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How I conduct interviews

Published March 21, 2024 

Note — every mention of “subject” in this article refers to the interviewee, not the general topic at hand.



I've interviewed hundreds of artists, entrepreneurs, and leaders throughout my career, and have had the opportunity to mentor several of my peers in the craft.


What I've found is that the best interviews aren't just a series of questions and answers; they create a dynamic space for dialogue, debate, and discovery. At their best, they can spark new ideas, inspire new actions, and change the way people think.


Below, I break down my four-part framework for conducting interviews. I'll focus primarily on the context of longform, in-depth reporting — assuming that you have anywhere from 30 to 120 minutes to sit down with a leader, entrepreneur, technologist, or artist, and explore their unique perspective on the world.


These are the kinds of interviews where you're not just looking for soundbites or factual information, but are also trying to develop a deeper understanding of a person's mind and motivations. You want to create room for insights to flourish, and for unexpected connections to be made.


It's a lot of work, but the payoff is worth it.



0. Understand your role


The best interviewers are always mindful of their role.


Conversation is a unique alchemy that can catalyze a shared journey of curiosity, connection, and respect between two people. An interview is a kind of conversation, with a specific purpose. Unlike a casual chat with a friend or a heated debate with an opponent, an interview is a deliberate, focused attempt to learn from someone who knows more than you do about a particular topic.


That means the interviewer has a unique responsibility. As an interviewer, your job is not to be the star of the show. It's not to impress your subject with your own knowledge or charm.


Instead, it's to be a conduit between your subject and your audience. You're there to ask the questions that your readers or listeners would ask if they had the chance, and to draw out the narratives that will help them better understand the topic at hand, in a new and revealing way.


This requires a tricky balance of engagement and detachment. While you need to be genuinely curious about your subject and their work — actively listening during interviews, following threads wherever they lead — you also need to maintain a certain distance. You're not there to be your subject's friend, or to validate their opinions. You're there to be an objective, impartial observer. That means being willing to ask tough questions, challenge assumptions, push back when necessary, and, most importantly, keep your own biases and opinions in check.


All of this makes an interviewer’s job uniquely tough. But when interviewers embrace this job with curiosity, humility, and diligence, it can lead to conversations that go beyond the informative and become truly transformative for their readers, and for their field at large.




1. Do your research


As the length of this article suggests, at least 50% of the work behind great interviews is rooted in careful preparation and research.

In line with my systems approach to reporting, I treat preparing for an interview like conducting a literature review for an academic paper. You wouldn't just dive into writing the paper without first taking the time to understand the existing research and theories in your field. You need to know where your own work fits into the larger discourse — including what's already been said, and what questions remain unanswered.


The same is true for interviews. Before I sit down with my subject, I do the necessary research to ensure I have a clear grasp on three core areas:

  • My subject’s background and influences, and the key themes and ideas that define their work.

  • The interests, needs, and challenges of the audience I’m writing for.

  • The larger landscape of my subject’s industry or field.

This kind of preparation takes time, but it's essential if you want to ask the kinds of questions that really push the conversation forward. It also shows your subject that you're taking the interview seriously, which can go a long way in building rapport and trust.


A. Know your subject


The first and most obvious step in preparing for an interview is to research your subject. This means going beyond just scanning their Wikipedia bio or social profiles; your conversation should build on and/or challenge ideas that your subject has already presented to the world.


Start by reading or watching any previous interviews, talks, or public engagements they've done. Look for the key themes that come up repeatedly, and pay attention to how they frame their own work and expertise.


See if you can also identify what your subject hasn’t said yet. Where are the gaps in your subject’s public persona? What questions have previous interviewers failed to ask?


These are the areas where you can really add value by pushing the wider discourse of your field in genuinely new directions. If you want your interview to stand out, make sure it's never happened before.


B. Know your audience


The second pillar of good interview research — and an often overlooked one, from my experience — is understanding your audience.


After all, you're not just having this conversation for your own benefit. Even if you’re publishing the interview to a newsletter with only two subscribers, you’re doing it because you think its underlying insights are worth sharing with other people.


So, before you sit down with your subject, you need to have a crystal-clear idea of who your intended audience is and what they care about. What keeps them up at night? What are they talking about on social media? What aspects of your subject's work or expertise are most relevant and interesting to them?


This is where market research comes in handy. If you're doing this interview for a particular publication, talk to your editor about who their target audience is, and how that might influence what they're looking for in a story. If you're interviewing for your own channels, take some time to analyze your existing or target readership, and the kinds of content that resonates with them. This can be as simple as visiting a social media account that you know your readers follow, and seeing which kinds of posts get the most engagement and why.


The goal here isn't to pander to the crowd, nor to compromise your own journalistic integrity. It’s to ensure that your conversation will be engaging and relevant to the people whom you are ultimately servicing in your work.


C. Know the landscape


The final pillar of interview research involves zooming out beyond just your subject’s individual work and expertise, and understanding the larger context in which your subject operates.


In your back pocket, you should have a good sense of the current state of the field, including how its big ideas and debates have evolved over time. What are the most pressing challenges and opportunities facing the field's practitioners today? The new technologies, business models, and cultural shifts that might disrupt the status quo?


The exact depth and breadth of this area of research will vary widely, depending on the nature of the interview and your own level of expertise. If you're interviewing someone in a field you know well — like I do with the music business — you may not need to spend as much time here.


If you’re relatively new to the field, fear not: Asking your subject for their opinion on the most pivotal issues at hand often makes for a great interview question, especially for a layman audience.


That said, at minimum, it's worth putting in the effort to develop a sense of informed curiosity about the world your subject inhabits. It helps you develop more insightful questions, and also helps your audience understand why your subject's work matters and how it fits into the bigger picture of their industry.


D. Prepare your own hypothesis


After you’ve finished conducting your research, take a step back and consider your overall hypothesis for the interview topic. What do you think are the most important issues to explore — and what do you expect your subject to say about these issues?


To be clear, having a hypothesis does NOT mean you should go into the interview with a rigid agenda. It's a starting point of inquiry, not an ending point of belief. The primary function of this hypothesis step is to help guide your questioning, and keep the conversation focused on what you believe matters most.


As you listen to your subject's responses, pay attention to how they line up with your initial predictions. Are they confirming your suspicions, or diverging from your assumptions? Are they introducing new ideas or perspectives that you hadn't previously considered?


If your hypothesis is confirmed, you have a clear, straightforward narrative to build your story around. And if it's challenged or upended, that's even more exciting: It means you've stumbled onto something unexpected that could shift your thesis in a whole new direction.




2. Ask the right questions


With your research and hypothesis in tow, you can start to craft a list of more specific questions to reference during your interview.


Some basic guiding principles that have served me well:


A. Start with the easy stuff


Begin with a few lighter, more casual questions to put your subject at ease. You could ask about their surroundings, or their day so far. Or, if you want to show that you've done your homework, you could reference something quirky or interesting they've posted on social media recently. The goal is to establish rapport, set a conversational tone, and demonstrate your engaged curiosity.

B. Then, go deep


After easing in, don't be afraid to pose more expansive questions that get at the heart of your subject's experiences, motivations, and beliefs. Ask about their hopes for the future of their field, the lessons they've learned from past career challenges, or the unsolved problems that keep them up at night.

C. Challenge assumptions — including your own


If there are commonly held beliefs or narratives surrounding your subject or their work, an interview is a ripe opportunity to interrogate those ideas. Ask questions that might compel your subject to reconsider their own assumptions, defend their positions in new ways, or even critique the hypotheses that you yourself have developed about their field. 

*In these situations, it's crucial to ensure that your questions are open-ended and not leading. This means avoiding questions that suggest a particular answer or bias, and instead framing them in a way that encourages your subject to provide their own unique perspective. For example, instead of asking, "Don't you think that the current narrative around your work is misleading?" which implies a specific viewpoint, you could ask, "How do you feel about the way your work is currently being perceived or discussed in your field?"

D. End with an open mind


As the interview winds down, ask questions that invite reflection, or open up new future lines of inquiry. What hasn't the interview covered yet that your subject feels is important to understand? Who else does your subject think you should talk to for additional insights, especially underrepresented perspectives that need to be heard?



3. Feel — and control — the flow


A great interview is a balancing act between preparation and spontaneity. You need a clear sense of what you want to learn, while also leaving room for insights and ideas to emerge in the moment. Every interview will have its unique flow based on the participants’ interests, moods, and personalities on that particular day.

For this reason, I rarely send interview questions to subjects in advance. This approach helps maintain the integrity of the conversation, ensuring that the subject’s responses are genuine, spontaneous, and not overly rehearsed. (There are a few exceptions, such as interviews for college classroom settings where focus and structure are paramount for effective learning experiences.)


The meat of the conversation is where your skills and preparation as an interviewer really come into play, when it comes to guiding and focusing the discussion effectively. There are a few key tips to keep in mind:


A. Remember your role


Once again: The interview is not about you. You are a conduit between your subject and your audience.


You can certainly express appreciation for your subject's work or show genuine interest in what they have to say. But ultimately, your job is to ask questions, to listen, and to steer the discussion towards valuable insights, not to compete with your subject for knowledge or airtime.


B. Listen actively and adapt


While an interview is a kind of conversation, the art of interviewing can also be understood as the art of listening.


You can't predict every response, and the most interesting moments often come from unexpected tangents. If your subject says something intriguing or surprising, don’t be afraid to follow up with "why?" or "can you elaborate?" Some of the best questions in an interview are the ones that build on your subject's previous answers, digging deeper into the motivations and insights that lie beneath the surface.


C. Bridge irrelevant tangents back to the core conversation


If your subject veers too off-topic or avoids a question, acknowledge their point and gently steer the discussion back. You can say something like, "That's fascinating, and I want to return to that later. But first, I want to make sure we cover X, which is something you mentioned earlier and that I think is crucial for our audience to understand."


If they still resist, be direct but respectful, emphasizing the topic's importance to your audience and to the field at large. Of course, if they won't budge, you can move on and find other ways to get the information you need.



4. Follow up


The responsibility of an interviewer to seek context and truth extends well beyond the interview itself. In fact, some of the most important steps in the interview process actually happen after you’ve said your goodbyes and stopped recording.

After every interview, I would recommend the following steps:

A. Send a thank-you note


This simple gesture demonstrates that you value your subject’s time and insights, and keeps the line of communication open for future interactions.

B. Schedule dedicated time for additional research


Explore the new or unexpected questions that you or your subject raised during the interview. This could involve deeper background context, contrasting perspectives, or other relevant case studies that can help you paint a more complete picture of the topic at hand.

C. Fact-check — then fact-check again


If your subject cited specific statistics or quotes during the interview, don't just take their word for it. Do your due diligence and verify the accuracy of that information with reputable sources. This follow-up work is a critical component of what separates a good interview from a great one — facilitating a piece of reporting that is comprehensive, compelling, and credible for your audience.



Conclusion: Why interview?

Whether you're a seasoned journalist, or just someone looking to have more meaningful discussions in your personal or professional life, I hope you find something valuable in this process.

Good interviewing is a skill that I am still mastering to this day, but one that I believe is accessible to anyone willing to put in the work. Especially in a world that often feels increasingly polarized and divided, the deep, empathetic listening associated with great interviews feels more important than ever. It can help us build bridges across differences, expand our own understanding of the world, and, ultimately, tell stories that matter.

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