The Most Important Question a Writer Can Ask

I’m an introvert.  I think that many writers are.  I sit back and watch the world, process what’s happening around me and spit it back out through the written word.  I write much better than I speak.  Cocktail parties are my nightmare because I don’t do small talk well.  But even my best friends will disagree with that statement.  The reason?  Although I’m naturally shy, I can carry on a conversation with a wall.  How? I’m an excellent questioner.

My motto has always been, “Live Curious.”  This motto manifests itself in my constant need to learn far-fetched facts about our world.  It also surfaces in my constant need to know more about people.  I’ve always been a natural interviewer. I just have a knack for getting people to talk… sometimes about things they don’t even want to talk about.

After years of “interviewing” people in order to learn more about them and deflect attention away from having to talk about myself, I finally got my big break.  I was offered the opportunity to start writing newspaper and magazine articles professionally.  No problem.  I’m a natural interviewer. Right? WRONG!  My first story was about a German Shepherd named Hercules who was discovered locked in a basement closet of an abandoned house.  I was scheduled to talk to the realtor who discovered Hercules and the veterinary assistant who cared for him in the first twelve hours after his rescue.  I was also assigned four other interviews to round out the story – local law enforcement, the veterinarian who ran the clinic, the lawyer who prosecuted the individual who abandoned the dog and Hercules’ new owner – the woman who adopted him after his intense rehabilitation.

I jumped in with both feet and spent no less than twelve hours on the phone with my six sources.  As is my natural tendency, I asked A LOT of questions – too many questions.  When it was over I found myself with pages of notes and the impossible task of organizing the information into a 1,000-word article.  The editor loved the final article, but my sources were less than thrilled that I’d spent two hours on the phone with each of them and their contributions boiled down to few lines each in the story.

After years of interviews and articles, I’ve learned that it is imperative to guide an interview so that the source’s time invested is equal to the coverage on the page.  This takes practice.  People love to talk about themselves, and too many open ended questions will leave you with cramped fingers.  Three hours later, you’ll still be  typing frantically in a desperate attempt to keep up with this source’s life story.  My advice is this:

1. Do your research: Knowing your article topic inside and out will allow you to pose carefully crafted questions.  Flailing about with generality-filled questions won’t get you to the heart of your article’s topic.
2. Plan your questions:  See above.  Approach every interview with a plan.  What do you need to know from this person and what is the most efficient way to glean that information?
3. Guide the conversation: People love to talk about themselves.  Be two steps ahead of your interviewee. As they are pontificating about the joys of offshore gambling boats, be prepared with the next question which can guide them back to the topic – the cruise ships’ effects on coral colonies in the area.
4. Keep your ears open for other storylines: Just because you need to keep your interviewee focused doesn’t mean you can’t be open to tangential story ideas.  My ears perk up when Bob starts talking about the mafia contingent woven through the underbelly of the offshore gambling boat industry.  But my editor expects me to write about the dying coral colonies.  I quickly tell Bob that I would love to table this discussion and ask if he would be open to discussing it at another time.  If his answer is yes, I refocus him on the plight of Caribbean coral polyps and finish the interview.  As soon as I hang up, I save my aquatic sealife interview, do my research, write my next article proposal “Al Capone Isn’t Dead! Just Hiding in the Bowels of an Offshore Gambling Boat,” and schedule a second interview with Bob.
5. Ask the ever important Last Question: The final question I ask in every interview is “Is there anything I haven’t asked you about that I need to know?”  I know I just scolded you for open-ended questions, but this particular open-ended gem is magical. Often sources will sit quietly for a beat and then launch into the perfectly crafted conclusion to my article.  The source’s brain will subconsciously summarize the “heart of the matter” and spit it back out back out in a well-crafted sound bite.  If I worked in radio, the interviewee’s answer to the Last Question would be the final quotation that puts a shiny red bow around the end of my story.  However, be forewarned.  You, as the writer, still need to do the work because sometimes… there’s no shiny bow.  Upon hearing the Last Question, Bob might launch right back into his story about a stellar round of Texas Hold ‘Em on seas with 16-foot waves.  If that’s the case see Step 3, and think twice about that Al Capone story.  Maybe another three hours on the phone with Bob just isn’t worth it!

Happy questioning and writing!