How to Ask Great Questions in Interviews

You've done the research. You've built the rapport. The subject is finally leaning in, ready to speak honestly. Everything you've prepared for — the knowledge, the relationship, the context — has led to this single moment. And now comes the thing that all that preparation makes possible: the question itself.

Because here's what most people don't realize: preparation and questioning aren't separate skills. The research doesn't end when the conversation begins; it transforms. It becomes the ground that allows you to ask with precision. The trust you've built gives you permission to go deeper. And the non-negotiables you identified before you walked in the door now become the backbone of how you design what you're actually going to say.

The question is the basic unit of the interview. Everything else — the preparation, the trust-building, the listening — exists in service of the moment when you ask something and another human being tells you something true. But here's the catch: asking a question that actually works is a craft. It has structure, principles, and a psychology as rich as any other element of the interview. Get the question right, and the interview opens up. Get it wrong, and no amount of charm or preparation will save you.

Open and Closed Questions: The Nuanced Reality

The received wisdom is simple: open-ended questions good, closed questions bad. Open questions invite narrative; closed questions get yes or no. Use open questions always. This is the advice in every journalism textbook, and it is — like most received wisdom — about two-thirds right.

The part it gets wrong is significant.

Open questions are better at generating story, texture, and unexpected territory. "What was that period like for you?" invites the subject to construct a narrative, choose the details, decide what mattered. You can't predict the answer, which is part of the point. The subject is handed the wheel and they drive somewhere you might not have thought to go.

But open questions have a structural weakness: they allow the subject to avoid. A politician asked "What's your position on housing policy?" can give you eleven minutes on the virtues of bipartisan dialogue without ever committing to a specific view. A CEO asked "Tell me about the company's culture" can generate a warm, glossy non-answer that sounds substantive and contains nothing checkable. Open questions are escape routes for the skilled deflector, and skilled deflectors know how to use them.

This is where the closed question — the one most interviewers have been trained to distrust — becomes a precision instrument.

Closed questions force commitment. "Did you know about the safety report before the product launched?" cannot be answered with a speech about corporate culture. It demands a yes or a no. And that yes or no becomes the foundation for everything that follows. Once a subject has committed to a factual position — on the record, in their own words — you have something to work with. You can follow the no with the document that contradicts it. You can follow the yes with "Then why did you proceed?"

The closed question is the investigative interviewer's lever. It locks the door of the room the subject was about to exit.

Closed questions also clarify timeline and fact. In a complex narrative interview, moments of ambiguity accumulate. You think someone is saying they left the organization before the incident; they might mean after. A closed question cuts through: "Just to be clear — were you still at the company when this happened?" That's not a sophisticated question. It's an essential one. Open questions build the story; closed questions verify the architecture.

Closed questions can, paradoxically, unlock emotion. This sounds backwards, but consider: "Were you frightened?" is a closed question with a yes/no structure. But in practice, very few people say simply "yes" or "no" to a question about their emotional experience. They say "yes, and —" and what follows the "and" is often exactly what you were trying to reach. The closed question gives the subject a concrete platform to push off from. Some subjects, especially reticent ones, find the open-ended invitation of "How did you feel?" overwhelming or overly intimate. The same subjects will answer "Were you scared?" readily — and then, once the door is open, they'll tell you everything.

The practical principle: use open questions to generate and explore; use closed questions to commit, verify, and unlock. The best interviewers switch between them fluidly, reading what each moment requires. Treating open questions as categorically superior is like treating a hammer as a better tool than a scalpel — the question is what you're building.

The Anatomy of a Powerful Question

Strip away the question type debates and you're left with fundamentals: what actually makes a question work?

Three qualities matter above all others: specificity, simplicity, and emotional resonance. They work together, and the absence of any one of them tends to produce a question that lands flat.

Specificity is the quality that separates homework from improvisation. Jodi Kantor, preparing to interview Barack and Michelle Obama, didn't ask, "What are your thoughts on gender equality in your marriage?" She had done enough research to understand that equality was a genuine tension in the Obama household — that the institutional weight of the presidency was not distributed symmetrically. So she asked: "How do you have an equal marriage when one person is president?" That question could only have come from someone who had done real work. And because it was specific, it was nearly impossible to answer with something generic. Specificity corners people — not in a hostile way, but in the sense that it removes the escape hatches.

