23 Interviews: Conversations with Risk

Eric Thomas

Learning Objectives

After reading this chapter, you will be able to:

  • Define what it means for interviews to be conversations with risk.
  • Articulate risks that interviewers can take during an interview.
  • Understand how to prepare questions for interviews that are conversations of risk.

Stepping It Up A Notch

The preceding chapter presents guidelines for beginning interviewers about how to prepare for and conduct solid interviews.

This chapter picks up where the first chapter leaves off, and presents advanced interviewing ideas for those who have some practice following basic interviewing strategies.

From Boring to Good Interviews

At the outset, let’s agree on what is an interview, what makes an interview boring, and what is a good interview.

An interview is research. It is research in that it is the gathering of fact, the gathering of opinion and the gathering of emotion from people and sources surrounding us.

But interviews that use only pre-scripted interview questions are boring and predictable.

Why are they boring and predictable? Because the people we are interviewing are going to say interesting things. And if we have a list of 20 questions that are going to inspire our next question, then we are never going to be responding to what the person says. If someone says something interesting, and we simply move on to the next question, we are not reacting to the interesting thing that they just said.

In contrast to boring, pre-scripted interviews, good interviews aim to gather new information, of course, but more than that, they are conversations.

But what is a conversation, and what makes a good conversation?

This chapter answers these questions with five audio clips from different podcasts. These audio clips demonstrate what makes a good conversation and, by extension, a good interview.

Good Conversations

The first audio clip shows what good conversations are like.

It comes from Slate magazine’s Culture GabFest podcast. Slate is an online magazine that, in addition to articles, puts out a variety of podcasts. This podcast talks about culture. In this episode, the hosts Stephen Metcalf, Dana Stevens and Julia Turner, discuss what makes a good conversation.

Listen to this clip: note what Stevens, Turner, and Metcalf define as good conversations.

These hosts say that good conversations involve humor and a bit of unexpectedness.

Conversations entail people saying things that are unexpected, off the cuff, and not scripted. In this, these hosts reinforce the idea that we shouldn’t be having these pre-scripted interview questions. Instead we, as interviewers, should be willing to take risks. This means being willing to say things that might offend, that might make people laugh, or maybe even that might confuse people.

Through all of this, we will enjoy and learn from our partners in the conversation.

Categories of Risk Interviewers Can Take

Here are five basic categories of risks that interviewers can take to turn an interview into a good conversation.

Be naïve. One of my favorites is to be naïve when you are interviewing. This means to act as though you don’t know the answers to questions that you already know. Being naïve in this way gets the person you’re interviewing, the expert, the person of authority, to give you their take on the issue at hand. This approach gives these people an opportunity to explain a basic concept in an unexpected way.

Be bold. The second risk that interviewers can take is to be very bold. This means saying something that could be construed as impertinent, or maybe even on the edge of being disrespectful. To have a bold take can be really helpful in taking a risk in interviewing.

Have your own theory. The third risk an interviewer can take is having your own theory: To present something as your own take. Normally, when we think about interviews, we think about just having questions formulated. But what if you were to walk in with your own theory of an issue or of how something happens, present that to your interviewee, and get this person to respond to that theory?

Be funny. Being funny in an interview is an incredible risk. There is perhaps nothing more intimidating than standing in front of people and trying to make them laugh. That’s a lot of pressure, but in taking that risk in an interview, that might be something that would elicit an interesting reaction that you could include in your research.

Be personal. The fifth and most obvious risk you could take in an interview is to be personal. This means not only being personal in the questions that you ask, but also being personal about your own experiences. What are the things you have gone through in relation to the topic of your interview that you could share with the interviewee? For example, say you are talking to a student athlete about a particular win or loss that they have just experienced. Being personal, and talking about your own past win or loss, might help your interviewee connect with you as a peer with a shared experience.

One Conversation Filled With Risks

The second interview that we will listen to is from Terry Gross, the famous radio interviewer who hosts NPR’s daily program “Fresh Air.” In this podcast, Terry Gross is interviewing Uta Hagen, an actress and a drama teacher.

As you will hear, Gross takes some particular risks in her interview with Hagen. As you listen, keep this central question in mind: What type of risks does Gross take during this interview?

Gross takes three main risks in this interview.

The first risk she takes may not seem very risky at all in terms of what we generally mean by risks and that is the idea of being informed. Gross sat down with Hagen’s books, she read the books, and likely researched Hagen using other sources as well. Gross did all the preparation that was needed, and that takes time.

Any occasion that you take time to research something is a risk because you could spend time researching something that doesn’t end up being relevant to your interview. But Gross has taken the risk of being informed and taking the time to be informed. The result was that Gross was able to ask informed questions and, as we will discuss, engage in a conversation with Hagen as an informed person.

The second risk she takes is the risk of being quiet and of listening actively. Consider how personal Hagen’s criticism of Gross asking Hagen about acting technique could have seemed to Gross. Hagen basically attacks everything Gross does for a living, but Gross just sits there and takes it.

If you ever had to sit there and be lectured to, and not defend yourself, you understand that it takes a huge amount of restraint from Gross to be submissive.

Remaining quiet and listening to Hagen’s perspective granted Gross a keen insight into the mind and opinion of a great acting coach, and time to use her prior knowledge of Hagen to formulate her response to the thespian. This leads us to Gross’s third risk.

The third risk that Gross takes is the risk of defending herself. Once she has listened to Hagen, Gross defends her question and fights back in a way, and explains her opposing argument. That could have further inflamed this situation and made Hagen even more offended by what Gross was asking and saying.

But, as you may notice, Gross is able to pull from her years of experience as an interviewer and her research of Hagen to explain why she asked the question that offended Hagen. In response, Hagen is convinced that Gross’s question wasn’t flippant but a thoughtful attempt to improve her own and her listeners’ understanding of the acting craft. In the end, Hagen sounds apologetic and almost flattered, and the two return to a congenial conversation.

Terry Gross later explained her thinking during the interaction:

“What I liked about [Uta Hagen] challenging me is that sometimes interviewing is like question, answer, question, answer, and that’s fine. But other times there’s this real whammy that’s thrown at you, and I like it. First of all, it really forces me to think, and second of all, in her case, it was challenging the basic premise of the interview. In a situation like that, if somebody is either hostile or challenging, I like to examine the problem and talk that through — I think that makes for provocative radio.”

Studs Terkel on the Train

The next podcast is from “The Studs Terkel Program.” Studs Terkel was a famous author and radio producer from Chicago. This clip is from Aug. 27, 1963, so you need to do a bit of time travel to understand the risks that Terkel takes here.

This clip is called “This Train.” It is from interviews that Terkel conducted with individuals on the way to a Civil Rights March in 1963.

The question I would like for you to keep in mind while listening to this clip is: What type of risk is Terkel taking? Again, focus on particular things that he says, and particular ways he sets up the interview that might be risky.

I see Terkel as taking one major risk in this interview.

The risk he takes is by simply being there, on location, in the train station, at the event. He took the risk of leaving the newsroom. This is something that is incredibly easy to avoid. You might be tempted to stay away from the personal interaction that might take place. He could have just picked up the phone, even back in 1963, and attempted to do these interviews over the phone.

However, the difference between being in-person and being over the phone is huge. Being there is an incredibly helpful thing to do in regard to doing the interview. It allows you to see and hear things firsthand. You directly interpret things instead of asking for someone else’s spin.

I think we can all agree that in 1963, as people were marching on Washington to advocate for civil rights, that this was not a topic that was seen as simple or easy to cover. This would have been something of great controversy. To add to this, Terkel was a white man covering an event that greatly impacted African Americans. By taking the risk of leaving the newsroom, Terkel improved his ability to find sources and to better obtain their trust to share their experiences.

So Terkel went out of the newsroom, found people where they were, and asked them about something that could be incredibly offensive to them, or incredibly controversial to them. All of this involved risk.

Telling a Story

The fourth clip is from the podcast “Radiolab.” This episode is titled “Dark Side of the Earth.” We are going to listen to a short interview with astronaut Dave Wolf, conducted by hosts Robert Krulwich and Jad Abumrad. The interview was posted Oct. 12, 2012.

This clip needs a little bit of a setup. What Dave Wolf, the astronaut, is going to explain here is this: He is trapped outside of the International Space Station, hovering out in the solar system, and the cooling unit of his space suit has failed. And so he is essentially slowly cooking from the outside in. It is a situation that is very likely to kill him unless he finds a way to get back into the space station.

He has already failed to get into one of the entrances of the space station. So, he is going to try another entrance into station.

He is getting so hot within the space suit that his perspiration and body heat is fogging up the front shield of the space suit, which he uses to look out of. You’ll hear him figure out a way to look through that shield so that he can see what he’s doing.

Again, what risks do interviewers Krulwich and Abumrad take in this interview?

Of course, the interviewers are being quiet, in a way that we talked about previously, to allow Wolf to tell a personal story.

But they take one key risk that we haven’t discussed previously. This risk is allowing Wolf to tell a story from beginning, to middle, to end. That is really, really tricky to do, to get someone to tell an interesting narrative story. And they’ve taken that risk of asking him to tell his story, and then given him the space and time to do so.

