The Ultimate Guide To Interviewing

Over the past five years, I’ve talked with more than 400 of the world’s most influential thinkers, doers, and leaders for my podcast, The Learning Leader Show. It has been a life-changing experience that all started as a side project for me to pursue my curiosity and obsession with excellence.

One of the unexpected benefits of this work has been the creation and evolution of my operating plan for conducting effective interviews. Listeners often ask me about the behind-the-scenes work that goes into a great interview. For example, Chad Simpson recently asked me on Twitter:

Chad’s question made me realize something. While I have refined my process and follow it habitually, I have never documented it. Immediately, I recalled a great piece of advice from a recent conversation I had with Morgan Housel, whose best-selling book, The Psychology of Money, was published in September: “The best way to crystallize your thoughts? Write about it.”

So, for Chad and anyone else out there who wants some ideas for conducting meaningful conversations with people they hope to learn from, here is my framework:

Preparation

Before every interview, I always do my research, consider a focus, and write a rough outline of potential topics.

By research, I mean I read, listen to, and watch everything I can find about the person. This includes books and articles—both written by my guest and about them—YouTube videos, keynote speeches, etc. The goal is to know as much as possible  so that when it comes time to talk, it flows and never feels like I’m grasping for what to say next. This is also a great time to home in on fresh and exciting questions so I’m not asking them the same questions everyone else asks them.

If possible, I ask a friend of theirs, “What is something unique about this person that I can’t find on the internet?” For my episode with rocket scientist and best-selling author, Ozan Varol, I asked our mutual friend and founder of Contently, Shane Snow, and he said, “Ask him about why he likes to get DVDs from Netflix instead of streaming.” I closed the episode with this question, and it ended up being the most memorable moment of the conversation.

Guest or Topic?

Next, I consider the focus of the interview, which I narrow into two options: “guest” or “topic.” Sometimes, I’m most curious about the guest’s topical expertise than the guest themselves.  Conversely, sometimes their expertise doesn’t matter and it’s the person we want to know. This is a decision I typically make prior to the interview, but I’m prepared to go with either route.  With “topic” episodes, I focus on the guest’s material  (their books, speeches, area of expertise) and less on their personal life or story. For the people who have a shocking story, I try to focus on them and not so much their place in the world or the politics of their profession.

However, I never know how the conversation will go, so I’m always prepared—just in case— to talk about either. That’s what my research is for. Rather than being an issue, this uncertainty is part of the fun. When I talk with Simon Sinek, for example, we almost always focus on the topics of his books (Start With Why, Together Is Better) and rarely talk about his life. The same is true for Charles Fishman—90% of our conversation focused on his book about the Apollo 11 moon landing. But with NBA great Clark Kellogg, our talk was 100% about him, his life, his story. John Maxwell (prolific leadership author and speaker) was a combination of both. Choosing a “guest” or “topic” focused episode alters the conversation, as I’m curious to learn about what’s most fascinating, and it forces me to think about that beforehand rather than just leap in headfirst.

The Flow

Instead of writing questions, my outline  is packed with notes and quotes. This helps me create more of a conversation and less of an interview. An interview can seem impersonal. A conversation, on the other hand, is two people getting to know one another, even if one person asks more questions than the other. The best  episodes feel more like a conversation between a mentor and a mentee.

In preparing for these conversations, I list all possible topics I might explore, and format them like this:

• Overarching topic I want to talk about
  • What they’ve said on the topic (quotes or excerpts from books, articles, speeches, appearances)
  • My thoughts/questions on it
  • A parallel story from a previous conversation

The parallel story is particularly important. Over the years, I’ve worked to develop pattern recognition: this involves matching the information received in the moment with prior knowledge from previous conversations. Doing this can take a conversation to a deeper level. Mentioning associated information can engage the guest’s own curiosity, and thus turn an interview into a conversation. On a recent episode with Ryan Holiday, for example, I made a comment that built on something he said, and he followed up by saying, “Hold on a second, I need to write that down. I’m going to use that.” Creating moments like these builds credibility for me, and helps not only with the current conversation (“Oh, this host has learned some things”) but for future ones. Referrals or testimonials from previous guests help my podcast grow; they tell their friends to listen, for example, or to be a guest.

