Asking good questions is hard. In most interviews I’ve done and read, I tend to hear a lot of the same questions. It seems that people either don’t research their guest before interviewing them, or they do light research and repeat what we all know in an effort to prove they did light research.
Both approaches result in a boring experience for the person being interviewed and a boring read for the audience. It’s why (among other reasons), even though someone asking to interview you is a great honor, many people who are often interviewed come to dread it.
I’m no pro at interviewing people, but between my NTMY podcast and the ongoing interview series we do on this blog, I’ve learned what separates forgettable interviews from memorable ones.
"Get as much context as you can and then think about what you still want to know."
Research the hell out of your guest
We spend a couple hours (at least) researching our guests, their work, industry, history, culture, clients, Tweets, etc. before we interview them. We find and read all the interviews they’ve already done. We read what Wikipedia has to say. We read whatever they’ve written themselves. We do everything short of stalking them at their local grocery store.
When beginning to write your questions, write down every question you have about your guest. As you research, eliminate the questions you find answers to. Get as much information as you can and then think about what you still want to know. This is what helps you ask great questions. It also helps you avoid questions they’ve already been asked. Eliminating those questions is your goal because 1. Your audience can or has already read about it elsewhere 2. Your guest has already said all they can say about it (unless of course, the story has developed since those interviews).
With almost every interview I’ve done, I’m asked a question I could easily answer by linking to another interview or article I wrote. I can see why this happens – people know you have an opinion on that subject so they want you to speak about it on their platform, whether or not you’ve already said it before. But even if you do want to discuss a topic someone often speaks about, try to find a fresh angle. Your guest and audience will thank you for it.
Think about the answers you want to receive
When preparing your questions, think about what you want your reader to say. This doesn’t mean you should write leading questions that back them into a corner. It means you should set your guest up to give you the best, most sparkling answer possible. Here are the questions to strike from your list immediately:
Question to avoid: “What’s your story? How did get where you are today?”
Why: Do you really want a paragraphs-long autobiography from your guest? Does your guest want to spend the time summing up their whole life’s journey for this interview? Does your audience want to read it? No. Asking for someone’s life story is like asking them to recount their “crazy” dream from last night. You’ll be bored and regret it immediately. Besides, the goal of your interview is to reveal their story. Not for them to tell their same-old version of it.
Question to avoid: “If you had to do/be/choose/go [insert whatever here], which/who/where would it be?”
Why: This type of question is lazy and results in a one-word, hollow response. Who cares what color your guest would be if they had to be a color? Who cares what they’d do if they had to choose between a tank full of sharks and room full of spiders? This rarely reveals anything meaningful about a person.
Question to avoid: “You’ve mentioned X in the past. Can you please expand on that?”
Why: Asking your guest to “expand” on something they said in another interview isn’t really asking a question. It results in your guest simply rephrasing the thing they’ve already said. Besides, there’s likely something specific that sparked your interest in that topic in the first place. Ask a question about that. Be more specific.
With every question you ask, you should be thinking about the answers you want to receive and the story you want to tell with this interview. What side of this person do you want to explore? What's the angle? Starting here will help you shape a cohesive narrative around the interview, rather than asking random, unrelated questions simply for the sake of asking them.
"Avoid questions that feel insidery or complex. They spend all day talking about that shit, and your audience won’t understand it anyway."
Make it fun for your guest, not just your audience
Make this the best interview they’ve ever done. The more positive experience your guest has, the more they will open up and give you great answers. Plus, you may be giving them exposure but this interview is also a favor to you. Be considerate by keeping the following in mind:
Remember your goal isn’t to impress the person you’re interviewing.
Be straightforward and ask your question in simple, conversational language. Avoid questions that feel insidery or complex. They spend all day talking about that shit, and your audience won’t understand it anyway. Give them a break from it. Make your conversation a refreshing escape from their everyday.
Be straightforward. Don’t talk around your question.
Don’t make your guest have to guess what you might be getting at or ask you to repeat the question.
Refine and condense your questions.
Long interviews are fine if the questions are all killer. Long interviews with filler questions and redundancies are not only a waste of everyone’s precious time (your guest, your editor, you), but will also flip the “off” switch for your guest and your reader. Your guest will get tired and your audience will tune out.
When preparing for your interview, ask yourself: What kind of questions would you want to answer?
Of course, one format can't apply to all interviews and shouldn’t. Sometimes, a live interview is necessary to capture the scene, the emotions or the immediate, unedited reaction from a person. A live interview also makes for more natural conversation and allows for easier follow-up questions. Other times, a written interview provokes better, more thoughtful answers because the person has more time to think in an environment that makes them at ease.
For most of our magazine's interviews, we usually have our guests answer our questions via email. One reason being, many of our guests speak English as a second language so this gives them to formulate their thoughts and say what they really want to say, rather than putting the pressure on in-person. Plus, it allows them to answer on their own time, which makes busy people more likely to agree to the interview in the first place. Again, it depends on your goals and the format of your platform.
Be willing to go off-script
It’s easy to write up your questions, have your guest fill in the blanks and call it done. This is one downside to a written interview format – any follow-up questions are more inconvenient and don’t flow naturally in a conversation. But no matter the format, it’s worth asking those follow-ups. Your interviewee may mention something as an aside that could open up a whole new direction for the interview. Let it go there. You might hear something in their answer that piques your interest. Try digging a little deeper. If you are doing the interview via email, this is as easy as shooting a quick note or making a comment on a shared doc.
It’s tempting to plow through your script, whether you’re nervous in person or you just want to get the job done. But if you pause to absorb your guest’s answers and take time to ask the follow-ups, you may discover much more about the person or subject than you would otherwise. Don’t feel obligated to stick to a template.
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There’s much more to learn depending on the type of interview you're conducting. A TV host may give you different advice than a news journalist. A blog writer will take a different approach than a podcast host. But generally, I’ve found these rules lead to better questions and as a result, better interviews.
