University of Arkansas

Walton College

The Sam M. Walton College of Business

The World Still Needs Contrarian Leaders

4 white paper airplanes flying and 1 red paper airplane flying another direction
October 26, 2023  |  By Stephen Caldwell

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Note: This is part of a series of reviews of classic books on business and leadership.  

The halls of academia aren’t known as a breeding ground for contrarian leadership, but, when you think about it, where else would it make more sense to find it? Universities are charged with developing thought leaders who, with their research and best practices, reshape the world for the better. That can hardly happen without chasing new and different ideas in new and different ways. 

Too many universities, however, settle into the status quo, embracing the same-old, same-old in the name of tradition and at the expense of innovation. Those universities risk extinction or, worse, irrelevance. And the same is true for leaders in other industries.  

The need for leaders to approach challenges with an open mind is what keeps Steven Sample’s 2002 book, The Contrarian’s Guide to Leadership, so relevant. Sample served from 1991 to 2010 as the president of the University of Southern California, and during that time helped the tradition-rich institution grow in several significant areas, including its commitment to research and strategic planning. He also regularly taught classes, including “The Art and Adventure of Leadership” with Warren Bennis

Sample’s book shares his approach to leadership, which I would describe as respecting the past while exploring the future.  

“By contrarian I don’t mean counter to all conventional wisdom,” he wrote. “Indeed, much of the conventional wisdom about leadership … is absolutely true. … (But) you can’t develop your full leadership potential, or even fully appreciate the art of leadership, by slavishly adhering to conventional wisdom.” 

Sample’s respect for history shows up in his recommendation to study what he called six “supertexts” that every leader should read: Machiavelli’s The Prince, Plato’s Republic, Shakespeare’s Hamlet, Shakespeare’s Othello, Sophocles’s Antigone, and Dante’s Divine Comedy.

Those might not qualify as classics on leadership, but, as Sample notes, “Go where your competitors don’t go and read what they don’t read.” 

Perhaps Sample’s most memorable and applicable advice is what he calls “thinking gray,” which can run counter to the idea that all great leaders are bold and “strongly governed by their passions and prejudices.” In reality, great leaders only act boldly when it’s time to act boldly, not before. 

The essence of thinking gray, he said is, “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.” 

Thinking gray, he said, is primarily necessary for the “weightiest of issues,” not routine decisions. 

Sample also makes a strong case for hiring capable lieutenants and serving and supporting them and for building a reputation based on your values. And, of course, he shares a few “counterintuitive hooks” – short statements that sound false but are absolutely true. For instance, … 

  • “Anything worth doing at all is worth doing poorly. It may be worth more if it’s done well, but it’s worth something if it’s done poorly.” 
  • “The very notion of perfection is almost antithetical to effective leadership.” 
  • “The radar-equipped find it hard to stay on course long enough to get anything accomplished, while the gyro-equipped are liable to run into an iceberg at full steam.” 

Sample’s approach to leadership helped USC thrive, and the principles he taught are easy to see in many of the leaders at the Walton College. That’s good news, because in a world that’s constantly changing at a rapid pace, contrarian leadership isn’t just helpful, it’s essential.  

Matt WallerStephen Caldwell is Chief Word Architect for WordBuilders, Inc., where he spends most of his time helping clients discover, craft, and share the messages of their hearts. In addition to writing and editing for newspapers, magazines, and on numerous book projects, he has developed leadership and functional training for Fortune 500 companies. He lives in Fayetteville, Arkansas.