Retired 4-star Gen. Stanley McChrystal tells a story about a battalion commander in a backward T-shirt to illustrate his top 2 pieces of leadership advice

Gen. Stanley McChrystal walks with American and Afghan forces in Afghanistan.

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Gen. Stanley McChrystal walks with American and Afghan forces in Afghanistan.
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U.S. Air Force photo by Tech. Sgt. Francisco V. Govea II via Wikimedia Commons

  • Stanley McChrystal is a retired four-star general in the US Army who led America’s Joint Special Operations Command and NATO forces in the war in Afghanistan.
  • McChrystal said the two greatest attributes a leader can have are empathy and self-discipline.
  • An anecdote from his time on the battlefield shows how leaders must be aware of the influence they possess.

Stanley McChrystal has always been fixated on the study of leadership. When he retired from the US Army in 2010 and began working on his memoir, he took time to reconsider his own successes and failures and what universal truths were reflected in his experience.

This year, he published “Leaders: Myth and Reality,” which he cowrote with Jeff Eggers and Joe Mangone, as a way of dismantling the popular “Great Man Theory” of history, concluding that teams benefit from humble leaders, not those put on a pedestal.

“When I think about the two things that I hope leaders have, first is empathy,” McChrystal said in an episode of the Business Insider podcastThis Is Success.” “And then the second part is self-discipline.”

He shared a story from his military career that illustrated both.

The power of influence

Before serving as the commander of Joint Special Operations Command and then the American-led forces in the War in Afghanistan, McChrystal served in several Army battalions.

When he joined one of them, he found the lieutenants all wearing their T-shirts backward. “And I’m going, ‘All right, what’s going on here? Did they get up after drinking all night or something?'” he said.

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It turned out that the battalion commander started wearing his own shirt backward because he thought that the small amount of noncamouflaged, exposed chest in the shirt’s front would make him an easier target for the enemy (“I didn’t think that was that smart an idea,” McChrystal said), and without being asked, his lieutenants followed his lead.

“Just the power you find that if you are charismatic and whatnot, anything you do, how you treat people, how you think about things, the little things, you’ll start to see it mimicked by people through your organization, and there’s great power in that,” McChrystal said. “And you’ve got to be careful with it.”

Be empathetic

Regardless of whether the commander’s decision to wear his shirt backward was useful, McChrystal had the impression that the commander didn’t recognize his own impact on his direct subordinates. It’s necessary for great leaders to “put yourself in their shoes,” McChrystal said, whether you’re dealing with your own team or an opponent.

As the head of special operations, McChrystal led the assassination of al-Qaida leader Abu Musab al-Zarqawi in Iraq. In his mission to track and take out Zarqawi, he grew to understand and even came to greatly respect his leadership skills, despite his horrific brutality. It’s an extreme example, but to a lesser extent applies to something as mundane as an office disagreement.

“Understanding that if you’re sitting on the other side of the table you have a different perspective, and they might be right,” McChrystal said. “Doesn’t mean you agree with them, doesn’t mean you approve, but being able to see it is really important.”

Be disciplined

The battalion commander’s lieutenants were watching every move he made, for better or worse. Leaders need to hold themselves to higher standards, McChrystal said.

In the interview, he discussed the way that a Rolling Stone article, which portrayed him as “The Runaway General” with aides who didn’t respect Vice President Joe Biden and other White House officials, led to his resignation. He found the article’s representations unfair, but knew immediately he had to apologize to Biden and offer his resignation to President Barack Obama. Negative quotes were not attributed to him, but he believed he had to take responsibility for the article’s existence in the first place. “And so on the one hand I thought that that wasn’t fair; on the other hand I’m responsible, and we have this negative article about a senior general show up on the president of the United States’ desk.”

It’s a decision he said hurt, but one he knew was right.

As he explained regarding his advice: “Most of us know what we ought to do as leaders. We know what we shouldn’t do. It’s having the self-discipline to do those things, because you’re leading all the time.”

Subscribe to “This Is Success” on Apple Podcasts, Stitcher, or wherever you listen. You can find the full McChrystal episode below.