If you don’t ask the right questions…
I long thought writing and journalism were about fact-finding and observation. You had to live the story, to have an interesting life, and as a result, great writing would just happen. If I chased the story, the story would just pour out of me.
I’m here to tell you, I’ve been in some crazy situations where the words that followed were far from compelling, and I’ve managed to turn seemingly boring bar conversations into some of my best prose. The secret for me has been in the art of asking questions. The right questions get to the real story.
All too often, I’m chatting with a writer or a reporter and they ask the obvious questions, and in turn, they get the obvious answers. Those that dig a bit deeper are the ones that will get their subjects to open up in new and interesting ways.
The Masters: Tim Ferriss and Cal Fussman
I’m a huge fan of Tim Ferriss’ podcast. He interviews the “world’s top performers” in an effort to get to the habits that have made them so successful. One could argue Tim is not a journalist, but he is a master at getting highly interesting people to open up about things they wouldn’t normally talk about.
In one episode of his podcast, he interviews Cal Fussman, the writer from Esquire and New York Times bestseller, about how he too became a master at asking questions. Cal shares his story about traveling around the world on a shoe-string budget. He’d get on a train somewhere, and he’d walk down the aisle with the intention of sitting next to someone that might invite him into their home for a meal or a place to sleep wherever it was that he was going. He’d pass by beautiful women he could sit next to, knowing full well that he had a better chance of getting a free meal from the old guy sitting by himself in the back.
Once he sat down, it was on – he had to bridge language and cultural differences in an effort to make such a deep connection with this person that he might score a bed or a dinner out of the deal. It was in those interactions that he learned to ask the questions that helped hone his craft as a journalist. Check out the podcast episode for the incredible story of how he used this same tactic to get Mikhail Gorbachev, Former General Secretary of the Communist Party of the Soviet Union, to turn a 10-minute interview into a three-hour conversation.
People love to talk about themselves. I’m no exception but rarely do I open up to someone just for the sake of conversation. If someone asks me about myself, my opinions, my beliefs, I’m happy to share if they’re genuinely interested in listening. But I hear the same questions all the time: “Who are you, what do you do, etc.” The same is true of most interview subjects. If they’re worth interviewing, they’ve been asked the same handful of questions hundreds of times, and when all you get is canned answers, don’t be surprised.
Question the familiar
I’ve found one of the best places to practice my question asking skills is on people I already know well. We all have a history with the people that we know and love, but how much do we really know about the people we surround ourselves with. There are hundreds of thousands of stories your parents, siblings, lovers have never told you. They may not even be aware that you don’t know these stories, so try asking them different questions next time your sitting around the dinner table. Instead of the age-old “how was your day today,” come out of nowhere with something like “tell me about the thing that terrifies you the most?”
Leading questions are another blog post altogether. If you can find the answer to your question in the public domain, that means the subject you’re interviewing has heard it too many times. Don’t be afraid to google a bit before an interview, but instead of looking for what they’ve already talked about, look for what they haven’t shared.
Tell me about Israel
I’ve recently been working from Tel Aviv, Israel for a few weeks. I’m not Jewish, and I have a very surface level understanding of the history of the country, the current political atmosphere, and the tensions between Jew and Arab. As a writer, I long to understand. The best way for me to do that is to have deep and meaningful conversations with people. I’ve been learning to ask the right questions to get people to open up about their politics, their hopes, and fears for the future. In this particular situation, ignorance is actually a gift, as I’m able to lead without a preconceived set of beliefs, whereby my “subject” can freely open up without fear that I’ll disagree with their opinion.
I have started many a conversation by asking for a history lesson. As that history creeps closer to the modern day, I’m able to inject the little “well what do you think”. As a result, I’m starting to understand the different ways through which modern Israelis view their country. Perhaps my questions will need to change when I go to Palestine.
Questions are one of the greatest tools we have as writers. It’s often said that you don’t think as well as you think you do if you can’t write it down. I’d go a step further and say that your story isn’t as interesting as you think it is if you can’t ask the right questions. Like anything else, asking questions is a skill, one that must be practiced. Head out into the world today and ask someone, anyone, a question that puts you out of your comfort zone as the asker, and see where the conversation leads. I think you’ll be amazed what you discover.