Starting the Conversation and Keeping It Rolling

Excerpted with permission from the 6th Chapter of “Talk to Me: How to Ask Better Questions, Get Better Answers, and Interview Anyone Like a Pro” by Dean Nelson

Starting the Conversation and Keeping it Rolling IT MAY SEEM OBVIOUS, BUT the best questions are the open-ended ones, where the source has a chance to explain something, and even provide an anecdote to illustrate it. If you prepared properly, you won’t need to ask a closed-ended question like “Where did you serve in World War II?” or “What is voodoo?” On the other hand, you don’t want to ask questions that are so open-ended that they paralyze the interviewer into giving meaningless answers. You may be headed in a direction, but you want to have a clearer sense than just knowing whether you are north or south of the equator.

The quality of your questions will have a direct impact on the quality of your interview.

I mentioned in Chapter 2 that my father spent a year in a weather station on the Arctic Circle during World War II. If you want to see him hem and haw and clear phlegm awkwardly and furrow his eyebrows and look out the window, ask him, “What was it like being on the Arctic Circle for a year?” That kind of a vague question won’t get much of a response other than something equally vague, like “Cold.” Why? Because nothing is like being on the Arctic Circle for a year. To get the kind of answer you’re hoping for, you have to ask this question differently. Something like, “What did you do for food up there?” Or, “What was the most difficult part about being there?” Or, “What was the most fun part about being there?” “Did you date any of the indigenous women while you were there?” I really did ask him that last one. He gave me a politically incorrect response that I can’t really share here, but the short answer is “No.” Those kinds of questions will get you into topics such as loneliness, seeing polar bears, trading cigarettes for ivory carvings—something that will provide insight, not just an obvious fact.

This presumes, of course, that you have done enough preparation that you will have the kind of questions that will lead your source into saying something interesting. If you were going to interview my father, for instance, then you would probably already have found out where he was during the war, which means you would have done some reading about what the conditions were like up there, what the hardships were, who the inhabitants of that region are. If you know those things going in, then you’ll be more prepared to ask him to give you some insight, some understanding, some anecdotes.

Leaning forward, keeping eye contact even when taking notes, giving nonverbal cues to keep talking, looking quizzical if something doesn’t make sense—all are part of conducting an interview. Effective interviewers know how to keep the conversation going. And that’s what an ideal interview really is—a conversation.

The Tao of How

If you want to conduct a good interview, you simply must know a great deal about the topic before you start. Then when the interview does start, you can lead it more intentionally and get something useful, rather than a vague platitude.

Interviews after Olympic events are prime examples. A runner or a skier or a skater or a gymnast has just completed something that only a freak of nature could complete—something the athletes have been obsessing about for the last four years of their lives, and the interviewer asks, “What was it like to be out here?”

I rarely shout at my television, but I almost get hoarse during the Olympics. Note to reporters who interview Olympic athletes: Nothing is like being there. Ask a better question. Ask “How you were able to focus after that false start?” Ask how this victory or loss ranks with other wins and losses in that athlete’s career. Ask about the impact of having a child during training two years ago and whether it made them a different kind of competitor. Lead the conversation with specifics. The vaguer your question, the more pointless the answer.

Doing your homework allows you to ask questions that begin with “Why” or “How,” which are guaranteed to get you further than “When” or “What” or “Who” or “Where.”

Still at a loss? Here are some other tried and true paths of inquiry that are sure to get your source talking:


The line “Would you rather . . .” is the first line of a fun conversation-starting game, where you come up with strange and unrelated topics, just so the person will explain how he or she feels about something. But it’s also a good interview question.

Ira Glass was asked on a podcast what he does when he doesn’t get a satisfactory answer from a source, and one method he uses is to give people something to riff on: He’ll propose a theory to the source just to get the person thinking and responding. “I find myself in a lot of interviews saying, ’Well is it more like this or is it like this? I can imagine it would be this way or this way. What is it?’ . . . They’re forced to go somewhere—to bat away one of your theories and to run at one of the others,” he said.

I asked a tangent to this question to a former NFL player who is now the pastor of a megachurch. “Which is harder,” I asked him—“playing professional football or being a pastor?” He gave me a strange look when I asked him, because those two things aren’t even close to being related. Finally he said, “That’s a serious question?” I nodded. He thought for a few seconds and gave me a great answer about the similarities and differences of a profession where people are trying to crush you, and playing professional football. Kidding. He really did give me a thoughtful response, and it was because of the juxtaposition of the two elements. Then I followed it up with “How are they similar and how are they different?” which was just a way to get him to amplify what he previously said. The Noah Adams Ira Glass once said in an interview that if he’s ever feeling stuck, he thinks of public radio journalist Noah Adams and remembers that there is one question that you can always, always count on: “How did you think it was going to work out before it happened? And then how did it really work out?” The question works so well, Glass said, because it always yields two stories in response. “You get ’Here’s how I thought it would go,’ which is one story. And then ’Here’s how the reality is different than the dream of that.’ The jump between the two is just kind of interesting.”

“What first got you interested in . . .”

I asked this of Deepak Chopra regarding his early interest in medicine. Since I knew the answer already—the novel Arrowsmith was a big influence—it gave us a chance to discuss the power of reading, of literature, and of identifying with a character. I’m pretty sure that the band Aerosmith had little to no influence on him.


Asking sources how they want to be remembered is a chance for them to tell you what is really important. It goes right to their values and helps them formulate what they consider their greatest contributions.

