Brian Casel
Brian Casel

What The Best Interviewers Get Right

by Brian Casel · Subscribe

I love a great interview.

I’ve been fascinated with interviewers for as long as I can remember. For years (and to this day) I tuned into Charlie Rose and Howard Stern, two of the best interviewers in the business, in my opinion.  Their interviewing styles are very far apart from one another, yet both are incredibly effective and engaging.

Rose methodically gets his guest to take us step-by-step to a deeper understanding about whatever the topic is. He knows the right questions to ask, and the precise way to phrase them, that will make highly technical or complicated material accessible to a broad audience. You can’t come away from watching a Charlie Rose show, and not feel smarter than you were an hour earlier.  A few favorites are his interview with Jeff Bezos, all of his interviews with Thomas Friedman, and just last night I caught his conversation with Evernote Co-Founder, Phil Libin.

Howard has a very different approach and keeps his audience engaged in a very different way. He makes his guest feel surprisingly comfortable and take their guard down, and then picks just the right moments to catch them off guard with a highly revealing question. He also knows how to inject humor, but also get serious and down to business. Above all, he has an incredible talent for sensing when his audience is getting bored and knows how to direct the conversation and guests accordingly. Look past all the “shock jock” labels and listen to any full-length Howard Stern interview, and you’ll know why that label misrepresents him.  A few favorites that come to mind are his interview with Sacha Baron Cohen (the first interview he ever gave “straight”, not in character), and his interview with Biz Stone.

Web Interviews… Hit or Miss

On the web, interviewing has become one of the most popular forms of content, especially on business blogs and podcasts (see my recent post about what the best podcasts get right).

Unfortunately, interviewing on the web has become very hit or miss.  Interviewing has caught on as an effective form of traffic and link-bait.  Anybody with a blog or podcast can invite a web celebrity on for an interview to make their post title more attractive and score a Tweet sent to the guest’s massive following.

But just getting a big-name guest to come on your show won’t guarantee your audience will receive the value they’re expecting when they clicked your link, or in some cases, paid to access the interview.

The best interviewers know that it takes a lot more effort, preparation, and years of experience to become a great interviewer.  It has been fascinating and inspiring for me, following along with Andrew Warner’s journey as he interviewed nearly 900 entrepreneurs over the past few years.  While even his early interviews kept me engaged for the full hour, he has clearly improved and honed his craft as the years went on, setting the bar for what a quality entrepreneur interview should look and sound like.

What Makes For a Great Interview?

As my new podcast, Bootstrapped Web, gets off the ground, with interviews playing a big role, I’ve been giving this question lots of thought.  Here are few things that I think separate the typical, run-of-the-mill web interview from the truly value-packed and engaging interviews.

Focus on a topic

The best interviewers have a specific objective when they set out to interview a guest.  They invite them on the show for a reason (not just for their name).  They pick out the most interesting topic that this guest can speak to, and make it their mission to get to the bottom of this topic over the course of the interview.

The “life story” interviews are rarely interesting.  Most of a person’s life isn’t interesting to us.  We’re most interested in one thing that person has done, which takes up a small portion of their life.  So I’d prefer to hear more about that one thing and less about everything else that came before it.

Be selfish

One thing I love about Andrew Warner’s interview style is that he’s selfish.  He asks the questions that he personally wants to know the answers to.  He digs and searches for tactics and lessons that he himself can use to improve his own business.

The reason this selfish approach works is because Andrew truly knows his audience — because his target audience is people just like him!

As I’m preparing my questions for interviewees on Bootstrapped Web, the number one thing going through my mind is what do I really want to know about this person.

Background research

The best interviewers will do their research on the guest, before they hit record.  They’ll Google them, read their blogs, watch their past interviews, and learn everything there is to know about the guest.  This lets them identify the most interesting and relevant areas to dig into.  Without this background research, the interviewer is just grasping at straws, hoping to hit on something interesting.

Get something new from the guest

When you book a high-profile guest interview, chances are they’ve been interviewed on many other programs too.  And chances are there is quite a bit of audience overlap between your program and those other programs.  So when I tune into an interview with someone I’ve heard interviewed elsewhere, I want to hear about something new.  Give me a story or insight or topic that other interviewers haven’t dug into yet.  The best interviewers know how to seek these “never-before-heard” nuggets from well-known guests.

Prepared questions & unprepared followup questions

First, a good interviewer will have a list of prepared questions they plan to ask a guest.  This is good because it prevents any awkward gaps in the conversation, and those annoying “lets see, what should I ask you next?” moments.

But a great interviewer will be attentive enough to latch onto the guest’s answers, and dig in with followup questions based on what they’ve just said.  This is a lot harder to do than it seems, because the interviewer must mentally prepare for the next question, while also listening closely and processing everything that the guest is saying.

Ability to change course, when necessary

This is where truly experienced interviewers shine.  When the prepared questions lead to unforeseen points of interest, the interviewer knows when to call an audible and change the direction of the conversation.  They have a feel for knowing when to take this risk and when to stick to the plan.

Not afraid to interrupt

This is something I personally struggle with as I’m trying to become a better interviewer.  When I’m casually chatting with someone, I generally try hard not to interrupt them.  It’s rude and makes for an awkward conversation.

But during a recorded interview, things are different.  The guest will oftentimes ramble on and on and spend 15 minutes answering the first question.  The best interviewers aren’t afraid to cut in and take control of the conversation, keeping the audience interested and keeping the storyline of the interview intact.

Demand clarity

Sometimes guests can be a little unclear in their answers.  Or sometimes they’re knowingly trying to dance around a tough question.  Audience members pick up on this quite easily, and if they don’t get the clear answer they’re waiting for, it will be very frustrating for them.

It’s up to the interviewer to sense when a guest isn’t being totally clear, and to pull the answer out of them one or another.  Sometimes it’s a direct re-asking of the same question.  Sometimes they’ll re-phrase the question in hopes the guest will be more forthcoming when they answer it from a different angle.

This is where a pre-interview can help smooth things out.  Figure out beforehand what is fair game and what is not, so that during the recording, your audience isn’t left with half-answered questions.

What do you think?

Who are your favorite interviewers and what do you think makes for a great interview?