Dear Writer: Advice on conducting a great interview

We asked Alicia Kennedy to share her advice on interviewing. She calls From the Desk of Alicia Kennedy Podcast, her weekly podcast that’s part of her food newsletter, “a curated conversation series.” She recently wrote about her belief in unscripted, unedited interviews here. Read on for her advice, or listen to her read it aloud above.

Dear writer and podcaster, what’s the secret to a good interview? 

My podcast always begins with the same question: “Can you tell me about where you grew up and what you ate?” This establishes the conversation in some straightforward biography, while also grounding it in the flavors and food philosophies that have shaped the guest’s life. From there, the audience and I will get to go deeper, but the guest sets the terms of the conversation by choosing what and how much to share. Do they become wistful and nostalgic, or do these memories seem painful? Are they tinged by grief and loss, or by joy and whimsy? The question sets the tone and tenor of the rest of the conversation.   

To me, a good interview is governed by the same thing as good nonfiction writing: curiosity. I’ve made mistakes before by doing interviews with people whose work I, frankly, was not curious about, and that means I’m just going through the motions. But what makes an interview good for the audience—whether a listener or reader—is that the people having the conversation are actively engaged with each other, and ideally with each other’s work. As an interviewer, I want the people listening to feel like they’re overhearing a natural conversation, something that would happen spontaneously after the plates are cleared away from the dinner table and all that’s left is some wine and cake.

There also needs to be a spirit of generosity on the part of the person being interviewed. When people come on who’ve never bothered to listen to a past episode and don’t respond generously to good-faith questions, it can feel like pulling teeth. I’ve learned for myself, whether I’m the host or the guest, that I shouldn’t show up unless I can get locked into having a generous conversation. This means being curious and being engaged, of course, but also believing that every question is a good question, a worthwhile question, and if I think perhaps it hasn’t been phrased well, that I can reframe it in my response. 

I want the people listening to feel like they’re overhearing a natural conversation, something that would happen spontaneously after the plates are cleared away from the dinner table and all that’s left is some wine and cake.

In order to facilitate better conversations, I send my guests the questions a week ahead of time. This provides not too much time to overprepare and thus kill spontaneity, but it does allow them to get a sense of the trajectory of the conversation and tell me whether they’d prefer to go in another direction. I want guests to be comfortable and know that it will be a safe space for anything they wish to talk about, and I like to establish their boundaries ahead of time. 

I try to ask big, open questions, too, so that the guest feels free to take their response in any direction. Specific questions, I’ve found, lend themselves too easily to simple answers. The worst feeling is to receive a “yes” or “no” in response. Though sometimes one can want to flex just how deep they’ve researched in their questions, I find it better to be looser and to let the guest guide the conversation a bit, because their spontaneity will also be more compelling to the listener. 

In writing these bigger, more open questions, I dive into