KIRK DOCKER
5 INTERVIEWERS WORTH WATCHING
There are many types of interviewers and interviewing styles. I count therapists, hostage negotiators, detectives and lawyers as interviewers in a way. Their work inherently focuses on people, and they all strive to extract information, ask questions, listen, and find out things that others could not.
Each profession has their own individual aims and outcomes they’re trying to achieve. In the same way a shock jock interviewing a politician has different aims to a long-form profile interviewer speaking to a legend of the screen. They also all work under different circumstances. A detective asks questions of people that may want to hide the truth whereas a late-night talk show host’s guests are generally spruiking themselves and a product.
All this being said, I’m going to suggest five interviewers worth watching, where you can leverage their techniques for your own interactions and deepen your communication skills. These interviewers lean towards longer form content with open-style questioning, although each has their own style and strengths. They also all work in the media, so their work is readily available. I’m currently working on a podcast series called ‘Interviewing Interviewers About Interviewing’ – it’ll focus on people who ask questions – not just media types. If this interests you, sign up here to find out when that comes out.
There are many more names I could have included, so I’ve named a few extra shout-outs at the end of this list. And I’d love to hear who you rate! Let me know via LinkedIn.
andrew denton
When you think interviewer in Australia, for a long time Andrew Denton’s name was #1. For good reason, his hour-long interview show Enough Rope ran a whopping 33 weeks a year between 2003 and 2008. Andrew went deep into the lives of people such as Bill Clinton, Steve Irwin, Esther Perel and Jerry Seinfeld, often getting them to open up in a way the world had never seen. Having worked with Andrew for a number of years and to this day enjoying his company as a friend, what’s true about his nature is that he is curious, thoughtful, playful and courageous in his question-asking. All that is evident when watching him. What isn’t as obvious is his meticulous research.
The reason he gets great reactions from his guests is because he asks questions that are outside the norm. Celebrities and people of profile that are interviewed often are repeatedly asked the same questions. An interviewer that puts the time and care into going deeper can elicit dynamic, emotional, real performances from people that are usually experts in controlled responses.
The example I’m going to show here however is not from Enough Rope. It’s from Andrew’s podcast Better Off Dead, an investigation into assisted dying. It’s a subject he’s not only passionate about but has since successfully campaigned for change in Australian state laws. It’s also an example of meticulous research, one on full display when he goes head-to-head with the founder and director of HOPE, an organisation dedicated to preventing euthanasia and assisted dying. He tackles two of their key accusations – that assisted dying safeguards don’t work and that the elderly and disabled were threatened. What results is a masterclass in killing them softly.
louis theroux
There was a time in the late 2000s where every up-and-coming content maker wanted to be like Louis Theroux. The types of worlds he infiltrated (think Nazis, pornstars, UFO abductees) and the courageous questions he asked were very inspiring. But there is great skill to what he does. Replicating the type of content he makes is not easy, but there is lots to learn from the way he goes about asking questions.
Louis’ skill is his ability to somewhat ‘play dumb’ or rather, be comfortable to appear to not know all the answers. He goes in looking to understand, and will ask things that he may already know the answer to or suspect he knows the answer to, but wants to hear what his subjects have to say for themselves. In this very famous example, he spends time with what he calls ‘the most hated family in America’ – the family at the core of the Westboro Baptist Church. They were notorious for placarding Amercian soldier funerals with signs reading hateful messages such as “God Hates Fags” and “Thank God For Dead Soldiers”.
WATCH: Louis meets Shirly Phelps, daughter of the family patriarch and day-to-day boss of operations.
In what’s a typical display from Louis, he listens, challenges and despite pushback, continues to ask questions to a subject that most of us would suggest makes zero sense or is at least sprouting lies. His manner not only keeps them onside but also allows us, the audience, to see them for who they are. Not only that, he is unflustered and supremely level-headed in his unpacking to understand.
Adding to his disarming inquisitiveness is his willingness to be honest about his own values. It’s not a stretch to assume that to build rapport with someone with such extreme beliefs you need to keep ambiguous about your own values, particularly if you disagree with them. But by being true to his values and asking questions to understand, Louis can never be accused of being untruthful if he challenges them. In a way, by being true, Louis demands that they are true. (this almost gets him in hot water when challenged by Neo-Nazis about whether he’s Jewish).
louis theroux
There was a time in the late 2000s where every up-and-coming content maker wanted to be like Louis Theroux. The types of worlds he infiltrated (think Nazis, pornstars, UFO abductees) and the courageous questions he asked were very inspiring. But there is great skill to what he does. Replicating the type of content he makes is not easy, but there is lots to learn from the way he goes about asking questions.
