The Contrarian’s Guide to Leadership | Notes & Review

Steven Sample. The Contrarian’s Guide to Leadership. Jossey-Bass, 2002. (197 pages)

…one of the most important and contrarian points 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 int he same context at a different time. | The very concept of leadership is elusive and tricky. (1)

But just as you can’t become an effective leader by trying to mimic a famous leader from the past, so you can’t develop your full leadership potential, or even fully appreciate the art of leadership, by slavishly adhering to conventional wisdom. The key is to break free. (3)

1. Thinking Gray, and Free

…contrarian wisdom argues that, for leaders, judgments as to the truth or falsity of information or the merits of new ideas should be arrived at as slowly and subtly as possible — and in many cases not at all. (7)

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… (7-8)

There are three very real dangers to effective leadership associated with binary thinking. One is that the leader forms opinions before it is necessary to do so, and in the process closes his mind to facts and arguments that may subsequently come to his attention. The second danger is flip-flopping. … | The third danger relates to an observation by the German philosopher Friedrich Nietzsche, to the effect that people tend to believe that which they sense is strongly believed by others. A well-developed ability to think gray is the best defense a leader can have against this kind of assault on his intellectual independence. Leaders may want to nurture a herd mentality among their followers, but they should never succumb to such thinking themselves. (9-10)

Thinking gray is decidedly not the same thing as thinking skeptically. … A close cousin of thinking gray is what I like to call thinking free — free, that is, from all prior restraints. (12)

Congenital naysayers are among the greatest stumbling blocks to thinking free. Rather than imagining how a new idea might possibly work, they instinctively think of all the reasons why it won’t. They sincerely believe they’re doing everyone a favor by reducing the amount of time spent on bad or foolish ideas. But what they really do is undermine the creativity that can be harvested from thinking free. … Thus, the key to successful invention often lies in getting one’s brain to imagine new combinations of existing elements that solve a problem in a way no one has ever thought of before. (13)

2. Artful Listening

The average person suffers from three delusions: (1) that he is a good driver, (2) that he has a good sense of humor, and (3) that he is a good listener. (21)

A contrarian leader is an artful listener, not because it makes people feel good (which it does), but rather because artful listening is an excellent means of acquiring new ideas and gathering and assessing information. (21)

Minds are of three kinds,…One is capable of thinking for itself; another is able to understand the thinking of others; and a third can neither think for itself nor understand the thinking of others. The first is of the highest excellence, the second is excellent, and the third is worthless. – Machiavelli

“seeing double” | The contrarian leader prizes and cultivates his ability to simultaneously view things from two or more perspectives. (22)

A leader’s inner circle of advisers should be founded on mutual understanding and trust. It should be comprised entirely of individuals who are committed to the institution’s and the leader’s best interests, and whose filters, prejudices and attitudes are well understood by the leader. Toward that end it is usually best to keep one’s inner circle of advisers relatively small — typically no more than eight. (22)

The contrarian leader never takes such counsel at face value; the first question she asks is, “Who is saying what to whom?” (27)

Thus it is the leader’s responsibility to ensure that the person who is speaking to him is not inadvertently misled by the leader’s genuine efforts to understand and appreciate what’s being said. Achieving this delicate balance is a fine art. (29)

One final aspect of listening gray is that a leader shouldn’t make up his mind about people’s credibility unless and until he has to. (31)

3. Experts: Saviors and Charlatans

…how can a modern leader use experts to his or her advantage without being used or used up by them? (37)

…every profession is a conspiracy against the laity. – George Bernard Shaw

…a leader should pay close attention to experts but never take them too seriously, and never ever trust them completely. (39)

As a general rule, leaders are much more interested in technology than they are in science. (43)

No amount of experimentation can prove me right; a single experiment can prove me wrong. – Albert Einstein

…it’s not important whether a particular scientific theory is really “true” in some ultimate sense; rather, what counts to leaders are the practical technologies that can be wrung from that theory. (45)

My friend Warren Bennis believes that, while only a tiny fraction of the population are practicing physical scientists, essentially everyone is a practicing social scientist. (46)

A lot of what can be counted doesn’t count, and a lot of what counts can’t be counted. – Albert Einstein

4. You Are What You Read

I’m sometimes asked to identify those of the supertexts which in my opinion are the most valuable for modern leaders. After The Prince, I would choose the stories of four of the greatest leaders in the Bible: Moses (in the book of Exodus), David (in 1 and 2 Samuel), Jesus (in Matthew) and Paul (in Acts). Next on my list would be: Plato’s Republic for the way it brings out the best in us; Shakespeare’s Hamlet for giving us a terrifying look inside ourselves, and his Othello for a view of a leader undone by an evil lieutenant; Sophocles’ Antigone to help us see the pitfalls of rigidity in a leader; and all of John Ciardi’s translation of Dante’s Divine Comedy for its portrayal of the full range of human triumphs and foibles. (58)

The key contribution of the supertexts is not a set of timeless truths about leadership, but rather some timeless truths about human nature. …Moreover, the supertexts are important not only for what they say but also for how they say it. (59)

The man who never looks into a newspaper is better informed than he who reads them, inasmuch as he who knows nothing is nearer to the truth than he whose mind is filled with falsehoods and errors. He who reads nothing will still learn the great acts, and the details are all false. – Thomas Jefferson in a letter to John Norville

This remark was later polished into the well-known maxim: “The man who reads nothing at all is better informed than the man who reads nothing but newspapers.” (60)

But, as with quitting smoking, after a few weeks I felt a new-found sense of freedom and autonomy. I realized that I (along with nearly everyone else in America) had become addicted to the popular media, and that in so doing I had given over a big chunk of my intellectual independence to a group of editors and reporters whose core values and interests were not necessarily congruent with my own. | Moreover, I was stunned to find that, within twelve hours of a story’s first appearing int he popular press, I was often better informed about the facts of the story than those of my friends and colleagues who were still addicted to reading newspapers. How could that be? Simple. I was getting my news orally from people (such as my principal advisers) whose biases were well known to me and who had my best interests at heart. (61)

It isn’t just the text of a news story that can mislead us; it’s also the choice of which stories get covered at all, and by whom, and where they’re placed in the paper… (62)

The question for each leader then becomes: how much total time do you wish to devote each day to reading …and how do you wish to allocate that time across the spectrum of published materials? (67)

5. Decisions, Decisions

Probably the most critical decisions made by leaders relate to the hiring, nurturing and firing of lieutenants. (71)

…the contrarian leader’s approach to decision making can be summarized in two general rules:

  1. Never make a decision yourself that can reasonably be delegated to a lieutenant.
  2. Never make a decision today that can reasonably be put off to tomorrow.

…the leader who delegates is forced to build coherence by putting together a team of lieutenants who have shared values and common goals. If he’s successful in this regard, his organization can survive the loss of the leader himself. (74)

First, the leader should reserve to himself the hiring, compensating, motivating, molding, assessing and firing of his chief lieutenants. | Second, the leader himself should make those decisions which have the greatest potential impact on the organization or movement he’s leading. (74)

Identifying the really crucial decisions is sometimes referred to as distinguishing between the urgent and the important, which sounds easy in theory but isn’t in practice. (75)

Machiavelli points out that a leader should never become too predictable, lest his lieutenants and other followers be able to manipulate him too easily. (75-76)

This is the paradox of leadership in a legal system — it asserts authority by deferring to it, as Washington wielded power by giving it up. – Garry Wills

Another contrarian discipline with respect to decision-making is to completely ignore any so-called sunk costs — i.e., costs incurred (or mistakes committed) in the past. Decisions made by a leader can only influence the future, not the past. (88)

6. Give the Devil His Due

Until philosophers are kings, or the kings and princes of this world have the spirit and power of philosophy, and political greatness and wisdom meet in one, and those commoner natures who pursue either to the exclusion of the other are compelled to stand aside, cities will never have rest from their evils. – Plato

Many have imagined republics and principalities which have never been seen or known to exist in reality; for how we live is so far removed from how we ought to live, that he who abandons what is done for what ought to be done will rather bring about his own ruin than his preservation; for a man who strives after goodness in all his acts is sure to come to ruin, since there are so many who are not good. Hence it is necessary that a prince who is interested in his survival learn to be other than good, making use of this capacity or refraining from it according to the need. – Machiavelli

…people are more likely to take advantage of a leader who is only loved than they are one who is feared… (98)

7. Know Which Hill You’re Willing to Die On

Most people confuse good leadership with effective leadership, but the contrarian leader knows that there is an enormous difference between the two. Hitler, for example, was an extraordinarily effective leader (at least during his rise to power and for the first decade or so of his reign), but few would cal him a good leader; indeed, most of us would say he was a monstrously evil one. (107)

Once you know which hill you’re really willing to die on, keep it to yourself. If you as a leader reveal to everyone the areas of moral behavior on which you are absolutely unwilling to compromise under any circumstances, your adversaries will almost surely use this knowledge to ensnare or undermine you. (112)

In order for a leader to know which hill he’s willing to die on — to know where his adamantine core is located — he needs to be consciously aware of his own moral beliefs and what the basis is for those beliefs. If not religious (or at least transcendental) in origin, one’s core moral values may prove very unreliable in a clutch, especially if they are in some sense altruistic. (114)

Nothing is good or bad, only thinking makes it so – Shakespeare in Hamlet

Ethical leadership requires that the leader choose one set of moral values over all others, and then take full responsibility for his actions based on those values. (119)

8. Work for Those Who Work for You

The best executive is the one who recruits the most competent men around, tells them what he wants done, and then gets out of their way so they can do it. – Teddy Roosevelt

Since so much of effective leadership involves bringing in the best talent possible, we should take note of an almost universal human truth: most people tend to hire people who are weaker than themselves. Moreover, this rule of thumb is nonlinear in practice — that is, excellent people tend to hire people only slightly weaker than themselves, while weak people tend to hire people who are much weaker than themselves. Or to paraphrase an old saw, “A’s hire A-minuses, and B’s hire C’s.” (123)

There’s no such thing as ‘the right man for the job.’ The appropriate question to ask is, ‘Is he the best man available for the job within the time frame in which I must fill the position?’ – Fred Hovde

Contrarian leaders know that it’s great people, not great job descriptions, that make an organization successful. (125) [VIA: Don’t great job descriptions assist, however, in finding great people? I think there’s a paradoxical inverse relationship here between subject and object]

I recently turned sixty, so I’d be the last person in the world to favor or practice age discrimination. But time and again I have been advised by successful leaders that, between two roughly equal candidates, one should always choose the younger. (126)

The contrarian leader understands the difference between statistics and stereotypes. (128)

9. Follow the Leader

To paraphrase Harry Truman, leadership involves getting others to willingly move in a new direction in which they’re not naturally inclined to move on their own. (142)

The contrarian leader knows that an effective salesman must sell himself first and the product second, and that similarly, an effective leader must sell himself first and his vision or policies second. (143)

Effective leaders are able to create, manipulate and exemplify not only stories but symbols, slogans, and mantras as well. All of these help define in the minds of followers the essence of the leader’s vision and his character (148)

Your actions speak so loudly I cannot hear what you say. – Emerson

The contrarian leader knows that the human brain is prewired at the deepest levels in favor of the spoken word; if you wish to really inspire your followers and touch them at their emotional core, you must speak to them. (149)

leaders are sentenced by their sentences. (150)

A contrarian leader…is always searching or what I like to call “leadership leverage”; that is, ways to inspire and motivate those of his followers whom he’ll never come to know personally or who will never (or only rarely) hear him speak firsthand. One of the most effective means of achieving such leverage is through the establishment of multiple “people chains” through which the leader’s goals, vision and values are transmitted orally and personally to every follower. (155)

