The popular leadership literature contains countless, conventional leadership books available at the click of an Amazon purchase, an audible subscription, or best of all, a trip to your locally-owned, retail bookstore. This list is different. We’ve compiled a handful of outside-the-box reading suggestions to improve a dynamic leader’s reservoir of appropriate skills. Here are some classic, unconventional leadership books.

Thinking, Fast and Slow, Daniel Kahneman


The bible of decision making. Thinking, Fast and Slow, describes two fundamental systems of thinking that people, i.e. leaders and teams, utilize to make choices and solve problems. The rub is that all the choices we make and solutions we craft, arise from either instinct or critical thinking. And immense value lies in recognizing the difference. Leadership and its success rest on the choices a leader makes and thus, Thinking, Fast and Slow can be a wildly valuable leadership tool.

The War of Art, Steven Pressfield


Get your ass in gear. The War of Art is one writer’s attempt to coach himself, not in the act of writing, but in the act of doing. Pressfield’s idea is that initiative drives inspiration, that effort is the prime mover of creativity, not the other way around. You don’t need to be inspired to start, you just need to start, and the inspiration will come. Leaders may value this book for its empathetic solution to the fear and paralysis brought by expectations. Quite possibly the most urgent book ever written.

Man’s Search for Meaning, Viktor Frankl


Not light reading. A chronicle of Frankl’s experience in concentration camps and the development of his theory that finding meaning in life is the central human motivation. Frankl argues that meaning defines human existence and that our ability to connect with meaning is a derivative of our ability to believe in a better future.


Between stimulus and response, there is a space. In that space is our power to choose our response. In our response lies our growth and our freedom.”


Leadership can require inspirational and motivational talents. As a leader, sometimes the most effective action is teaching people to hope.

Moneyball, Michael Lewis


The lifecycle of a better idea. Billy Beane of the Oakland A’s leads his organization through a fundamental philosophical and operational shift. All the while defying the common wisdom, the skeptics, and the derision of entrenched ideologues. A roller-coaster account of bold, counter-intuitive action with high stakes. A book on how to do the opposite, and a classic of analytical decision making.


Leadership From Broad Experience


Successful leaders are flexible, broad thinkers, adapting their teams and processes to the adversities and vagaries of the moment. Leaders and teams that draw wisdom from every learning experience and opportunity are the ones that drive to succeed. That said, we hope these unconventional leadership books can bring value to present and future leaders and teams.


P.S. We have not included amazon links in the hope that people get out there and support their local bookstore, even if it smells a bit funky and the coffee is bitter.