For each outline, I typically have 5-8 topics with each of the above three bullet points—and always in the same order. This is the material I review many times prior to recording, which helps me avoid looking at my notes (too much) during the conversation.

Pre-Show Chat

Prior to hitting record, I spend a few moments building rapport with my guest. “I want this to feel like two people who are becoming friends meeting for lunch,” I tell them. “I’d like to call you by your first name, and you’re welcome to call me Ryan.” This sets a friendlier tone and helps take them out of “interview” mode and more into a conversation. I’m not a journalist and not trying to be one. I like having—and learning from—conversations, and to me it feels more like a conversation when we call each other by our first names.

I also make sure they know they can trust me. It’s crucial that my guests feel completely at ease with being transparent about what they think. “If you say something you regret,” I offer, “then tell me, and we’ll edit it out. Nobody will ever hear it.” This distinction—between the role of journalist and conversationalist—is key for me and for my guests. My purpose in these conversations isn’t to find news and report it; I’m just a guy wanting to learn from a variety of excellent people, and to do so fairly and graciously with those who are generous with their time and thoughts. I said this to John Mackey, CEO of WholeFoods, prior to recording. At times, he’s lost trust with journalists for taking his words out of context. Knowing where I was coming from in our conversation put him at ease. He laughed, relaxed, and even mentioned it while we were recording.

I also make sure to share a brief history of my show, as well as the type of people who listen (“A lot of emails I receive are from leaders in mid-level management positions, or people who desire to be in one of those roles—anyone from a front-line manager to an SVP of a large organization.”). This helps them understand the audience. While I am the person they’re speaking with, the audience is who we’re both speaking to. Picturing who they are helps us both.

What’s Your Hook?

Best-selling author Ryan Holiday offered me this advice after reading an early draft of my first book: “Grab your audience by the throat from the instant they open the book. Use a story that hooks them.” Beginning a podcast interview is no different. Starting off a conversation with, “So… tell us about your story. What do you do and how did you get into that?” is super boring. Why waste their time asking for information anyone could Google in five seconds? Instead, I like to ask a question with substance: “What are the commonalities you’ve found among people who have sustained excellence over an extended period of time?”  This forces the guest to bring it immediately, and gives me something useful within the first two minutes of the conversation. This has become an anchor—something for the audience to smile about when they press play on a new episode. Additionally, my guest’s answer typically gives me a good follow-up question to get even more specific (“Who do you think embodies those characteristics and behaviors?”)

How To Respond

Preparation, pre-show chatting, and hooks aside: the initial response after an answer is what makes or breaks an interviewer. I have three primary ideas when it comes to my response:

• Build on what they say. Take their answer and be additive to make the point even stronger.
• Disagree with them. This can be delicate, but when done with thought, it can create a dynamic conversation. That said, it must come from an authentic place and be your real opinion—there is no advocating for the devil here. There are talk shows all over TV where the hosts “choose sides” in order to have constant disagreement and create division and outrage, and I think we’ve seen where that leads. That’s not what I’m talking about. But I do strive to have real, substantive conversations, and that means we don’t always agree.
• Move on. Don’t say, “Oh, I love that” and ramble about how incredible your guest is. If you don’t have anything to add, go to the next question.

While keeping an eye on my outline, I’m simultaneously listening to what my guest is saying and preparing to respond to that answer. If I want to go deeper because they’ve piqued my curiosity, I immediately go for it. Sometimes, it’s a simple one-word question or short phrase of encouragement: “Really?” or “Tell me more…” or “And then what happened?” These moments are the challenging parts of interviewing—and the moments I love. I never know the right move beforehand and have to make instinctive decisions all the time. These decisions are the difference between a good show and a great one. This becomes more instinctive the more I do it. Like most things, it’s about repetition, purposeful practice (getting feedback after the repetitions of many shows), and adjusting.