Jesus was extraordinarily effective in achieving leadership leverage through people chains. He recruited a dozen principal followers, who in turn recruited hundreds of others, who in turn recruited thousands of others, and so forth to a cumulative total of billions of followers over the past two thousand years. It’s important to note that the vast majority of Jesus’ followers during these two millennia have been recruited through the spoken word. (156)

Therein lies a great contrarian principle: followers, be they soldiers, assembly-line workers, faculty members or voters, are not standardized units, to be counted as so many widgets on a shelf. Rather, each is a unique human being who must be recognized and treated as such if the organization or movement you’re leading is to flourish over the long haul. You as the top leader may not be in a position to provide this kind of individual attention yourself to each of your followers, but it’s essential that someone in your organization does so. Otherwise your ability to motivate your followers will surely erode over time. | Leaders don’t really run organizations (although we often use that term in describing leadership). Rather, leaders lead individual followers, who collectively give motion and substance to the organization of which the leader is the head. The contrarian leader never loses sight of this fact, which is often a major reason for his success. (157)

10. Being President Versus Doing President

Anything worth doing at all is worth doing just well enough. (168)

When a person first attains a top leadership position, he’s often dazzled by the perquisites and deferential treatment which accompany high office; indeed, these may well be the things that motivated him to seek the top job in the first place. But soon these ephemeral glories fade and he’s left with the realities of his job — the nitty-gritty of day-to-day leadership. It’s then that Vern Newhouse’s insight, cited at the beginning of this chapter, comes into play. Does this person want simply to be president, or does he really want to do president? If the latter, he might contribute something great and lasting to his followers and the organization they comprise. But if he only wants to be president, the sooner he’s removed from office the better for everyone concerned, including the leader himself. (170)

11. The University of Southern California: A Case Study in Contrarian Leadership


  1. Think gray: try not to form firm opinions about ideas or people unless and until you have to.
  2. Think free: train yourself to move several steps beyond traditional brainstorming by considering really outrageous solutions and approaches.
  3. Listen first, talk later; and when you listen, do so artfully.
  4. Experts can be helpful, but they’re no substitute for your own critical thinking and discernment.
  5. Beware of pseudoscience masquerading as incontrovertible fact or unassailable wisdom; it typically will do nothing to serve your interests or those of the organization you are leading.
  6. Dig for gold in the supertexts while your competition stays mired down in trade publications and other ephemera; you can depend on your lieutenants to give you any current news that really matters.
  7. Never make a decision yourself that can reasonably be delegated to a lieutenant; and never make a decision today that can reasonably be put off to tomorrow.
  8. Ignore sunk costs and yesterday’s mistakes; the decisions you make as a leader can only affect the future, not the past.
  9. Don’t unnecessarily humiliate a defeated opponent.
  10. Know which ill you’re willing to die on, and realize that your choice may at some point require you to retreat from all the surrounding hills.
  11. Work for those who work for you; recruit the best lieutenants available, and then spend most of your time and energy helping them to succeed.
  12. Many people want to be leader, but few want to do leader; if you’re not in the latter group you should stay away from the leader business altogether.
  13. You as a leader can’t really run your organization; rather, you can only lead individual followers, who then collectively give motion and substance to the organization of which you are the head.
  14. Don’t delude yourself into thinking that people are intrinsically better or worse than they really are; instead, work to bring out the best in your followers (and yourself) while minimizing the worst.
  15. You can’t copy your way to excellence; rather, true excellence can only be achieved through original thinking and unconventional approaches.

Every act of theirs, which appears to them an act of their own free will is in an historical sense involuntary and is related to the whole cause of history and predestined from eternity. – Leo Tolstoy

And contrarian wisdom would argue that that is the morally preferable approach: A leader should always act as though he himself, not history or fate, is responsible for his actions. (192)

…managers do things right, while leaders do the right thing. – Warren Bennis

About VIA


  1. Really excellent synopsis. I saw the title and thought to myself… there’s a book I should really read but won’t. Thanks buddy, now I don’t have to : ) Guess that’s the point huh….

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