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“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 alclass="underline" 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: