provides readers with a more in-depth look at what it takes to be an effective leader. He focuses on 21 different qualities that he believes are essential for any leader who wants to be successful. If you're looking to improve your leadership skills, then this book is a great place to start. You'll learn about qualities like initiative, decisiveness, and courage and understand how to develop them in yourself.
8. ‘Own the Room’ by Amy Jen Su and Muriel Maignan Wilkins
Focusing on what it means for leaders to connect easily with people and communicate authentically in order to make an immediate impact in a company, “Own the Room” is a masterclass in leadership. Su and Wilkins offer frameworks and actionable steps that entrepreneurs can use to improve their communication skills and develop a personal presence. You'll learn how to tell your story in a way that engages others, ask questions that lead to productive conversations, and give feedback effectively.
9. ‘Wooden on Leadership’ by John Wooden
Often considered one of the greatest college basketball coaches of all time, John Wooden's book on leadership is a must-read for any entrepreneur. Wooden applies his successful coaching methods to the business world and offers insights on how to build a winning team. Follow Wooden’s 12 lessons of leadership and his Pyramid of Success model that helps leaders build mental, emotional, and physical toughness to lead teams to success.
10. ‘From the Sea to the C-Suite’ by Cutler Dawson
As the leader of the Navy Federal Credit Union, the largest in the country, Dawson has plenty of experience in leadership. In “From the Sea to the C-Suite,” he offers insights on how to build a strong team and create a collaborative culture. His insights on customer service and creating systematic approaches to leadership will help you integrate the lessons into your own business practices.
11. ‘Dare to Lead’ by Brené Brown
Brown's alternative take on the same principles that help entrepreneurs become successful leaders is worth the read. Brown's focus is on developing brave leaders and offers readers a new perspective on what it means to lead with courage. In “Dare to Lead,” you'll learn how to embrace vulnerability, cultivate empathy, and build trust within your team. These are essential qualities for any leader who wants to create lasting change.
12. ‘Learn How To Take A Punch’ by Brett J. Fox
Focused on the issues and problems entrepreneurs might face when growing a successful company, “Learn How To Take a Punch” is a great resource for anyone who wants to learn how to be a better leader. You'll learn how to handle difficult conversations, manage stress, and make decisions under pressure. These are all essential skills for any entrepreneur who wants to scale their business.
13. ‘Start with Why: How Great Leaders Inspire Everyone to Take Action’ by Simon Sinek
With one of the most popular TED Talks of all time, Simon Sinek leads by example and challenges the quid pro quo of leadership books. Sinek's focus is on starting with the why, not the what in order to inspire people to do the things you want them to do. In “Start with Why,” you'll understand how to connect with people on a deeper level and create long-lasting relationships.
14. ‘Beyond Happiness: How Authentic Leaders Prioritize Purpose and People for Growth and Impact’ by Jenn Lim
Another book that focuses on challenging traditional leadership methods, “Beyond Happiness” by Jenn Lim offers a new perspective on what it means to be an effective leader. You'll learn about the power of purpose and how to create a positive culture within your team. This book is essential for anyone who wants to create lasting change within their organization and lead a new generation with modern leadership qualities.
15. ‘Radical Candor’ by Kim Scott
Kim Scott looks beyond the common workplace culture to develop new ideas on how to communicate with employees and build a successful team. In “Radical Candor,” you'll learn how to give feedback that is both honest and kind, as well as how to manage difficult conversations. These are essential skills for any leader who wants to create a productive and positive work environment.
16. ‘Startup Leadership’ by Derek Lidow
Focused on the incredible challenges startups face, Derek Lidow’s “Startup Leadership” offers insights on how to overcome them. You'll learn about the importance of customer focus, building a team of experts, and creating a culture of innovation. Entrepreneurs will be given real-life advice on how to navigate the struggles of startup culture while still implementing a strong team and always believing in themselves.
17. ‘The Five Dysfunctions of a Team’ by Patrick Lencioni
Breaking down leadership into five dysfunctions that every entrepreneur must master, Patrick Lencioni offers a comprehensive guide on how to build an effective team. In “The Five Dysfunctions of a Team,” you'll learn about the importance of trust, conflict, commitment, accountability, and results. The story of Kathryn Petersen is used as a way to understand how leadership is as much about courage as it is about skills.
18. ‘Primal Leadership: Unleashing the Power of Emotional Intelligence’ by Daniel Goleman
The traditional vision of a great leader is one that is stoic and holds fast through all tribulations. In “Primal Leadership,” Goleman offers an alternative take that highlights the importance of emotional intelligence in leadership. You'll learn how to be more self-aware, understand the emotions of those around you, and use that information to create a more positive work environment.
19. ‘The Dichotomy of Leadership: Balancing the Challenges of Extreme Ownership to Lead and Win’ by Jocko Willink and Leif Babin
As Navy Seals, both Willink and Babin have long understood the value of taking extreme ownership in order to be a successful leader. “The Dichotomy of Leadership” outlines the importance of this dichotomy and how it can be applied to business. You'll learn about the need for effective planning, decision making, and execution in order to achieve success. The authors help integrate the lessons from both leading and following in order to create successful teams that get the job done.
20. ‘Originals: How Non-Conformists Move the World’ by Adam Grant
It has often been said that the greatest leaders in the world are those who think outside the box. In “Originals,” Adam Grant embraces this notion and offers a new perspective on what it means to be an effective leader. You'll learn about the importance of taking risks, being creative, and thinking differently in order to create lasting change within organizations.
21. ‘Leadership: In Turbulent Times’ by Doris Kearns Goodwin
Success stories of entrepreneurs come with much praise and accolades, but the road to success is paved with hardships and challenges. In “Leadership: In Turbulent Times,” Goodwin offers a glimpse into the lives of some of America's most successful presidents and how they navigated times of turmoil. You'll learn about their leadership styles, the qualities that made them effective leaders, and how you can apply those same principles to your own life.
22. ‘Drive: The Surprising Truth About What Motivates Us’ by Daniel Pink
Great leadership is about learning how to motivate and inspire people to take on projects bigger than themselves, and in “Drive” by Daniel Pink, you'll learn exactly how to do that. Instead of focusing on rewards like traditional leadership might highlight, Pink offers a different look and offers guidance on the skills it takes to lead. Directing our own lives, creating new things, and believing we can do better are all skills you'll learn how to teach others in Drive.
23. ‘Upstanding’ by Frank Calderoni
With a career that touches some of the biggest companies in the world, including IBM and Cisco, Calderoni believes leadership is just as much about your personal character as it is about your professional accomplishments. In “Upstanding,” he walks the reader through his leadership journey and the challenges he's faced along the way while also teaching how to develop your own personal code of ethics.
24. ‘EntreLeadership’ by Dave Ramsey
Dave Ramsey is well-known as a financial guru but it's his business advice that shines in “EntreLeadership.” Ramsey has built a multimillion-dollar company from the ground up and in this book he offers his advice on how to build, grow, and manage a successful business. He also teaches the importance of hiring the right people, delegating tasks, and holding employees accountable for their actions.
What’s your favorite leadership book? Let us know in the comments!