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Leadership Books: The Best Books on Leadership for Every Stage of Your Career

Andrew Langat
November 16, 2023
a man reading a leadership book
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“There is more treasure in books than in all the pirate’s loot on Treasure Island.”- Walt Disney.

If you search "leadership books" on the world's largest online bookstore,, you will get over 60,000 results. It's not difficult to see why leadership books are in high demand.

Many leaders strive to improve their skills and aspiring leaders want to learn the "secrets" of effective leadership.

At every level of leadership, there is always something to learn and improve. Even influential leaders — in politics and business — understand the importance of leadership books.

For example, Bill Gates periodically recommends leadership books and Barack Obama's annual summer reading list has a fair share of leadership books.

Regardless of your career stage, leadership books can be an invaluable resource. They can enable you to overcome challenges, win friends, lead high-performing teams, get a fresh perspective, or simply learn what effective leadership entails.

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What Is a Leadership Book?

A leadership book offers tips, actions, and theories on how to be a better leader on a variety of leadership topics.

By reading these books, you get to learn about important topics such as what leadership is, emotional intelligence in leadership, networking skills, managing work-life balance, case studies, organizational culture, leadership behaviors, and how to practice effective executive presence among others.

Leadership books are applicable in each career stage: exploration, establishment, mid-career, late-career, and decline.

Here is our recommended book for the first four career stages:

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Best Leadership Books for the Exploration Stage

The exploration stage is when your career starts. You may be trying out different jobs, networking for new options, or trying to win friends. However, this does not mean that you cannot offer leadership.

Depending on your job role, you may find yourself leading teams or managing up, which calls for practical leadership skills.

The following books offer actionable advice on how to navigate the exploration stage.

1. Leaders Eat Last by Simon Sinek

In this book, Simon Sinek emphasizes the importance of creating psychological safety in a team. This is achieved by building strong team relationships that enhance trust enabling the team to collectively work as a unit.

What this book will teach you:

In the exploration stage, as a new leader, the pressure to prove your mettle might affect your judgment. You will often work with new leaders and teams and face uncertain challenges ranging from creating effective team dynamics to dealing with biases or even handling tough conversations.

By reading Leaders Eat Last you will learn the elements of emotionally intelligent leadership that put the best interests of team members first. This borrows heavily from servant leadership. Moreover, you will learn the importance of encouraging collaboration by creating a culture rooted in trust.

This might interest you: Emotional intelligence in leadership.

2. Dare to Lead: Brave Work. Tough Conversations. Whole Hearts by Brené Brown

In this book, Brené Brown advocates for embracing vulnerability, authenticity, and courage in leadership. This is because leadership often takes responsibility and involves establishing new paths making tough calls – and admitting mistakes.

This leadership challenge requires vulnerability and courage. Getting these skills at the exploration stage sets the stage for successful leadership.

What this book will teach you:

Dare to Lead is essentially a manual for leaders who wish to foster environments in which employees may do their best work while feeling supported, respected, and empowered.

As a leader in the exploration stage, the book will teach you to lead from the heart, embracing your humanity and vulnerability. Moreover, you will learn how to combine the responsibilities of leadership with the ideals of authenticity and compassion, resulting in greater outcomes for both team members and organizations.

This might interest you: What's the purpose of leadership?

3. The Lean Startup by Eric Ries

During the exploration phase, you will be testing new concepts with minimal resources, as is the case when running a startup.

Eric Ries's book explains the notion of a lean approach – making the most of minimal resources. Due to inexperience, there may be a lot of self-deception or lack of self-awareness at this time. This can result in discrepancies between when to create your minimal viable product (MVP) and how to allocate resources.

Iterative learning, customer-driven growth, quick experimentation, and flexibility are all emphasized in this leadership book. These ideas are critical for leaders who are experimenting with new tactics or company models.

What this book will teach you:

As one of the most referenced leadership books of modern times, The Lean Startup will teach you how to build sustainable leadership through validated learning and the Build-Measure-Learn Cycle. This is important in the exploratory stage where experience is lacking and there is a great need for strategic thinking to avoid making costly mistakes.

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

Reading the 7 Habits of Highly Effective People at the start of your career may lay a solid foundation for personal and professional development.

The behaviors detailed in the book can assist you in developing the necessary attitude, work habits, and communication skills to effectively navigate your profession from the outset.

What this book will teach you:

This book will teach you seven habits of being highly effective that include being proactive, starting with the end in mind, putting first things first, thinking win-win, seeking first to understand, then to be understood, synergizing, and sharpening even the best teams saw.

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Best Leadership Books for the Establishment Stage

At this stage, you have established a career path that you are passionate about and are starting to build your experience and expertise.

You may be taking on more responsibility and moving up the ranks and your confidence is growing.

Some of the recommended books at this stage include:

1. Good to Great: Why Some Companies Make the Leap and Others Don't by Jim Collins

Good to Great provides research-based insights from research done on 28 companies over 30 years on how firms shift from good performance to excellent performance.

What you will learn from this book:

This book covers important concepts universal principles and strategic tactics for optimizing operations, establishing a clear goal, and developing a strong organizational culture and why good is the enemy of a great leader.

