May 24, 2022

Asking Great Questions

What is that question that you should never ask on a podcast?

For the answer, you will need to check out today's episode, but in the meantime, let's talk about what makes a great interview on a podcast. We often don't realize the full power of a great interview as a listener until we are behind the microphone.


Like all skills in podcasting, it's a muscle that needs to go to the gym and get stronger.

But what are some of those easy tips that we can apply right now without learning the hard way? Is a question Mathew gets often. So these are precisely the questions we dive into today on the show.


·     Facebook exits Podcasts (1:40)

·     What does the podcast world want from social media (7:42)

·     The art of a good interview (11:42)

·     Managing exhaustion during an interview (13:00)

·     How to pull out a good story (17:07)

·     Is asking questions or having a conversation better (25:45)

·     What does an excellent pre-interview checklist look like (28:21)  

·     How to avoid painful topics with a guest (31:27)

·     Learning to advocate for yourself as a guest (37:15)

·     What never to do on a podcast interview (42:31)

Thanks for Listening!

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Speaker 1 (00:02)

Hello and welcome to Podcasting Anything and ask me anything for all things podcasting. I'm your host, Ben CLOY, and I'm joined here in the studio with Mathew Passy. The podcast control Matt, and I wanted to move the conversation beyond the Podcasting 101 topics and move into the intermediate to advance podcasting strategy. To reach your goals, to interact with the show, submit your questions to be answered live, book a podcast audible with Matthew or find the notes from today's show. Head on over to Welcome back to Studio Three. Here I am live with Mathew Passy here talking about the news, a deep dive that, you know, every interview podcast is going to need tying to questions, and we're going to wrap up with a question. Matthew, welcome to Podcast again. And you gave me that weird awkward look of like he did it again.

Speaker 2 (00:48)

Well, the real thing is remote location. So am I really in Studio 03:00? A.m.? I in three B. Three A. Right. Is this still Studio Three?

Speaker 1 (00:58)

Here it is still Studio Three. And if anybody's wondering, this is also the studio where they record The Tonight Show with Jimmy Fallon.

Speaker 2 (01:05)

I see.

Speaker 1 (01:05)

Yeah. This is a big primetime podcast studio.

Speaker 2 (01:10)

Okay. Well, then I'm excited to be here, as always.

Speaker 1 (01:13)

Back only thing we're missing is Rockefeller Center. Although I think Jimmy Fallon recorded from Rockefeller Center, I don't think it's in somewhere else in New York City.

Speaker 2 (01:23)

If he's doing it through NBC, then yes, I don't think it empties out onto into Rockefeller Center. We're not going to go over the geography of the NBC.

Speaker 1 (01:33)

We'll continue to work our analogy and our cat talk introduction of Studio Three.

Speaker 2 (01:39)

That's fair.

Speaker 1 (01:40)

Well, Mathew, we got kind of some sad news today or actually, it came out last week. And it's just the downside of the podcasting world is because everybody tries to play in it and then they try to get out of it because they can't figure it out. And the news that we're talking about is Facebook is quite abruptly, not even really like gradually got an email just even yesterday, June 3 is the day podcast will no longer be published on Facebook. How did you take that news?

Speaker 2 (02:09)

Not shocked at all. They announced it. I don't know. It felt like two months ago that they announced that you couldn't could add your podcast to your branding page. And the rollout was clunky and difficult, and we filled a lot of questions about how does this work? Where does it show up? Personally, I put calls pods attached to the call spots. Facebook page, couldn't find it for four days, kind of gave up on it. Then one day somebody was chatting about on one of the Facebook groups. I was like, I wonder how it's doing there. It was like, oh, I guess it's here. But really, I don't think they really gave it a chance, emphasized it. I never actually tried to play a podcast via Facebook while I was meaningfully scrolling on the network. So I'm not surprised at all that they are killing it. However, I do want to make one thing clear because I got a couple of emails actually after Facebook sent that email out, which is some people were like, so can I never post my podcast to Facebook? No, you can post your podcast to Facebook. It's just not going to be built into your page anymore.

Speaker 2 (03:14)

And I don't really get why they are killing it. I saw something about they want to refocus their audio offerings and something about the Metaverse, but what does it really cost them to include it on our pages? The way we include other information is about a tab that people barely saw. So I guess another short lived stint for podcasting that I think so few people are going to mess except for the podcasters who had to go through the struggle of uploading it to their.

Speaker 1 (03:46)

Page one moment because I had it connected from me. And I did have one actual listener, homeless, religiously, every single day because I published a daily episode. He would always like the post. So Facebook figured that out put in front of him every single day. The one annoying thing though was you could never share the episode to the story. Like the only thing you could do is share it to your feet. And I'm like, I don't want my feet littered with a bunch of podcast episodes. I'd rather just put it in a story because I post so many everyday had they had done that, it was a decent audiogram and had decent visuals, they didn't spend any time understanding how it could be beneficial in getting it into the normal workflow. And I feel like the first time they coded it, they fix some of the bugs and then like, a lot of things. And I was really also thinking like, can you imagine how short sighted it would have been if the early podcasters would have been? Like, you know what? I like doing this. It probably has potential, but we're not getting any results and we're out.

Speaker 1 (04:42)

I mean, the reason why there's Pod fade at ten episodes every time is because people get tired and they look at the results they're getting and they're like, you know what? I'm out instead of like, maybe if I just tweaked a few things or ask for help or maybe brought in a consultant to figure out what could we do with podcasting? It's just a lot of irony, I think, tied to podcasting and how Pod fate occurs.

Speaker 2 (05:06)

Yeah. I mean, I think there could be a lot of frustration there that people are putting their heart and soul and effort into creating content and then they're finding it difficult to generate and grow an audience. And we try and talk to people about what are ways to do that. But truthfully, more and more I am seeing more memes and posts and tweets and online content where there is this perception of podcasting and it's facetious in nature, but it's out there that most podcasting is just a bunch of people rambling into a microphone with no real purpose. And why would we want to consume that stuff? And yeah, I think if you are just a bunch of people who are rambling into a microphone with no real purpose unless you are really funny, really entertaining, have super high value chemistry, yeah, you're probably not going to find an audience because nobody has time for that nonsense. It's just not productive content and our time is valuable. There's just not a lot of mass appeal for a bunch of people who think they're hilarious talking around the table, shooting the proverbial shit or whatnot, and thinking that they're going to grow an audience.

Speaker 2 (06:24)

Are there shows like that that exist and are successful? Yeah. But for everyone that is successful, there's probably another 30,000 that are not. The same is true for people who are getting into radio and people who are creating music and people who are doing YouTube channels and people who are writing books. There's no guarantee that just because you think you're entertaining or special or funny that you are going to be successful and there's no guarantee that truthfully. Oftentimes the people who are successful and famous and rich and everything like that off the stuff aren't all that good. Sometimes it really is just a bunch of luck. Now, on the other hand, if you are doing this with purpose, right, if you are trying to provide specific value, if you're trying to answer specific questions, if you are catering to a specific niche, if you are filling a void, right, if you don't need the kind of numbers that people are craving so they can sell mattress ads on their show, then yeah, by all means, it's still a great platform for sharing content and distribution, but it doesn't mean you're going to become the next Joe Rogan.

Speaker 2 (07:34)

Not that that's necessarily a good thing for everyone.

Speaker 1 (07:37)

You know, the other thing that would be hopefully not something we have to discuss here, but the YouTube announcement of their deep dive into podcasting that hopefully the death of podcasting and Facebook doesn't persuade YouTube to pull back before they ever get going. And then two, hopefully the lessons of Facebook's podcasting journey is enhanced within YouTube. But then even more. This is probably what to get excited about. Youtube is primed to be that one social media platform that does it well and automatically and creates a spot for that content to live in a place that doesn't just get canceled and doesn't make, doesn't add complication to the process and also supports content creators in a way that we want.

Speaker 2 (08:19)

Well, I think the other thing about this is that it's less about how we share our content. I think for so many of us, the idea of Facebook. Bringing podcast to the platform was great. Another way for us to share our content. And what I think so few people are really and this is really on the tech and the Facebook and the platform side is it's not really about that. What would make this work better is if it was just easier to consume the content on that side. I don't necessarily need to be able to access content on every Facebook page. What I need is a standalone player or a way to add episodes to, like Reals or my save list. That then when I go onto Facebook, I can just hit a button that says, yeah, what's in my Facebook podcast queue. Right. Or pull from my Apple podcast subscriptions or things like that without that being part of the focus. And I hope that's sort of what Twitter is looking to do. I'm just not sure what's going to happen.

Speaker 1 (09:31)

Do you mean to say Twitter or do you mean to say YouTube there?

Speaker 2 (09:36)

Sorry, I actually meant to say Twitter, because both Twitter and YouTube are kind of showing and hinting and dropping things about the fact that podcast could be coming to those platforms as well.

Speaker 1 (09:47)

And the Twitter angle also has the Elon Musk angle of wherever that could add into of changing the focus and priorities as well. So that one maybe could lose steam. But whatever gets off the ground as well.

Speaker 2 (09:59)

Yeah. I don't know if you I'm not sure how I feel about the whole, like, does Musk make it better or worse? I just don't know where that's going to go with him. I don't know. Does he listen to podcasts? I know he appears on a few of them and lights up a Doobie with Joe Rogan, but I still don't know if that means he consumes them regularly or cares about them.

Speaker 1 (10:21)

Yeah, that would be the thing. When he's flying around on the jet, is he having business meetings on the jet? Is he reading books on the jet or is he listening to a podcast that would almost be like his number one spot where although his brain probably never turns off, I feel like that's one thing. Elon Bryan is never off to slow down and listen to a podcast, so he's probably not. He's probably got something else he's doing on the airplanes.

Speaker 2 (10:42)

True. And my sense is he's mostly just working. Right. He's managing a lot of different companies, a lot of different teams, a lot of different deals. And so my guess is there's not really a lot of downtime where someone is not trying to get a hold of Elon and get his approval or his take on something that's happening.

Speaker 1 (11:02)

Yeah. Well, with that, let's go ahead and put a bowl on Facebook killing off podcasts and move into our deep dive today, which is kind of simplistic, but it's also one that there's a reason why people like Barbara Walters and George Stephanopoulos become these people that are Premier interviews of the most elite people in the world. It's because it's a practice. It's an art. It's something you have to improve. It's not just something you wake up every day and ask good questions or ask the right questions to get the answer that the audience knows they need. So first question up the bat here on the steep dive. When you are listening to a podcast that's come to you for a consultant and you're trying to find out and listen to the quality of their questions, how do you even evaluate from an outside consultant view if this person maybe has a funk in the quality of the questions they're asking or Kink maybe is another way to say it.

Speaker 2 (12:01)

It probably happens as a you probably based their ability on the results. So if you are asking the wrong questions, then you are getting a very disjointed and poorly thought out story out of that conversation. So good interviewers, good podcasters we've talked about in the back, they're really good listeners and they're paying attention what the person is saying and they're shifting. But also they are using the time as a way to tell a narrative or a way to pull out a narrative. And so there's kind of like a it makes sense. There's an arc to what they are trying to accomplish. And I think one thing you hear podcasters who are not great interviewers do is they just kind of go all over the map. They often lose their train of thoughts and they often lose like the train of processing. And it's funny, I'm saying lose their train of thoughts as I'm trained.

Speaker 1 (13:04)

You've got this on mode where you have this train of consciousness going for a 60 Minutes thing and trying to keep it all tied together is how I feel sometimes, which is also exhausting doing.

Speaker 2 (13:13)

Yeah, you'll see, this often happens when people try and do their intro before they've recorded their podcast. They'll be like, today on the show we're going to talk about Facebook asking good questions and what's going on with YouTube. And then they go into the interview and they start talking about topic one, and they never get to topic two or three because they are not staying on topic. They are not focused. They're not trying to tell a story. They are just trying to fill enough time to put out a decent episode. And so us as the listeners were like, well, I wanted to hear about B and C, the topics that were there, like what happened to those? And you quickly realize, well, it's because the person isn't really their thoughts aren't organized. They are not prepared to do the interview and they are probably waiting to talk and not really listening, whereas really good podcasters and we've talked about this before as well. They will have a set of questions, a set of things that they want to get to right because they've done some research ahead of time. They've prepared themselves for the conversation that is coming up.

Speaker 2 (14:17)

There are things that they specifically want to highlight or focus and listen. Sometimes plans go awry because you think you're talking about A, B and C and you're like, you know, Ae and F was actually more interesting, but it's interesting in the scope of what we were trying to accomplish. Right? We have a goal for this show. For example, a lot of people do successful entrepreneur show, right? And they get the chance to talk to Elon Musk and instead of talking to him about being a successful entrepreneur, they wind up asking him questions about Tesla or smoking weed with Joe Rogan or buying Twitter or messing with people on Twitter. Those are interesting, but that's not the goal of your show. That's not the focus of your show. That's not the value that you are promising your audience that you are going to get from your show. What it means is you are just excited to talk to this person and you cannot keep your train of thought, your stream of consciousness, your focus in the right place, and that's going to get you really good podcasters have a mission, have a goal in mind, have value that they want to deliver and they use that time to deliver it.

Speaker 2 (15:28)

Even if they find value in something different than what they expected, they are still working towards the ultimate goal of we want our audience to take this away from the show. And that's where I think a lot of people get in trouble. And that's why so many people who like, yeah, we just sit around the table and talk and have fun. It's like, okay, but are you always having fun? Are you sometimes fighting? Are you going on tangents? Are you doing inside jokes? Are you just making fun of people when you don't have a real solid focus or a real solid understanding of why you're doing this and what value you want to give the listeners? It's easy to just create mindless content. And truthfully, nobody wants to listen to mindless content, correct?

Speaker 1 (16:10)

There is already enough mindless content in a lot of other places on the internet. Even though you're watching the stuff that my kids watch for YouTube. To me, that's mindless content of people doing challenges over and over and over and just doing crazy things. And it's got to be just exhausting trying to redefine crazy and then having people have their almost numbness to the craziness. The one question that hit me when you were talking about it and I think this is what you were hinting on with Elon Musk that can be also just as tricky is unique ability to the question like, is this a question that he's rehearsed because he's been asked 400 times and his juice and excitement behind the question is very mediocre at best? Or is it unique to the point where you're going to get a story or maybe have you heard him tell a story? And you're like, I feel like there's a story behind that story. And I think maybe even that's what the pros that the news stations essentially do is they understand that there's these stories behind the story in your business and radio and just doing podcasting for so long, is there any secret weapon that you've discovered to help inquisitively, hear or look for or ask a question to get to a story behind the story?

Speaker 2 (17:26)

I think what it requires is knowing what stories are out there. So if you are going to interview an Elon Musk, right, you are going to have to listen to some of the other content that is out there. And you're going to have to realize that I don't want to repeat the same questions because if people wanted to hear the answer to that question, that content already exists out there. Also. Same thing we were just saying. Right. Do those questions actually add to the value you are trying to create or are you just filling the time? But really, when you're doing radio or when you're doing television and you know what, where this comes up a lot is people who start their interview with so tell me about yourself. Where are you from? Where do things begin? Let's go all the way back. Right. Good presenters, good storytellers. Like you said, they'll provide that information quickly. Succinctly. Right. Ben is a former military professional. Now he's a dad. But what we really want to know today is this. And to your point, like Bill, find the things that you would have talked about and find the angles of those stories that matter to the overall objective.

Speaker 2 (18:41)

How did your military service prepare you for fatherhood or whatnot? How does being a podcaster improve on your entrepreneurship today? Or how do your kids impact your entrepreneurship as opposed to just saying so you have kids, right. That's the question of someone who isn't prepared and isn't ready to get a deep dive into someone. Right. If we can read most of the stuff on the Wikipedia page, it's not that interesting. But how do you feel about it? How did that impact you? What made that so different from other things that have happened about those kinds of questions are the ones that are going to draw interesting things out of a person. And again, they have to be in the context of what you are hoping to accomplish with your content. This also happens, by the way, if you stop interviewing the same people that everybody is interviewing. Yeah, it seems easy. Oh, I get Elon Musk on the show. Well, everybody knows Elon Musk, too. It's about I've got a big audience. Yay. Yeah. That sometimes happens. Pick up a few. Right. A little bit. Mostly Elon Musk fans listen for Elon Musk and then they move on and they find the next show.

Speaker 2 (20:03)

No, they're not sticky fans. What you really should be doing is finding the stories. Finding the people who are not being spoken to, who are not all over the place and tell their stories is what I think would be help people be more successful in this space.

Speaker 1 (20:20)

I think there's another angle that I often use in my podcast where someone's telling their military story and I'll detect like, a feeling, like oftentimes where they're an overachiever in the military, they are defined by their accomplishments, their ribbons, what they've done, like where they've started, what places they'll talk about going to Officer Academy, West Point. That was what I was thinking of. I feel bad for not thinking of it right away. But West Point, and I'll be almost thinking like, it sounds like you were just trying to prove something or like you were trying to run from something. Like, a lot of times, speed in life is proportional to what they're trying to leave behind. So I'm like, what was life like before you went to the military? Because it seemed like you were trying to define something that was different and realizing those are often like the stories of before the heroic story, there is a moment of like, yeah, life was kind of a dumpster fire and figuring out those little struggles within their life. I feel like that's where you also get a lot of juice. And I'd like to take the next question to you, which initially is hard.

Speaker 1 (21:26)

The answer is kind of default to you ask. But one thing I still struggle even have many conversations I've had understanding in the moment livestream in your mind what question the audience wants to ask this person.

