Everything I know about interviewing

From my advice to the CAJ mentorship program

When I’m able, I participate in the Canadian Association of Journalists’ mentorship program for young journalists. It gives ambitious young journalists a chance to learn from some of the country’s best. Sometimes a few of them ask for time with me instead. There’s no accounting for taste.

For the latest round, instead of general advice, I offered tips on three specific elements of the craft: Interview skills, structuring a long feature article, and developing a distinctive voice as a writer. I promised my mentees — an awkward term; maybe younger colleagues? — some tip sheets, and I decided to publish them here in case other colleagues find them interesting.

Note that these are, essentially, discussions of technique. I figure there are a million other places to debate doctrine, ethics, workplace challenges, or correct attitude toward the latest headlines. A lot of those discussions are really interesting! But I’m not sure people who wonder how to do this are well-served. So that’s how I’m trying to help.

With that preface in mind, here are my tips on interviewing.

1. It’s just an interview.

Don’t worry too much about how good you are at interviewing. The biggest variable in your ability to get a good interview is the subject. If they’re willing to talk, and they’re a great talker, it’ll be hard for you to screw the interview up. If they’re neither, you can only get so far. You can improve your results a lot with good technique, but in the end if they don’t want to talk you can’t make them. I find this knowledge liberating.

2. It doesn’t have to sound like a conversation.

A great conversation is an interaction between two good talkers. In an interview, half of this dynamic is, to some extent, optional. Any effort you put into sounding impressive is wasted. If you fluff a question, just start over. If you realize 20 minutes later that your subject made an interesting point, come back to it. You don’t have to be artful about it: “Can we get back to what you were saying about that thing in 2011? I just thought of something I want to know about that.” 

Above all, don’t hesitate to ask the dumb questions. “Why did you do that?” “How do you do that?” “Was this before or after the other thing?” “Wait, I’m not sure, how could it come before? Explain it to me.” Your goal isn’t to impress the subject, it’s to get them to say the words. And since sometimes the obvious answer isn’t the actual answer, they should get a chance to give a real answer to the obvious question. 

A transcript of your questions will probably read like a mess. That’s fine. You won’t publish a transcript of your questions. Your goal is to get the subject talking. Whatever you have to say to get that to happen, don’t worry about it. Your words and delivery are for making the subject talk, not for being independently impressive.

3. Decide beforehand what the interview’s about.

One of the saddest stories I know is about the late-night host Conan O’Brien, who was so eager to interview the Johnson biographer Robert Caro that he launched a podcast, just in case Caro said yes. He was famous for telling jokes on TV but all he really wanted to do was ask Robert Caro about writing. He pestered Caro’s publicists for years. The New York Times wrote a story about his Caro-quest. Finally Caro gave him an interview. Listen to it. It’s terrible. O’Brien spends the first 20 minutes or more explaining Caro’s books to him. I’m pretty sure Caro knows what’s in his books. Conan’s questions, when he finally starts asking some, are variations on “— Isn’t it cool that you did this thing I noticed, which I will now explain?” In all his eagerness, Conan never asked himself a basic question: “What’s Robert Caro’s role in my Robert Caro interview?” 

Say you’re interviewing a famous scientist who just won a prize. You could ask how they got into science. You could ask when they felt most alone. You could ask how government policy could have better supported research like theirs. You could ask what the big unanswered questions are that they still want to tackle. You could ask how they came up with the design of their breakthrough experiment. Until you pick a theme or a couple of themes, it’s not obvious which is the best question, or sequence of questions. It becomes obvious when you decide what key themes you hope to get them talking about. 

Say you eventually decide, in your interview prep, that you mostly want to know about their biggest experimental insight, the breakthrough moment. Okay then. Where were they when the moment happened? How had the day been going? What about the two months leading up to that day? Were they feeling frustrated? Did they do something specific to break the logjam? Did they take a break, or confide in friends, or buy better equipment, or have a snack? Were they on high alert, or kind of distracted, expecting another lousy day? When did they realize this wasn’t that? Who else was there in the room? Who said what first? And so on. Your preferred focus makes many of your choices about specific questions much easier.

4. Prepare a list of questions. Be ready to ignore it.

The first part is optional, the second mandatory. You have a list of questions for the same reason military generals have a battle plan: to be prepared and confident. You also have the same expectation they do: something will happen, probably early, to make the plan obsolete. From there, your next question is based on the subject’s answer to the last question. If you need to, you can get back to your list later. Once you start basing your questions on their answers, you probably won’t need to.

5. Short questions are better.

“Prime Minister, you’ve said you favour a policy of blah-dee-blah, but last week Mr. Jones said that couldn’t be so. He says there’s a limit to the amount of blorp diddy blorp. Understanding that the premiers are divided on this, and time is running out, do you think you can keep doing X or do you still have time to derpity derp a doo? Can you also answer in French, please, and have you made a bet with the president about the big game?”

