Ask More: The Power of Questions to Open Doors, Uncover Solutions, and Spark Change

CHAPTER 4

FROM THE INSIDE OUT

Empathy Questions

I SAT DOWN WITH four young moms. They arranged themselves in a semicircle so we could all see each other. They were polite, soft-spoken, nicely dressed, and anxious to talk about themselves and their children. A diverse group—black and white and Hispanic—all of them were single moms and receiving some form of public assistance.

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I was there to do a story for CNN on welfare reform from the perspective of those receiving the benefits—the people we don’t hear from very often, the people we talk about, but seldom with. I wanted to hear about their lives and explore with them how the proposed changes would affect them. The welfare reform law, known formally as the Personal Responsibility and Work Opportunity Act of 1996, sparked heated debate and controversy. It placed time limits on welfare benefits, required recipients to find work, tightened child support enforcement, and tried to discourage out-of-wedlock births by limiting benefits for young single parents. I had heard an endless parade of politicians and experts sound off on the issue. But I was curious: how did these proposed changes look through the eyes of the people who would be directly affected by them? So I asked.

What difference will this new law make?

What kind of job do you want?

How will a job help you make ends meet?

They all said a job would improve their lives and their finances. A job would give them self-respect and a steady income would help them be better parents. But they still needed to take care of their children. They still needed healthcare. They worried about whether their paycheck would be enough to feed the whole family. They wanted to work, but they had valid concerns—and a lot of questions.

As the conversation unfolded and I learned about their lives, I discovered a much more complicated reality than I had imagined. Three of the women had struggled with alcohol or drug issues. One had six kids, including a son who was born with a heart defect and needed frequent medical care. None of these women had gone to college. One said she could barely read.

One of the moms told me about a job interview she had coming up at a local hospital. She was excited and preparing for it. What was the job? I asked. Working in reception or something, she replied. What did it pay? Minimum wage, she thought. How would she afford childcare on minimum wage? Would she have healthcare? How would she get to and from work? She had no idea.

As the conversation unfolded, I realized that the real story here was how much we didn’t know and couldn’t imagine. These women lived fractured and difficult lives, filled with struggle and pain, sometimes of their own doing. I did my best to capture the conversation, but I wished the public could have been there, asking these questions and hearing the answers for themselves, because these women—despite every expectation and stereotype—were inspiring in their determination. You got a different perspective if you asked:

What do you see when you wake up each day?

What are you feeling, fearing, and thinking?

What do you want for your children?

The questions that have always interested me the most are the ones that explore people as three-dimensional beings, each with a unique and layered story. They are questions that mine the most complex human elements, revealing depth of soul and experience. They are questions that foster understanding of someone you don’t know or who is very different from you.

These questions—empathy questions—explore what makes people tick, think, fear, and feel. They focus unselfishly and spring from genuine interest. The simple act of asking, of listening without comment or judgment and letting a silence linger or a free-form thought coalesce, invites a person to reflect or think out loud. It might even prompt a revelation.

Empathetic questioning helps you connect with a friend who is going through a divorce, a family member who has cancer, a teenager who is struggling with grades and social hierarchy, or a welfare mom. Use this line of inquiry when a colleague needs to talk through an argument at home or politics at the office, or when you want to reach out to someone who comes from a different place, background, or perspective.

In this chapter, I explore empathetic questioning through the prism of example and from the perspective of those who’ve studied it and done it for a living. They know how to use questions to enhance trust, reinforce relationships, and improve our understanding of ourselves. This form of questioning pays off in a number of ways. Research shows empathetic bosses inspire more productive workers. Empathetic doctors are more effective. A variety of studies has linked empathy to better health outcomes and lower stress levels. A study published in the Journal of the Association of American Medical Colleges in 2011 found that diabetes patients did a better job regulating their blood sugar when being treated by empathetic doctors. Other studies have found that cancer patients had greater trust in doctors who responded to them empathetically and reported less depression and better quality of life.

Using questions to establish empathetic relationships involves seeing and asking from another perspective. Ask to:

Try new shoes. Empathy involves taking the perspective of another person. What is he thinking? How is he feeling? If you switched places and stood in his shoes, what would you see?

Leave running room. Start with big broad questions to get people talking. Invite them to engage on ground where they’re most comfortable and most familiar.

Listen beyond words. The deeper you go, the more you need to listen for cues and tone and mood. Pauses and hesitation have meaning, too. So do body language, facial expressions, and eye contact.

Establish intimate distance. Convey compassion and interest. But maintain enough distance and detachment so you don’t judge and can offer objective questions or advice.

The Good Professor

Helen Riess is a clinical professor of psychiatry at Harvard Medical School. She studies empathy and teaches doctors how to incorporate it into their work with patients. I got to know her through the Middlebury College board we both served on. From the moment I met her I was struck by her instinctive ability to listen intently and to represent diverse viewpoints with depth and sensitivity when she spoke at our meetings. When she mentioned student life, for example, she conveyed a special awareness of the pressures college students face, engulfed by technology, plugged in to always-on texting, dealing with mountains of debt and uncertain employment in a hypercompetitive global economy.

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.

“You can ask questions about their childhood and find out, were they sick, were they well?” she says. “Just all those things that create who you are.”

Were they outgoing or inhibited?

Were they good in school, and did they like school?

What were their parents like, and where were they from?

How were they parented?

Did they like to read?

Did they go to the movies?

What were the first records they bought?

In a powerful interview with comedian Tracy Morgan, Terry dug down to the roots of a troubled adolescence that nurtured Morgan’s latent creativity. Notice how she framed her questions without judgment but without hesitation.

GROSS: So I just wanted to get back to your childhood a little bit. When your father died of AIDS when you were in high school, you dropped out of high school, and you needed money. So you say you started selling marijuana and then eventually started selling crack.

MORGAN: Yeah.

GROSS: But—so I’m wondering. Did you take Al Pacino’s advice from Scarface—don’t get high on your own supply?

MORGAN: No, I never did drugs. My drug of choice was beer, was liquor. As far as narcotics, no. I would smoke weed and drink beer like any other—like Michael Phelps do that. But I never did no narcotics—never. My father had died from that. So I already knew better. You know, I’m a very smart person. I was able to see that. As a child, I was able to know that I wanted a better life.

GROSS: You say that it was helpful to you as a comic to sell crack because of all the characters that you met. What do you mean?

MORGAN: Well, it wasn’t helpful for me to sell crack, especially to my old community, and it still bothers me today, but it’s something that I did. It was survival. Now I’m living. Now I don’t have to do any of that stuff. I’m a grown man now, but when I did, I wasn’t good at it. So I had my fledging attempt at being a drug dealer.

GROSS: So, tell me really, how did you feel when you were selling crack, knowing that you were selling a drug that destroys lives?

MORGAN: I was a kid. I had no fear. I was crazy, and when you don’t have fear, you’re crazy.

Terry’s questions penetrate gently but insistently. She is interested in creative tension, setback, and adversity, but she does not try to embarrass or trip up her guests. Her voice is warm and her listening accommodates the ranges of emotion she encounters:

“I’m not looking to shame somebody. I’m not looking to have them say anything that’s going to keep them awake at night, regretting that they said it. I’m not looking to have them say something that’s going to end up with their mother or their child or their best friend hating them for saying it.”

Terry Gross prefers to let her guests take the lead when questions get personal and the emotions get rough: “I don’t just sit down and ask people about their sexual orientation or their religion or their fear of death, unless it comes up organically in some way through their work or through something that they said.”

That’s where empathy plays a vital role. “I try to imagine what is it like to be that person,” Terry explains. “What might they have been feeling when they did this or experienced this? And is there anything like that in my life, not because I want to talk with them about my life, but because I want to be able to understand it in a way that might make sense to me.”

When Terry interviewed renowned author Maurice Sendak, her empathetic questioning produced a remarkable moment.

Sendak, the beloved children’s author of Where the Wild Things Are and other books, was a famously complex character. He could translate dark reality into a playful children’s adventure. An avowed atheist, he was introspective and deeply creative. He came out as gay late in life. In September 2011, as the New England fall was setting in, Sendak spoke with Terry by phone. He was eighty-three and in failing health. His partner was gone, and loneliness was his companion. But Sendak had just published Bumble-Ardy, a book about a pig who, on his ninth birthday, throws himself his first birthday party. The story is a fable about growing up and staying young, about celebration and convention, about love and forgiveness. Terry had interviewed Sendak many times before. They’d known one another for years. He trusted her. You can hear the affection in her voice.