Speaker 2 (21:42)

You know, podcasters who are really good at this and who have built up an audience and those who are a little bit more savvy, they don't have to anticipate what question the audience wants to ask. They will actually give the audience a chance to ask their question. I work with a podcaster right now who started a Patreon, and literally at the beginning, I think he was doing A-2-A month Patreon thing where you could be one of his patrons for $2 a month. And for $2 a month, you would find out who the guest is ahead of time and be able to submit your question and he'd read them on the air to the guest. And it's a big thrill for someone to have their question asked of someone Uber famous in their space. Right. And not only that, it helps you create great content and gets you an understanding of what people are looking for. But to your point, in general, if you are not at the place where you can have paying members and offer your community advanced notice of who the guest is and get questions like that, it's just about being curious.

Speaker 2 (22:49)

Right? If you already know the answers to the questions, why are we asking them. What you really have to do is you really have to be listening and following a lot of it is just gut. Right? You said, I had a feeling. I just had this idea just popped into my head. And that idea probably popped into your head because you were genuinely interested and empathetic to this person and curious about this person and passionate about learning about them. So many people are doing this right now and it's just become habit, routine mechanics, muscle memory, and they're just going through the motions of asking the same questions. Yeah. So tell me more about that. Oh, that's interesting. But they're not genuinely curious or passionate about the person. If you're really passionate about the person, if you are really empathetic to that person, if you really care about what it is, what value you're trying to deliver for your audience, you'll know the questions they want to hear because as you're listening, they're the same questions that you would ask if you were listening to this person. That's why it sometimes drives me nuts when you have the people who are like, we have ten questions we ask everybody and we ask them in a row because you might have asked out of the first four questions, the fourth question, he might have given an answer like, wait a minute, I would like to learn more about that.

Speaker 2 (24:19)

But you're answered question number five and it doesn't really matter because you're just reading off question five because that's what you think you do.

Speaker 1 (24:25)

I will never forget there was a listener way back, probably like month two military veteran dad after launching. And he's like, I wanted more from that answer. But you were more focused on the next question because in the beginning I started with questions, I had ten questions, and it was running through it, and I was less focused on deep diving or throwing out the questions, which is probably something. Also the Pro News Network interviewers do they probably have a list of questions even themselves going into those interviews? And at some point they might throw it out in their head and you're like, okay, we're going in a different angle because you want to even interview to the flow of energy in the room. You don't want to get a flow of energy going in direction and then yank it back. Like the listener feels that I could easily see that happening in their life or in the listeners minds of like, man, we were going that way and then all of a sudden we yanked it all the way. And I think sometimes it's okay to resent her if you get off on a tangent.

Speaker 1 (25:23)

But I think doing it for the sake of question, like, you have a script that could probably be a danger zone. I actually want to ask something I do to you quite often, and I think it's a bad habit, but I want to just talk about here and riff on it for a little bit. Often times where I'm focused on just having a conversation, I don't always ask a question. It's almost just like a tag you're at thing where each person talks about something or responds to something or adds something to the topic and then the other person responds back to it. Do you see any benefit or is it a balance towards that or is that something that I really need to learn to let go and focus on giving the person I'm listening or talking to a question? Or is it okay that if you dive deeper into it and then they just have a moment to add to it, respond or go in a different direction?

Speaker 2 (26:12)

I think it comes down to feel and chemistry like you and I think we could both kind of read our physical cues. We can read our verbal cues, right? I can read the tone of your voice and kind of know when you are getting to the end of a point without a question or about to actually ask a question. I do that often too, which is I don't always ask a question. I kind of state something and hope that they are going to respond to it. But you have to be pretty quick on your toes and read the room and kind of realize, oh, I said something interesting. And if they don't respond right away, you've got to realize I better jump back in and refill the gap now and now actually turn that into a question and not do that anymore because clearly they are not going to respond. So I better turn around and actually ask pointed questions so that this person knows where to go and listen. Some of that is chemistry. Some of that are guests who they're just not. They're quiet, they're shy. Whatever it is, there are some people just like, I'm here to answer your questions.

Speaker 2 (27:18)

So if you don't ask me a question, I'm not answering, there could be a million reasons why that doesn't work. But yeah, in a good conversation where you have that chemistry, like where you are developing this relationship, it is okay to be able to just finish a thought and see what the other person has to say.

Speaker 1 (27:39)

There is a thought that I was also thinking about in the negative of what we were talking, like asking a good question. Because the worst case scenario for an interview is when you literally have to pull the value out of the person where you kind of hinted at it, where it's just like that question should have been a paragraph and they gave you two sentences and then you're like, man, this is going to be the longest 45 minutes of my life here. Because if that's the case, my mind in trying to lift myself and you in this interview to actually make you sound good and look good, it's going to be exhausting. And so I'm also wondering, what is your best recommendations to a pre interview before you hit record? Because I think a lot of maybe the dead air, the bad questions, bad paragraphs could come from you just went into a place, he's not comfortable or she's not comfortable. So what do you recommend for a pre interview? Checklist to talk with someone before you get into the interview.

