Best Leadership Books - Peter Boolkah

Leadership is not merely a title or a position, but a combination of qualities, skills and, perhaps most importantly, the ability to inspire others towards a shared vision. Just as a well-crafted book can transport you to new worlds, the best leadership books can transform your approach to business, enriching your perspective and equipping you with the knowledge to navigate your entrepreneurial journey successfully. In this article, we delve into an array of exceptional books that are not just shelves of information but lighthouses guiding you through the tumultuous seas of leadership.

Whether you’re a fledgeling entrepreneur or a seasoned business veteran, this list of the best leadership books will surely spark your imagination, challenge your perceptions, and ultimately, amplify your approach to leadership.

The Importance of Leadership in Today’s World

In today’s fast-paced business climate, effective leadership isn’t just some buzzwords. It’s more crucial than ever. It is the driving force behind a team’s morale, productivity, and consequently, a company’s success. Great leaders inspire everyone to take action. They can mold diverse team members into a cohesive unit, focused on achieving common objectives.

They also foster an environment where innovation thrives, encouraging individuals to step outside their comfort zones, take calculated risks, and come up with groundbreaking solutions. Furthermore, in challenging times, experienced leaders provide stability and direction, promoting self-awareness and instilling confidence in team members and stakeholders alike. In essence, leadership is not just about making crucial decisions; it is about inspiring, motivating, and empowering others to deliver their best.

Best leadership books - Peter Boolkah

List of Best 20 Leadership Books of All Time

1. The First 90 Days – by Michael Watkins

“The First 90 Days” is an internationally acclaimed bestseller by Michael D. Watkins, who is a renowned expert on leadership transitions. Every great leader should read this expanded and updated edition that presents effective strategies for overcoming the challenges often associated with assuming a new role, making it invaluable whether you’re starting out in a new job, moving up within your current organisation, or taking on an overseas assignment.

Watkins acknowledges the demanding nature of today’s professional landscape, where changes are frequent and expectations are high. This book is important for leaders and serves as an indispensable guide to successfully navigating the crucial first 90 days of a new role and beyond.

2. The Leadership Challenge – by James Kouzes & Barry Posner

“The Leadership Challenge” is an exceptional business book that has stood the test of time, with its first edition penned in 1987. Authored by the esteemed leadership experts, Jim Kouzes and Barry Posner, the book has carved its position as one of the best-selling leadership books ever. This third edition has been revised and updated to address the challenges presented by our unpredictable global business environment.

Rooted in extensive research, it gathers insights from leaders across public and private sectors globally. The authors emphasise that while the context of leadership has evolved over the decades, the fundamentals remain unchanged, affirming that leadership is not a passing trend but a timeless necessity.

3. The 21 Irrefutable Laws of Leadership – by  John C. Maxwell

The 25th Anniversary Edition of John C. Maxwell’s New York Times bestseller, “The 21 Irrefutable Laws of Leadership” is a great read for business leaders. It boasts a comprehensive, fully revised, and updated guide to effective executive leadership in the modern world. This insightful book illuminates key principles such as vision, influence, responsibility, and commitment, providing a roadmap for setting goals and maintaining emotional balance during challenging times.

Maxwell’s personal experiences lend practicality and inspiration to each leadership law. The book has been meticulously updated for the next generation of leaders with new insights and relevant examples while preserving the timeless leadership truths that have empowered many over the last quarter of a century.

4. Leaders Eat Last – by Simon Sinek

Both seasoned and new leaders need to read “Leaders Eat Last”. This insightful masterpiece from the acclaimed author Simon Sinek is not just for leaders striving for self-improvement but for anyone seeking to enhance their interpersonal skills and career trajectory. This book, now available in paperback, comes with an expanded chapter and appendix on leading millennials, inspired by Sinek’s viral video “Millennials in the workplace”. The primary focus of the book is the creation of an optimal work environment, where individuals feel valued, trusted, and fulfilled.

Through his experience working with various organizations worldwide, Sinek identifies that the most successful teams are those fostered by leaders who create a “Circle of Safety” – a safe space that encourages trust and cooperation, protecting the team from external challenges. With narratives ranging from military operations to investment banking, Sinek illustrates the profound impact of great leadership.

5. Dare to Lead – by Brené Brown

“Dare to Lead,” a New York Times bestseller by Brené Brown, emboldens us to manifest bravery in leadership. Drawing from her groundbreaking research with leaders and cultural innovators worldwide, Brown elucidates how to translate daring concepts into actionable practices within leadership roles. The book eschews the traditional perception of leadership as a title or status, instead defining a leader as one who nurtures potential and courageously acts to develop it.

It entices leaders to have the courage to be vulnrable and foster empathy – uniquely human traits that set us apart in an era increasingly dominated by machines and AI. Brown’s book is a treasure trove for anyone wishing to cultivate courageous leadership, whether you’re a seasoned reader of her work or new to her transformative insights.

6. Start with Why – by Simon Sinek

Bestselling author Simon Sinek delves into the heart of effective leadership in his influential book, “Start with Why”. This compelling read explores the truth that outstanding leaders and organisations are those that begin with a clear ‘why’. Probing into the leadership of icons like Martin Luther King Jr., Steve Jobs, and the Wright Brothers, Sinek unveils a common denominator – they all started with ‘why’. He introduces “The Golden Circle”, a robust framework for constructing successful organisations, leading movements, and inspiring people.

The book emphasises that while any company can describe ‘what’ it does and ‘how’, only a few can articulate ‘why’ – the core purpose, cause, or belief that underpins everything they do. This idea transforms the way we understand successful leadership and marketing, urging us to lead not by manipulation but by inspiration. Sinek’s engaging narrative, culled from a vast array of real-life stories, outlines what it truly takes to lead and inspire. “Start with Why” is a must-read for anyone aiming to inspire others or seeking that spark of inspiration themselves.

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

“The 7 Habits of Highly Effective People” by Stephen R. Covey is a classic read for leaders who continues to command the bestseller lists, and for good reason. The book’s enduring appeal lies in its focus on timeless principles such as fairness, integrity, honesty, and human dignity, bypassing fleeting trends and superficial psychology. One of the most influential books ever written, “The Seven Habits of Highly Effective People” has stimulated and guided readers for over three decades, contributing to the transformation of millions of lives across all age groups and professions.

Covey posits that regardless of one’s competency, sustained and lasting success can only be achieved if one can effectively lead themselves, influence, engage and collaborate with others, and continuously enhance and renew their capabilities. These elements form the bedrock of personal, team, and organisational effectiveness.

8. Execution: The Discipline of Getting Things Done – by Larry Bossidy & Ram Charan

“Execution: The Discipline of Getting Things Done” by Larry Bossidy and Ram Charan is a tour de force in leadership literature, specifically addressing how to translate strategy into tangible results. The authors assert that execution relies on a distinctive set of behaviours and an organisational culture deeply immersed in three core intertwined processes: people, strategy, and operations. Through hands-on leadership, Bossidy and Charan argue, leaders can make swift decisions, delegate effectively, and ensure follow-through by hiring ‘doers’ who can invigorate others.

The book emphasizes that informed leaders, who comprehend the nuances of markets, customers, and resources, should be at the helm of the strategy process, employing the operations process to devise new schemes and link performance to incentives. These three crucial processes, as the authors contend, form the bedrock of a competitive edge.

9. Good to Great – by Jim Collins

“Good to Great” by Jim Collins is a seminal work that explores how ordinary companies transform into extraordinary performers. Drawing upon a rigorous research study spanning fifteen years, Collins and his team identified companies that had drastically outperformed the market, turning long-term mediocrity into superiority. These ‘good-to-great’ companies, as Collins coins them, unleashed phenomenal cumulative stock returns, surpassing even the world’s most successful enterprises.

The book contrasts these companies against a set of comparison companies that failed to make the leap, carefully examining the factors that differentiate the truly great from the merely good. Groundbreaking findings, such as the requirement of specific leadership to achieve greatness, the importance of simplicity within the three circles, a culture of discipline combined with entrepreneurial spirit, and a unique perspective on the role of technology, are shared. “Good to Great” is a must-read, providing valuable insights into the best strategies and practices for managing people.

reading book in office

10. The Lean Startup – by Eric Ries

If you are looking  for a good read to amplify your leadership skills, “The Lean Startup” by Eric Ries needs to find its place on your list. This book provides vital insights into the creation and management of startups by leveraging lean principles and agile development. The book underscores the significance of continuous experimentation, seeking customer feedback, and swiftly adapting to create products or services that genuinely cater to customer needs.

Ries introduces the concept of a Minimum Viable Product (MVP), a basic version of a product that can be tested with customers, further enhancing decision-making processes through data-driven experiments. The author aptly discusses the concept of ‘pivoting’ – altering a startup’s trajectory based on customer feedback or market conditions. Packed with illustrative case studies and examples, the book demystifies what strategies work and what do not in entrepreneurship, and how to gauge progress through a focus on learning and experimentation.