She congratulates him on the book and asks simply:

How have you been?

Sendak sounds fatigued and resigned.

“It’s been a rough time,” he admits. He’s gotten “quite old.” He is still working but it doesn’t matter if he ever publishes again. What time he has left is “for me and me alone.” Sendak speaks about the death of his publisher and his publisher’s wife. “My tears flow,” he says. “I am having to deal with that and it’s very, very hard.”

There can be art in a question. Terry’s next one paints with a deft stroke. Having heard Sendak’s loneliness, feeling his mortality, she asks:

Are you at the point where you feel like you’ve outlived a lot of people who you loved?

“Yes. Of course,” he answers. “And since I don’t believe in another world, in another life, that this is it. And when they die they are out of my life. They’re gone forever. Blank. Blank. Blank.”

Terry acknowledges the thought: “Having friends die tests our faith.” She knows Sendak does not believe in God and rejects religion. Still, she wonders whether he feels any spirituality as he considers his own death.

Is your atheism staying strong?

“Yes. I’m not unhappy about becoming old,” he says. “I’m not unhappy about what must be. It makes me cry only when I see my friends go before me and life is emptied.” He reflects on the hundred-year-old maple trees just outside his window. “I can see how beautiful they are. I can take time to see how beautiful they are. It is a blessing to get old.”

As Terry thanks Sendak, thinking she is bringing the interview to a close, the conversation takes its most interesting turn. She hears more than his words. She picks up on his tone of voice, the way he paces his thoughts. She hovers on the moment.

GROSS: Well, I’m really glad we got the chance to speak because when I heard you had a book coming out I thought what a good excuse … to call up Maurice Sendak and have a chat.

SENDAK: Yes, that’s what we always do, isn’t it?

GROSS: Yeah. It is.

SENDAK: That’s what we’ve always done.

GROSS: It is.

SENDAK: Thank God we’re still around to do it.

GROSS: Yes.

SENDAK: And almost certainly, I’ll go before you go, so I won’t have to miss you.

GROSS: Oh, God what a …

SENDAK: And I don’t know whether I’ll do another book or not. I might. It doesn’t matter. I’m a happy old man. But I will cry my way all the way to the grave.

GROSS: Well, I’m so glad you have a new book. I’m really glad we had a chance to talk.

SENDAK: I am too.

GROSS: And I wish you all good things.

SENDAK: I wish you all good things. Live your life, live your life, live your life.

Nearly poetic, Sendak spoke from his most solitary place, staring directly at the mortality that we are all destined to confront. Terry told me it was one of the most emotional interviews she has ever done.

“What struck me about him in that interview is that he opened the door without me even knocking, to talk about the things that I was uncomfortable even asking my parents about when I knew they were dying.” Terry picked up on Sendak’s cues. She followed him through his thought process. She asked gently. Perhaps without even realizing it, she stood in Sendak’s shoes—alone, vulnerable, and exposed. She asked about hard things and conveyed her willingness to hear whatever came back. Then, she asked for more.

“That’s the thing about interviewing,” Terry explained, “You’re there for the special thing, which is to dig deep and get to the essence of what it means to be you.”

Whether you’re a radio host, or a friend, a concerned parent, or a trusted colleague, empathetic questions can lead to discovery and surprise. They help you dig deep and do a little perspective-taking. They can also be achingly difficult because they may visit some intensely private places. Conversations that build on empathetic questioning require patient, skilled, and focused listening. Terry listens for the revealed moment, where an inner thought, emotion, or expression of the human condition unfurls. She listens for reflection, acknowledgement, or a telltale pause. She listens for illuminating stories that haven’t been finished or heard before.

She creates what I call intimate distance. The intimacy is expressed through her evident interest in her guest. It is authenticated by her questions, which embrace human complexity and frailty. She maintains distance by sitting back, withholding judgment, letting silence linger, and retaining an outsider’s eye. Intimate distance allows Terry to engage emotion without getting trapped by it or drawn in so that she forfeits her observer status.

Maurice Sendak died eight months after his interview with Terry Gross.

He published one more book after Bumble-Ardy. But it is the words from his most famous book, Where the Wild Things Are, that resonate and connect to Sendak’s own journey through life.