Simplicity is the quality that beginning interviewers most consistently underestimate. The longer a question is, the more surface area it gives a subject to wander into. A short, clean question creates a kind of narrative pressure — the silence that follows it belongs to the subject, and they have to fill it. "What was that day like?" is almost uncomfortably simple. It's also almost impossible to answer briefly. Whereas "Can you walk me through the sequence of events that led to your decision and describe what you were feeling during that period?" gives the subject so many places to hide that you'll get a press release in response.

Emotional resonance is the hardest quality to engineer deliberately, because it depends on genuine understanding of your subject's experience. A question resonates emotionally when it names something the subject actually cares about — not what you assume they should care about, but what the research and conversation have revealed they care about. This is why cookie-cutter interview templates produce cookie-cutter answers. A question that could be asked of anyone lands differently than one that could only be asked of this person, in this moment.

graph TD
    A[Powerful Question] --> B[Specificity]
    A --> C[Simplicity]
    A --> D[Emotional Resonance]
    B --> E[Removes escape routes]
    C --> F[Creates narrative pressure]
    D --> G[Names what subject actually cares about]
    E --> H[Surprising, honest answer]
    F --> H
    G --> H

The Compound Question: A Self-Inflicted Wound

Nothing kills an interview faster than the compound question. You know the one: "Can you tell me about your childhood, and how that shaped your career, and whether you think you'd have made different choices if you'd grown up somewhere else, and also what advice you'd give to young people today?"

The subject answers the last part. Or the easiest part. Or the safest part. The interviewer doesn't know which part they answered, so the follow-up goes sideways. Two minutes have been wasted on a question that generated nothing useful.

The compound question is almost always a sign of anxiety — the interviewer's anxiety. You're not sure which question to ask, so you ask all of them. Or you're afraid of silence, so you keep talking until the question has enough cushioning to feel comfortable. The cure is what the writing teacher tells the student: kill your darlings. You have three questions? Ask the best one. Trust that the others will find their place later, or won't need to be asked at all, because the first one opened something unexpected.

Investigative journalist Julian Sher calls these "double-barreled questions" and identifies them as one of the most common ways interviewers inadvertently give subjects an escape route. If you ask two things at once, the subject can answer one and you have no legitimate way to demand they address the other — they've technically answered your question. It's a gift you gave them without meaning to.

The discipline here is brutal and necessary: one question at a time. Always. Even when it feels rude. Even when the silence afterward makes you squirm. Ask one thing, then stop talking.

Question Sequencing: The Interview as Narrative Arc

A great interview has a shape. It isn't just a list of questions fired in sequence until the time runs out. It has movement — something like the arc of a story, with an opening that establishes trust, a middle that generates depth, and an end that reaches for meaning.

Max Linsky, who interviews professional interviewers on the Longform Podcast, describes long interviews as having three acts: "Know where you want to start, where you want to end, and how you want to get there." This isn't just structural advice — it's psychological. When you have a sense of where you're going, you can afford to let the conversation roam. You're not anxious about covering ground because you trust the shape. That trust communicates itself to your subject.

The classic sequencing principle is the funnel technique: start broad, narrow to specifics, and know when to reverse.

The opening questions should be low-stakes and expansive. You're warming up the room. The subject is testing you — figuring out whether you're trustworthy, whether you actually know what you're talking about, whether they'll regret agreeing to this. Big, easy questions at the start serve two purposes: they give the subject a chance to establish their voice and comfort level, and they give you time to calibrate. "Tell me how you got started in all this" is a good early question not because it's artful, but because it's genuinely useful — and almost everyone has something to say about their origins.

As the interview develops, you narrow. The broad "tell me about your work" becomes "tell me about that particular decision." The "what was that period like for you" becomes "what were you thinking on that specific afternoon?" Specificity increases as trust increases — the subject becomes willing to go to places they wouldn't have visited in the first fifteen minutes.

Then, paradoxically, you broaden again at the end. This is where you reach for the reflective questions: What does this mean to you now? What would you do differently? What do you want people to understand about this that they never ask about? These questions give the subject permission to step back from the narrative and reflect — and that's often where the most memorable material lives.

graph LR
    A[Opening: Broad, Low-Stakes] --> B[Middle: Narrowing to Specifics]
    B --> C[Deep: Maximum Specificity]
    C --> D[Closing: Broaden to Meaning]
    A --> |builds trust| B
    B --> |generates depth| C
    C --> |unlocks reflection| D

Hypothetical and Reflective Questions: The Power of Stepping Sideways

Some of the most revealing questions are ones that technically don't ask about what happened. They ask about what might have happened, or what the subject now understands that they didn't then. These are the hypothetical and reflective questions, and they have a particular magic that direct questions sometimes can't achieve.

"What would you have done differently?" is one of the most underrated questions in the interviewer's toolkit. On the surface, it's asking about a counterfactual — something that never occurred. In practice, it's asking the subject to evaluate their own choices from a position of hindsight. That evaluation requires vulnerability. It requires them to name what they got wrong or what they wish had been different. And because it's framed as reflection rather than accusation, subjects will often answer it far more honestly than they'd answer "Why did you make that decision?"

The reflective question works because it changes the subject's relationship to the material. Instead of defending a position in the present, they're examining a moment from the past. The emotional distance is slightly greater, and people tend to be more honest at a slight remove.

Hypothetical questions work differently. "If you were starting over today, knowing what you know now, what would you do?" isn't just a thought experiment — it reveals what the subject values, what they've concluded, what their real priorities are. Structuring this kind of question carefully, as part of a deliberate approach to interview design, is something the best science journalists do routinely — not as a gimmick, but because hypotheticals unlock reasoning that purely factual questions never reach.

A note of caution: hypothetical questions can feel abstract or untethered if used too early. They belong in the later stages of the interview, after you've established enough concrete ground that the hypothetical feels meaningful rather than floating in air.

The Follow-Up: The Most Underrated Question in the Room

Here is the honest truth about most interviews: the prepared questions are table stakes. They get you in the room and give you a structure. The interview itself is made of follow-up questions — the ones you couldn't have written in advance, because they respond to what the subject actually said rather than what you expected them to say.

A follow-up question is simply: "I heard what you just said, and I want more of it." It might be as simple as repeating the last phrase the subject said with a questioning inflection. It might be "Can you say more about that?" Or it might be a genuine leap — you heard something in their last answer that connects to something you know from your research, and you chase it.

The mechanics of a good follow-up are specific. You are building a new question directly out of the subject's last answer — not returning to your list, not pivoting to a related topic, but drilling into the precise word or moment that snagged your attention. The subject says, "It was a difficult transition." You heard the word transition. What were they transitioning from? To? What made it difficult rather than merely complicated? The follow-up zeroes in: "When you say 'transition' — what were you moving away from?" That question could not have been prepared in advance. It exists only because you were actually listening.

This is also where the closed question re-enters with force. A subject gives you a rich, open-ended answer — and somewhere in it, they implied something significant without quite saying it. The follow-up closed question pins it down: "So when that happened, were you still in the role?" "Did you tell anyone at the time?" The follow-up closed question takes the gift of their open answer and secures the specific fact that makes it meaningful.

The follow-up is the test of whether you're actually listening. If you're looking at your notes when the subject is saying something extraordinary, you'll miss it. And if you do miss it, you'll move on to the next prepared question while the real story sits unasked.

Real-Time Improvisation: Letting Go of the List

Every working journalist has had the experience of walking into an interview with a carefully prepared question list and watching the subject say something in the first five minutes that changes everything. Maybe they reveal something you didn't know. Maybe they use a word that carries a weight you want to unpack. Maybe they tell a story that connects two things you had thought were separate. Whatever it is, the prepared list suddenly feels like last year's map.

This is not a failure of preparation. It's preparation working correctly. You built the question list to understand the territory well enough to improvise inside it. Now you're improvising.

Max Linsky puts it plainly: "Do your research and write down tons and tons of questions. Only bring 15-20 to the interview. Only ask 10 of them. If you need to ask all 20, you're not having a conversation." What fills the space left by the unasked questions? Real-time responses to what's actually being said. The list was never the interview; it was the scaffold you use to erect the interview, and scaffolding comes down.

The discipline of real-time improvisation is harder than it sounds, because you're doing several things simultaneously: listening to what's being said, assessing what it means, connecting it to what you know, and formulating a response — all while maintaining the social surface of a relaxed conversation. It's genuinely difficult, and the interviewers who make it look effortless have done hundreds of interviews to build that fluency.

The key is maintaining what you might call your throughline — the central question your interview is trying to answer. Not a specific question on your list, but the deeper animating inquiry behind all of them. What do you actually want to understand about this person? As long as you're moving toward that, you can afford to follow tangents, chase unexpected revelations, and set aside large sections of your prepared material. The throughline will pull you back.

The Open Notebook's guide on steering interviews describes this as the difference between being in control and being controlling. The best interviewers are in control — they know where they're going and can navigate back there from almost anywhere. But they're not controlling in the sense of forcing the conversation along a predetermined path. They allow the unexpected, because the unexpected is usually where the story actually lives.

