Great storytelling is built on revealing interviews. Are yours falling flat?
Stop skimming the surface. Here's how to show up.
Independence Pass coming out of Aspen, Colo. At 12,096 feet, it’s the highest paved road in the state.
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“We kind of coast through life. You know, how's the weather? How are the kids? Where’d you go on vacation? Cool, cool. See you next Friday. Right?” — Nikki Boyer, Dying for Sex and Near Death
Hi storytellers —
How happy are you with your interviews? How about stories that you write or produce based on those interviews?
If you’re like most of us, you make gems. But not often enough. Most of the time, you’re wondering why there’s such a gap between what you’ve made and your much bigger ambitions to create something that makes listeners gasp with recognition and resonance. I’ve been there many times. We all have, no matter how long we’ve been at this.
I have a solution for all of us. Let me explain by way of a story.
Did you listen to the hit series Dying for Sex? In this six-part Wondery podcast, host Nikki Boyer and her close friend Molly walk us through Molly’s journey with terminal breast cancer. But it’s not a downer: Determined to get the most out of the time she has left, Molly leaves her unhappy marriage and has as many sexual escapades as possible.
By turns, it’s hilarious, provocative, and poignant. (It’s now being made into a TV series starring Michelle Williams.)
Last year, preparing for a Sound Judgment interview with Nikki, I listened to Dying for Sex. My husband and I were crossing out of Aspen, Colo. over Independence Pass, the highest paved road in the state and, at 12,096 feet, one of the highest in the country. I had one eye on the heart-stopping drop offs and one ear on the podcast. Molly was describing having a strange man suck her toes. That was the least racy thing she would share.
I was with my husband, the person I love most in the world, and part of me was concentrating on, um, staying alive. And the way I reacted was to the podcast was…odd. Inhibited. When it comes to becoming a great storyteller, keeping your guard up is an obstacle almost as high as Independence Pass.
Nikki and I talked about that moment in this Sound Judgment episode.
Here’s an excerpt.
Elaine Appleton Grant
I bet a lot of people never hear, in their normal lives, any deep conversations at all.
Nikki Boyer
Right. Because we kind of coast through life. You know, how's the weather? How are the kids? Where’d you go on vacation? Cool, cool. See you next Friday. Right?
Elaine Appleton Grant
Yeah.
Nikki Boyer
How often do you walk into the room, and someone says, you know, are you really fulfilled with your relationship? And then the wheels start turning and then two days later [the person says]: ‘So, I wanted to tell you something that I was thinking about.’ And not that we need to put people's feet to the fire, to be like, are you happy? Is your relationship good? But asking the deeper questions, of what did that mean to you? And how does that feel? And is that what you wanted? And are you disappointed? I really like getting the shovel and digging a little. And it doesn't make everybody comfortable, and that's okay. Some people are like, Whoa, this is too much.
Elaine Appleton Grant
Well, I gotta say, when I heard the first episode of Dying for Sex—
Nikki Boyer
What did you think?
Elaine Appleton Grant
Well, I was in the car with my husband. Listening to the first episode of Dying for Sex, which is very racy. And I was a little embarrassed, you know? And he was listening very intently and having no expression on his face at all.
Nikki Boyer
Right. Yeah, no, I am curious. Like, why were you—what was embarrassing about it for you?
Elaine Appleton Grant
Oh my gosh.
Nikki Boyer
I mean, it’s pretty kinky.
Elaine Appleton Grant
Yeah. Well, it is, it is. But you're also reminding me of another guest that I had last season. Dana Black, who has a great podcast you would like. It's called I Swear on My Mother's Grave. And she is a memoirist, and also an actor, like you. And she did the same thing. She's like, ‘Oh, but Elaine, I need to ask you questions.’ I’m like, whoa, hold on.”
(Listen to the audio version of this newsletter here or on the podcast for a clip. It’ll make you laugh.)
I never did answer Nikki — I learned the skill of regaining control of an interview years ago, not to mention deflecting attention off of myself, the journalist. While controlling an interview is a critical talent, if I had it to do all over again, I would have answered.
What I’m about to recommend feels like breaking the rules
Lately, the conversations I had with Nikki and Dana Black keep returning to me. They’re teaching me important things that, with a few telling exceptions, I did not learn from the journalists on my show.
The most critical is this: In America, we’re experiencing a crisis of belonging. A majority of the population feels disconnected to others. We are dying to feel close and connected, which happens when we feel seen and heard — and when we give the gifts of our curiosity and presence to others. Don’t you love that human who makes you feel like you’re the only person in the room? I do.
What’s love got to do with it?
“Attention is the rarest and purest form of generosity,” wrote the author Simone Weil in First and Last Notebooks, a collection of essays published in 1970. Author David Augsburger put it more plainly: “Being heard is so close to being loved, that for the average person it is almost indistinguishable.”
Wait! Love? You’re talking about love in a newsletter that has its foundation in journalism?
Yeah. I am.
Because wanting candor and getting it are two entirely different things. And the way journalists have approached this problem for decades creates a problematic power dynamic: We ask everything from our sources. We give nothing of ourselves in return. Those are the rules. Not only is this often unfair, it’s often far less effective than we have been trained to believe.
But only a minority of storytellers are journalists. Neither Nikki nor Dana are. They bring different skills and rules to their work. As actors, they’ve been trained that the energy of any conversation arises from the relationship created between people.
Nikki and Dana both possess an uncanny ability to relate to people. They each made me feel as if I’d known them for years. That warm bond is apparent in their shows. You’ll also hear it in the narrative show Last Day, hosted by Lemonada co-CEO Stephanie Wittels Wachs, another actor, and in the spectacular podcast Shelter in Place with Laura Joyce Davis, a novelist.
But you’ll hear it as well from Anna Sale, host of Death, Sex and Money. She’s a superb example of a reporter who has mastered the art of candid, intimate presence while holding tightly to journalistic ethics, in case you were worried that the two don’t mix. (They do and they must.)
In creating that rapport — that warm, respectful bond — right from the start, these storytellers get tacit permission to ask anything they want. More often than not, people respond with relief, often sharing stories that have been pent up for years.
But how, you’re asking? Is it magic?
How to do this well is another story. There’s no single way; there are numerous. But if I have one piece of advice, it’s one I tell myself every day: Drop the “professional” guard. Don’t hide behind the old journalistic training that you should appear nowhere in any story, as if it’s being reported by a ghost, or, these days, a bot.
Be as open as possible to the person in front of you. Listen and observe so closely that you can follow up on a sigh, a shake of the head, a change in tone of voice. Take a chance on reflecting your observations back to them without judgment: “You looked amused just now. What’s that about?” Ask the question about feelings that occurs to you, the one you might normally suppress.
Allow silence.
And see what happens. I think you may be astonished at the result.
# # #
Tell me about an interview you conducted that you can’t forget! Maybe it was so heart-stoppingly good that it’s imprinted in your brain like the best dream you ever had. Or maybe it was so humiliatingly bad that it made you wonder about your life choices. In either case, what did you learn?
When you share in the comments or in Substack Notes, you help our whole community learn from your experience! (Feel free to link to your show, feature story, book or speech.)
New training on the way
Want to transform your storytelling by improving your skills at conducting these deeper, meaningful interviews? The techniques that help you interview for the real story of people’s lives are best learned and practiced in community. I’m developing a four-session, by-application-only course that will help you hone your curiosity, courage, and connection. I’ll announce it shortly. Don’t miss it! Join the Sound Judgment Workshop Waitlist now.
Your Next Steps
Your homework this week: Listen to the following Sound Judgment episodes and the podcasts that inspired them. They’re full of lessons on conducting emotionally resonant conversations, not to mention transforming your audience into a community of avid listeners or readers.
How to Capture an Audience with Near Death’s Nikki Boyer
How to Tell the Truth: The Art of Memoir with Dana Black
How Anna Sale Invites Listeners In
Emotional Bravery on Last Day with Stephanie Wittels Wachs
Finding Your Voice with Shelter in Place Host Laura Joyce Davis
🏆 Learn from the best
Fellowship opportunity: I’m honestly thrilled to tell you about today’s offering. Many years ago, I had the good fortune to attend the Medicine and Media seminar at Dartmouth College in Hanover, N.H., then run by Dr. Steven Woloshin and his late wife, Dr. Lisa Woloshin. I learned volumes about how to report medical research accurately and how not to fall for misinformation.
Dr. Steven Woloshin is offering the Medicine and the Media fellowship again from August 26-29. The seminar itself is free and subsidies are available for lodging. Learn more and apply here. The deadline to apply is July 12.
Read: The Marginalian, a long-running newsletter by the eloquent and insanely well-read Maria Popova. Thanks to The Marginalian for bringing Simone Weil to my attention.
New Resources Section coming
Every day, I search for helpful resources — podcasts, articles, books, groups, and more. So I’m starting a standing resources section! This newsletter is free for everyone right now, but the resources section, along with some other things up my sleeve, will soon be for paid subscribers. Have a resource you’d like to share? Just hit reply to this newsletter.
I love hearing from you, no matter what’s on your mind.
As always, it is a joy to be with you.
Elaine Appleton Grant