It will teach you leadership advice that is not found in many business books. The author has taken time to research what makes companies and industry leaders move from good to great.

This includes the core values that make great leadership, for example: the flywheel effect, level 5 leadership, discipline, and how to own negative emotions and confront brutal facts.

2. Scaling Up: How a Few Companies Make It... and Why the Rest Don't by Verne Harnish

Scaling a business while preserving efficiency and effectiveness is a significant problem for many companies. For example, only 8% of companies manage to scale.

Scaling up provides leaders with tangible ideas and strategies to help them develop their organizations while maintaining quality and culture.

What this book will teach you:

At the establishment stage, you get to take extreme ownership of your projects. Senior management has probably trusted you with more responsibilities including scaling up projects. In this endeavor, having key questions you can draw from will help guide your thinking. For example:

Scaling up people. Key question: Are all stakeholders (employees, customers, shareholders) happy and engaged in the business – and would you “rehire” all of them?

Scaling up strategy. Key question: Can you state your firm’s strategy simply — and is it driving sustainable growth in revenue and gross margins? The strategy should be clear and concise.

Scaling up execution. Key question: Are all processes running without drama and driving industry-leading profitability?

Scaling up cash. Key question: Do you have consistent sources of cash, ideally generated internally, to fuel the growth of your business?

3. Execution: The Discipline of Getting Things Done by Larry Bossidy and Ram Charan

The most important component driving effective executive development in the early phases of setup is successful execution. Leaders are charged with the critical job of transforming strategic ideas into tangible results. This is because when good leaders execute great ideas effectively, they become great leaders.

This book is a practical guide, providing essential insights into how leaders understand the complex process of aligning individuals, strategic objectives, and operational complexities.

Organizations may achieve smooth execution of their plans by integrating these insights, driving them to triumphant successes and general improvement.

What this book will teach you:

This book will teach you how to execute effectively by teaching the following: why execution is needed, the building block of execution, and three core building blocks of execution. The latter is perhaps the most important aspect of execution as it includes:

People: It is critical to ensure that personnel within your team are assigned to the appropriate tasks/jobs. This starts at the recruiting stage, skill development, and recognizing and elevating start performance with a proven record of delivery.

Strategy: The world's greatest managers create strategies that are clear, realistic, and focused. This helps in making a conscious choice that helps to provide a clear roadmap for the organization's actions.

Operations: This is translating strategy into specific measurable actions that the company employees can implement.

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Best Leadership Books for Mid-Career Stage

This is the stage when you are at the peak of your career and are making significant contributions to your organization. You may be in a leadership position on a successful team and are mentoring others.

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

In this book, Daniel Pink explores the science behind human motivation and how it relates to leadership. He presents a new framework for understanding what drives individuals to excel in their work, which goes beyond traditional notions of rewards and punishments.

Pink's insights are precious for mid-career leaders seeking to create environments that foster intrinsic motivation, autonomy, and innovation within their teams.

The 5 Levels of Leadership by John C. Maxwell

John C. Maxwell presents a framework for leadership development that spans five levels, from position-based leadership to the highest level of leadership influence.

He outlines practical steps to progress through each level, focusing on building relationships, leading by example, and empowering others. This book offers mid-career leaders guidance on how to evolve their leadership skills and expand their impact within their organizations.

Lead from the Outside: How to Build Your Future and Make Real Change by Stacey Abrams

Stacey Abrams needs no introduction. She has distinguished herself as an author, civil rights advocate, and one of the foremost leaders of today. Her Book Lead From The Outside is a compelling read for anyone who wants to take extreme ownership of their leadership and make widespread impact.

What this book will teach you:

As you navigate your mid-career, you will have gained significant experience and probably you will be assuming more challenging roles that may make you feel like an outsider. On the other hand, you might be experiencing a plateau in your career and need professional development. At this career stage, by reading this book, you will learn:

  • Self-Advocacy: this is a central theme in this book. Abrams advocates taking proactive action in asserting yourself by taking ownership of your career, proactively seeking opportunities, building a support network, overcoming self-doubt, and learning effective communication.
  • How to Lead When Facing Adversity: In the course of your career, you may face adversity from your colleagues, boss, or even external factors that you have no control over such as economic downturns or layoffs. Abrams understands this and offers not only personal anecdotes but practice tips for navigating adversity.
  • Use Passion to Fuel Your Career: In your career, what are you passionate about? In Abrams's case, it is voting rights. By identifying your passion, you can go above and beyond your job description, which will enable you to move up the career ladder.

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Best Leadership Books for Late Career Stage

This is the stage when you are nearing retirement and winding down your career. You may be transitioning to a less demanding role or starting a new chapter in your personal change in life.

The Second Mountain: The Quest for a Moral Life by David Brooks

In this book, David Brooks explores the concept of the human being and "the second mountain," representing a more profound sense of purpose, self-improvement, and fulfillment that individuals often seek in their later stages of life.

While not exclusively a leadership book, its insights into personal growth, values, and meaningful contributions can be highly relevant for leaders looking to transition from achieving professional success to making a lasting impact and leaving a legacy.