Louis’ skill is his ability to somewhat ‘play dumb’ or rather, be comfortable to appear to not know all the answers. He goes in looking to understand, and will ask things that he may already know the answer to or suspect he knows the answer to, but wants to hear what his subjects have to say for themselves. In this very famous example, he spends time with what he calls ‘the most hated family in America’ – the family at the core of the Westboro Baptist Church. They were notorious for placarding Amercian soldier funerals with signs reading hateful messages such as “God Hates Fags” and “Thank God For Dead Soldiers”.
WATCH: Louis meets Shirly Phelps, daughter of the family patriarch and day-to-day boss of operations.
In what’s a typical display from Louis, he listens, challenges and despite pushback, continues to ask questions to a subject that most of us would suggest makes zero sense or is at least sprouting lies. His manner not only keeps them onside but also allows us, the audience, to see them for who they are. Not only that, he is unflustered and supremely level-headed in his unpacking to understand.
Adding to his disarming inquisitiveness is his willingness to be honest about his own values. It’s not a stretch to assume that to build rapport with someone with such extreme beliefs you need to keep ambiguous about your own values, particularly if you disagree with them. But by being true to his values and asking questions to understand, Louis can never be accused of being untruthful if he challenges them. In a way, by being true, Louis demands that they are true. (this almost gets him in hot water when challenged by Neo-Nazis about whether he’s Jewish).
esther perel
Esther Perel is a psychotherapist and relationship therapist. She is Jewish and grew up in Belgium post World War II. It was here she noted the very different ways Jewish families in her neighbourhood dealt with the genocide of the Jewish people – some, like her own family, rejoiced in being alive and lived for every day, while others locked themselves away, ever-alert, in fear that something terrible could happen again. It was from these early days she was interested in people and their relationships.
Esther’s interviews aren’t in the style of typical media interviews, but recorded one-off therapy sessions broadcast on her podcasts Where Should We Begin? and How’s Work? Couples come to her wanting to explore an issue. Esther is a master question-asker. It’s worth listening to her just to take in her questions. Her opening in the example I’ve included below is, “If this was a helpful conversation and you left here and said, ‘This really made a difference’. What would it be? What needs to happen?”
Being a therapist, her questioning is about exploring emotions and interpersonal dynamics, so her questions are probing and challenging, but she asks them with warmth and humour which puts her subjects at ease. She’s also tough but fair, often flipping the tables on someone that thinks they are wholly in the right while their partner is in the wrong. She rarely lets anyone off the hook!
An interesting component in Esther’s podcast is that she will interject her sessions with her own analysis, to give you an understanding of why she decided to go in the direction she did, her breakdown of the particular people she is working with, and critique her own methods. In this episode I Don’t Mean To Be Mean But…, Esther struggles with one of her clients and finds the way she interacts with her partner frustrating. In her analysis, she explains what’s going on for her:
“And as I listen to this myself, I realise that I was doing to her what I was telling her, she was doing to him. And that’s when I knew I’m inducted in the system. I was talking to them in the same tone as they were talking to each other. This is where I felt that I had lost some of my therapeutic stance. That said, therapy is filled with surprises. Sometimes I think I have done the most beautiful intervention and it falls completely flat. And sometimes I cringe at my voice or my tone or at my own intervention, thinking that was so not helpful and then I find out, that landed exactly when it needed to land. And that is an unknown that every therapist lives with.”
gay talese
Gay is a writer, considered the pioneer of the feature profile piece. He gained attention with his artful magazine pieces for Esquire in the sixties, including “Frank Sinatra Has a Cold,” an article that interviews the people surrounding Sinatra, (people impacted by the fact he has a cold) to paint a portrait of him, without speaking to the man himself. Since then, he has written many books, one I particularly enjoy is Thy Neighbors Wife, a romp through America’s modern sexual history in which Gay, in the section exploring swinging, becomes a character himself. He is a founder of what is called New Journalism, an innovation where he applied techniques from the craft of fiction writing to his newspaper and magazine stories, giving them the shape and life of short stories. I was a fan of his work far before I was aware of how he interviewed. In particular I marvelled at the intimacy he achieved with his subjects.
When he was interviewed about his technique on the Longform podcast, (something I highly recommend you listen to) one of the things that struck me was his description of an early defining moment that shaped the way he began to understand stories and people. He grew up living above a hair salon during World War II. His mother would be doing the hair of ladies whose husbands were away fighting and he would eavesdrop on their conversations. His early understanding of the war was not through traditional news outlets, but through these women telling stories of their husbands – second-hand sources but nonetheless close to the action in a very specific way. Observing, watching, and listening became a cornerstone in his understanding of people and how there are many ways and angles in which you can unpack an idea or a person.
