Interviewing skills I’ve learned along the way

In 2016, I journeyed to Singapore to speak with Andrew Fastow, former Enron CFO, in his first interview following his release from prison. I prepared and researched meticulously beforehand, as I would do with any subject-matter expert (SME) interview. I watched the film “Enron: The Smartest Guys in the Room,” read any news article I could get my hands on, and even sought insights from my brother-in-law — a certified public accountant — about the intricacies of Enron’s fraudulent schemes.

Securing the most ideal interview spot was paramount. I arranged a quiet conference room at the venue where Fastow was speaking to ensure uninterrupted dialogue and ease of transportation. However, post-talk, he was hungry, so he proposed we conduct our discussion over lunch. Suddenly I was faced with the prospect of distractions and background noise beyond my control. I adapted on the spot, knowing that his comfort superseded my plans and would likely result in a more candid conversation.

We ended up at a corner table in Beijing Number One, a restaurant in the Marina Bay Sands Hotel mall. Over a shared Peking duck, Fastow provided me firsthand insights into one of the most notorious fraud schemes of our time. In the unassuming ambiance of the eatery, I believe he felt more relaxed as he delved into the depths of corporate scandal.

I learned an important lesson that day: properly preparing for a SME interview is critical, but staying flexible and being open to change is equally imperative.

Lessons learned in real time

I’ve conducted countless SME interviews during my career as a professional copywriter, and they’ve all taught me something new, whether about the subject itself or the process of interviewing.

These lessons have made me nearly unflappable when things don’t go according to plan. When I interviewed Steve Murphy and Javier Peña, the DEA agents who inspired the Netflix show “Narcos,” I remained composed during Javier’s video and audio issues on our Zoom call.

I’ve been given impossibly short windows of time with some SMEs while others have taken me on twisted and long tales. Dr. Sam Foote, the whistleblower who exposed corruption within the Arizona Veterans Affairs Department, took me on an hours-long phone call detailing his experience to such an extent that I spent days combing through the details to cobble together the correct timeline.

No matter the situation, the uncharted course, or the nature of the content, proper preparation and sound interviewing principles have never failed me. Our field guide, Tips for Interviewing Subject-Matter Experts, breaks down these tips and principles that help you conduct a successful interview.

The following are notable examples of how I’ve used some of these tips in my career:

1. Actively listen

My experience with Dr. Foote certainly required strong active listening skills. During our discussion, he would often go off on tangents or mention details that I’d need to clarify on the spot (or note for fact-checking later). Had I not been so actively focused as he spoke to me, I’m sure I would have missed important information or failed to bring us back on track when necessary.

2. Build rapport

One of the most impactful and important interviews of my life was when I spoke with Matthew Caruana Galizia, the son of murdered Maltese journalist Daphne Caruana Galizia. I needed to approach our discussion with the care and compassion it deserved. Though the meat of my article was going to be about corruption in Malta and the events that led to Daphne’s death, I took my time getting there. Instead, I started by asking Matthew about his mother — who she was as a mother, a person, a friend. I didn’t immediately ask him to relive a traumatic event, which gave him time to settle into the interview and get comfortable talking to me. And when it came time to write my article, his words about his late mother inspired my lede.

3. Embrace the pause

Nobody likes uncomfortable silence, but as an interviewer, silence can be golden. After a SME finishes answering a question, wait for what feels like a second too long before asking the next question. Your subject will want to fill that uncomfortable silence, and the result could be a juicy detail they might not have shared otherwise.

For example, I was tasked with ghostwriting an article about a specific technology for a vice president at a large corporation. He knew the gist of what I was hoping to achieve but expressed his concern that the topic wasn’t strong enough to warrant an article. I said, “Well, why don’t I start by asking some questions and we’ll see where this discussion takes us.” During each uncomfortable pause he’d say something like, “And you know, actually …” He would then continue down a train of thought that was insightful or informative in some way. Needless to say, I got what I needed to write the article.

4. Don’t ask “yes” and “no” questions

When I interviewed Theranos whistleblower Tyler Shultz, he’d already done so many interviews that much of what I was likely to learn had already been reported. I had a wealth of information to work with — I knew the machinations of the fraud, the details of Shultz’s life, and the role he played in uncovering the scheme.

As a result, it would have been too easy to ask something like, “I’ve read that Theranos’ signature blood-testing machine was nicknamed ‘Edison’ after the famous inventor. Is that correct?” He could have easily replied, “Yes, that’s correct.” And where would that have left me? With no new information and scrambling to follow up with the right question.

Instead, I asked, “I’ve read that Theranos’ signature blood-testing machine was nicknamed ‘Edison’ after the famous inventor. Tell me about the characteristics or nuances of the machine that inspired this nickname.” This question forced Shultz to go into detail about the technology. And within that detail, new and illuminating insights inspired my follow-up questions. 

Practice makes perfect

Interviewing is an art and a skill. It didn’t come naturally to me when I first started but over time, I have honed my skills and done my best to perfect this part of my craft. There are certainly times when an interview doesn’t go as planned or the way I wanted it to — and that’s okay!

But if you properly research and prepare with the right list of questions and go into the interview with patience, focus, and flexibility, you’re likely to come out of it with what you need to craft a compelling narrative. Armed with these insights and our handy field guide, seize every opportunity for captivating storytelling.