11. Emotional Intelligence –  by Daniel Goleman

“Emotional Intelligence” by Daniel Goleman is an enlightening exploration of our emotional sphere and its profound influence. The book is a great read for industry leaders at all levels. It delves into the nature of emotions, their purpose, and how we can hone our abilities to manage them effectively.

Goleman makes a compelling case for the importance of emotional intelligence both in our personal lives and at work, shedding light on how our emotional responses can shape our relationships and experiences. Furthermore, he posits that our collective capacity to navigate emotions may have far-reaching implications for humanity’s well-being. A crucial read for anyone seeking to understand and improve their emotional landscape.

12. On Becoming a Leader – by Warren Bennis

“On Becoming a Leader” by Warren Bennis is a rich reservoir of insights on leadership. Central to the book’s theme is the idea that genuine leaders seek to express themselves, not just prove themselves. Bennis contrasts the restrictive vision of self-proofing with the expansive and engaging pursuit of self-expression by leaders.

Such leaders, according to Bennis, view life not as a competition, but as an opportunity for self-actualisation. The book emphasizes that leadership can’t thrive if there’s lack of commitment to life. Leadership requires vision and often involves the entirety of one’s life. A compelling read, it challenges the reader to overcome mediocrity, embrace challenges, and truly lead by expressing their authentic selves.

13. The Art of Possibility – by Rosamund Stone Zander and Benjamin Zander

“The Art of Possibility” by Rosamund Stone Zander and Benjamin Zander is a transformative read, addressing the pivotal distinction between individuals who lead lives brimming with fulfilment and those who perceive happiness as an elusive future state. The book suggests that an attitude of abundance and embracing possibility are key to achieving a truly gratifying life.

It urges readers to keep an open door in their minds for life-altering opportunities, experiences, and all the goodness life has to offer. Zander delves into the art of possibility, demonstrating that life is a beautiful journey, worth living to its fullest when we dare to invite possibility into our existence.

14. Immunity to Change – by Robert Kegan and Lisa Laskow Lahey

“Immunity to Change” by Robert Kegan and Lisa Laskow Lahey is a groundbreaking book that provides a unique approach to both personal and organizational transformation. The authors focus on mindset change, enlightening readers on overcoming blind spots, identifying competing commitments, and freeing themselves from limiting assumptions.

The book’s strategies have been successfully implemented in educational institutions worldwide, helping faculty and administrators enact lasting change. Kegan and Lahey continue to offer resources and programs through their consulting firm, Minds at Work, including webinars on navigating crises. A highly recommended read for anyone seeking to drive meaningful change in their lives and organizations.

15. The Hard Thing About Hard Things – by Ben Horowitz

“The Hard Thing About Hard Things” by Ben Horowitz is one of the best titles among the books published by industry experts. It’s an entrepreneur’s handbook, addressing the realities of running a business that most guides won’t touch. It offers a frank exploration of the challenges faced by CEOs in both peacetime and wartime, emphasizing that there’s no recipe for success, a silver bullet to solve problems or perfect business. The most valuable lesson learned from anyone that has read this book is that the struggle is part of the journey, and only by embracing it can we make the greatest difference.

With insights like the importance of fostering a culture of trust, handling worst-case scenarios, and prioritizing people, products, and profits respectively, this book is a favourite among entrepreneurs. It exposes the raw truth of the leadership journey, with its dizzying highs and crushing lows, encouraging readers to face difficult decisions head-on and never give up. Horowitz also offers advice on hiring, fostering an effective work environment, and avoiding organisational pitfalls. It is an invaluable resource for those seeking to understand the real-world challenges of entrepreneurship.

16. Dealing with Darwin – by Geoffrey Moore

“Dealing with Darwin” by Geoffrey Moore is an exceptional guide for innovation management. In this book, Moore enriches the technology life-cycle concept introduced in “Crossing the Chasm”, extending it further to the category life cycle. This offers invaluable insight into managing innovation in mature markets.

Moreover, he expands on the core/context concept from “Living on the Fault Line”, transforming it into a tool for resource repurposing and innovation funding. Moore also explores the impact of two disparate business architectures, namely complex systems and volume operations, on innovation strategy. The book ultimately illuminates the perpetual evolutionary forces driving category maturity and renewal.

17. The 11 Laws of Likability – by Michelle Lederman

“The 11 Laws of Likability” by Michelle Lederman is a riveting read that unravels the secret behind successful business relationships: likability. Lederman convincingly argues that people tend to do business with individuals they find appealing. This book is her quest to demonstrate how to be successful by revealing what is inherently likable within us.