I want to know how people did what they did. And I want to know how that compares with how I did what I did. That’s my whole life. It’s not really a life. It’s a life of inquiry. It’s a life of getting off your ass, knocking on a door, walking a few steps or a great distance to pursue a story. That’s all it is: a life of boundless curiosity in which you indulge yourself and never miss an opportunity to talk to someone at length.
Gay Talese, 2007, A Writer’s Life
gay talese
Gay is a writer, considered the pioneer of the feature profile piece. He gained attention with his artful magazine pieces for Esquire in the sixties, including “Frank Sinatra Has a Cold,” an article that interviews the people surrounding Sinatra, (people impacted by the fact he has a cold) to paint a portrait of him, without speaking to the man himself. Since then, he has written many books, one I particularly enjoy is Thy Neighbors Wife, a romp through America’s modern sexual history in which Gay, in the section exploring swinging, becomes a character himself. He is a founder of what is called New Journalism, an innovation where he applied techniques from the craft of fiction writing to his newspaper and magazine stories, giving them the shape and life of short stories. I was a fan of his work far before I was aware of how he interviewed. In particular I marvelled at the intimacy he achieved with his subjects.
When he was interviewed about his technique on the Longform podcast, (something I highly recommend you listen to) one of the things that struck me was his description of an early defining moment that shaped the way he began to understand stories and people. He grew up living above a hair salon during World War II. His mother would be doing the hair of ladies whose husbands were away fighting and he would eavesdrop on their conversations. His early understanding of the war was not through traditional news outlets, but through these women telling stories of their husbands – second-hand sources but nonetheless close to the action in a very specific way. Observing, watching, and listening became a cornerstone in his understanding of people and how there are many ways and angles in which you can unpack an idea or a person.
I want to know how people did what they did. And I want to know how that compares with how I did what I did. That’s my whole life. It’s not really a life. It’s a life of inquiry. It’s a life of getting off your ass, knocking on a door, walking a few steps or a great distance to pursue a story. That’s all it is: a life of boundless curiosity in which you indulge yourself and never miss an opportunity to talk to someone at length.
Gay Talese, 2007, A Writer’s Life
oprah winfrey
On December 14 1986 Mike Wallace of 60 Minutes interviewed the rising star Oprah Winfrey when her talk show went from Chicago based to national broadcast. From day one, Oprah’s style was evident and articulated beautifully in the following exchange:
Mike Wallace: I understand that when you prepare for a broadcast. You don’t really prepare, in that you don’t have a script, you don’t have questions. Do you wing it?
Oprah Winfrey: Yeah basically I do.
MW: Why?
OW: Because I think that I’m a surrogate viewer and I feel really connected to the women who are out there watching me.
MW: I know, but having said that, still if you’re going to be a proxy, you have to ask the questions that they want the answer to.
OW: (in unison) They want the answer to!
So, that’s what I do. I ask the questions that I want the answers to.
I love this. It sounds so simple, but we often forget to do it. Ask questions that we actually want to know the answers to. Oprah is obviously doing something right to be the icon she is for so long, but what? I want to highlight a couple of things.
oprah winfrey
On December 14 1986 Mike Wallace of 60 Minutes interviewed the rising star Oprah Winfrey when her talk show went from Chicago based to national broadcast. From day one, Oprah’s style was evident and articulated beautifully in the following exchange:
Mike Wallace: I understand that when you prepare for a broadcast. You don’t really prepare, in that you don’t have a script, you don’t have questions. Do you wing it?
Oprah Winfrey: Yeah basically I do.
MW: Why?
OW: Because I think that I’m a surrogate viewer and I feel really connected to the women who are out there watching me.
MW: I know, but having said that, still if you’re going to be a proxy, you have to ask the questions that they want the answer to.
OW: (in unison) They want the answer to!
So, that’s what I do. I ask the questions that I want the answers to.
I love this. It sounds so simple, but we often forget to do it. Ask questions that we actually want to know the answers to. Oprah is obviously doing something right to be the icon she is for so long, but what? I want to highlight a couple of things.
First, she comes from a place of respect and love, that’s why people speak to her. They feel they are going to be treated right, fairly. They know they can have a deep conversation with her and she can handle it. They know that she will at times figuratively (metaphorically) and literally wrap her arms around them. But if you look at the questions she asks, she doesn’t shy away from asking the hard stuff. In the interview with Meghan Markel in 2021 she asked:
You said in a podcast, that it became “almost unsurvivable”, and that struck me, because it sounded like you were in some mental trouble. What was going on?
