I wrote a three-part series for Drew McManus’ site ArtsHacker earlier this year, and this got my brain going: what if I also put out some “pulling back the curtain” podcasts about how I do all of this and what I’ve learned in the process? So that’s what today’s episode is. I’m breaking this into two parts: today I’m covering “the art of the interview” and seven lessons I’ve learned about interviewing. Next time we’ll go deep into the tech behind recording, editing, and putting these episodes out.
Podcasters like me end up having this strange skill set where they’re half Jay Leno and half IT guy. While some of the bigger podcasters split these duties into various team members, the vast majority of podcasters (myself included) fill both of these roles.
Early Days: Discovering Podcasts
I discovered podcasts not too long after getting my first iPod Video in 2005. My first podcast was This Week in Tech with Leo Laporte (who I’ve actually seen live! my wife and I went to the TWiT studio in Petaluma last year to see a live taping of This Week in Tech). I was hooked from the get go, and it wasn’t took long before I thought, “What if I did my own podcast?”
I filed that thought away for a year. My blog was starting to grow, and I was having a good time riding that wave. But the more I got into blogging, the more I thought about how cool it would be to have a podcast. I was loving listening to interview shows, and I had broadened my listening to include about 20 podcasts at that point. It was basically all that I listened to outside of some music. It had totally supplanted any other form of talk radio or television.
As 2006 progressed, I resolved to start my own show, and the last few months of that year were spent purchasing gear, setting up a website, getting hosting for my new podcast, and learning how to use my gear to record and edit. I did some unreleased test episodes at the end of 2006 and put out my first podcast on January 1st of 2007.
Getting My Sea Legs
Recording yourself makes most people self-conscious, and listening back to yourself as a host can be particularly awkward. Like most people, I hated how I sounded on the mic, and I didn’t really know how to use any of the gear that I had that well, so it was trial by fire for sure. I had this questionable Acer laptop at the time, with caused all sorts of problems early on, but I’ll save those details for the tech episode next time.
I put out what I thought was a pretty decent first episode, just stating the purpose of the show and what I hope to do. The funny thing is that I have done pretty much exactly what I said on that first episode! I went back not too long ago and listened to that episode, expecting some truly cringe-worthy material, but to my surprise it was actually pretty tight.
My first three episodes had no guests—they were just me rambling into the microphone, and it’s amazing to hear how stiff and stilted my delivery was. It was all new to me, and that’s the first big lesson I have for this episode: no matter how well-versed you may be in public speaking, it takes time to find your own rhythm and your own voice in front of the microphone for a podcast. Imitating someone else may work at first, but ultimately you have to find your own style. It’s tough!
My First Guests
I finally got a guest on episode 4—Andy Anderson from the Lyric Opera of Chicago, and I am eternally thankful to him for being willing to take a chance on something like this. Andy is an incredibly open guy, which was amazing for a first guest. He made it so easy for me. I can think of a lot of other people I interviewed after that which would have been much more challenging interviews, but Andy was amazing and was really helpful for building my confidence. I mean, I really didn’t know what I was doing.
I had listened to podcasts for a while at that point and had taken in a lot of interviews, but doing your own interview is not the thing entirely. It can feel kind of formal and weird—I actually think that it’s one of those deceptively difficult skills that seems easy when done well but is in reality incredibly challenging to do at a high level.
Lesson #1 – Starting an Interview
I hear moments of quality interviewing even in those first episodes, but I cringe as I hear what I call extended resume-type questions: then you went to this school, then this school, then you auditioned for x, y, or z, etc.
I still start basically all interviews with some talk about the musician’s early years, but I no longer expect to talk about each minute detail of their progression through school, training, and employment. It’s not necessarily that interesting… I mean, sometimes it is, and if so that’s cool, but what I do now is listen intently to what they are saying and listen for any sort of interesting twist in their path or any extra passion in their voice about a particular aspect of their upbringing.
A tip I picked up from Tim Ferriss that I pretty much always use these days: talk with a person for at least 10 minutes (especially if you haven’t met in the past) before starting the interview. This makes for a way less stilted conversation. The concern that most people have is that you’ll “blow” all the good content in the pre-interview and it will be stale when you’re actually recording, and while this can be kind of true, the benefits of chatting for a while far outweigh the disadvantages.
I have also stopped being so formal with the beginnings of interviews. It just feels more natural to me. If you’ve listened to the podcast for the long haul, you’ll notice that, at a certain point, I quit “welcoming my guest to Contrabass Conversations.” It just seemed too stilted and didn’t really add anything to the podcast. If anything, it hurt the podcast because it made people clamp up a little bit.
Lesson #2 – Coaxing Out Good Content
My philosophy is that people I’m interviewing have a story to tell, and if I can’t get that out of them then it’s my fault as an interviewer. I have to ride the wave of discussion and pick out what is most interesting.
That can be easy or stupidly challenging depending on the guest. Fortunately, I’ve picked up a few techniques from some of my favorite interviewers (most notably Tim Ferriss, Chris Hardwick, and Marc Maron). Questions like “tell me the story of….” or even something as simple as “what was that like?” work really well. Questions that can be answered yes/no are also a little dangerous because there’s not a clear call for the guest to elaborate. Some will, others won’t.
Also, some people are just more reflective/verbal than others. With time, you start to pick up within minutes (and that’s why you don’t want to just dive into the interview immediately–get to know them and make the environment relaxed) what sort of guest they’ll probably be. Regardless, I feel like it’s my job to suss out the interesting content from them.
So… how to figure out what is going to be interesting from a particular person?
That’s where research comes into play.
Lesson #3 – Research Strategies
For me, researching is key to doing a good interview. I start the process with a new note in Evernote for the upcoming guest. I then devour anything and everything that I can find online about that individual. My Evernote document quickly becomes filled with biographical information, YouTube links, photos, audio examples, and the like. As I read, watch, and listen, questions start to formulate in my mind. Through this process, I’m looking for the key things that make that person’s story unique.
Lesson #4 – Formulating Good Questions
I used to send every interview guest the same set of stock questions. This led to the same kind of interview formula for everyone. Over time, I quit using that list, approaching each new interview with a totally blank slate. Even though guests will have certain commonalities (education background, career path, musical genre, etc.), I find that I get a better interview if I start from scratch every time. I think that things got a lot better in terms of content when I quit trying to shoehorn everybody through the same ringer of questions.
Lesson #5 – Plan Like Crazy, but Improvise in the Moment
I write a lot of potential questions for a guest before an interview. I will sometimes share these if requested by a guest or if I feel that it will enhance the interview. If a guest doesn’t request them, I’ll typically not send them unless I find something a little off-the-beaten-path in my research that I think would be interesting to dig into. I never want to surprise a guest with something way out of left field, but I’m also trying to balance preparation and spontaneity, and I don’t want things to be overly scripted. It’s a balancing act that is a little different for every guest.
In the interview itself, I almost never look at those questions. I try to go with the flow and will only look if i feel like we’re grinding to a halt. At the very end, I do look just to make sure that we didn’t skip any key topics, and I try to remember to ask my guest if there was anything we didn’t talk about that they wanted to cover. This has been a super helpful thing to ask!
Lesson #6 – Give Your Guest “Final Edit”
The intent of my podcast is never for it to be a “gotcha” kind of show. The intent is to make my guests look good and learn their unique story. With that in mind, I let them know that I edit, so anything that they want to restate can be easily changed. Also, they can listen to the interview before it goes out and suggest any changes. They have final edit on anything I put out.
That knowledge takes pressure off of the guest to phrase everything perfectly, and it also allows us the luxury of exploring tangents and taking chances. If these tangents don’t lead to interesting content, they can always be chopped out in the editing process.
Lesson #7 – Talk About Myself
Talk about myself? How egotistical.
Actually, this is a wicked technique when used correctly because it encourages the guest to be more open. If I start by relating something that I’ve struggled with, if make it more likely that my guest will feel comfortable sharing in similar fashion. This leads to a more open and honest conversation and much better content.
I try to use it with discretion lest the podcast turn into the “Jason Heath Show,” but it works wonders with making a human connection and encouraging honesty. Tim Ferriss is a master of this technique and articulated this lesson eloquently on his podcast. Though I’ve done this subconsciously to a certain extent throughout the life of the podcast, I’ve practiced this lesson more consciously in recent months.
For me, interviewing is like any other skill, requiring practice and repetition. I find it both satisfying and quite challenging. One cool side benefit of the whole interview preparation and execution process is that it requires me to formulate questions, which helps me ask better questions of myself. It’s a self-education process as much as anything, and I’ve grown to appreciate the whole process more over time.
I’ll be digging into all the dirty details about the technology behind podcasting and sharing some humorous missteps that I’ve made along the way.