“What do you make of . . .”

This gives you a chance to bring up an issue that your source can expound on. But it can’t be so narrow that it’s paralyzing. A good question would be, “What do you make of the people who say that climate change is a hoax?” I asked that of the environmental writer and activist Bill McKibben, and it launched him into a deep, articulate response. If I would have asked him, “What do you make of climate change?” he would have looked at me like my dad looked at people when they asked what it was like being in the Arctic for a year.

“What would you take if you . . .”

There are many varieties to this question. It could be the cliché “What would you want with you if you were stranded on a desert island?” or “What would you grab if you had to evacuate your home quickly?” We have had to face that question twice because of wildfires in our neighborhood, and we had little time to get out. It’s very revealing. A different riff on this was when I auditioned for a reality television show that was going to be recorded and broadcast in Sweden. That’s right, it was a Swedish reality show, and I wanted in! I made it to the second stage of auditions, thanks to a video testimonial that my son recorded of me making the case. When it came time for the Skype interview with the Swedish producer, we had a delightful conversation, but I could tell that she lost interest when she asked me, “If you come to Sweden to be part of this show, what would we find in your suitcase?” It’s a fair question. A good one. Because it reveals something about my personality. And that’s where I blew it. I said I would have lots of books and a journal. In retrospect, I know that answer put a big label on me that said “BORING!!!” (more accurately, the word in Swedish is “tråkigt”), which meant I would be a horrible reality show candidate. What should I have said? IKEA gift cards?

The Jeopardy! question

I have used this question several times, and have seen it used in job interviews. It’s “If you were a contestant on Jeopardy!, in what category would you excel?” It’s a great way to get a person talking about his or her interests, expertise, and passion.

“Help me understand . . .”

This puts your source in the role of expert, which is usually useful. If there is a difficult topic, saying something along the lines of “Help me understand how virtual currencies work” will get you further than “What is Bitcoin?”

“Excuse me?”

Use this when you really don’t understand what the person said, or if the person said something outrageous and you want to give her the opportunity to explain. It’s a great follow-up to something complicated, offensive, puzzling—it’s an invitation for the person to keep going.

“How would your life have been different . . . ?”

I love asking this question, because it makes the source consider alternatives to how his or her life turned out. It reveals a lot about the person’s personality and interests. I asked, only jokingly, this question of Kareem Abdul-Jabbar when we discussed his love for writing. “Did you ever think about how your life would have been different if you would have pursued journalism instead of basketball?” I asked him. “You could have been somebody!” He clearly saw that I was kidding, and said, “Yeah, we’ll never know.”

“You have said . . .”

This takes preparation, because it means you have read what this person has written, or listened to comments. But bringing up something someone said in the past is a chance for the person to show that he still feels strongly about the topic, or (even better) that he has changed his perspective.

“What is your favorite unimportant thing to do?”

This gets your source evaluating a number of things at once, and it often creates something personal and revealing. The interviewer Jesse Thorn asked this of the documentary filmmaker Werner Herzog. Herzog said it was watching soccer, which then allowed Thorn to delve into what interested Herzog about the sport.

Your mom was right

But there’s more to it than just asking good questions. How you ask the questions will affect the answers as well. Your mom was right—it’s not just what you say; it’s how you say it.

Remember, a good interview is a conversation, not an interrogation.


When you ask questions, you want to show your source that you are listening with your whole body. Eye contact matters. Try to keep looking at your source, while only occasionally looking down at your notes. This takes practice. When your source is speaking, lean forward a little. Let your facial expression show that you are agreeing or confused or challenging. The occasional “Mm-hmms” and “Uh-huhs” are encouragements for your source to keep going. Be very aware of whether you are cutting the person off. You will learn a lot about whether you interrupt, cut off, disrupt, or dominate the conversation if you listen to a few of your interviews. It’s humbling and instructive. That’s why you should do it.

Keeping eye contact while taking notes is an acquired skill. Like texting and driving. Wait. Bad example. Anyway, you aren’t born with this ability. But if you work at it, you’ll get better.

Those nonverbal “Uh-huhs” will keep the source going. When you relax, they relax. If the purpose of your interview is to get more than just a fact or two, then the kinds of questions you ask and the way you ask them will have a great impact on whether you hear anything useful.

That’s true for any profession. If you’re a human resources person conducting an interview with a job candidate, and you see on the person’s resume that she rode a bicycle across the United States, or climbed Machu Picchu, or won a gold medal in cup stacking (it’s a thing—I know a guy who does it), that’s a better place to start than asking “What was your first job?” At the beginning of an annual physical, my doctor (who must have looked at my chart before coming into the exam room) said, “So you’re still teaching journalism, eh? Why? I thought journalism was dead!” He didn’t say it in an aggressive or mocking manner. He said it as a means to get us open with each other.

Note from Bob:  Dean Nelson’s book was a “Page-Turner” for me.  Dean shares one fascinating story after another!   You will want to click HERE to purchase your “Talk to Me” book today! 


Dean Nelson


Dean Nelson  is the founder and director of the journalism program at Point Loma Nazarene University in San Diego. He writes occasionally for the New York Times, the Boston Globe, San Diego Magazine, Westways, Sojourners, and several other national publications. He has won several awards from the Society of Professional Journalists for his reporting, and has written or co-written 14 books. Nelson is a frequent speaker at writing workshops and retreats.


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