When you abandon your question list, don't abandon the physical list. Glancing at it periodically anchors you and signals to the subject that there's structure to this conversation. The list is a security blanket you're allowed to put down and pick up. The difference between a professional and a beginner is that the professional knows when to put it down.

Question Brevity: Why Shorter Is Almost Always Better

There's a counter-intuitive principle at work here, and it's worth stating plainly: the longer your question, the shorter the answer tends to be. The shorter your question, the longer the answer tends to be.

This works because of where the narrative pressure falls. A long question exhausts itself. By the time you've finished asking it, the subject has already started mentally drafting their response, and because your question was complex, their response will address the complexity — efficiently, defensively, in as organized a way as possible. A short question, especially one with emotional charge, creates pressure that the subject has to relieve by talking. The vacuum demands to be filled.

Think about the simplest questions you've ever been asked. "What happened?" "How did that feel?" "Then what?" They're almost embarrassingly uncomplicated. They're also nearly impossible to answer in a single sentence. They hand the conversational responsibility entirely to the subject, which is exactly where you want it.

Investigative journalists learn this the hard way: loaded questions — questions stuffed with the interviewer's assumptions, adjectives, and framing — give the subject something to argue with rather than something to answer. "Basic is beautiful," as Sher puts it. Strip the question down to its essential request, and you'll often be surprised how much more you get.

The practical exercise: after you write a question, count the words. If it's more than twenty, see if you can cut it in half. If it's more than forty, something has definitely gone wrong.

The Unasked Question: Implication and What You Don't Say

There is a category of question so advanced it barely deserves the name — the implied question, the half-finished thought, the statement that stops just short of asking anything and waits for the subject to complete it.

This technique works because of how language creates pressure. When a sentence trails off, or stops at a point where more is clearly expected, a gap opens in the conversation. People are wired to close gaps — not through silence, but through speech. If you make a statement that implies a question but don't complete the question, a significant portion of your subjects will complete it for you — often in a direction more honest than anything they'd have said in response to a direct question.

A direct question is, by definition, a thing the subject can see coming and prepare to deflect. An implied question doesn't give them a visible target. "I imagine that period must have been complicated" isn't a question. But watch what follows it: the subject will tell you what kind of complicated it was, often in detail they wouldn't have offered if you'd asked "Was that a difficult period for you?" The implication invites; the direct question can feel like a gate to push through.

There's a version of this that borders on theater: the journalist who makes a slightly incorrect statement to prompt a correction. "So you resigned from the company" — when you know they were fired — draws out a more detailed and emotionally charged account than "Tell me about your departure from the company." This technique requires care; used manipulatively, it damages trust and sometimes produces false information. But used judiciously, it's a way of giving the subject something specific to respond to, something they can't simply accept and move on from.

What you'll notice is that all of these techniques — the trailing statement, the strategic misstatement, the half-question — create a certain kind of pressure in the conversational space. That pressure is real, and it's distinct from silence itself. Silence creates a different kind of discomfort: a social vacuum that demands to be filled. The psychology of how subjects respond to silence — why they keep talking when an interviewer stops, and how that moment of wordlessness can be more powerful than any question — is worth its own exploration, and we'll give it exactly that in the next section.

For now, the principle: language can be as productive at its edges as at its center. A sentence that doesn't quite complete itself, a statement that leans toward a question without becoming one — these are linguistic tools that belong in the advanced interviewer's kit.

Putting It Together: Question Design as Ongoing Practice

The craft of question design doesn't resolve into a checklist. There's no formula that will produce a powerful question every time. What develops, over hundreds of interviews, is something closer to taste — an intuition about which kind of question the moment requires, a feel for when to push and when to wait, an ear for the word in the subject's answer that deserves to be chased.

But taste can be cultivated deliberately. The working practice is simple: after every interview, review your questions. Which ones generated the most? Which ones fell flat? Which ones do you wish you'd asked but didn't? Amanda Hess's observation applies here as much as anywhere: "I don't think I've ever regretted asking a question, but I've regretted a bunch of questions I didn't ask." The question you were afraid to ask is almost always worth asking. The question you kept softening to make it more comfortable is almost always less effective than the direct version.

The deepest principle here connects back to what this course is really about: the interview is a relationship, and questions are how you signal the nature of that relationship. A vague question signals that you haven't really thought about this person. A compound question signals that you're anxious. A precise, simple, well-placed question — whether open or closed, prepared or improvised — signals that you have been paying attention: that you understand something about who this person is and what they've been through. That signal changes what you get back.

Specificity, in a question, is a form of respect. And respect, as it turns out, is surprisingly good journalism.