Art of the Interview: Asking the right questions, part II

Art of the Interview is an occasional series designed to help young journalists build critical interviewing skills.

The man in the red jumpsuit was like a secret written in code. And I couldn’t find the key.

As his appointed guard sat in the corner of the room, doodling on a notebook and obviously weary of the interview that had lasted for nearly an hour, I kept peppering my source — a convicted drug dealer — with questions. I knew what had landed him in prison, when he’d been convicted, and where he’d hoped his career would take him. But, I had the nagging feeling I didn’t know who he really was.

The interview was for the final installment of a series I was writing about drug trafficking on Interstate 80. I’d covered the issue from a variety of perspectives, but for this last piece, I wanted to make the story human. And, for that, I’d have to get into the mind of a person who’d sold drugs for a living. That task was proving harder than expected.

Finally, in an act of desperation, I asked the most obvious question I could think of: Why?

His answer opened up the story. His career in selling drugs, he replied, was rooted in his lifelong desire to be a businessman. Suddenly, I had a new way to approach the story. I had a glimpse into my source’s motivations, which stemmed from a real human desire to succeed and belong. He was no longer a piece of a problem, but a person with whom readers could identify.

In part I of this piece, we examined the basic questions that ensure you understand an issue completely and accurately. Now, we’ll look at questions that can help you dive deeper and reveal the human side of any issue.


Our deepest motivations are rooted in beliefs, values, and emotions. By sounding a person’s motivations, then, you’re actually tapping into the core traits that make us human.

They can be hard to uncover, though. Our beliefs, values, and emotions are deeply personal, so we often mask them with more mundane explanations for our decisions. It often requires patience and persistence to coax out someone’s deepest motivations.

Some questions that seek to understand motivation include:

  • Why did [this thing/action] appeal to you? Why did you do it?
  • Why did [this thing/action] repel you? Why did you choose to not do it?
  • What did/do you hope to accomplish by doing this? What did/do you hope will happen as a result?


Our emotions don’t only motivate us. They can also thwart us, confound us, pain us, or give us pause. Asking about a person’s emotions — even the so-called “negative” ones that we tend to downplay — can yield rare insights.

Tactfully asking this kind of question requires delicacy and common sense. You want to convey your source’s most difficult emotions with dignity and respect, not cause them pain by asking artless questions about their suffering.

For people who are grieving, ask them what the deceased meant to them. What about them do they remember? What made their lives meaningful? What did they learn from that person? These questions will yield richer human insights, and they allow the survivors to remember them in they way they want them to be remembered.

Emotions are deeply personal things, so it requires time and patience to draw them out. When probing into a source’s more powerful emotions, asking questions that obliquely point to those feelings are often more effective than direct questioning. These questions include:

  • What was going through your mind when this happened? What was the first thing you thought of?
  • How has this experience changed you?
  • Where do you see yourself going from here? What’s next for you in your life?

Being human

If you want your sources to open up to you, you have to be willing to open up to them a little, too.

My best memories from my newspaper career are the interviews that felt more like conversations. When you allow yourself, the interviewer, to be human, you give permission for the interviewee to be human, too.

Photo credit: Pixabay


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