How To Freelance Tuesday: Conducting an Interview
If you’re a freelance writer, you’ll probably need to do an interview or two or a dozen in your time, whether you’re writing a profile or feature on a person and their work, or simply need some experts for an article. I’ve been doing interviews for a few years now for my site the Boston Book Blog, but I’ve also interviewed my fair share of job candidates as well. (They used to pull me in to help because I was so good.)
There are some folks who love interviews, and there are some that are terrified by it. I’m honestly nervous when it comes to interviewing folks (not sure why, I’m not doing the talking!), but I always have to remember that it’s not an “interview,” it’s a “conversation.” And if you know the simple trick to conversation — asking questions — then you’ll be set.
Here’s my process for conducting an interview.
Figure out who and why
This is the easy part. Maybe there’s a new initiative in town and you want to find out more, or you want to talk to an author you like, or you need an expert opinion. Knowing who is going to be straightforward, but at the same time, you need to know what piece you’re writing. Just need a quote for an article you’re already working on? Or want to write a 2000 word profile on them and going in cold? Knowing the end result is going to determine your questions and approach.
Reach out and schedule
Reach out and introduce yourself, and tell them about your project. Don’t say, “Would love to pick your brain!” but be focused: “I’m writing an article on x, y, z and since you’re an expert in the field, I’d love your input,” or, “I heard about that thing you’re up to and I’d love to feature it in _____.” This shows that you’ve thought it through, and you have an actual proposal to give them. Also, be professional because you are, and be gracious because they are taking time out of their schedule for you. Because of that, be willing to be flexible with your time and availability, too.
Choose a format
I actually like to meet people for a coffee and do the interview that way (pre-COVID, obvi). You can read body language better and there’s a better back and forth. But it does take up more time (travel, etc.), and may cost money (always always buy the coffee because they’re doing you a favor). BUT in this new age of COVID, remote interviews are the thing now, so phone is fine, just make sure you have a way of recording. I haven’t done an interview on Zoom yet, but with their recording function and pretty great platform, I’m sure I’ll be doing a lot of them that way in the future!
Prep the hell out of it
Now that you’ve arranged a time and place, you need to prep the hell out of the interview so that it goes seamlessly. Read everything you can about your interviewee. Read their website. Track them down on social media, especially LinkedIn. Google search them and read interviews they did in the past, or places where they might have been quoted in the news, or references to them from alumni magazines. It’s pretty stalkerish, but you may find some really fascinating thing, like a former career, interesting writing they’ve done, or fun fact that you can ask them about.
Ask good questions
As you prep, you’re going to start to shape your article in your head, and then you can list your questions in a storyline. You want one question to lead to the next, to follow a natural flow of conversation. You also now know on a more micro level the sections you want to write about, so can tailor your questions in that regard. My interviews are actually incredibly controlled and precise — but you would never know that because they flow so easily! Additionally, make sure to be thoughtful about the questions you want to ask. Instead of, “How did you write your book?” ask “Why did you want to include the theme of nostalgia/hope/family dynamics in your book?”
Make the interviewee feel comfortable
Once you get to your interview, or get on the call, you want to immediately create an environment of friendliness and trust for the interviewee, so they’ll feel comfortable talking to you. Take the time to small talk, ask them about their day, mention a fun fact you found, mention a colleague or connection, thank them again for helping out, and turn on the excited tone in your voice. I usually give my interviewees an overview of what we’re going to talk about so they know the trajectory of the conversation. The big idea here is that you’re taking care of them, and shepherding them through this experience.
Record it, and tell them you’re recording it
I record my interviews, and you should too. (I think most people do at this point.) There’s two reasons why: The first is so that I can give my interviewee my full attention, and be focused on what they’re saying to me so that I can listen and ask them things, rather than be furiously taking notes. The second is easy: So I can get quotes right later. I have an app on my phone called VoiceRecorder, and it’s free and phenomenal. (It also looks like an old school cassette tape recorder, so I like that!) It has a phone recording option as well, but I just turn my phone on speaker and record through the app on my iPad. But here’s the thing: You need to legally tell your interviewee that you’re recording them, especially on a phone call.
Ask questions lightly
You have your list of questions, you have all the targets you want to hit, you know what you want to talk about, so start asking — but use just a few words. We’ve all been at the events where someone gets up to ask a question, and they do a long ramp up and ask their question, then ask their question constructed differently, then ask their question a third time constructed differently. You not only want your interviewee doing most of the talking, but you want them to be creative in their answer. By asking a simple question and then letting it hang — “Tell me about the time you were a field reporter,” or, “Was taking that step hard for you?” — you’re giving them room to answer, to be thoughtful, or spontaneous. You also need to be comfortable with silence, as it draws out more from the interviewee. The more you talk, the more you narrow the answer for your interviewee.
Listen, listen, listen so you can go off book
Some of the most cringeworthy interviews out there are when the interviewer doesn’t listen and can’t riff. You’ve seen it: The interviewer asks a question they planned, the interviewee responds, and then there’s awkward silence. The interviewer usually responds, “That’s great,” or “Cool,” and asks the next question on their list. What you should be doing is having a conversation, so as the interviewee is answering, listen to them for points to expand upon, neat facts or stories you can ask about, or ways to let your interview unfold itself.
Try to keep it a reasonable amount of time
I’m sorry to all the people I’ve interviewed where we’ve gone an hour or longer. I guess the good thing is it doesn’t feel like it…? A half hour interview for consultations, facts, and pull quotes is good, and an hour is right if you’re featuring a person and their work. It may go longer, and that’s fine if everyone’s on board, so always check in with them and be respectful of time. Be sure to ask at the beginning as well if they have a hard stop.
Back up your stuff right after
The scariest moment ever ever ever is testing that audio to make sure you got the interview. The second scariest might be worrying if you have it only saved in one spot. My app allows me to upload the interview audio to Dropbox or iCloud, so I always do that immediately afterwards to have my interview in two places.
Thank them
Thank them then, thank them in an email later. Be gracious, and let them know that you’re appreciative of their time and contribution. Then, be communicative about your timeline, when the article’s coming out, if you need anything more, etc.
Write your article
The hard work’s done, and then the hard work begins! Now’s the time to write the article. What I do (which is probably crazy) is before I start writing, I transcribe the entire interview myself. Yes. It takes forever (not that long; I can transcribe at half speed), but as I’m writing out the interview, I’m going over it again and crafting it in my mind. Also, having a transcript gives me accurate quotes that I can work from, so I can let the interview shape the article — not just relisten to pull quotes I think are going to serve me.
Once you start doing more interviews, you’ll get more comfortable and you’ll start paying attention to reporters, podcasters, and talk show hosts that do it well — and you’ll start to notice the ones who do it poorly, and take notes to refine your process.
