How to Conduct a Great Interview: The Craft Behind the Conversation

The interview is the most common form in contemporary journalism and the most commonly done badly. Every day, thousands of press rounds, podcast appearances, and media interviews produce exchanges that are essentially elaborate non-communication: two parties performing their expected roles — the reporter performing curiosity, the subject performing openness — while saying almost nothing that either party would not have said in a prepared statement.

A great interview is something entirely different. It is a conversation that produces genuine knowledge — about the subject, about the world the subject has moved through, about human experience as seen from a position that most listeners and readers do not occupy. Great interviews are among the most valuable documents we have of how particular people thought, what they felt, what they believed. The archives of The Paris Review, of the Playboy Interviews, of Studs Terkel’s oral histories — these are primary historical documents, not just journalism.

The craft that produces them is specific, learnable in its outlines if not entirely replicable in its execution, and worth understanding whether you aspire to practice it or simply to read it more intelligently.

The Great Interviewers and Their Methods

Studs Terkel: The Art of Making People the Protagonist

Louis Studs Terkel (1912-2008) spent most of his working life conducting oral history interviews with Americans about their experience of the major events of the 20th century: the Depression (Hard Times, 1970), World War II (The Good War, 1984), work (Working, 1974), race (Race, 1992), and death (Will the Circle Be Unbroken?, 2001). The interviews he produced — with farmers, factory workers, civil rights activists, corporate executives, veterans, criminals — constitute one of the most important archives of American experience from the mid-20th century.

Terkel’s method was deceptively simple. He prepared extensively — reading everything available about the person and their context before the interview — and then, in the interview itself, he shut up. His questions were short; his follow-ups were often not questions at all but affirmations, small sounds of agreement, brief repetitions of the last thing the subject said. He was, in the most literal sense, the world’s most enthusiastic listener.

What Terkel understood was that most people never have the experience of being genuinely listened to — of knowing that someone is paying full attention, is interested in what they have to say, and will not use what they say against them. When that experience is provided — by a warm, non-threatening, visibly delighted conversational partner — people produce material that they didn’t know they had. They tell the true stories rather than the official ones.

Terkel’s genius was also his editing. The recorded interviews were often two to four hours long. What appeared in print was thirty minutes of selected exchange, and the selection was where the artistry lay. Terkel could identify the moment in a long conversation when a person’s guard dropped, when they moved from the performance of their experience to the experience itself, and he built his excerpts around those moments.

His Working — the most widely read of his oral histories, still in print and still used in labor history courses — is built from hundreds of such moments: the moment when a hooker explains with complete seriousness and some pride that her work is a skilled profession, the moment when an executive admits that the decisions he makes determine other people’s lives and that this weight keeps him awake, the moment when a migrant farm worker describes the physical sensation of work in language of startling beauty.

Alex Haley: The Long Game

Alex Haley’s great achievement as an interviewer was patience — specifically, the patience to return to the same subject over months or years, building a relationship of trust through which genuine revelation became possible.

His interviews with Malcolm X — which began in 1962 and continued until Malcolm’s assassination in 1965 — exemplify this method. The early interviews were guarded, the subject presenting the polished Nation of Islam version of his views and his history. As the relationship deepened, as Haley demonstrated through hundreds of hours of conversation that he was genuinely interested rather than adversarial or exploitative, Malcolm began to speak more honestly about his doubts, his conflicts, his evolving understanding of his own life.

The book that resulted — The Autobiography of Malcolm X — is technically an autobiography but is functionally a product of Haley’s interviewing, because the questions shaped the narrative, the relationship enabled the honesty, and the editing organized the material into a coherent life story. Haley is the invisible but essential presence in the book.

Haley described his method for the Playboy interviews — which he conducted with figures including Miles Davis, Martin Luther King, Jr., and George Lincoln Rockwell (the American Nazi leader) — as requiring that he spend as much time as possible with the subject in their own environment, observing before interviewing. He wanted to understand how a person moved through their world before he asked them to describe it.

This observational preparation served a specific function: it allowed Haley to notice discrepancies between the subject’s stated self-understanding and their actual behavior, and to ask, diplomatically, about those discrepancies. When a public figure says one thing and does another, the gap is where the most interesting material lives.

David Remnick: The Well-Read Guest

David Remnick, who became editor of The New Yorker in 1998 but is also one of the best magazine interviewers of his generation, represents a different approach: the interview as an act of equal intellectual partnership.

Remnick comes to an interview having read everything the subject has written, watched everything they’ve done, and formed his own detailed views about it. The conversation then proceeds as a genuine exchange — two people who have thought seriously about the same subject talking to each other, with Remnick making arguments and the subject responding to them.

His long profile of Barack Obama in 2014, built from a series of interviews over multiple settings, is a masterpiece of this approach: Remnick challenges Obama’s optimism directly, presents contrary evidence, refuses to accept generalities, and the result is a portrait of a man who is more complicated and more interesting than the public persona suggested.