Which brings me to my next point. Oprah seeks clarity as a way of affirming what she’s heard and acknowledging that she understands them. For someone that’s answering the question, it’s affirming to know that you aren’t being misinterpreted and you also have the opportunity to correct the record if you have been.
When people answer these sorts of questions (truth around mental health), often they will talk around the point. This is not to say they don’t want to answer, it’s just sometimes hard to work out how to answer. In Meghan’s case, she answered the question:
I just didn’t want to be alive anymore.
Many of us in this moment would reel back, feel we’ve heard enough, “we get it”. But after listening deeply to the extended answer, Oprah came back to that point.
Wow, you didn’t want to be alive anymore. What do you mean by that? Were you thinking about harming yourself? Were you having suicidal thoughts?
I think the biggest takeaway from Oprah is that she makes her guests feel heard, understood and valued through deep listening and giving a shit. Which results in a meaningful connection with her interviewees and often a transformative experience.
First, she comes from a place of respect and love, that’s why people speak to her. They feel they are going to be treated right, fairly. They know they can have a deep conversation with her and she can handle it. They know that she will at times figuratively (metaphorically) and literally wrap her arms around them. But if you look at the questions she asks, she doesn’t shy away from asking the hard stuff. In the interview with Meghan Markel in 2021 she asked:
You said in a podcast, that it became “almost unsurvivable”, and that struck me, because it sounded like you were in some mental trouble. What was going on?
Which brings me to my next point. Oprah seeks clarity as a way of affirming what she’s heard and acknowledging that she understands them. For someone that’s answering the question, it’s affirming to know that you aren’t being misinterpreted and you also have the opportunity to correct the record if you have been.
When people answer these sorts of questions (truth around mental health), often they will talk around the point. This is not to say they don’t want to answer, it’s just sometimes hard to work out how to answer. In Meghan’s case, she answered the question:
I just didn’t want to be alive anymore.
Many of us in this moment would reel back, feel we’ve heard enough, “we get it”. But after listening deeply to the extended answer, Oprah came back to that point.
Wow, you didn’t want to be alive anymore. What do you mean by that? Were you thinking about harming yourself? Were you having suicidal thoughts?
I think the biggest takeaway from Oprah is that she makes her guests feel heard, understood and valued through deep listening and giving a shit. Which results in a meaningful connection with her interviewees and often a transformative experience.
others worth checking out
Sarah Ferguson: Australia’s most unflinching current affairs reporter. She never backs down from a tough question, whether it’s to obfuscating politicians, sexually abusing priests or making Sidney Powell walk out of the interview (her questions are brutal!). Her work is legendary on Four Corners and now you can see her daily, hosting 7.30 on ABC.
Mike Wallace: The original “tough” interviewer and the face of 60 Minutes for decades. In the film Mike Wallace Is Here, he’s asked, “Is it hard to ask those questions?”
Mike: No not at all.
Interviewer: How do you do it?
MW: I’m nosey. And insistent. And not to be pushed aside.
I: And confident.
MW: Confident that when I ask the question, there’s a reason for it being asked. It’s not a question picked out of the air. You ask tough questions to get behind the facade. To try and get an understanding of what’s really going on behind the scenes.
Dick Cavet: The talk show host you’ve probably never heard of. Rather than the typical talk show interview of “anecdote, anecdote, plug”, Cavet is both relaxed and himself as he asks legitimately curious questions to the biggest names in the world, often resulting in news grabbing revelations. Here he has the only interview with Marlon Brando after he rejected his Oscar in 1973, in which he asked a native American woman to go up in his place in protest.
Quentin Sommerville: An amazing war correspondent — in pretty hectic situations. I think he might be the best war correspondent in the world right now. He gained worldwide attention when accidentally got high while reporting in front of a huge pile of burning opium & hash. But he is best known for his work in the midst of the action. Incredibly, here he is with Ukrainian soldiers right in the front line.
Richard Fidler & Sarah Kanowski: Conversations deliver a treasure trove of fantastic interviews each year, and more often than not with people you’ve never heard of. Impressively they broadcast five interviews a week on the ABC, with the interviewing role rotating between the consistently excellent Richard Fidler and Sarah Kanowski. These interviews are tight, well researched, respectful and always entertaining.
final thought
The idea of this list is to get you looking at question askers with a critical eye. Observing the way they listen, ask questions and follow-ups, the sort of research they do. Do they make their guests at ease, do the interviewers spend a lot of time talking about themselves or do they truly focus on their guests? Finally do they take chances with their questions and get new revelations?
I have a monthly newsletter called Questionable Advice where I write about what I’ve learnt interviewing 1000s of people. Sign up here if you’d like to receive it.
Most up-to-date information about me can be found at kirkdocker.com