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As I learned about her background and her interests, I discovered that Helen was an expert on empathy. She researched it, taught it, wrote about it, practiced it, and coached it. I wanted to know how she thought the rest of us could better leverage empathy through the questions we asked, so I went to see her in Boston.

We met at a restaurant near her office, a few blocks from Massachusetts General Hospital, where she was director of the Empathy and Relational Science Program. Helen practiced what she taught: As we sat and talked, she leaned in, locked eyes, and maintained a relaxed and comfortable demeanor. She listened intently—no smartphone intrusions here—and did not break her gaze, barely looking down at her lunch.

Helen described empathy to me as “the ability to listen and take another person’s perspective.” It empowers you not just to understand the other person but also to imagine you are the other person, she said. “Perspective taking” is a way of asking people to assume another person’s viewpoints, emotions, behaviors, and thoughts—to see through their lens in order to understand their point of view.

“This is where imagination and curiosity come in,” Helen told me. “This is the intentional act of moving yourself out of your shoes and into the shoes of the other person.” Empathy is not asking “What would it be like for me?” she explained, but “I wonder what it would be like for him?” Her empathetic questions reflect that “perspective taking.”

What’s it like to experience what that person’s going through?

What are other people feeling?

Scared? Jubilant? Vulnerable?

What is it like for them to be who they are?

Helen works with doctors. She tells them to start with a broad question to establish an empathetic relationship. It is the simplest of questions, yet if it is meant sincerely, it can both solicit useful information and convey genuine concern.

How are you doing today?

But Helen tells her doctors that they have to do more than just ask. They have to listen, closely and sincerely. They have to hear more than words. They must listen to voice tone and inflection and watch for reactions and body language. She coaches them to maintain eye contact and scan the other person’s face to see if they seem relaxed, anxious, frightened, or stressed. If they hear strong emotion, they should respond to it directly and ask compassionately.

What are you most concerned about?

Helen urges her doctors to stay off the computer when a patient is talking, interrupt as little as possible, and stay calm and respond reassuringly when a patient expresses emotion or fear. Tune into their words and cues. Focus intentionally and supportively to establish empathy and convey it.

Helen believes it is the questioner’s responsibility to take in fully what the patient is communicating. This affects outcomes; patients who don’t experience empathy are less likely to trust their doctors and they’re less likely to adhere to the treatments that are recommended. They are much less satisfied. Helen’s research has corroborated these findings.

“We did a study, a systematic review and a meta-analysis … that showed that low empathy and communication in patient-doctor relationships actually leads to worse health outcomes, statistically significant worse obesity, hypertension, asthma, osteoarthritis pain. These are hard health outcomes that are affected when there’s a poor connection.” Helen explained that one of her graduate students found that doctors’ stress levels also improved when they had empathetic relationships with their patients.

Empathy ratifies our humanity. Walt Whitman captured its essence when he wrote, “I do not ask the wounded person how he feels. I myself become the wounded person.” The best questioners take Whitman’s words to heart.

Which is why I went to talk to Terry Gross.

The Empathetic Interviewer

WHYY radio is located in downtown Philadelphia. The station offers twenty-four hours of programming, but one voice is known to millions.

As host of NPR’s Fresh Air program, Terry Gross has interviewed thousands of people. Her questions have a signature quality, clear and curious, understated, and often deeply empathetic. Her questions draw out her guests, allowing her to get inside their heads and connect. Some 4.5 million people every week hear her show on more than 400 radio stations and countless podcasts across America. Terry has developed a special style and voice for interviewing creative types: authors and artists, actors and musicians, thinkers and theoreticians.

Rail thin and barely five feet tall, Terry’s physical presence belies her stature as one of the most gifted interviewers in broadcasting. She greeted me in the lobby and took me to one of the station’s main studios. Having started my career in radio, I felt at home in this dusky, unadorned box of a room dominated only by a desk, a few chairs, and a couple of microphones on extension arms that could swivel as needed. We settled in for our conversation, a couple of believers in the magic of radio and the revealed secrets of interview. There is something intensely private about radio. There are no distractions, no bright lights or cameras that will catch you off guard. People are more relaxed in radio. The listener paints his or her own picture of the faces that go with the voices.

Interviewing on the radio was an unexpected career for Terry. As a girl, she was shy, quiet, and not inclined to share anything personal, especially information about herself or her family. Her grandparents were Russian and Polish Jews who escaped to America. They did not discuss the dark times or details about family members. They felt that “there were a lot of things historically you just don’t tell people.”

Terry started to find her voice when she got a job in radio in Buffalo, New York. The station featured programming for women. For her job application, Terry had to write sample questions for one of the station’s hosts, a feminist lawyer, who was doing a show about women and divorce. Terry was going through a divorce herself, so the questions came quickly and easily. She got the job.

Because it was the 1970s, a college campus, and blissfully egalitarian public radio, everyone got a shot. Terry started doing some hosting. She loved it and the job loved her. She recalled a show featuring the feminist take on women’s undergarments. Did they objectify women? She did another discussing women as sexualized victims in popular culture, with a sadomasochistic consideration of Dracula as a public sex offender. The old vampire “was so S&M,” Terry told me with a mischievous grin.

Two years later she moved to Philadelphia and WHYY. The station has been her home ever since.

Terry’s first rule of interviewing is “know your guest.” Find the most interesting parts of their lives and stories. Read, listen, and watch them. “The more you know about someone, and the more you genuinely care about them, the more likely they are to trust you with their story,” she explained. Put yourself in their place. Do some perspective taking. “The more they trust you with their story, the more they’ll open up. The more they open up, the more fascinating they will be.”

Terry asks her guests about their experiences and ideas. She wants to know their origins and what inspires them. She asks about the things that shape people, especially creative people like artists, musicians, actors, authors, thinkers. She finds that breaking her questions into small pieces is an effective way to generate specific answers that connect to stories and prompt reflection.