If You Could Only Have 10 Leadership Books

A man (we’ll call him “Bob”) gave me a challenge:

“If you could only have 10 leadership books for the rest of your career, which 10 would you pick?”

My criteria:

Proven for at least a few years; no trendy flash-in-the-bestseller-list entries
Sufficient depth so that I could gain new insights each time I reread it
Speaks to timeless principles, rather than tactics which will become outdated
Resonates with me personally (the “2×4-to-the-forehead value”)
I’ve recommended to others, and know they also benefitted
Would be good for the leader of a Mars colony
I’m ruling out biographies

My top 10 books, in no particular order:

The Effective Executive (Peter Drucker) – Prescient when written, still completely relevant. Effectiveness at the personal and organizational level is crucial.

The 80/20 Principle (Richard Koch) – Once you get this you’ll see 80/20 everywhere, and use it to maximize the value of your time and energy. Though the world is becoming 95/5, the principles still apply.

The Fifth Discipline (Peter Senge) – Thinking and Deciding in systems is an essential skill for leaders in complex situations.

Warfighting (US Marine Corps) – The best book on strategy, with applications in the corporate and non-profit world as well.

Proverbs (King Solomon) – 31 chapters of principled insights about moral relationships.

Influence: The Psychology of Persuasion (Robert Cialdini) – The classic, research-based text on what moves people to change behavior. Leaders are always in the business of shaping the behavior of others to get results.

Seeking Wisdom: From Darwin to Munger (Peter Bevelin) Leaders must leverage proven mental models for assessing situations and making decisions, because the gap between cause and effect has destroyed many leaders.

The Prince (Machiavelli) – The oft-maligned but classic text on ruling. Geopolitics and Realpolitik are factors in a complex world of global business.

The War of Art (Steven Pressfield) – Leadership is grounded in self-leadership, and anything you create is going to require a battle. Procrastination, fear, and self-doubt are only defeated when we create our work and share it with the world.

Complete Plays of William Shakespeare – Every person you will ever work with is in at least one of his plays. The Bard paints vivid pictures of the strengths and foibles of man.

These have all stood the test of time and multiple readers. I could happily reread each one every year and confidently learn from them. Collectively they speak to the think-decide-communicate responsibilities of leaders in every generation. Added joy: none of them have leadership in the title!

Selecting just 10 was difficult because I treasure so many books. I would be hard-pressed to limit myself to just 10 biographies of leaders! There are many good books on leading change and communication, but none good enough to displace a book on my top 10 list.

In the Fiction category, I have three additional recommendations because fiction often speaks to us in ways non-fiction can’t deliver:

The Lord of the Rings – classic big story with multiple examples of great and poor leadership

Ender’s Game and Dune – how truly smart people think about complex situations

Of course, there are many great books I’d recommend that almost made the top 10. Man’s Search for Meaning and Durant’s The Lessons of History are classic, as are Sun Tzu’s The Art of War and Marcus Aurelius’ Meditations.

A handful of excellent books are published each year. Let’s see how Start with Why, The Five Dysfunctions of a Team, Ray Dalio’s Principles, Tribes, Drive, Execution, Team of Teams, Made to Stick, The 48 Laws of Power, Leading Change, Deep Work, Ego is the Enemy, Primal Leadership, On Becoming a Leader, Team of Rivals, Leadership and Self-Deception, The Personal MBA, Lean In, The Effective Manager, The Truth About Leadership, Extreme Ownership and others fare in 20 years.