How Empathy Gets Tricky — And What Leaders Can Do About It

An excerpt from Rethinking Empathy: How to Share Support When You Don’t Share Another’s Experience, a bonus chapter to Transfluence.

American Airlines Flight 715 inched its way forward in the typically long line of jumbo jets waiting to take off from LaGuardia Airport. Dawn had broken and blue skies awaited. We would soon be soaring toward Dallas, where I would take part in our fall board meeting at Prologis.

As chief financial officer of the company, I had plenty of work to keep me busy on the three-hour flight, and I was anxious to get airborne.

It was a little after 9 a.m. when I glanced out the window and noticed we had moved up to third in line. But that’s as far as we got. The giant airliner moved forward slowly and then, instead of pivoting toward the runway, it turned the other direction toward the terminal.

Every frequent traveler knows that feeling.

What now?!

But before I could speculate about what was wrong and how long we might be delayed, something unusual caught my eye — a huge plume of smoke rising into the otherwise clear skies over Manhattan.

We returned to the gate with very little information. It wasn’t long, however, before I learned the devastating news: Two jetliners had crashed into the twin towers of the World Trade Center.

A million thoughts raced through my mind as I made my way to the United Airlines Club to regroup and formulate a new plan. It was there that I saw the unimaginable on a television screen — at 9:59 a.m., the 110-story South Tower succumbed to its damage and collapsed to the ground. My heart fell with it. Dust and debris filled the air, and people wandered the streets in a dazed panic.

This was no accident, I thought. This had to have been a terrorist attack.

I wasn’t sure exactly what to do, but I knew I had to leave that airport. I called my assistant, who answered as she was driving to work in Denver. I asked her to pull over immediately, briefly explained what I knew of the situation and asked her to call and book me a car. Then I packed myself into an already overstuffed shuttle bus to get to the rental car center — and away from the terminal.

By the time I arrived, there must have been two hundred people in line. I walked to the front, got the attention of an agent, and said, “I realize everyone wants  a car, but I already have one booked.” Thankfully, the agent came through and I quickly left LaGuardia, hoping to get out of the city.

I made my way to Interstate 678, listening to the radio as more and more details of the attacks emerged. Then, with only a quarter mile between me and Whitestone Bridge, I learned that it — and every other bridge or ferry that would get me off Long Island — had been closed. My only option was to backtrack deeper into Long Island and look for a place to stay. Eventually, I found a rat trap of a motel that would become my home for the next two days.

As I checked in, I could still see the black smoke hovering over lower Manhattan, and my mind continued to race from one concern to the next. My appointments the previous day had been in New York City, so I wondered if any of those people had been hurt — or worse. And one of our directors ran Coca-Cola’s operations in Russia and was on a flight to the United States for our meeting, so I thought about his safety. Then, a surreal idea hit me: What if one of the passengers on my flight was a terrorist? Was I that close to being a passenger on a highjacked plane? Was I that close to becoming a pawn in a terrorist’s plot? Was I that close to death?

At one point during my emotional rollercoaster of a drive from the airport to that motel, I received a call from Dane Brooksher, our CEO.

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“I have no idea what it must be like to be in New York right now,” he said. “All I want to know is that you are OK.”

He was right, of course. There was no way he could know what it was like. The chaos, the anxiety, the uncertainty, the fear. It was unimaginable then, and it still feels impossible to describe. But Dane didn’t need to know how I felt to do what any good leader would have done — reach out and let me know he cared.

Many leadership experts will tell you that Dane was modeling the most important trait you can develop as a leader — empathy — but the truth is, he wasn’t empathetic at all.

Concerned? Yes. Compassionate? Absolutely. But empathy is defined as “the ability to share someone else’s feelings or experiences by imagining what it would be like to be in that person’s situation.” Some dictionaries use the word “understand,” as in “the ability to understand and share the feelings of another.”

That’s where empathy gets tricky.

We often can have an intellectual understanding of a situation. We can know the details and facts even if we weren’t involved, and we can know the event likely would have caused someone to have an emotional response. We can even imagine how that person might have felt. But we can’t always have an empathetic understanding where we know or feel what another person is going through. Our limited imaginations often won’t let us share in the emotions they are experiencing.

Thankfully, innate abilities can come to our aid, according to Helen Riess, chief scientific officer of Empathetics and an associate professor of psychiatry at Harvard Medical School. Brain research, she notes, shows that empathic people can “exhibit unconscious mimicry of the postures, mannerisms, and facial expressions of others to a greater degree than individuals who are unempathic.” In other words, some people express empathy just by intuitively reflecting what they see in others.

Involuntary responses aside, I’ve come to believe that real empathy is great, but it’s elusive. Empathy is a complex ability that requires understanding another’s emotional state. For most leaders, in fact, empathy may feel unnatural. And in many situations, it might actually feel impossible.

On that traumatic day in 2001, Dane couldn’t display true empathy because he simply couldn’t fully imagine my situation. And he couldn’t understand or share my feelings or experiences, just as I couldn’t understand or share the feelings or experiences of the people who were around Ground Zero during that attack

And that’s the challenge for leaders today. Because even when we can’t be empathetic — when we can’t possibly understand the other person’s emotional experience — we still need to respond appropriately. How we respond in a world that increasingly seems like a powder keg with a lit fuse will define us as leaders. Will we make things better? Or will everything blow up around us?

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