One thing I would encourage every interviewer to do is to have a “tell me a story” question at the ready.

It is very easy for people to avoid telling us stories if we ask them questions like, “How was your day?” “How was your presentation?” “How did the budget meeting go?” They can answer very easily by saying, “Good,” or “OK,” or “Not so great.”

But if we say, “Tell me a story about the budget meeting,” then they are very unlikely to just respond quickly. They’re going to be forced by social manners and also by our question to tell us a story, and we likely will get much more out of it by asking that question.

Back to Middle School

The next podcast is from the radio program “This American Life. This episode, “Middle School,” focuses on the embarrassment, the fun, and the awkwardness of being a middle-schooler. This was produced by This American Life’s co-producer Ira Glass, and it was first published on Oct. 28, 2011.

You’re going to hear a variety of interviewers here. The risks that these interviewers take are very similar to the risks taken by the previous interviewers. So I’m going to ask you to keep a different question in mind. While listening, ask yourself: What are the specific things that the interviewers do and ask here that are particularly good?

I think one of the most striking moments comes from the interviewer who asked, “Take me through it minute by minute.” That prompt, that follow-up question that she asked, allows the boy in this case to explain exactly what happened, and to feel OK about indulging the interviewer in this minute-by-minute of what life is like for him.

There are other risks that these This American Life interviewers took:

  1. They enter their sources’ most comfortable space. They find them among their friends, at their school, they find them outside of their school in places that put the interviewees at ease.
  2. They don’t have pre-written questions. Instead, they have impromptu, of-the-minute follow-up questions. They ask questions based on what the previous question to the answer was. It takes years of practice to get to this point, though. Below we will give you some tips on how to build up to this level of mastery.
  3. They also ask lots and lots of confirmation questions. They ask and re-ask the same questions, and in doing so they are asking their sources to dive deeper into their experiences, and say things in a more detailed way.
  4. This American Life producers take incredible risks with the actual questions they ask. These are adults who go into a middle school with a microphone and ask students about petting, dating, boys and girls at their school, and dances. In doing so, they ask some incredibly sensitive questions. In other words, the producers go out of their comfort zones to ensure that their interviewees feel comfortable enough to be their authentic selves.

Preparing for Conversations With Risk

So, if we are trying to do all of this conversational interviewing do we just walk into an interview unprepared?

I think we already know the answer to that: No. But we are going to prepare for a conversation differently than we would for a pre-scripted interview.

The following process comes from Bill Tammeus, who is a former long-time journalist with the Kansas City Star. He presents this as a step-by-step process for preparing for a conversational interview.

Focus. The first thing Tammeus says that we should know is the focus of our story. Make sure that your focus is narrow enough for the time and space we are given, or that it is broad enough to fill the time and space we are given. For instance, we shouldn’t be trying to answer a huge question about our culture with a 200-word brief. Similarly, we shouldn’t try to answer a very, very narrow question with a 10,000-word story we’ve been assigned. We should make sure that our focus is appropriate.

Research the story. We should do as much factual research as we can on our topics, much in the same way that Terry Gross researched acting and knew tons and tons about it. We should do lots and lots of research on the story we are hoping to research.

Research the interviewee. We should do as much factual research on the interviewee as we did on the topic or story. Remember how Terry Gross read all of Uta Hagan’s acting books? You may not have to read books, but taking a glance at the interviewee’s LinkedIn account or another biographical source should be a good starting point.

We shouldn’t need to ask the interviewee where they went to school or how many years they have been in their careers, or how to spell their names. We should know all those things heading into that interview. We shouldn’t be surprised by any of their answers. We should be asking more interesting and more conversational questions that will get our source to tell us something interesting.

Prepare questions. This is going to seem absolutely counterintuitive, but you should write down 20 to 25 questions to ask. Now, we just said that we would not ask our subject 20 to 25 questions in a pre-scripted way. That is still true. The point of writing down these questions is to get our questions on paper and into our minds. Then, we will go through a mental exercise.

Group questions. We are going to group all of those questions into five or six subject areas that will dominate our questions. So in the end, we are not going to ask those exact 20 to 25 questions, but rather we are going to talk about five to six the major subject areas.

Throw questions away. You now have all of those questions in your head. There is no reason why you need to go into an interview with your written-down questions. If you do, you will likely rely on them and likely ask questions that seem stilted, and not seem responsive to the person you are sitting in front of. So instead, allow those five or six subject areas guide you.