The technique requires something that most interviewers don’t have: genuine intellectual substance. You cannot argue intelligently with a subject about their work unless you understand their work as well as or better than most readers. This is rare in journalism, where the pressure to cover many subjects limits depth, and it is why Remnick’s interviews are as distinctive as they are.

Terry Gross: The Permission Structure

Terry Gross, who has hosted Fresh Air on NPR since 1975, operates differently from any of the above: her format is radio, her time is constrained, her audience is general, and her subjects range from film directors to scientists to politicians to musicians. What she has developed across fifty years is a specific conversational architecture — a permission structure — that makes people comfortable enough to say things they didn’t intend to say.

Gross begins interviews with factual questions — where did you grow up, what were your parents like, how did you start doing this — that seem biographical but are actually establishing what she calls the “emotional through-line.” By the time she reaches the substantive questions, she has assembled a portrait of the person’s formation that allows her to ask about the present in terms of the past: “You’ve said you grew up in a household where feelings weren’t discussed — is that why you write about them so directly now?”

This move — connecting the present to a formation narrative the subject has already given her — produces a kind of confessional candidness because the subject has already told her the relevant context. They are not being asked to reveal something new; they are being asked to make explicit a connection that they implicitly drew themselves.

Behind the differences in method and style, the great interviewers share a set of practices:

Preparation Without Script

Every great interviewer prepares obsessively and then sets the preparation aside. The research serves two purposes: it ensures that the interviewer can ask intelligent follow-ups and can recognize when a subject is being evasive; and it allows the interviewer to appear fully present rather than consulting notes, which changes the emotional register of the conversation.

The script is the enemy. An interviewer who is working through a list of prepared questions is not listening; they are waiting to ask the next question. The subject knows this and acts accordingly — they give scripted answers to scripted questions, because the exchange has established itself as performance rather than conversation.

The Productive Silence

Every great interviewer has learned to sit with silence after an answer. The natural human impulse is to fill silence — to ask the next question, to affirm what was said, to add something. But silence after an answer is an implicit invitation to continue, and subjects who continue beyond their prepared answer almost always say something more interesting than what they said first.

Terkel used silence most deliberately. In interviews that produced twenty pages of published material from two hours of conversation, significant portions of the recorded exchange were simply Terkel listening while the subject developed a thought further than they originally intended.

The Apparently Naive Question

The most effective questions are often those that appear naive: “Why did you do that?” “What did that feel like?” “What were you thinking at the time?” These questions give the subject permission to start from the beginning, which is where the authentic account lives. The sophisticated question — the one that demonstrates the interviewer’s knowledge and intelligence — tends to produce sophisticated answers, which are often performed rather than genuine.

Haley was a master of the apparently naive question. His interview with George Lincoln Rockwell — the American Nazi leader — is remarkable because Haley, who was Black, spent hours in the room with a man who believed Black people were inferior, and asked him, with every appearance of genuine curiosity, to explain why he believed what he believed. The resulting interview is disturbing and illuminating in equal measure, because Haley’s refusal to perform outrage gave Rockwell the space to reveal his ideology in its full, self-contradictory complexity.

The Moment of Exposure

Every great interview has a moment — often just a few sentences — where the subject says something they hadn’t planned to say, something that reveals rather than represents. The interviewer’s job is to recognize this moment and create the conditions for it.

The conditions are specific: the subject must feel safe enough to be honest, which requires sustained non-judgmental attention; the subject must be talking long enough that the performed version exhausts itself and the actual version takes over; the subject must encounter a question that their prepared material doesn’t address.

The third condition is the most technically demanding. It requires asking about the gap between the subject’s stated self-understanding and what the interviewer has observed — the discrepancy, the contradiction, the unresolved tension. Done gracefully, this produces the most revelatory moments in journalism. Done clumsily, it produces defensiveness and withdrawal.

Why the Form Matters

The interview is not simply journalism’s means of information extraction. It is a form with its own aesthetic and its own epistemological claims.

The claim of the great interview is that the truth about a person’s experience is accessible through conversation in ways it is not through any other method — not through biography, not through their own writing, not through third-party observation. This is because conversation is interactive: the interviewer’s responses shape the subject’s answers in real time, creating a collaborative construction of meaning that neither party could have produced alone.

This is also what makes the form treacherous. The “truth” produced in an interview is a co-creation — shaped by the interviewer’s questions, the subject’s performance, the recording and editing that follows, the context in which the piece is published. The great interviews acknowledge this implicitly by foregrounding the relationship between interviewer and subject, by making the conversation itself part of the story.

The Miles Davis interview works because Haley makes his own uncertainty visible — you can feel him adjusting his approach, trying different angles, following threads that don’t resolve. The resulting conversation is not Davis giving prepared answers to prepared questions. It is two people with different histories and different purposes trying to produce genuine exchange, and the effort itself is part of the record.

That is what a great interview is. That is what the form can be. And it is why it is worth taking seriously as a form, and worth reading carefully when it is done right.

Further reading on Playboy-X: