Asking the Question People Have Been Waiting their Whole Lives to Answer

John Adams on posterity

This is part III of a series on interviews. Part I revealed the secret to how great interviews are the stuff of legends. Part II with some examples of worst and best interviews centered on increasing value with networking and practice. Sometimes we arm wrestle a little in conversation, until we find the sweet spot, the entry point to a person's story and they relent to tell their version of it.

So it's a matter of energy and life force, as Marc Pachter put it. But there are also questions more related to empathy. In many cases, they are the very questions people “have been waiting their whole lives to be asked.”  One such opportunity was an interview Pachter did with one of the great American biographers,  Dumas Malone. He says:

He did a five-volume biography of Thomas Jefferson, spent virtually his whole life with Thomas Jefferson, and by the way, at one point I asked him, Would you like to have met him?

He said, Well, of course, but actually, I know him better than anyone who ever met him, because I got to read all of his letters. So, he was very satisfied with the kind of relationship they had over 50 years.

And I asked him one question. I said, Did Jefferson ever disappoint you?

Here is this man who had given his whole life to uncovering Jefferson and connecting with him, and he said, Well, he said, I'm afraid so. He said, You know, I've read everything, and sometimes Mr. Jefferson would smooth the truth a bit.

Which meant this was a person who lied more than he wished he had. He had seen the letters.

He said, But I understand that. We southerners do like a smooth surface, so that there were times when he just didn't want the confrontation.

And he said, Now, John Adams was too honest. And he started to talk about that, and later on he invited me to his house, and I met his wife who was from Massachusetts, and he and she had exactly the relationship of Thomas Jefferson and John Adams. She was the New Englander and abrasive, and he was this courtly fellow.

An even better example was an interview Pachter did with Agnes de Mille, one of the great choreographers in American history. De Mille created the dances in Oklahoma, transforming American theater.” There one a question that people thought was audacious and cruel. Says Paxhter, but it was the right question:

At the time that I proposed to her that by the way, I would have proposed to her; she was extraordinary but proposed to her that she come on. She said, Come to my apartment. She lived in New York. Come to my apartment and we'll talk for those 15 minutes, and then we'll decide whether we proceed.

And so I showed up in this dark, rambling New York apartment, and she called out to me, and she was in bed. I had known that she had had a stroke, and that was some 10 years before. And so she spent almost all of her life in bed, but I speak of the life force her hair was askew. She wasn't about to make up for this occasion.

And she was sitting there surrounded by books, and her most interesting possession she felt at that moment was her will, which she had by her side. She wasn't unhappy about this. She was resigned. She said, I keep this will by my bed, memento mori, and I change it all the time just because I want to. And she was loving the prospect of death as much as she had loved life. I thought, this is somebody I've got to get in this series.

De Mille agreed to do the interview. She was on a wheelchair, with half the body immobilized, but still groomed for the occasion.

but this was a woman in great physical distress. And we had a conversation, and then I asked her this unthinkable question. I said, Was it a problem for you in your life that you were not beautiful?

And the audience just you know, they're always on the side of the interviewee, and they felt that this was a kind of assault, but this was the question she had wanted somebody to ask her whole life. And she began to talk about her childhood, when she was beautiful, and she literally turned here she was, in this broken bodyand she turned to the audience and described herself as the fair demoiselle with her red hair and her light steps and so forth, and then she said, And then puberty hit.

And she began to talk about things that had happened to her body and her face, and how she could no longer count on her beauty, and her family then treated her like the ugly sister of the beautiful one for whom all the ballet lessons were given. And she had to go along just to be with her sister for company, and in that process, she made a number of decisions. First of all, was that dance, even though it hadn't been offered to her, was her life. And secondly, she had better be, although she did dance for a while, a choreographer because then her looks didn't matter. But she was thrilled to get that out as a real, real fact in her life.

Sometimes we dance around the real story with soft ball questions. We're either not sure how to ask the question we want to ask, or we hope that the person in the conversation with us will volunteer the information without us asking. If we're not present to that moment, we'll miss the opportunity of a lifetime.

Questions are good at getting us started, then generating momentum.

When we are not afraid to ask, of opening the door for humanity to rush through, we generate energy, the life force. Curiosity and empathy are our allies.

All it takes to get to the real story is often a well timed question. It's the slip people need, the permission to give us a glimpse of what it's like to be who they are. In some respect we are all waiting for others to discover us, to ask us the important questions, so we can tell the truth about what influences our lives.

Empathy is the key to helping people reveal themselves. There's an art to asking, and as we practice, we learn to ask better questions. Which gets us to the information we seek faster.

Next up, we'll talk about simple ways to draw insights from interviews.