Note sections. What do you do with those five to six subject areas? You go ahead and put them in bullet point in the corner of each page of your note-writing materials. If you put them up there, you will be able to ask those questions without needing to refer to those exact questions. It will allow you to work through each of those subject areas one by one, without having to ask questions that are pre-formulated. And it will allow you to ask follow-up questions that are more  conversational.

Subject conversation. During the interview, have a conversation about those bullet-point subject areas. Allow this conversation to be free-flowing, take the risks of being naïve, being bold, being funny, coming up with your own theory, and all the things that we talked about in this chapter.

Finish up. How do you finish this? You finish this by asking the interviewee: What did I forget to ask? This is often a really good question to finish with, because it flatters the interviewee a little bit. This question signals to them that that they probably know the topic better than you do. Their answer to this question may help you to generate your next story idea.

Double-check preferences. Double-check how your source wants their name to appear in your writing. I said before that we don’t need to check the spelling of someone’s name, but someone might prefer to be Jen instead of Jenny of Jennifer, so it’s always good to learn of someone’s preferred title and how they would like their name to appear. You may also ask how they wish their professional title to appear, and if they have a pronoun preference (i.e., he/his, her/her, they/them/theirs).


What are we seeking from interviews? We are seeking news. We are seeking something that few people already know. We want something unexpected, and we want something that is unknown. And we are much more likely to get this very unknown information if we ask questions using a conversational approach rather than pre-scripted Q & A. We are always looking to have a conversation that hinges on risk.

A Practitioner’s View


Zak Beasley

KU Journalism, B.S. 2007, M.S. 2014; KU Law, J.D. 2015

U.S. Marine Corps Captain

I’m a judge advocate in the Marine Corps, which is just another way of saying I’m a Marine lawyer.

As part of my job, I have to interview people in order to understand their side of the story, as well as their recollection of events. It’s not unusual to interview someone weeks or even months after an event has happened, which makes the interviews that much more difficult.

How to select individuals. If a person is likely to have relevant information to my case, I want to talk to them, period. If there were five witnesses to a crime, you better believe I’m trying to talk to everyone.

How to conduct interviews. First, deciding the proper tone of the interview. If I’m talking to a victim of sexual assault, my tone is going to be entirely different than if I’m talking to an expert witness about how cocaine affects the body, or with a person suspected of committing a violent crime. Establishing the proper tone creates an environment where the interviewee feels comfortable and gives the impression that I am a professional. Typically I always take time to thank the person for their time upfront and tell them the importance of their interview.

Second, tell the truth. Without failure, I always stress the importance of telling the truth. I don’t care whether the facts I get from a person are good for my case or not: if I don’t have reliable information, then I can’t do my job.

Sometimes people feel pressured that they have to give a certain answer, so I do my best to make sure they know their only obligation is to tell the truth. This comes in handy if the interviewee/witness is testifying, and the veracity of their prior statements ever comes into question.

Third, don’t be afraid to ask lots of questions. The importance of having a firm understanding of a person’s recollection of events or expert opinion cannot be overstated. I typically spend a good portion of my morning reviewing investigations, case law, and prior witness statements in order to maximize my understanding of the case and the relevant issues.

I like to outline topics and sub-topics I want to cover with the interviewee to make sure we cover those areas. I like open-ended questions when conducting interviews so I can let the person talk without having to interrupt them, and then ask more pointed questions on the back end.

Don’t be afraid to ask the same question a couple of times. Never leave an interview being unsure about what the person was trying to convey.

Fourth, don’t be afraid to ask hard questions. Typically, those are the most important ones to ask. I always like to preface those questions with a disclaimer and why it’s important for me to know. At the end of the day, I can’t do my job if I don’t have all the facts.

Activity 1:

Find an audio or video clip of an interview conducted by a journalist. Answer the following questions through a presentation: Does this interview exemplify a conversation with risk? What risks are present in this interview? What risks could the interviewer have taken during this interview? How could/did these risks contribute to the interview? Write 1-2 pages double spaced explaining your impression.

Activity 2:

Choose a topic you are passionate about and a key person related to this topic you would want to interview. Following Bill Tammeus’s process: research and prepare questions for a conversational interview. How does this preparation process ensure that your interview will be more conversational? Include 2-3 specific risks strategies you could include in the interview. What are the strengths and weaknesses in regards to using these risks? Provide drafts of your question-writing process with notes explaining your decisions.

Activity 3:

Select 1-2 of the clips or podcasts from this chapter. Based on Bill Tammeus’ process, how did the questions in these interviews make these interviews conversational (or not)? Does it seem like the interviewers researched the topic or story ahead of time? How so? What were the major subject areas covered in the interview?


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