I am holding the book now, tattered and worn, the binding barely holding the pages in place. I read this book so many times to my children when they were young that when I close my eyes I can feel those little people next to me, nestled with their innocence and wonderment against my younger self. I see the journey now, having completed so much of it.

Where the Wild Things Are tells the story of Max, the book’s adventurous boy traveler, who put on his wolf suit, made mischief, and sailed away to rumble with the wild things. And when he decided it was time to go home, Max “sailed back over a year and in and out of weeks and through a day and into the night of his very own room where he found his supper waiting for him … and it was still hot.”

It is that sense of place and that rhythm of the journey that Sendak was relaying to Terry Gross. What kid doesn’t stand in Max’s shoes and imagine—and empathize?

Therapeutic Inquiry

You don’t need a degree to be a disciplined listener and an empathetic questioner. You just need to know who you are talking to and be able to imagine what the world looks like through their eyes. Terry explains that it’s like mining what’s beneath the surface.

“When I’m interviewing somebody,” she says, “I’m drawing on the self-knowledge they already have. I’m not presuming to be a therapist and lead them to questions that will enable them to reach self-knowledge that they don’t already have.”

Terry is right to recognize that, however adept her questioning, traveling to the depths where the psyche holds its secrets, insecurities, repressed memories, and Freudian trappings is not what she’s paid to do. That’s someone else’s job. Which is why I decided to see a therapist, someone trained to go to those places—carefully and over time, an empathetic questioner by definition.

I met Betty Pristera at the airport in Raleigh-Durham, North Carolina. She pulled up in her little Honda Civic, a fitting vehicle for this compact spring of a woman, who, I soon learned, was also a competitive ballroom dancer. She bounded out of the car to greet me.

“Welcome to Raleigh-Durham,” she said with a beaming smile, “How are you?” She shook my hand, directed me to the passenger seat and began asking about my life before we were out of the airport. We headed to a nearby restaurant for a late breakfast, where we were waist-deep in conversation before the eggs hit the table.

A friend had introduced me to Betty after I’d mentioned to him that I wanted to explore how therapists use empathetic questioning to help people discover and heal. My friend had been through a rough time, and Betty helped him through it. He said she had listened and guided and empathized. She didn’t judge. She drew him out and asked him to explore his life and his experiences in profoundly reflective ways. She helped him discover secrets he kept from himself so he could reconnect and get his life back on track. She maintained intimate distance.

I wanted to know how the rest of us could apply these techniques in our own questioning. What could we learn from this empathetic therapist to become more effective questioners?

Betty came from a large Italian family. She grew up in New Jersey. Her father was a chemist, her mom a housewife. She was nurtured on the traditions, flavors, and smells of southern Italy. There was always food and family in the house. And music. Everyone played something. Her father and brothers played the violin, her mother and sister played the piano. Several family members sang. Betty learned piano early. She was performing by the time she was nine. There was talk that she should go to Juilliard and make music her career. But she was drawn to people.

When Betty was eleven, she watched her grandfather die. Her mother maintained a bedside vigil, and Betty was nearby. The young girl witnessed her mother’s “heart and courage” as she bore the pain of the dying man. Betty took the experience as a calling and became a hospital volunteer. Ultimately, she went to nursing school, earned a master’s degree in social work, and studied marriage and family therapy. Her first job was at an adult day program at the Eastern Pennsylvania Psychiatric Institute, where she led group therapy sessions. When her husband was accepted at the University of North Carolina for an advanced degree, Betty got an appointment in the UNC department of psychiatry and began doing clinical work in marriage and family therapy. Within a few years, she hung out her own shingle and established a thriving private practice.

Betty’s practice has changed as families have changed. She works with straight couples and gay couples, blended and step families. Modern families. She listens with intensity, and while her eyes lock, they never judge. She sees it all: anxiety, depression, problems with parents, children, addiction, and tragedies. Betty is gentle and sure. She describes her approach with her patients as precise and purposeful.

“I have a broad definition of a relationship and what constitutes family,” she explains. She asks in order to learn, and to get people to talk.

Where are you hurting?

What’s troubling you?

What have you tried?

Betty enjoys helping people, guiding them so they see and understand themselves more clearly. Her objective is to steer them toward “compassion and empathy for themselves,” she explains. “Therein lies a lot of the healing.”