Speaker 2 (28:36)

I'm not a big pre interview person. I know there are lots of podcasters who want to chat with the person before they chat with the person. I would hope that when I am requesting that interview or when people are requesting to be on the show, they have a sense of what we're going to do. They've listened to an episode, we've given an FAQ or something like that that makes it clear what is going on and what we're trying to get to. And so I'm not big on that for cause pods. Pretty much. If I see somebody as a show that's interesting. That's about the topic that we like. I say, great, we'd love to ask you about it. Give them the link to the form, let them fill it out. If they email a question, I tell them, yeah, we're just going to ask you about your calls and your show and what you've learned as a podcaster, and we'll take it from there. And truthfully, I try and keep it casual and light and understanding. And by the time we hit record, I've kind of went through all the motions of, yeah, it's pretty easy.

Speaker 2 (29:32)

Listen, no pressure. If we go 15 minutes, fine. If we go 30 minutes, cool. If we only go ten, we go ten, right? Don't try and make it such a big deal on the person that they can relax and they can open up. And to your point, if you're asking questions and you're not getting good answers, okay, listen, you can try all you want to get in there, but you're probably going to get frustrated with the response. So ask your questions. Get your responses. If you're not getting a good one, ask a follow up. Ask them to clarify or just realize to yourself, not all these are going to be winners, right? You don't have to fill 40 minutes of content every single time. Maybe you put out a 20 minutes episode. Maybe you put out a 90 minutes episode because the person was so good and there were so many things that you were able to get into and all those different things. So anyway, what do I do for a pre interview? I make sure the person who I'm talking to wants to be there. Really? If I've got to force them to be there, if I've got to hold a proverbial gun to their head to get them there, they're not going to enjoy themselves.

Speaker 2 (30:39)

Yeah, maybe every so often you crack that egg and you get the person to open up and it becomes a lot of fun. But for the most part, if you are twisting their arm to be there, they're going to answer your questions, they're going to dance for you, and they're going to leave as quickly as possible. So I'd say don't worry about it and find somebody else. There's plenty of other guests in the ocean. I guess it would be the analogy there fish in the sea, guests in the ocean. Kind of true.

Speaker 1 (31:04)

It definitely works because you have to remember there are seven and a half billion people on this planet. And just because you had one dud doesn't mean that the next one is going to be a dud. And podcasting is this repetition not done in one single episode? You don't go viral because you publish one, and then you're done it's because you sequentially make a lot of content that sounds good and feels good, and people keep coming back. One thing that I learned back in I think it was 2020, maybe 2019, definitely, probably 2019, because nothing really happened exciting in 2020 podcast, or at least from a conference point of view, which is where I'm going. This person on stage talked about interviewing from the scars and not the wounds. And so as a person who interviews a lot of people that might have a traumatic story, that really hit me to remind myself that not every story is ready to be shared yet. And it's also like an interesting question that I sometimes lead with is realizing, is there any story that's just kind of too fresh for you? Not because sometimes I describe like if I get curious, I might go into a place that I don't want to go unless I know you're okay going there.

Speaker 1 (32:03)

And if there's a place off limits, maybe they don't like talking about their dad, or maybe there's some story that maybe they got divorced is another uncomfortable one that maybe not everybody is ready and making sure that you're interviewing from the right place in their timeline. And if there's any places in their timeline off limits, that's also what I have found to just kind of make you feel comfortable that you don't have to worry about questioning your head. Is that a safe question or not? But then you also are giving the other person permission to tell you that there's not. And then it also makes them more comfortable when they show up. Have you seen that come up with cause pods or any of the other?

Speaker 2 (32:40)

I get a little nervous sometimes on cause pods because some folks who are talking about this stuff, it might be very fresh that we are talking about it, but I have the privilege of knowing that if they weren't comfortable talking about this stuff, they would have launched a podcast on in the first place. It was probably a lot harder when I was working in radio or for folks who work in news when tragedy strikes and you're running up to somebody who is literally covered in dust or soot or smoke or God forbid blood or something like that and you're trying to ask them questions about something that happened and that's really fresh. Truthfully, I don't know how people do that and I'm glad that I'm not the one who has to because I couldn't. Right. I could not put somebody through that. So the fact that most of the content that I produce and work on is not in such a delicate nature. It's not really something that I've thought about too much. But to that point, unless you are live streaming and truthfully, even if you were live streaming, I think what you have to do is one give that person permission to say I can't talk about it right now because truthfully, that's an answer onto itself and that is a very powerful answer.