When To Close

For every conversation, I want to end at a point where I’m still eager for more. I want my listeners to say, “Ah! I wish that episode were longer.” Why? Well, I’d rather sprint than walk across the finish line. I want to want more. I want my listeners to want more. I tell my guests, “I’d love to continue our dialog as we both progress” to ensure they hear me say, “Let’s keep this going.” Part of why I do what I do is to build meaningful relationships with great people.

Additional Tips

Aside from the process points noted above, there are a lot of other techniques and tools to help transform your time with someone from an interview into a conversation:

LISTEN

Patrick O’Shaughnessy is the CEO of O’Shaughnessy Asset Management and the host of “Invest Like The Best.” He offers a great image for the flow of an interview: “The role of the person asking the questions is to create and sustain momentum. I have this visual of a rush of water running down a maze of tubes which have hatches that open and close. If the water hits a closed hatch, everything stops. My job is to anticipate by listening very carefully and get ahead of the water to open doors to keep the momentum going.” Two of the world’s most effective leadership development trainers, Dr. Jack Zenger and Dr. Joseph Folkman said, “Good listeners make you feel better not merely passively absorbing, but by actively supporting. This lets you gain energy and height, just like someone jumping on a trampoline. So remember, if you want to be a better listener, be sure to actually pay attention and interact with the person talking to you.”

The best questions are follow-ups. A good follow-up question takes a surface level comment and goes deeper.

Look At The Camera

If it’s on Zoom, I work to look into the camera as much as possible. This feels weird because I want to look at my guest (on my screen), but it’s more important that they feel as if I’m looking at them. And to do that, I have to look directly into the camera.

Also, if you watch my episodes on YouTube, you’ll notice that if I’m not talking, I’m probably writing. I write a loose transcription in real time, which serves multiple purposes:

• Handwriting what’s being said helps me retain the knowledge
• Having their ‘in the moment’ quotes at my fingertips creates opportunities for call backs later in the conversation
• It helps me type the show notes (which I later publish for each episode)

Read The Acknowledgements

For guests who have written a book, I start my search with their acknowledgements section. I remember writing that section of my own book, which was an emotional process. (When Doug Meyer asked me about this segment of the book. I started crying.) I wanted to thank everyone who had helped me. I know the same is true for most authors. Because of this, I search for important people in the lives of my guests, and usually ask about them early in the interview. Most guests do not get asked about the acknowledgements in their book, and it can be a welcome reprieve from talking about the contents of it. Setting the tone with something personal creates a more engaging (and loving) conversation.

Draw Out The Story

For John Mackey, I wanted to know how he felt when one of his best friends tried to take his job. To get to that place, I asked about the failed experiment he conducted with WholePeople.com. Then I asked about his move back to Austin, and the surprise meeting with the board when the coup was in process. It was emotional, raw, and real. Later in the conversation, I asked John what qualities he looks for when hiring a leader. When he said loyalty and trust, it tied back to this earlier story. It was a callback to the raw and emotional part of our conversation. It humanized him and illustrated the why behind his most important values. Don’t just take the story as told, react, and move on: take the time to probe for the details that make it come to life. In doing so, you do the same for the storyteller as well.

Be Purposeful

Saying as much as possible with the fewest number of words is a crucial skill for stand-up comedians. As Andy Sanford put it, “You have an allotted amount of time where you can only say so much, so every word should be pertinent. That doesn’t mean that every sentence has to be funny, but it must serve a purpose.” The same is true for an interview. Each question must move the conversation forward and help the guest share an insight. I try not to wander. This is something that takes time and a lot of practice, but the effort is worth it. Make every question count.

Make the Moments Come to Life

“It’s 1999. You’re sitting at a table across from the leaders at Yahoo! negotiating a deal to sell Broadcast.com to them. What was going through your mind as you walked in the door? What did you say to them? How did you and Mark celebrate after the deal closed for $5.7 billion?” I want to help my guest take me inside those rooms and inside their mind. This is where preparation pays off. Without it, you won’t know where those “moments” reside. Sometimes, you may have the fortunate luck of stumbling across one during the course of your conversation. “Wait… You met with Jeff Bezos at his house for the initial talk to sell him Whole Foods? Tell me more…” Listening well is the key to seizing on these gifts of chance.

