On Contrarian Leadership

I recently finished reading The Contrarian’s Guide to Leadership by Steven B. Sample.

As the author best states: “The purpose of the this book is to get you to think about leaders and leadership from a fresh and original point of view – from what I call a contrarian perspective…The Key is to break free, if only fleeting, from the bonds of conventional thinking so as to bring your natural creativity and intellectual independence to the fore.” He further argues that: “One of the important and contrarian point we can make about leadership is that it is highly situational and contingent; the leader who succeeds in one context at one point in time won’t necessarily succeed in a different context at the same time, or in the same context at a different time.”

The principles of such leadership are then discussed over ten (10) chapters as follows: 1) Thinking Gray, and Free 2) Artful Listening 3) Experts: Saviors and Charlatans 4) You Are What You Read 5) Decisions, Decisions 6) Give the Devil His Due 7) Know Which Hill You’re Willing to Die On 8) Work for Those Who Work for You 9) Follow the Leader 10) Being President Versus Doing President. The author then concludes the book with an illustrative example through his experience at the University of Southern California.

A great recommended read that brings fresh perspective on servant leadership!

Below are key excerpts from the book, that I found particularly insightful:

3- “The essence of thinking gray is this: don’t form an opinion about an important matter until you’ve heard all the relevant facts and arguments, or until circumstances force you to form an opinion without recourse to all the facts.”

4- “…clients who benefited most from my services were leaders who never became too dependent on me, who always maintained their intellectual independence, and who never kidded themselves that expertise could be a substitute for leadership.”

5- “The key contribution of the supertexts is not a set of timeless truths about leadership, but rather some timeless truths about human nature. One of the great fallacies of our age (and perhaps any age) is the belief that we are fundamentally different from our ancient forebears, that we have somehow outgrown the barbaric and benighted practices of centuries and millennia past…we are every bit as human, and no more human, that the characters in the Old Testament or the people of sixteenth-century Florence.”

6- “All leaders, whether contrarian or otherwise, are heavily influenced bu what they read. Indeed, in many cases leaders are directed and inspired as much by their readings as they are by their closest advisers…In reading as in so many other areas, maintaining one’s intellectual independence is an essential prerequisite for effective leadership.”

7- “The contrarian leader’s approach to decision making can be summarized in two general rule: 1) Never make a decision yourself that can reasonably be delegated to a lieutenant. 2) Never make a decision today that can reasonably be pt off to tomorrow.”

8- “The challenge for the leader isn’t to delude himself into thinking that people are intrinsically better or worse than they really are; rather, it is to find ways to bring out the best in his followers (and in himself) while minimizing the worst.”

9- “An outstanding candidate (for an open position) must be at least two notices above the leading insider in order to be a good risk.”

10- “In the long run the most difficult part of building a diverse team of lieutenants is to integrate people whose intellectual and moral perspectives cover a wide spectrum and are not simply isomorphic with those of the leader.”

11- “It has been my experience that money is often as essential element in attracting and retaining outstanding people…however I don’t believe money is a very effective tool for inspiring people to reach for and achieve extraordinary goals; rather, the actual motivation in such instances seems to be pride or the desire to beat out the competition.”

12- “The challenge is for the person at the top to be such an excellent supervisor – fair, supportive, demanding, a good listener, motivating, and inspiring – that these values will be internalized and replicated via people chains at every level in the organization.”

13- “The contrarian leader knows that he himself must answer the question of what’s right both a worldly and a moral perspective. This at times will make his experience more exhilarating than that of other leaders, and at times more excruciating. But it will always be his experience – one for which he willingly takes responsibility  And what could be a greater or more meaningful adventure in leadership than that?”


Omar Halabieh

The Contrarian’s Guide To Leadership


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