Speaker 2 (34:00)

Or if you are recording it. Right. I always say when I'm starting off cause Pods and Ben sometimes hears it on the tape and sometimes I hit save before I actually hit record. But what I always say to the guest is listen, if I have a question you don't like, just tell me, Matthew, that's a terrible question. I'm not answering it and I'll move on. Right. It's not my goal to make people uncomfortable or to make them upset or to open a fresh wound. So it's a little bit easier. But I also know good interviewers, right? You started with Barbara Walters and Stephanopoulos and even Oprah to an extent their super power in a way is getting people to talk about the things that are uncomfortable because that's what we are craving. Right. If we want the facts, the facts are out there. We kind of know what we usually want from these interviews is how did that feel or why did they do it or what was the motivation? It's that piece of information that nobody does know or nobody can understand. So I think either A, you have to be very brave in order to ask that question.

Speaker 2 (35:12)

Know that every so often you might get punched in the nose or somebody might walk out on your interview because it's too fresh or you're not being sensitive enough in the way that you are asking the question. And sometimes what you have to do is ask the question. Maybe you don't get a response, ask a few more, get them to open up a little bit more and then go back to that question. Right. You've also got to good interviewers, also do a good job of building rapport with the guest. And so if early on you try and attack that question too early, the person is like, I don't know, you don't answer that question. But if you've been talking to them for 40 minutes or so and you've gotten them to open up and to laugh and to bring up things that maybe they haven't had to talk about another podcast or YouTube cast or whatever, then you come around to that question. You ask it a different way. You might be able to maybe catch them off guard or get them more comfortable with answering your question. So it's persistent, it's feel. It still goes back to, I think, having empathy.

Speaker 2 (36:11)

And it also just goes back to being brave enough to ask it and knowing that the response might be go F yourself and you're not getting what you want from that person or the person leaving in a Huff.

Speaker 1 (36:25)

Two things that I'm taking away from this deep dive. One is understanding that as an interviewer, realizing that you need to kind of take an inventory of maybe where the muscles aren't so strong in your ability, at least just recognizing them and then even learning about how do you get better in those things? Because I think taking that inventory of maybe you're not okay talking about sensitive things and making sure that this podcast aligns to my strength as an interviewer. And if it doesn't align that, it's actually someplace where I want to grow. I think as an interviewer in a podcast, we often maybe discredit that or we don't put enough value into that. But also as a guest, what you also gave me was advocate for yourself in a way that doesn't just make you this person on the other end, where this person's talking down for you, advocate for yourself in a way that you are still a person talking on a podcast, you don't always have to be a perfect answer person. You can also just say, like, can you reassess that question? Because I don't really get it advocating to get the better answer.

Speaker 1 (37:26)

That's probably something I don't hear enough. Well, one, it's probably edited out, but two, I know I don't do that. I'm often trying to play off whatever they're saying. And if I do think it's a bad question, I'm not pausing and saying like, hey, can you ask that in a different way? I'd like to give a really good answer, and I don't currently have a depth to it to get there. Yeah.

Speaker 2 (37:48)

And maybe it's also again, you might just have to give it more time, right? If they say, I don't know, let me think about it. All right, keep going with the interview and then come back to it or re approach it. But also it does mean that as a guest, you have every right to ask what I don't like you. I don't like the idea of guests preparing their responses. So I'm not a fan of sending people the actual questions ahead of time because what they don't want somebody reading off the script and saying, my podcast is about this. It is a lot of that's not going to be interesting to anybody, but I do want to give them a chance to know what kind of topics are there, where we could be going and listen, give them the chance to say all that is fine, except I can't talk about this or maybe even give them the chance to say, you know, while we're talking about all this stuff, can we also touch on this? Yes. Like, these people are helping you, right, with your platform. They are giving you content. They are creating engaging materials so that you can grow an audience and sell that audience or sell your product or whatever else it is that you want to do.

Speaker 2 (39:09)

But many times they're going to get something out of this, too. So let them kind of use the platform as well if there's something they want to talk about, as long as it's not completely out of left field.