In this enlightening journey, she helps you discover your authentic likability, which isn’t about maintaining an unrealistically happy facade but about fostering genuine connections. The book guides you in creating candid, enjoyable interactions that result in beneficial outcomes for everyone involved, thus underscoring the critical role of likability in business success.

18. Five Dysfunctions of a Team – by Patrick Lencioni

“The Five Dysfunctions of a Team” by Patrick Lencioni is an unconventional take on management literature, providing insights through a fictional narrative. Utilizing a fable to illustrate the challenges faced by even the best teams in their collaborative efforts, this book provides practical tactics to surmount issues of the absence of trust and workplace politics. The ultimate aim is to empower employees to be team players and to attain their vital objectives with unity and effectiveness.

The story chronicles Kathryn Petersen’s endeavours to foster a healthy team environment in the imagined business, DecisionTech. As the plot unravels, Kathryn introduces her executives to the Five Dysfunctions of a Team Model, attributing these dysfunctions as the cause of the team’s shortcomings. This model, represented as a pyramid, illustrates the interconnection of the dysfunctions, where each impacts the one above. Lencioni also includes a theoretical part in the book, summarising his thoughts and providing an evaluation tool to assess a team’s susceptibility to dysfunctions.

19. Lean In – by Sheryl Sandberg

“Lean In: Work, Women, and Will to Lead” by Sheryl Sandberg offers an incisive commentary on the burning business topic — the stark gender inequality that persists in today’s society. With a mere 4% of Fortune 500 CEOs being women, Sandberg addresses the glaring disparities head-on.

Drawing on personal experiences from her illustrious career at Facebook and Google, she presents vulnerable moments as teachable instances to provide leadership training to all female leaders. The book serves as a clarion call, urging women to ‘lean in’ and harness their full potential to reach new heights, whilst providing actionable advice to effect change in this unequal landscape.

20. GO: Put Your Strengths To Work – by Marcus Buckingham

“GO: Put Your Strengths To Work” by Marcus Buckingham is an empowering guide that helps leaders recognize the value of leveraging our strengths for optimal productivity, creativity, and resilience. Grounded in research involving 2 million people, it reveals an alarming statistic: only 17% of people feel they utilize their strengths in their professional lives. The book, therefore, aims to help readers identify, label, and effectively deploy their personal strengths.

Each copy includes an online profiling assessment based on the Clifton StrengthsFinder profile. Buckingham suggests starting with a “SET” assessment to gauge current and future engagement with your strengths. By actively following the book’s tasks, readers can expect a marked shift in their “SET” scores, signifying more efficient utilisation of their strengths.


What is the best book to read on leadership?

The ‘best’ leadership book is subjective and largely depends on your personal leadership style and the challenges you’re currently facing. However, a universally acclaimed book would be “The Hard Thing About Hard Things” by Ben Horowitz. This brutally honest book offers practical advice on managing tough situations, making it a valuable resource for leaders. It provides a candid exploration of the ups and downs of entrepreneurship, emphasizing that struggles are part of the journey and that only by embracing them can we truly lead effectively.

However, to broaden your understanding of leadership, it’s recommended to read various books that offer diverse perspectives, such as “Dealing with Darwin” by Geoffrey Moore for innovation management, “The 11 Laws of Likability” by Michelle Lederman for mastering business relationships, and “Five Dysfunctions of a Team” by Patrick Lencioni for understanding team dynamics.

How many leadership books exist?

The exact number of leadership books is difficult to quantify. Countless books on leadership, management and business success have been published over the years, each offering unique insights and perspectives. It’s estimated that thousands, if not tens of thousands, of leadership books are available globally.

However, the sheer volume of books shouldn’t deter you. Instead, focus on finding the ones that resonate with your leadership style, the unique challenges you face, and your personal and professional growth goals. Remember, the best leadership book is the one that inspires you to become a better leader.

Are there any books that focus on leadership in nonprofit organizations?

Indeed, there are several books that focus on leadership within the context of nonprofit organizations. A standout recommendation is “The Nonprofit Strategy Revolution: Real-Time Strategic Planning in a Rapid-Response World” by David La Piana. This book challenges traditional strategic planning with a flexible, real-time approach tailored to the fast-paced, constantly changing world of nonprofits. It provides a dynamic, iterative process that engages staff and board in a program of systematic learning and management.

Another excellent book is “Forces for Good: The Six Practices of High-Impact Nonprofits” by Leslie R. Crutchfield and Heather McLeod Grant. It identifies successful strategies and practices of high-impact nonprofits and delivers practical tools for organizations to amplify their impact. These books, among others, offer invaluable insights for effective leadership in the nonprofit arena.

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