Tips and tricks for asking good questions that get good answers.

What is most important about the water cooler.

In our latest edition, Sidekick taught you everything you need to know about the technical side of podcasting. Now let’s explore storytelling, specifically the art of interviewing. Because behind every compelling story is a talented interviewer, and these skills carry over from journalism to the corporate world and beyond. If you can get people talking about themselves, there’s no end to what you can learn from them.

To learn more about the art of conducting a great interview, Sidekick spoke with legendary journalist, author and New Yorker contributor, Ken Auletta; Spotify podcast host and storyteller, Leah Palmieri; and former CNN executive editor for international features and current editor of Spotify-owned channels, Neil Curry.

Before starting an interview, strictly why you are talking to the person and what is the purpose of the interview. Meaning: What do you want to get out of the conversation?

Once you know this, do your research author of Hollywood edge Ken Auletta told Sidekick. “Research the subject’s online profiles, read any previous interviews they’ve given, and find out what questions they’ve already answered. Talk to his peers and critics to get a broader understanding of who you’re interviewing.”

Neil Curry and Leah Palmieri shared similar advice with Sidekick. Currie relies on research to help him find new angles on old stories that might reveal new information. Palmieri studies the subject’s Instagram and Twitter posts to get an idea of ​​what the interviewee is thinking, which helps her figure out how to start the conversation.

Curry and Auletta both agreed that the key to a good interview is that it feels conversational and approachable. In Auletta’s experience, the best interviews start with simple questions before diving into more complex topics.

“Start with the softer questions—questions that make people feel like you’re not messing with them,” Auletta told Sidekick. Let people know you’re there to understand them, not chase them, and ask intelligent questions so the subject feels confident, he suggested.

Here are some more tips from our experts:

  • Listen carefully. You may have questions asked, but remember to let the conversation flow. “[When] you’re really listening to that person, at that point you’re having a dialogue. And you’re taking them to areas that maybe they haven’t been to. So you might get some surprising answers,” Auletta said. But also read the room, Palmieri advised. Assess if the person is comfortable sharing more and then ask questions accordingly.
  • Don’t rush to fill the silence. Wait for a moment of silence during your interview, Auletta advised. Often interviewees will talk more to fill in the blanks themselves. “They will sense that you are not satisfied with their answer … and they will want to satisfy you with an answer,” he said.
  • Know your questions well. Connecting to the topic and keeping a calm back-and-forth conversation is important, but having a clear understanding of what responses you want to elicit helps keep the conversation moving in the right direction, Palmieri said. If the subject goes off topic because they contacted you, give it a moment and then bring it back.
  • Be agreeable. “When people feel comfortable with someone in a conversation, they tend to be more open,” Auletta said. Palmieri and Curry agreed: Set the scene and make light conversation or ask someone about their interests, but be approachable. Let your body language and demeanor reflect that you are open-minded and willing to listen to their story without judgment.
  • Interview with confidence. “No matter who you’re interviewing, don’t be afraid,” Curry said. “You have a right to be in this room. They sit with you and listen to your questions… and don’t be afraid of the clichés [like] ‘How did you feel?’ This is the main question of most interviews.
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When you get to know someone, you won’t learn everything about them in one conversation. This is as true in life as it is in interviewing. But if you follow this advice, whoever you interview will tell you stories that will give you a glimpse of who they are.

For Auletta, one of those defining moments came when he interviewed entrepreneur and CNN founder Ted Turner for the New Yorker. Turner has spoken about his father’s suicide in the past, but in his interview with Auletta, he revealed the contents of the obituary and shared how that moment shaped his life and career. Through carefully prepared questions and purposeful silence, Auletta made a very private and successful man feel comfortable enough to share incredibly intimate details.

The memorable moment from Palmieri’s interview looked a little different. She spoke to 14-year-old singer Sarah James shortly after she rose to fame with her appearance on America is looking for talent. New to fame and still building her career, James shared details with Palmieri about her new life in the Checking the microphone podcast and Palmieri was able to witness the young singer record a single in real time.

In both cases, careful interviewing led to compelling stories culled from a wealth of information. Readers and listeners were on the edge of their seats, and interviewees discovered themselves in perhaps entirely new ways. It is good interview.—SS

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