Feel and Think

Some people are more cognitive; some are more emotional. I want to draw out both sides of their experience and wisdom, so I use these questions intentionally: “How did you feel?” and “What did you think?” These are not the same questions, and they don’t generate the same kinds of answers. If you can credibly peel the two apart for the guest, you may uncover an insight that normally goes unsaid.

Tell Me…

Instead of asking, “How was your trip to India?” Say, “Tell me about your trip to India.” If you ask your kids, “How was your day at school?” their answer is: “It was good.” But “Tell me about your day at school” forces them to think of what they actually did. It’s more open-ended, and open-ended questions get more information. (h/t Alexandra Carter)

What and How

I try to ask what and how questions whenever possible. A why question can put someone on the defensive, whereas a what or how question comes from a place of curiosity. Instead of saying, “Why did you decide to hire that person?” ask, “What was it about that person that compelled you to hire them?” (This also makes the question about the qualities of the person they hired instead of about the hiring manager. If I’m trying to learn about the qualities of an excellent person for that role, this is a better question.) With that said, there are exceptions. Sometimes a simple Why? can be the perfect follow-up. As Picasso said, “Learn the rules like a pro so you can break them like an artist.”

Get Tactical

My interviews go from high-level overviews to down-and-dirty tactics. I find it important to get practical guidance for my listeners—tangible takeaways they can implement immediately. In my conversation with the former CEO of Nasdaq, Robert Greifeld, I asked, “What is your exact hiring process at Nasdaq? What specific questions do you ask in the interview process? What are you looking for in a candidate? What is it about those qualities that you find useful? When have you made a mistake? What caused that mistake? What did you learn from it?”

Don’t allow high level theories only. It’s OK to start there, but it’s best to ask for an example that can take you deeper. David Epstein told me, “We learn who we are in practice, not in theory.” Like my listeners, I want to learn from something that happened, not just a theory.

Silence

This is a next-level skill that I still struggle with. Sometimes the right answer is to be quiet. Let the answer sit. Often, the guest feels compelled to fill the space and will build on the point they just made. In addition, sometimes a little quiet allows them to reflect and go deeper, or to express a thought more fully.

My Process

It’s important to reiterate that this is my process, meaning it’s what has worked best for me. The combination of researching/preparing, having the conversation, handwriting notes, and listening to the final episode helps sear that knowledge into my brain, which allows me to recall it when I need it. Yet the only real constant in my process is that it evolves and changes as I learn.

Improving upon any process is a combination of doing the work and studying the greats. I am always on the lookout for great interviewers (on TV, podcasts, talk shows, etc.) and am constantly deconstructing the formation of questions they ask and how they get their guests to open up. For example, watch this conversation between Anderson Cooper and Stephen Colbert. Both are world class interviewers, supremely prepared, and agile in the moment. Watching them work inspires me to be better.

Listen to Terry Gross share her process. She’s been one the greatest interviewers in the world for more than 40 years! Or Howard Stern, Joe Rogan, Guy Raz, and on and on. Each has undergone a continual process of learning and of doing the work. Nobody’s perfect , but as with most professions, purposeful practice (getting the reps AND constructive feedback) will certainly make you better.

 

Ryan Hawk is a keynote speaker, author, advisor, and the host of The Learning Leader Show, a podcast with millions of listeners in more than 150 countries.  He is the author of WELCOME TO MANAGEMENT: How To Grow From Top Performer To Excellent Leader.

A lifelong student of leadership, he rose to roles as a professional quarterback and VP of Sales at a multibillion-dollar company. Currently, as head of Brixey & Meyer’s leadership advisory practice, Ryan speaks regularly at Fortune 500 companies, works with teams and players in the NFL, NBA, and NCAA, and facilitates “Leadership Circles” that offers structured guidance and collaborative feedback to new and experienced leaders.