Betty often begins with one of those simple open-ended questions that just invites people to talk.

What brings you here?

Then she listens. She listens for how the patient defines her problem or talks about her struggle. She “listens” with her eyes, looking for signals and signs of stress or anxiety. The color of someone’s face may change. Their nose may get red. They may look like they’re fighting back tears. And she might say:

What are you feeling right now?

Are you sad now?

Some will say yes. Some cry. They share a powerful, intimate moment.

“Some people will tell you the tears have been there and I haven’t been able to cry them. Or I haven’t been able to access this emotion. Or … I haven’t been able to cry and I also don’t sleep very well.” Betty believes such an experience represents a gift for therapist and patient alike. “It’s an acknowledgement the patient is feeling safe,” she says, “safe enough with you to be vulnerable, to reveal themselves to you and to themselves.”

Betty often follows up with one of the most effective questions you can ask, and it isn’t even a question.

Tell me more.

That’s what got the patient we’ll call Roger to open up. Roger revealed that his marriage, which has been rocky for a few years, has gotten even worse lately. He and his wife barely talk. He had a brief affair a few months ago, but it’s over now. He wasn’t looking for someone to get involved with; it just happened. He knows he’s at a crossroads. He is sorry about the whole situation, but he finds himself lost and confused. As for the affair, he thinks maybe it happened because his marriage left him feeling isolated and unloved. Maybe he was just vulnerable and met someone who was captivated by him when his wife was not. He doesn’t know where things went wrong. He’s trying to figure it out.

Now Betty can ask:

Did you want the marriage?

Do you want to deal with it?

Have you had therapy?

She explores Roger’s level of awareness, whether he is tuned in to his own feelings and to others. She wants to know how he sees this marriage and what kind of conversation he’s had with himself.

Has your spouse been unhappy, too?

What is your picture of the marriage?

What’s your picture of yourself as a husband?

Have you said to your spouse, “I think we’re in trouble. I think we need help”?

Betty wants Roger to talk about his feelings, goals, and values.

How far out of integrity are you with your own vision of who you told yourself you were going to be as a husband?

How does that feel?

How do you talk to yourself about that?

Where do you want to be with yourself now?

Betty is following a line of inquiry she calls “accessing the internal dialogue.” She wants her patients to examine and question themselves: “I might say, it sounds like you’re having an internal conversation, argument, or dilemma with yourself. Who’s talking and what is each part saying? Do any of those voices sound like anyone else you know?” This perspective taking looks inward. It’s where her patients explore their own empathy and how they apply it to themselves and others.

Betty gets people talking—to her, to themselves, to one another. She tries to get couples face-to-face. She issues a challenge: Sit and listen for two minutes without responding or rebutting. Maintain eye contact. Try to relax. Ask questions rather than accuse. Try to understand the other person from the other person’s perspective. She calls it “slow and careful and tender work.”

“I often tell people you have everything you need and plenty to spare to solve this. And I say I will help you. I’m trying to empower them.”

Betty asks a therapist’s questions. These questions are designed to explore. They search for understanding to locate a happier, healthier person. They reflect Betty’s empathy and they encourage it in her patients.

License and Limits

Empathetic questions generate some of the most personal conversations we have. They can be tricky, though, because there is no clear end point. One person’s relieved revelation is another’s do-not-touch secret. Knowing how and when to respect zones of guarded privacy is a tough call. It’s why Betty Pristera sometimes defers to “tell me more” as she gets to know her clients. That’s why Terry Gross has subjects where she follows rather than leads.

When I interview people, I feel I have license to ask just about anything. Most of the individuals I question are public figures. They expect to be asked and are skilled at telling you when you go out of bounds. Even so, there are things I won’t ask about unless it is germane to their public lives or performance. I won’t gratuitously ask about a person’s personal life. I won’t ask about pain someone has experienced just to hear them talk about it. I ask about illness or grief only if it’s relevant or sheds light on a person’s character.

For all these reasons, empathetic questioning requires close and constant listening for words and tone and mood. As Helen Riess and Betty Pristera noted, listening empathetically involves more than your ears because people send signals in a variety of ways about how they’re feeling. They may talk freely or they may clam up, fearful of what they may discover. Reading those signals, asking openly, and listening intently is a big part of empathy itself.