At some point, a question becomes so long it’s impossible to answer in good faith. Long questions offer all kinds of hiding spots. If a question’s in three parts, the interviewee will just answer the easiest part. Or they’ll “pivot to message,” which means they ignore your word salad and just say the thing their PR team wants them to say. “Well, heh-heh, I don’t know about all that, but one thing I do know is…” Long questions are always easy to answer. And the answers they produce are usually boring. 

When I was young, before I was really sure I even intended to become a journalist, NBC had a guy named John Chancellor who’d been their main news anchor many years earlier. They would still bring him out for big interviews with newsmakers. He’d ask questions like, “You’ve said now is not the time to engage with China. Why not?” It’s basically impossible to find a place to hide in a question like that. You have to answer it, or make it plain to everyone that you’re not answering it.

Even in much less confrontational settings, short questions can be powerful. “I never had a great relationship with my parents.” “Why not?” There’s no way to know where that story will go. So don’t try to guess. Let your subject tell their tale.

6. Help your subject say their thing.

It’s fair to contradict your subject, fact-check them, press them. In some circumstances it can even be brilliant. (This interview with singer Eddie Vedder helps illustrate why David Marchese is considered a model interviewer. He’s constantly prodding Vedder, not letting him off the hook. But the vibe isn’t “You’re in trouble,” it’s “I love you, but this is my job and I’m not going to let you take this hour off work.”) If all you give a subject is contradiction and pressure, the message they’ll get is definitely “You’re in trouble,” and they’ll react defensively. Congratulations, you’ve defeated your purpose when that happens. Most of the time, you should be encouraging.

I had a colleague who would routinely say, “That’s so interesting,” with great conviction, whenever a subject said something interesting. It’s like sunshine on a flower. If you can find ways to make your next question entirely about the last thing they said, it’s even better. “That can’t have been easy,” when they’ve begun to describe how hard something was. “He said that, after everything you’d been through?” “So what you’re telling me is that this whole thing began two years before the big blow-up?” 

Obviously sometimes you’re going to do an essentially confrontational interview. But even then, you mostly don’t want it to feel like a siege. You want the antagonist in your story to have every fair opportunity to explain what they were doing. And if you can manage not to be grudging about that, if you can let them feel that they are being heard, you might uncover aspects of their action and their attitude that, while they might not change your mind about what they did, will at least add depth to the reader’s understanding of what happened.

Giving a subject about whom you plan to be critical a fair chance to tell their side of things takes humility. And humility takes courage. Courage improves with practice. 

7. Prepare, but wear it lightly.

The more you know about your interviewee and the topic, the better everything will go. You’ll know the main events in their life and how things got to this point. You’ll spot contradictions, evasions, evolutions in attitude that others might miss. You’ll be confident. So it’ll actually be easier to respond to surprises by improvising. 

Always remember, though, that you and your interview subject aren’t two experts who are trying to impress the world’s only other expert. You’re trying to inform an audience of people who aren’t experts. So don’t “jargon up” to your interviewee. Make sure the transcript at the end has lots of language anyone could understand.

8. The way the interview comes out isn’t quite the way you have to write it.

There’s a lot of debate about how much you can edit an interview. David Marchese (whose explanation of his method in this interview is really valuable) makes it clear that if the most interesting moment happens two-thirds of the way through the interview, he’s not shy about moving that up to the top of the written product.

Beyond that, you shouldn’t hesitate to cut everything that’s boring, confusing or useless. Even the first or last parts of sentences, as long as what you preserve is a coherent clause. Do you clean up grammar? I never hesitate to take out false starts. “What I, what I think is that, I think it all began in Sarnia…” becomes “It all began in Sarnia….”

But you have to preserve meaning. The subject has to read the interview and think, “That’s what I said, all right.” That means preserving sentence structure. On that, though, one more note: Nobody owns punctuation. Punctuation isn’t objective. Break up long strings of words into coherent sentences. Often quite short. Instead of: “Nobody owns punctuation, punctuation isn’t objective, break up long strings of words into coherent sentences, often quite short.”

Helpful links:

Taffy Brodesser-Akner explains her technique. 

Samantha Bee interviews Marc Maron (she misses some big chances to respond to his answers, so with great respect to Sam Bee, to me this is an example of how not to do it.)

Marc Maron interviews Kenneth Branagh (pairs with the Sam Bee interview to, I would argue, Maron’s great advantage) 

Frank Rich interviews Chris Rock. A spectacularly successful interview. Note how little of what Rich says is memorable. He’s there to help Chris Rock.