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For the vast majority of people, giving in to this natural compulsion toward binary thinking is relatively harmless. But for leaders it can lead to disaster.
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. A leader hears something in favor of a proposition and decides on the spot that the proposition must be true. Later that same day he hears an argument against the proposition and decides the proposition must be false. Many failed leaders have tended to believe the last thing they heard from the last person they talked to, thereby putting themselves and their followers through mental (and sometimes physical) contortions which were both unnecessary and counterproductive.
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.
Nietzsche’s point was beautifully illustrated by an experiment fashioned by psychologist Solomon Asch a half-century ago and repeated by others many times since then. In the experiment, eight subjects, supposedly chosen at random, were brought together in a room and shown a series of cards on which were printed four vertical lines. Each subject was asked in turn to identify which one of the three lines on the right side of the card was the same length as the line on the left side of the card. The experiment was arranged so that seven of the eight “subjects” were in fact ringers who, with conviction and sincerity, would each identify the same one of the right-hand lines as being equal in length to the left-hand line, when in fact it was not. The one true subject in this experiment was then faced with either going along with the judgment of
One must always keep in mind that leadership is an art, not a science. In this sense, leadership is more akin to music, painting and poetry than it is to more routinized endeavors.
the group and declaring as true something he knew to be false, or taking a position which was at odds with the consensus opinion of his peers. Roughly three-quarters of the subjects went against their better judgment and joined in with the false consensus at least once.
As in so many other areas that are essential to effective leadership, the popular media are a major stumbling block to thinking gray. There is no such thing as an unbiased article in a newspaper or an objective soundbite on television news. On the contrary, reporters and editors are trained experts at getting you to believe what it is they have to say and to adopt their point of view. Indeed, à la Nietzsche, the media want you to believe that everyone else (or at least, every other important person) believes what it is they have to say. It is precisely this patina of believability and respectability that makes the popular media so attractive to us, especially when their messages comport with our own passions and prejudices. And it is precisely this same patina that stands in the way of our thinking gray.
Thinking gray is decidedly not the same thing as thinking skeptically. The skeptic initially places everything he hears or reads in the “not true” box, with an implied willingness to move things to the “true” box if the accumulated evidence warrants such a transfer. There’s often a hint of cynicism about the skeptic that can be very off-putting to followers. It’s difficult for people to be inspired by a Doubting Thomas.
By contrast, the contrarian leader who can think gray doesn’t place things he hears or reads in either the “not true” or the “true” box. He is as open to enthusiastically embracing a new idea as he is to rejecting it. And he can truthfully compliment a lieutenant for having come up with a new idea or observation, without misleading the lieutenant as to whether he (the leader) believes it to be good or true or useful.


A close cousin of thinking gray is what I like to call thinking free – free, that is, from all prior restraints. It’s popular these days to talk about “thinking out of the box” or “brainstorming,” but thinking free takes that process of inventiveness to the next level.
The difference between thinking out of the box and thinking free can be understood when we imagine ourselves coming out of a heated swimming pool on a cool, brisk day. When we merely think out of the box, we stay in the cold just long enough to feel slightly uncomfortable, and then hastily retreat either back into the warm pool or indoors. But when we are truly thinking free, we stay out in the cold until we shiver and our teeth chatter. It’s the ability to tolerate the cold long after it becomes unpleasant – to forcibly sustain our thinking free for more than a fleeting moment – that leads to the greatest innovations.
The key to thinking free is first to allow your mind to contemplate really outrageous ideas, and only subsequently apply the constraints of practicality, practicability, legality, cost, time and ethics. As with thinking gray, thinking free is an unnatural act; not one person in a thousand can do it without enormous effort.
Here’s a simple example. A leader brings a group of people together who share a common goal (e.g., keeping their company afloat in a brutally competitive market), but who have widely varying opinions as to how the goal might best be achieved. The leader asks each person in turn to offer up an off-the-wall idea for achieving the goal, with the proviso that every other person in the group must respond with at least two reasons why the idea will work. The result is often surliness or sullen silence on the part of the participants. Most people are simply unable to force themselves to think positively for even a few minutes about an idea which they believe in their hearts is stupid, wrongheaded, immoral, impractical or illegal.
Now please do not misunderstand me; I am not suggesting that leaders should pursue evil or illegal or ridiculous ideas. On the contrary, I have found that one’s principles, passions and prejudices always reassert control after a few minutes of thinking free. But during those few minutes the leader or his or her associates just might come up with a truly original idea.

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Congenital naysayers are one of 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.

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