42. The right questions

Interviewing anxiety

I’m making every valiant attempt to write with more regularity this summer. If you missed the last two posts, catch up here:

40. Reunion

41. Death of a watch tan

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A little over three years ago, before I’d published much of anything, I had a phone conversation with a reporter at POLITICO who advised me against going to journalism school. I was so nervous to talk to this hotshot, and even more so when I felt the palpable tension of him trying to talk me out of the career plan I was considering. He cautioned me against going into the journalism industry itself, suggesting that I think carefully about what I found appealing about reporting, that perhaps I could get it somewhere else. 

I haven’t heeded much of that advice, given I’m halfway through a journalism program with every intention of becoming a full time reporter for as long as I can. But the scrap of wisdom I did take was that there are countless ways to learn how to be a good reporter; most of these resources are available outside of any formal education setting. He recommended I begin with the Longform Podcast. 

I’ve been a devotee of the show ever since. The hosts, Aaron Lammer, Max Linsky and Evan Ratliff, release a weekly episode in which they interview a nonfiction writer about their craft. In about an hour, they deconstruct the process of reporting and writing longform stories, even books. It offers a glimpse into the minds of writers I deeply admire, people I want to become. 

Last Friday I talked to a friend and fellow journalist about the Longform Podcast, and he said, “It’s almost too good.” 

It’s too good in the sense that everyone is articulate and brilliant and interesting and understandable. In the sense that they’ve released well over 500 episodes and each new one is still fascinating, still says something new. It’s too good in the sense that I have a fantasy of one day being invited onto the show, yet I’m saddled with the fear that I could never create what these writers have created. 

More precisely than that, the interviews themselves are too good, better than any series of questions I’ve ever asked. They demonstrate meticulous preparation; they draw the interviewee out; they build on each other; they drive toward some fundamental question, an arc of conversation the host has seemingly devised all along. Each episode is a masterpiece. Each episode, too good. 

The trend in journalism, or at least what most of my classmates and other early career reporters I know do, is to audio record all your interviews using transcription software, even if you’re not an audio journalist. Otter.ai, my software of choice, records and transcribes the conversation in real time, and you see your own words materialize on the screen before you. 

Later, I go back and review the recording, clean up the words the AI didn’t correctly transcribe, and listen to the tape of myself asking questions. Many people dislike the sound of their own voices. It’s jarring to hear ourselves outside of our own skulls. But I can get over that. What I can’t get over is hearing myself ask bad questions. Recorded and transcribed interviews let me review my speech in excruciating detail. 

I’ll listen to myself take a paragraph to ask a simple question, and I want to scream, “Spit it out!” Far more mortifying and counterproductive, I’ll hear myself say I know what something is when I don’t, afraid I’ll come off as unprepared. Of course, this leaves me as in the dark as I was, failing to ask the person on the phone to share whatever precious knowledge they have. Too late, I want to yell at myself, “Idiot! Ask the damn question!” Sometimes I provide too much context about what I’m working on, shaping someone’s answer more than I mean to. Sometimes I don’t provide enough. Many of my questions sound hesitant and anxious, which is accurate. I am nervous for absolutely every interview.  

Some of these things can, and will, get better with practice. Interviewing is a skill. But what fundamentally holds me back is that I want the people I’m interviewing to like me. I want them to think I’m smart and prepared. I want them to tell me that I’m asking great questions. At some level, at least for the duration of the conversation, I want us to be friends. 

This makes sense when I think big picture about where I am in my career: at this stage where I don’t feel like a confident interviewer, I seek reassurance, even praise, from the very people I’m interviewing. In wanting people to like me and think I’m asking good questions, I imagine what someone wants to hear, catering to my source rather than my reader—the person who needs me to ask questions that help me understand and tell the story, the whole story, to them. My own ego (or maybe it’s inexperience or shyness or insecurity or a combination thereof) gets in my way. 

I talked to another friend about our interviewing anxieties, and she recounted the experience of going out on assignment with a more experienced reporter, who asked blunt, direct questions—the kind of questions I sometimes think of as “stupid” questions. But stupid questions are something else: those where the answer is readily available elsewhere, meaning I’m wasting the time of the person talking to me, as well as my own. But when questions get to the heart of the matter without dancing around, without trying to sound erudite and overprepared, they are usually good questions. 

I sometimes joke privately that attending Yale gave me an inferiority complex. I was surrounded by thousands of people I assumed were smarter than me, and I walked into every discussion section scared to speak, embarrassed by my filler words and upspeak. Rather than rise to the level I perceived my classmates to be at, I spoke less and less frequently. When I did speak, I was sure I’d said something dumb.

Perhaps this is a natural human tendency, to assume others are doing it better than I am, asking the right questions while I’m muddling my way through several sentences wondering what it is I’m even asking. But then I’ll listen to my Otter.ai transcript and confirm for myself that, yes, I do say “like” quite a lot, and yes I do start many of my sentences with “um,” so I must have been right all along: I am not good at this. 

The recorded interview preserves my insecurities, which I can then play back at half speed and make myself feel twice as bad for twice as long.

On the flip side, sometimes I listen back to an interview and it flows. My questions build on each other and drive toward something and I’m not saying “like” every other word, or I do say it, but I don’t punish myself for it. I hear myself ask not only the questions that tell the story in broad strokes, but the questions that elicit description and detail, the ones that help me tell the story well. In those moments, I can believe I will one day stop soaking the pits of my shirt for every interview. And that maybe one day I can be good at this. 

I took a class last semester where the professor brought in numerous brilliant feature writers to talk with our class of ten students for an hour. Each of us was required to bring in three questions, “good questions,” and we had to ask at least one. This exercise was particularly well designed for someone like me: shy in any setting where I am less experienced and worried about broadcasting my naiveté. But the beauty of the classroom environment is that I am expected to know less. These people are offering their time to impart some small slice of knowledge, and my job is to soak it up. 

Indeed, one of the best things about journalism is that this extends beyond the classroom. The reporter never stops learning. In many of my stories, science topics in particular, I get to ask people who are excellent at what they do, who are creating new knowledge, to explain the world to me. I am expected to know less than them because I am not an expert in anything (lol). That doesn’t neutralize my fear of asking stupid questions, but it does take some of the pressure off asking the perfect questions. 

In my conversation with the POLITICO reporter, he told me that early in his career, he’d had an informational interview with one of the most revered public health scientists and writers in the world. The last thing I wrote in my notes from that call was “Atul Gawande gave him 90 minutes.” 

It is a gift whenever people give us their time, but that doesn't mean we have to, or even can, show up perfectly prepared. I don’t know what questions were asked and answered in that hour and a half, but I like to imagine that some of them were excellent, and some of them boring or bad or just okay. 

We ask from where we are and go from there.