Best Books on Leadership | Sources of Insight

“Leadership is influence.” — John Maxwell

These are the best leadership books that helped me the most at Microsoft to learn influence, leading change, and more.

When I think of leadership, I think of influence, change, connection, conviction, inspired action, empowerment, decisive action, forward-thinking, and vision.

The leadership books below help provide leadership skills, including mindsets, methodologies, and methods. I test many of the leadership books below while leading large scale programs, projects, and initiatives and distributed teams around the world.

I put the bulk of the list in categories so you can explore relevant leadership books and you can easily compare against your existing leadership books library.

The Top 10 Best Leadership Books

Here is a list of the top 10 best leadership books that will help you develop your leadership mindset, skillset, and toolset, as well as develop your leadership philosophy. Some of the key skills they will help you build include vision, execution, influence, emotional intelligence (QE), and more.

1. Emotional Capitalists

by Martyn Newman

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It’s one thing to know the basics of emotional intelligence. It’s another to apply it from a leadership perspective.

The best leaders have strong Emotional Intelligence. They get themselves and they get the people around them.

By the time I read this book, emotional intelligence (or EQ), was already popular idea around Microsoft as a component of personal and professional development.

This book made emotional intelligence real for me.

Martyn did a great job throughout the book of turning the idea of emotional intelligence into pragmatic development exercises that anybody can work on to grow their emotional intelligence understanding and skills.

2. Flawless Execution

by Michael Murphy

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This takes what fighter pilots learned about executing in life and death scenarios and brings it to the corporate arena.

This book took my confidence in execution to the next level through its frameworks and examples.

I loved the depth and detail around creating 12-Point Future Pictures to communicate vision and create compelling clarity.

It’s actually one of the most action-packed books on the art of execution I ever read, and I found myself referring to it for years at Microsoft.

3. Leadership Gold

by John Maxwell

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I was already a Maxwell fan but this was like having his greatest hits all in one place.

It’s 26 of his best lessons he learned over more than 40+ years of leadership study and practice.

The best thing about this book is it feels like Maxwell is a mentor, taking you through his best lessons in a very personable way.

4. Leadership on the Line

by Ronald Heifetz and Marty Linsky

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What a breath of fresh air. This was the first leadership book I read that really stepped into the dark and lonely side of leadership when you have to drive unpopular changes or put yourself on the line.

This is the book that taught me a simple framework for understanding whether a problem is a technical problem or an adaptive challenge

Just that one framework helped me jump to a new level of leadership and understand in a much deeper way how to pace myself for change and how to lead a team through big challenges.

Whenever I recommend this book to a mentee, they end up having a profound experience.

5. Principle-Centered Leadership

by Stephen Covey

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I think this is where I really learned to understand the distinction and value of principles vs. rules.

Covey defines 8 Characteristics of principle-centered leadership:

Continue to learn
Service oriented
Radiate positive energy
Believe in other people
Lead balanced lives
See life as an adventure
Synergistic
Self-renewal

I related to each of the principles and practiced them over the years at Microsoft. This is yet another example of how the essence of great leadership is timeless, and this is one of the best evergreen books ever written.

6. Start with Why

by Simon Sinek

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I was so lucky that one of my mentees introduced me to Simon’s work early on, as she was an early business partner with him.

If more leaders started with WHY, more orgs would be a better place.

Actually, if everybody started with their WHY, the world would be a better place.

When you know how to think, act, and communicate from the inside out, as Simon teaches, your inner game becomes the foundation for your outer success.

This is one of those life changing books that stands the test of time.

7. The 5 Levels of Leadership

by John Maxwell

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I like how Maxwell frames out levels and provides a roadmap for growing your leadership influence and impact.

Maxwell outlines 5 levels of leadership like so:

Position – People follow because they have to.
Permission – People follow because they want to.
Production – People follow because of what you have done for the organization.
People Development – People follow because of what you have done for them personally.
Pinnacle – People follow because of who you are and what you represent.

It’s now how I would lay out the levels, but I get the framework. At the highest level, I see leaders that know how to scale the work of others, live their principles, and inspire people through creative vision. I would expect any leader to master self-leadership, then model the way for others. I also expect leaders to focus on strengths and always bring out the best in each individual, so they bring out the best in the team.

8. The 21 Irrefutable Laws of Leadership

by John Maxwell

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And the hits just keep on rolling with Maxwell! This is one of my all-time, favorite books by Maxwell, and I think it might have been my first introduction to his work.

I love it when an author can distill their knowledge into sound principles, patterns, and practices.

This work is a solid example of turning insights and strategies into strategic operating principles in the form of “laws”.

I remember reading the book fast and absorbing everything so easily because of the way Maxwell explains in plain and simple language.

This book really informed my leadership philosophy early on and I think it is one of the best foundations to draw from.

9. The Essential Wooden

by John Wooden

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It’s a shame there isn’t an audio version. Wooden is a great speaker and, just like Covey, his words echo in your mind.

Wooden is the one that gave me confidence that any team can become a winning team if you bring out each person’s best.

Wooden was famous for his style of coaching.

Rather than generalized advice for the team, Wooden would journal for every single individual to continuously improve.

I really like how Wooden measured success as “peace of mind”, and how he would say that if you played your best, but lost, did you really lose, and if you didn’t play your best, but you won, did you really win?

And whenever I catch myself rushing through something, I remember how Wooden would say, “Be quick, but don’t hurry.”

This book is a true, evergreen, leadership classic.