Stillness Is the Key by Ryan Holiday

Ryan Holiday delves into the power of stillness and mindfulness in leadership. As you navigate the late career stage of primal leadership, finding moments of stillness becomes crucial for reflection, decision-making, and maintaining a balanced perspective.

This book provides insights into how leaders can cultivate inner calm and clarity to influence people make better choices and how best leaders lead with wisdom.

The Power of Moments: Why Certain Experiences Have Extraordinary Impact by Chip Heath and Dan Heath

Chip Heath and Dan Heath explore the significance of creating memorable and impactful moments in leadership. As you reflect on your career journey, this book can guide you in crafting meaningful experiences for yourself, your team, and your organization.

It emphasizes how great leaders inspire the potential to shape positive outcomes through deliberate, well-timed, and emotionally resonant moments.

The Extraordinary Power of Leader Humility: Thriving Organizations & Great Results by Marilyn Gist

If you want to lead well, The Extraordinary Power of Leader Humility: Thriving Organizations & Great Results is designed for you.

The book delves into the idea that humility in leadership is not a weakness but a strength – and one that can lead to exceptional outcomes for great leaders and their teams.

Key takeaways and leadership lessons from the book include:

  1. The Definition of Leader Humility: The book defines leader humility as the ability to recognize and appreciate the value of others, acknowledge one's limitations, and be open to learning from team members.
  2. How to Have a Positive Impact on Organizations: Leadership with humility creates a positive impact as it fosters a culture of trust, collaboration, and open communication. These enhance employee motivation and overall performance.
  3. Building Strong Relationships: Humility in leadership is essential for building strong and lasting relationships with team members and other stakeholders so that everyone feels valued and heard.
  4. Empowering and Developing Others: Humble leaders empower their team members and help them develop their own leadership potential. They are more willing to mentor and support the growth of others, which ultimately benefits the organization by fostering a culture of continuous improvement.

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What Other Leadership Books Should I Read?

If you are looking for the best leadership books to give you more perspective, try checking the following:

1. The Five Dysfunctions of a Team: A Leadership Fable by Patrick Lencioni

Patrick Lencioni's book will teach you what causes dysfunction in a team, including the absence of trust, fear of conflict, lack of commitment, avoidance of accountability taking responsibility, and inattention to results.

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

This book will teach you the 21 laws of leadership will teach you on how to be an effective leader. Maxwell argues that leadership is not limited to a select few but can be learned and developed by anyone willing to put in the effort.

3. Primal Leadership: Unleashing the Power of Emotional Intelligence by Daniel Goleman

This book will teach you emotional intelligence highlighting important key concepts such as Emotional intelligence, leadership styles, emotional contagion, and Emotional Intelligence Competencies.

4. True North by Bill George

True North will enable you to discover your authentic leadership style. The central theme of True North is the idea that authentic leadership comes from being true to yourself and your values. The book outlines the following key concepts: discovering your authentic self, leadership as a journey, developing a supportive leadership team, balancing values and results, and the role of courage.

5. The Likeability Trap: How to Break Free and Succeed as You Are by Alicia Mendez

In the workplace, many of us are often faced with the conundrum of how to exactly to carry ourselves, and how to navigate different situations while staying true to our values.

Be too warm and approachable, and you can be viewed as a pushover.

Be affirmative and outspoken and you risk the chance of being labeled as snobbish.

The result is that many of us often fall into the likeability trap. This book will help you avoid this trap by providing practicable tips and solutions on how to be your authentic and and practice authentic leadership.

6. The Rise: Creativity, the Gift of Failure, and the Search for Mastery by Sarah Lewis

This book helps us reframe success so we understand it as a process, and helps us reframe failure so we can appreciate it as a teacher. By referencing writers, painters, inventors, and entrepreneurs such as Samuel F.B. Morse, Diane Arbus, and J.K. Rowling, you will be inspired to explore your creativity and see how it can positively influence your leadership journey.

7. Act like a Leader, Think like a Leader by Herminia Ibarra

This book breaks down how to begin taking actions that reframe how you consider yourself as a leader, how to step into leadership roles and spaces, and how to expand and nurture the network you need on your leadership journey. Its mix of anecdotes, guided reflection, and concrete action steps will not just inspire you, but will also help you step into the kind of leader you want to be.

Inspiring, isn’t it ? Want to learn more about connecting self-awareness to professional development? Get in touch today.

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Reading and Coaching Can Make You a Better Leader

When we assume leadership positions, we chiefly aim to influence people. This does not come naturally to human beings, so we need to learn leadership behaviors that include emotional intelligence, accountability, and active listening.

Because we cannot learn all the rules of leadership through reading leadership books, coaching is one of the essential resources you should consider to refine your leadership skills.

At Highrise, you will learn essential leadership skills that include what true leadership is, practical steps for leading others, and how to own your leadership so you can really shine.

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Andrew Langat
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Andrew Langat is an experienced content specialist in Leadership, Productivity, Education, Fintech, and Research. He is an avid reader and loves swimming as a hobby. He believes that quality content should be actionable and helpful.