The Contrarian’s Guide to Leadership Summary

The contrarian leader thinks differently. While others see black and white, contrarians maintain intellectual independence and see many different shades between the extremes. Leaders who can conceptualize a range of ideas are more creative and intellectually open. What is the essence of “thinking gray?” Avoid forming an opinion until you’ve heard all pertinent facts and views, or until circumstances force you to form an opinion to move forward. Binary thinking, which is “black and white,” can lead to disaster because:

• You want to stay open-minded — Once leaders form opinions, their minds often close to new facts and information.
• You want to be decisive — The leader who forms an opinion yet remains open- minded will flip-flop, believing whatever case has been presented most recently.
• You want to think for yourself — People tend to believe whatever is strongly believed by other people. “Thinking gray” is the best defense against this herd instinct.

So, should you employ “gray-think” as a leader in all situations? Of course not. In fact, in most circumstances, it might be counterproductive. You could drive yourself crazy “thinking gray” about each of life’s routine decisions, but the deepest dilemmas demand it. A leader’s vision is important, but the ability to “think free” and to consider a range of ideas may be just as pivotal. For example, the leader must be able to envision how different organizational structures and combinations will affect a company’s development. You can be a leader without being terribly creative if you are able to nurture free thinking among your associates and are willing to implement their ideas.


Artful Listening

Most people think that what they have to say is more important than what they have to hear, and that’s why people are often lousy listeners. Contrarian leaders listen first and talk second. They genuinely want to hear different viewpoints and receive new data.


Machiavelli once observed, “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.” True leaders must be able to think for themselves and understand others’ thinking. That requires listening, the key to the contrarian leader’s intellectual independence. Listening enables leaders to “see double” — both through their own eyes and through those of their followers. The leader is never immobilized when confronted by conflicting points of view, and develops an ability to see two viewpoints simultaneously.

The leader’s inner circle should be based on confidence and awareness. Colleagues should feel free to constructively, candidly criticize the leader’s direction. However, this requires real trust between the parties, a level of trust that often takes years to develop.

To turn listening into an art, go beyond passive listening. You must be genuinely, intensely interested in what someone else is saying. Deliberately draw out the other person and seek additional details. Paraphrasing and active listening can help define the terms of the discussion. The leader who “thinks gray” must also learn to “listen gray.” That means listening to all types of input — anecdotes, briefings, complaints and puffery — without drawing any immediate conclusions or offering a definite response. Knowing when to stop listening is another rarely recognized component of artful listening. At some point, the leader must make a decision and take action. Taking the time to listen carefully at the beginning, however, can save a lot of wasted time at the end.

“Open communication with structured decision making” is one way to achieve a higher level of clear communication in a bureaucracy. Under this model, anyone at any level is free to communicate problems, opinions and concerns to anyone at any other level in the organization. If the janitor wants to address an issue with the CEO, that is permissible and, perhaps, even encouraged. However, the flip side of open communication is structure. That means that commitments, expenditures and decisions are made strictly through the operational hierarchy. This opens a free flow of information to the leader, but it avoids undermining the authority of subordinate managers.

Contrarian Authority Takes Its Time

When someone takes over an organization’s leadership, conventional thinking is that the new leader should seize the reins as quickly as possible. While this may be necessary during a crisis, the new leader really should have a few months to observe the organization before actually assuming control. CEOs who rush in to fix problems they do not fully understand risk making major blunders at a critical time.

Of Consultants, Saviors and Charlatans

Where would today’s leaders be without the gaggle of experts — consultants, analysts, attorneys and technicians — who tell them what to do? Just remember, you rarely hear about all the CEOs who stumbled because they listened to the wrong advice. As George Bernard Shaw once said, “Every profession is a conspiracy against the public.” The key to dealing with experts is to know your goals precisely.

If you feel any uncertainty, your views and direction will probably be subordinated to those of someone with greater expertise — even if you’re right. Thus, you must be sufficiently familiar with technological fields within your organization.

