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As I mentioned last time, nothing so determines the final shape and content of your interview as the questions you ask and the order in which you ask them. (For the previous installments begin here and then follow the links at the end of each installment.) Here’s how I have been going about putting together a question outline.

At first, I don’t worry at all about the order of the questions—I am more interested in brainstorming questions. Before I do any research at all, I draw on my initial curiosity about the guest that prompted me to do the interview in the first place. I’ll open a Word document just for questions and enter them. I like to keep the mindset that I probably will never have a chance again to speak to this person—so I remind myself not to hold back on whatever it is that I’ve always genuinely wanted to know about the guest or his or her work. There are some questions that I find that I repeatedly ask of my guests, because they are issues that I am obsessed about, and that I am genuinely curious about when I meet someone well known or unusually productive. I like to understand people’s lives from the inside, from their perspective,  so I often ask about the guests’ working process, and what they consider to be their most important understandings about their work. I am also curious how an artist’s working life changes with age, and I am often apt to ask questions about that.

But the bulk of my questions come as a result of research into the guest’s work. As I am reading about a guest, or reading a guest’s book, I have my computer file by me, and I am typing into it both salient points that are made, as well as points I would like to understand further. I will also make note of places where I disagree with the guest, places where there could be fruitful further conversation. If I am seeing a film or a theater piece that my guest is involved with, then I have a pad with me and I am taking notes as I’m watching. At a minimum, I become familiar with the guest’s latest project. But, really, ideally, it is much better when I am able to become familiar with a much wider range of the guest’s work, and can situate what the guest is doing within the context of his or her own work, and within the work of his or her contemporaries.

I double space each question, and through experience, I know that when I have about a page and a half of 14-pt type questions, I have enough for a 30-minute interview. Once I have all the questions down, I start moving them around into the order I want. Here, for example, is the final question outline I used when I was preparing to interview playwright and actor Wallace Shawn (I’ve included the intro [which was cut considerably in the editing process] and the outro):

Intro: Hi, I’m Jack Shalom. Actor, playwright, essayist Wallace Shawn has been provoking thought from audiences for over four decades. His memorable film roles have included co-starring in My Dinner with Andre, and his comic turn as Vizzini in The Princess Bride. His work as a playwright includes the Obie Award winning Aunt Dan and Lemon, The Fever, and The Designated Mourner; and his essays include the recently released Night Thoughts.

His 2015 play, Evening At The Talk House has been released as an audio drama, with a fine cast that includes himself, Matthew Broderick, Larry Pine, Jill Eikenberry, and Claudia Shear. It can be found gratis on the website of The Intercept online magazine. I’m happy to be talking with Wallace Shawn. (WAIT) Hi, Wally.

Tell us about Evening At the Talk House.

The play was originally done in London, then opened in New York. Did you see a difference between the London and NYC reception?

How did this audio version come to be, and how did it land at The Intercept?

How much did you have to change the play for audio production?

Many of your plays deal with a similar theme: The dark apparatus that it takes to maintain a privileged society. How is Evening At the Talk House different from your previous plays in its working out? Does it represent an evolution in your thinking about these matters?

The characters in Evening At the Talk House keep insisting that they are just trying to have a pleasant evening. In a sense, the play is what it costs the rest of the world for those people to have their pleasant evening. Do people give up their own comfort willingly?

It’s often the self-absorbed artists in your plays who are the people who seemingly can only relate to their own needs. You seem to target artists in particular in your works. Can you speak more about that?

Because this play shows the problems the privileged have in trying to square the contradictions of their wish to appear benign, I could imagine that some might complain that this work is in some sense privileging the problems of the privileged. Is that a fair criticism?

As complex and layered as your plays are, I find your essays on the other hand, remarkably transparent and lucid. When I read your essays, I say, well of course, why hasn’t anybody else explained it so plainly? How do you decide whether something is going to become a play or an essay?

I really enjoyed reading Night Thoughts. It’s like your communist manifesto. A short simple book that anyone can understand. Rather than talking about owners and workers, though, you speak of the lucky and the unlucky. Can you talk more about that?

You are not just someone who is interested in both politics and theater, but you see the two subjects as intimately entwined. A few years ago you wrote a wonderful essay called “Why I Call Myself a Socialist: Is the World Really a Stage?” Could you talk about some of the ideas in that essay and what in your view is the relationship of acting  to the necessity of socialism?

What’s the most important thing you know about playwriting?

Anything else you’d like to add, Wally?

 I’ve been talking with Wallace Shawn whose play Evening at the Talk House is now available as a free podcast at Theintercept.com. Thanks, Wally. (WAIT) This has been Jack Shalom with host Prairie Miller.

By looking at the outline above you can see how I structure the order of my questions. I generally want the guest to feel comfortable, and I want to situate the listening audience, so I start off by asking questions about the guest’s most recent projects. Next, I’ll move onto other projects I’m interested in, and then I use those projects as a springboard to ask about overall process and more personal questions. If I feel that the guest is amenable, at this point I’ll bring up disagreements or questions which might be a little more challenging. How far I go with that depends on the kinds of responses I get. Finally, I’ll tend to finish up with asking about future projects and where one can obtain more information about the guest’s work. I’ll also ask at the end if there’s anything else they wish to add—surprisingly, often the guest takes a thoughtful breath, regroups and comes out with some of the most interesting material here.

When the interview actually happens, do I stick to this outline?

Almost never.

But that’s for next week, when I talk about actually conducting the interview.

You can read the next installment here:

Radio Interview Production Workshop #7: Conducting The Interview