THE ART OF
At the time of writing, I’ve conducted over 500 interviews in my lifetime. I’ve interviewed NYT bestselling authors, CEOs, entrepreneurs, students, parents, friends, musicians, and frontline workers. In short: just about anybody who will give me the time of day.
My approach is inspired by the very best in the game – John McPhee, Tim Ferriss and Joe Rogan to name but a few. I’ve stolen like any great artist does. But, ultimately, I’ve tried to become a master of my own process.
KNOW WHAT’S BEEN SAID
Regardless of who I interview, my first step is always the same: listen to everything that person has said before. What makes an interview great is its ability to create a space with a topic, subject or person that has not existed before. And so step one is knowing what’s been said already.
Step one is a big part of the reason why I believe Joe Rogan is so successful. It’s not like his guests have never been interviewed before. In fact, the folks on his show are some of the most quoted, covered and scrutinized people on earth. And yet Joe has a knack of creating spaces with his guests that do not exist anywhere else in the world, so they do things they don’t do other places.
Case in point: Elon. Do I need say more?
Your only goal at the end of the day is to create a space where your guest feels safe, trusted and challenged – all prerequisites to having a conversation that’s never been had before.
Your only goal at the end of the day is to have a conversation that’s never been had before.
That’s my metric for all interviews — I don’t believe they are top quality unless I ask questions that haven’t been asked before. And so – to give myself the best chance of doing just that – I consume all the podcasts, articles and social media posts I can get my hands on.
I do this as I’m cleaning the house, going for a walk, or picking up groceries – constantly stopping the interview to make sure I have a good grasp of what they are saying. I compile all my notes into a Google document. And from there I can begin to piece together what I see as themes that are untouched.
This process can be arduous. But it enables you to truly understand where you can go deeper with the subject to create a space for a conversation that has never existed before.
Preparing to interview several executives at Kraft Heinz. Chicago, IL.
I start to ask myself: what do I want to hear? And how do I avoid monotonous answers?
HONE IN ON THEME
As I hone in the major themes, I list out the top 5, matching certain quotes or ideas to relevant sections. This way, I can begin to piece together certain themes and get a sense for how the interview might flow. Here’s an example of what a typical preparation document looks like.
Soon enough, the foundation of the interview reveals itself. But more importantly, you can see how much of what you’ve designed has or hasn’t been said before.
My take is simple: lean into the unsaid parts, even if you think your audience might not enjoy them. It’s where all the magic lies. You will earn some serious cred from guests for the novel research and your confidence to pursue something new will only compound with reps.
This is when I start to ask myself: what do I want to hear? And how do I avoid monotonous answers?
A little glimpse into the director’s chair. Chicago, IL.
DON’T GO ROUTE ONE
One way to avoid monotony is to not ask any direct questions of the guest upfront but rather focus on the people that they love and admire (e.g. family).
This serves three purposes: 1) you establish a great level of trust early on with your guest 2) you humanize them and take them ‘off their guard’ and 3) you actually learn way more about the guest than you would have by asking them about themselves in the first place.
It sounds counterintuitive, but it’s true: if you want to get to know someone, ask them about the people they admire.
If you want to get to know someone, ask them about the people they admire.
TO SEND OR NOT TO SEND?
It’s really up to you whether you send your questions to your guest ahead of time. I’ve had tremendous interviews both ways.
As I said, you’re optimizing for the creation of trust and content that is quality. So use your best instinct to achieve that goal. Even if you do send a list of questions, don’t be scared to go beyond or deeper. Especially if you feel like the guest is giving you rehearsed answers.
With that said, rehearsed answers aren’t always bad. Especially if they are on complex subjects. The audience often gets even more benefit out of a guest having had some time to think deeply about what they want to say on very nuanced subjects.
At the end of the day: let your heart guide you. Some people will review your questions. Others won’t look at anything. Part of me will always prefer something raw, and real. But trust your gut and always give your guest some idea of what plan to cover.
It never hurts to make sure your guest has a great time. Chicago, IL.
TAKES TWO TO TANGO
Finally, I always default to Tim Ferris’ line when the interview starts — “please do your best to include as much interesting information as possible. We can always edit content out afterward, but we can’t put more interesting stories back in.”
After all, interviews are just as much a reflection of your guest as they are you. It pays for you both to spend the time, effort and energy to make sure it’s as insightful as possible.