Thinking Gray: In Praise of Deliberative Leadership

Steven Sample, in The Contrarian’s Guide to Leadership, contends that effective leaders frequently “think gray.” In other words, they work hard to remain as open-minded as possible by not forming strong opinions when they encounter new concepts, people, or circumstances. Obviously, no one can think gray perfectly since doing so runs counter to our nature. It is a practice, like other imperfect but necessary skills, such as mindfulness or medicine. Driven by bias and other factors, we want to form opinions, make comparisons, leap to conclusions, and forge judgments whenever we encounter novel challenges. Good leaders, though, sometimes suspend their inclinations so as to remain neutral until such a time as they have to form an opinion, take a stance, or make a decision. They do so with intention and discipline. The advantages are substantial.

Thinking gray is difficult and seems anathema to what we typically regard as good leadership. Great leaders are imagined and portrayed as being preternaturally decisive. Proper leaders, we assume, take a stand in the face of doubt and stand by it whatever the odds. They defy convention, opposition, and even fear to hold a position or direction. We admire those whom we regard as such steadfast leaders. We laud their boldness, their resilience, even when we disagree.

And, on occasion, we need such leaders, particularly in times of true crisis. But times of true crisis–and I don’t mean times of great concern or festering paranoia or simple urgency–are fairly infrequent in the quotidian swirl of decisions and choices.

All too often, such leaders end badly because they are reactive and not deliberative. What we praise as steadfast may actually be stubborn. What we applaud as brave may in reality be heedless, reckless, or plain stupid. Having strong convictions and acting on them despite all evidence to the contrary has more in common with the mindset of toddlers than that of the fully formed adult. Young kids are spontaneous and willful in their spontaneity, and while we may enjoy their freedom and antics, we do not imitate them.

The true challenge, except in rare circumstances, is to withhold judgment. Not to react but to consider, to weigh. Such behavior can look like confusion, cowardice, or inanition to those who do not appreciate the virtues of consideration and evaluation. 

The deliberative stance is thinking gray, choosing not to choose the black or the white until such a time as a decision must be made and even then perhaps finding a compromise. After all, what is the virtue in making a decision in haste? If I can wait awhile to decide, why should I rush? It seems foolish to react suddenly without cause and outside of reason. Such reactions are inevitably prone to emotional bias and potentially are informed by partial knowledge and assumptions. Besides, what if something changes in the circumstances or in the context governing the decision? A quick, reactive decision–the decision of a rash decider–may precede the change, which could lead to avoidable error.

Deliberation, reasonably deployed, helps avoid such a situation, but by deliberation I do not mean avoidance or procrastination. A leader should run at challenges and problems but should not leap to conclusions unnecessarily. Nonetheless, quick decisions are frequently desirable or even necessary. Many solutions require only a rapid application of logic or even a flash of insight. Most choices are so minor or simple that we would be silly to delay them. For instance, lengthy deliberations over what to eat for lunch or whether to get a haircut or not would be a waste of time. These choices, like most, require a quick and slight exertion of brainpower. But complex or momentous decisions demand the practice of thinking gray.

By extension, the gray thinker will be willing to review, revisit, and revise decisions. Even gray thinkers will make mistakes, but the gray thinkers’ mistakes will be of a different kind and degree than the reactively decisive, the type more commonly associated with admirable leadership. The gray thinker’s mistakes, whatever the consequences, will remain steeped in principle and logic, so gray thinkers own their mistakes. We should not confuse deliberation and self-review with indecisiveness and self-doubt. The gray thinker has the discipline to withhold judgment and the strength to reconsider and change.

Too often we laud the shoot-from-the-hip cowboy making snap judgments, but that type of leader is out of place in our time. Life is not a cheeseball Western with clear, white-hat-black-hat delineations offering choices as the bullets fly. Our experiences can seem rapid fire, but they only seem that way. That is why regularly thinking gray is the mark of the true leader, the one to trust. Only the gray thinker will make the most consistently solid and correct decisions, and only the gray thinker will own mistakes and not just admit to them. The practice of gray thinking is less than exciting, but it is honest and true.

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