The Art of Asking Questions

creativityEarlier this week, Norman Hollyn and I gave a presentation to the LACPUG (Los Angeles Creative Pro User Group) on creating documentaries. Norman covered story-telling and editing, while I discussed interview planning and techniques.

In thinking about my presentation, I discovered some insights that I haven’t written about before that I want to share with you here.


Over the last 40 years, I’ve done more than 4,000 interviews for radio, TV and podcasts; both live and recorded. These have ranged in length from three to forty-five minutes.

Some have been a single guest for an entire program, others wove multiple guests into the same program, still others provided the audio commentary to illustrate a documentary.


The best attribute of an interviewer is curiosity. If you are interested in your subject, your guests will be interesting in return.

The second best attribute of an interview is an ability to enable your guests to relax. EVERYONE is scared of being on TV, of being recorded and potentially studied by others. The interviewer’s job is to get the guest to relax and focus on the conversation, not the technology surrounding them.

NOTE: At the end of this article are links to other articles I’ve written covering interview techniques for both interviewers and guests.


A documentary starts with a point of view. This flows into a log-line. The log-line evolves into your plan for the program. This plan then determines the types of guests you need and the questions you need to ask. The questions determine both your story and the emotional hook that underlies it. And the story is what viewers use to determine whether they want to invest the time to watch or not.

This doesn’t mean you can’t change your direction as you discover new ideas and guests. But, without a plan, no program will be successful; or completed.

Just as every documentary starts with a plan, every interview needs a point of view and a plan. For every interview I’ve ever done, I’ve written down what my goal for the interview is along with a series of questions that I want to ask.

Before every interview, I review:

This doesn’t mean that I can’t ask other questions. Just the opposite, if I truly stay focused on the guest and what they are saying – “in the moment,” as actors like to say – other questions will flow naturally. New thoughts and ideas will be discovered and discussed. However, my written questions form the backbone of the interview and provide me a way to make sure I ask the questions that I most want to ask.


My biggest suggestion is to stay focused. It isn’t how long the interview runs, its the answers you get during the interview that will determine its success. I never let an interview run longer than 30 minutes. By that time, everyone is tired and no one is speaking English.

If the subject is that deep or complex, take a break and come back. If you can’t get what you need in 30 minutes, your planning is wrong. Rethink and focus.

It is critical that you do your homework. Learn the subject you’ll be discussing. Not only does that improve your questions, it allows you to spot when a guest is finessing the truth and drill in deeper.

I generally structure my interviews to start with easy questions, then move into harder, more thought-provoking queries, then wrap up with the ones that focus on emotion. Why? Because the guest needs to trust you before they share anything meaningful; and trust is only built over time.

My first question for pre-recorded interviews is always: “What’s your name, title and company?” First, most people know the answer to that without any thought; though I have had a number of newly-appointed vice-presidents struggle trying to remember their title. Second, because the answer is so easy, the guest relaxes and says to themselves: “See, that wasn’t hard, I can do this.”

That relaxing is critical, if a guest is tense and second-guessing everything they say, you’ll end up with a very stiff, uninteresting interview. The key is to get your guests focused on having a conversation with you and ignore all the tech around them.

My first question for live interviews is almost always: “Describe the company you work for, what does it do?” Again, an easy question that gets the guest into thinking that this won’t be so hard.


Never ask “Yes” or “No” questions. If the guest is an amateur, once they answer “Yes,” they will stop talking. Not only do you have an answer you can’t use, but you have nowhere to go with the conversation. Everything comes to a dead stop.

For this reason, avoid questions that start with: “can,” “will,” “do,” “should”…

Much better words to use to start a question are: “who,” “what,” “when,” “where,” “why,” and “how.” In second place are: “describe,” “tell,” and “explain;” which are all variants on “what.”

The reason is that these Question Starters carry hidden emotional meanings. For example:


Thinking about this further made me realize there is an emotion arc to an interview and we can reinforce this with the questions we ask.

For example, I generally start with “What” questions:

This generally creates a fairly dramatic statement:

From there, I move into fact-gathering mode:

Next, I move into more thought-provoking, introspective questions:

Finally, after the guest and I have been working together for a while and things are going swimmingly, I get to the heart of the interview – why.


Let your interviews breathe. All too often, interviewers jump right on to the next question. Wait – ESPECIALLY if you are in the How or Why section. These are emotional and, often, the guest needs to work up the courage to share something personal or emotional.

Often, a pregnant pause gives birth to an amazing emotional response. Don’t be in a hurry to ask the next question. Silence often prompts the guest to say more, simply to fill the silence. There’s nothing wrong with waiting for a few seconds.

I never, repeat never, share questions with a guest. I may share the areas I want to discuss with them, but never the questions. Why? Because most guests will try to memorize answers; and that always comes out badly. The only time I violate this rule is if I’m talking with a regular guest and I need them to hit specific content points. But that is less an interview and more like a report.

If you are interviewing a hostile guest, there’s no harm in trying to build trust before you start slamming the hammer down. Still, if time is short and they are not interested, cut right to your most important questions – which is another reason I have a written list of questions with me so I can find and ask the most important ones, if necessary.

If you are interviewing someone who is very, very nervous, ask sidebar questions that are not pertinent, simply to get them talking about anything. I generally focus on what they do at work, which feels neutral and they start to feel comfortable talking on camera. Then, I quietly and without fanfare, return to the interview once they calm down and realize they are not going to die.

If you are interviewing a very experienced guest, they will often highjack the conversation to convey the points they want to make, rather than the points you want to cover. Most of the time, let them speak – you won’t be able to derail them anyway – you can always clean it up later in editing. Then re-ask the same question. Once they get the posturing out of their system, you can generally get some decent answers. However, in today’s world, there are many people who are all posture and no substance; in which case… um, good luck.

If you are interviewing someone who just gives yes or no answers, try to get them to open up with longer answers. If that doesn’t work, give up. I don’t lose many interviews, but if a guest just doesn’t want to cooperate by providing answers I can use, there’s no sense to have them sit there wasting the time of me and my crew.

Not everyone can, or wants to, be a television star.

Finally, if you need to stop and fix something, say something positive to your guest before you talk to the crew. They are the ones feeling exposed and wondering: “Did I do OK, coach?” Reassure your guests first, then deal with whatever chaos is breaking out on set.

When an interview is done, ALWAYS tell the guest they did a great job; even if they didn’t. If it was a solid interview, they deserve to know. And if it wasn’t, nothing they can do now will make it any better, so at least make them feel they were successful.


For me, the insights I discovered in thinking about this were the connections between the questions we ask and the quality and emotion level of the answers we get back.

Here are some other articles I’ve written on interviews that you may find useful:

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One Response to The Art of Asking Questions

  1. Larry says:

    it would be nice just to have some resources i can turn to on my phone.

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