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2 essential questions to ask if you want to be a better leader

“Knowing how the other side thinks is the most effective way to solidify your own line of thought.”

2 essential questions to ask if you want to be a better leader
[Photo: Garrett Sears/Unsplash]

In 2017, after nearly a decade spent building Uber into a household brand, Travis Kalanick yielded to pressure from investors who demanded that he step down as CEO. Shortly before offering his resignation, the scandal-plagued founder issued a statement: “For the first time I’ve been willing to admit that I need leadership help.”

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That was too little too late. And for such once-great commercial giants as Kodak, Blockbuster, and Blackberry, the unwillingness to solicit advice or consider potential pitfalls resulted in not only personal but corporate catastrophe.

A popular technique employed by trial lawyers preparing for legal combat is to construct arguments against their own positions. Anticipating both attacks and rebuttals from opposing counsel equips courtroom warriors to argue their cases better while defending against counterarguments.

Debate teams practice using the same device, proposing and defending positions that counter their own personal beliefs. Legislators and political strategists compose papers that contradict their own proposals and policies. Knowing how the other side thinks is the most effective way to solidify your own line of thought.

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And, occasionally, you may discover that you’ve been wrong and need to reevaluate your own position.

Unfortunately, in the politically charged culture of today, few of us have any inclination to seriously consider opposing views or to listen to them at all. And that mindset can have disastrous consequences in business as well as politics.

Two thousand years ago, two great academies of study debated the ancient laws of the Judean commonwealth. History records that the scholars of the House of Hillel and the House of Shammai argued with one another so passionately it was as if “they fought with swords and spears.” Each school had its own angle on higher truth, and each was committed to preserving the integrity of Jewish legal tradition.

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But when they left the study hall, they were fast friends. They married their sons and daughters to each other. Their different visions never became personal. And, occasionally, one school convinced the other that it was wrong.

Ultimately, it was the opinions of the House of Hillel that prevailed, and later authorities explain why. Not only did the scholars of Hillel always record the opinions held by the scholars of Shammai along with their own—they always recorded the opposition opinions first.

Only when we understand the other side of any argument can we truly understand our own. That’s why intellectual integrity demands that we ask ourselves these questions:

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  • If I don’t understand why you believe what you believe, how can I be sure that you’re wrong?
  • If I don’t understand why you might reasonably disagree with me, how can I be sure that I’m right?

I first learned this lesson as an undergraduate at the University of California. The best teacher I ever had was Richard Levin, who taught me to love and appreciate the plays of William Shakespeare. What set professor Levin apart from almost every other instructor was the eagerness with which he encouraged us to argue with him. He didn’t want to spoon-feed us information, nor did he want us to accept his interpretations as gospel.

He wanted us to engage, to think, and to reason.

As a cocky senior in the English department, I took up the challenge, enthusiastically formulating my own hypotheses and arguing them from the center of the front row. Invariably, professor Levin wiped the floor with me, drawing on his superior knowledge and experience. But he always refuted my arguments with a smile on his face and twinkle in his eye, without any trace of condescension.

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And, because he did, I came away with a deeper understanding and a profound appreciation for the timeless wisdom of Shakespearean drama. And, occasionally, I even impressed Professor Levin with an insight that had never occurred to him.

As a leader, when you encourage underlings to propose new ideas, challenge conventional thinking, and argue against the status quo, you are not promoting insurrection. Just the opposite. You are forging a culture of creativity, mutual respect, and intellectual integrity, one in which every contribution is valued and where a commitment to sound decision-making overrides investment in ego or personal prestige.

And that will drive you and your organization relentlessly toward success, not occasionally, but always.

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Yonason Goldson works with leaders to create a culture of ethics that builds trust, sparks initiative, and drives productivity. His sixth book is Grappling with the Gray: An ethical handbook for personal success and business prosperity.


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