For example, the way a leader handles lawyers is particularly important. Considering that businesses must function in a world where a woman in New Mexico won $2.7 million (later reduced to $600,000) for burning herself with a cup of hot coffee from McDonald’s, the attorney plays an important role in any enterprise. The job of knowing when you’re on safe ground and when you’re not is complicated by constant changes in the law and its interpretations. However, if any expert, including an attorney, says that a given matter is so complex that it is beyond explication to a layperson, a contrarian leader becomes immediately suspicious. Perhaps the expert does not understand the issue well enough to explain it. While experts may be necessary, the leader should not kowtow to every bit of their advice.

Contrary Reading Habits

Don’t get so caught up in current events that you overlook the timeless classics, the “super texts,” such as Machiavelli’s The Prince or Homer’s Odyssey. Authors whose influence has stretched across the centuries are very rare. They offer not so much timeless truths about leaders, as timeless truths about the nature of human beings. The notion that we are superior or even substantially different from our forebears is problematic. If The New York Times does not shed light on your circumstances, perhaps a return to the classics will help. One drawback of the modern media is that you may allow gatekeepers to make decisions for you. If newspapers are the first rough draft of history, the implication is that some events of historical significance are being roughly handled. A pretty good chance exists that the stories that are not included in the newspaper — such as those which document subtle but powerful social undercurrents — are often more important than the stories that are included. To cultivate a contrarian’s healthy attitude toward the press:

• Read newspapers primarily for entertainment.
• When the press attacks someone, assume that important facts in the person’s defense have been omitted.
• Always suspect herd mentality.
• Realize that newspapers pay little attention to the subtle gray shades of reality.
• Know that even the best newspapers occasionally get the facts wrong.

Select your reading material carefully because leaders are heavily influenced by what they read.

Contrarian Decision-Making

“To decide or not to decide?” can be the contrarian leader’s most important question. While the clean-desk mentality that demands dealing with each issue as soon as it arises may work well for bureaucrats and managers, it’s lousy advice for leaders. The contrarian rules say that when feasible, you should:

• Wait to decide — Never make a decision today that can be reasonably delayed until tomorrow. That’s not to say that you should procrastinate on important decisions. The key word, of course, is “reasonably.” Indeed, if you clear your decks for all but the most crucial decisions, you will be able to focus on those. Harry Truman always used to ask, “How much time do I have?” He understood that the timetable often influenced his decision-making. Beware, however, because you face a pitfall: the danger of waiting too long.
• Delegate decision making — Never make a decision you could delegate reasonably to staff. Military leaders follow this practice with the understanding that they retain responsibility for the tasks and decisions that they delegate to subordinates. Delegation accomplishes two goals: it frees up the leader’s time and it helps develop subordinates’ decision-making skills. It is no coincidence that dictatorial managers rarely leave able lieutenants who can replace them.

Proactive Leadership

Part of the fine art of leadership is creating circumstances that require you to take a course of action. Leaders trying to manage unwieldy bureaucracies often use this technique. A CEO, for example, may declare his intention of reducing the number of senior officers by 30% within two months without announcing who is likely to go. The leader of a nonprofit may decide it’s time for a whole new mission statement, assigning its creation to a vice president or advisory board. This can be a way to get an organization to respond without attacking it directly.

Occasionally a leader feels the need to appear to be doing something about a high profile situation without actually taking substantial action. On such occasions, all a leader can do is reassure people. Occasionally, a leader’s role includes acting against subordinates’ advice, even if they are unanimous. You must do this properly to avoid offending your most trusted assistants.

Machiavelli, the father of modern political science, had a few suggestions for today’s leaders:

• Remember that no policy is without risk.
• A leader is justified in resorting to almost any action to prevent civil chaos or foreign domination.
• If you do a man a slight injury, he will seek revenge; if you crush him, he cannot.
• Never compromise with or submit to evil to avoid war.
• Luck plays the biggest role and fortune favors the bold.
• In a newly conquered territory, commit harsh acts all at once, but distribute mercies and benefits gradually over time.
• The leader’s main job is to protect from foreign invasion.

A Hill to Die On

Always know which hill you’re willing to die on — that means knowing where your ultimate core beliefs reside, and what you’re willing to do to defend them. Without that clarity, you will lack ethical leadership and people will hesitate to follow you. Work hard on behalf of the people who work for you. Make sure that your direct reports have direct access to you. And be willing to put forth a concerted effort to remove the obstacles they face every day.