Speaker 1 (39:19)

So we're going to test something here with our question of this episode. And by the way, if you want to submit your question, head on over to and there's a little microphone in the corner to fill it out. And we will ask your question live here to Mathew and get you your answer in a similar way that we also just talked about, that if you have a question that you want to ask, Matthew and you'd love to hear a riff on whatever that question is, make sure you head over to And so, Mathew, I'm going to twofold here. I'm going to give you the question, and I'm going to give a reason why I asked this question. At the end of it. What was your favorite interview that you've ever participated in either as an interviewer? Like, I can't believe this opportunity presented itself, and I can't believe that moment actually happened.

Speaker 2 (40:02)

I'm going to let you finish why you're asking this question while I think about that answer, because I've done a lot of I've probably interviewed a thousand times at this point. And trying to come up with my favorite actual interview is a really, really tough question. I know there's been some really good cause pods out there that I thought were just special and interesting. There were people that I used to talk to when I was at the Journal who were just funny or we had a good relationship. And so anytime we were behind the microphone, it was just a good time. There were a few celebrities who were just like, oh, I get to talk to this person. That was a ton of fun. Category one that I always remember was I got to talk to Guy Fieti before he was really he was doing diners driving and dives. And you kind of knew who he was if you paid attention to Food Network. But I remember we got pitched in an opportunity to interview him. And most of the people in the office were like, I don't know who that is. And I was like, yeah, Guy Fieri from Dodge.

Speaker 2 (41:03)

My wife was a big Food Network person, and that's how bad it was. That when I did the interview. I was like, yeah, it's fierce here. I'm like, no, it's fiery. I'm like, oh, okay. But here's a celebrity guy who has this wacky personality and he's promoting something. It was a good cause, but he is out there promoting something and selling something, and is he just going to do this because he's doing a bunch of interviews and kind of be a jerk about it now? He was the sweetest guy in the world. He answered everything really well. I'm sure some of those answers were prepared, but we tried to give a slightly different angle than what they were really pitching, and he just went with it. And when I told you my wife loves watching you, and we're really big fans of the show, he was genuinely excited to know that people were paying attention to what he was doing.

Speaker 1 (41:51)

What podcast was that for? Cause Pods? Because you mentioned Causepods? Or is this some other podcast that doesn't exist?

Speaker 2 (41:57)

No, this was back when I was working at The Wall Street Journal. It was probably just a generic we put out interview podcasts. I probably was putting out like five or six different interviews a day.

Speaker 1 (42:06)


Speaker 2 (42:06)

Across the various fees that we had. So it was probably just like, they're doing an interesting story, we're going to use it on the news, and then we publish the whole interview anyway. So it's really hard to say what was the best interview experience I've ever had. It would be like asking someone what's their favorite movie or what's their favorite song. There's reasons why so many can stand out, and there's also reasons why I've done so many that it's hard to remember all the good ones. If I heard them, I'd rather be like, oh, yeah, that was a really good one. But right now I can't think of it.

Speaker 1 (42:45)

The reason why I asked that question and I teed it up. You hit it out of the park and it's going to bring this home is often, especially with, like, an Elon Musk is you're going to have these, like or another popular interview that I saw going around the circuit was Matthew McConaughey when he published his book. It opened up a very opportunity that a lot of people had. Matthew McConaughey on their podcast. And how many people is it just a cool thing to have Matthew McConaugh on your podcast and you're like, what's your favorite movie that you've ever been in as an actor? And he's probably going to have a similar answer that you did. And so the hint or the idea, like I said, you hit it perfectly is watch out for that impossible question that you may not have dropped it before, or if you are going to drop it, at least give them a chance to think about it, because I think this is where that rule would break down. But then also just realize you're going to create an awkward spot you're going to take him out of his thought process, you're going to destroy the energy properly.

Speaker 1 (43:40)

And there is a reason why at the end and you're going to have to try hard to get back on track because he just spent his last 30 seconds maybe going through his entire existence trying to find something and then he's no longer in this path and flow of conversation.

Speaker 2 (43:57)

Yeah. I think that was a fantastic question and a really good point that you bring up. And just to add to that, there's also this game that you have to play when answering a question like that, which is if I say this, am I pissing off this person? If I say this, am I pushing it? Did I forget to mention this person? It's not just a matter of will. I remember which one was really my favorite or if I say that working on Wilf of Wall Street was the best thing I've ever done. Like now are all the people who I have worked with on various movies, Dallas Buyers Club or whatever, they're like, what the hell, man? We want to ask you for that.

Speaker 1 (44:33)

Movie was our movie. Now you're saying it's another movie. Yeah.

Speaker 2 (44:39)

So I think that's a really solid point to stress, which is try not to ask open ended questions that you know you're not going to get the right answer. Be more pointed in your questions, be more specific and truthfully when you're interviewing him after ask him things that nobody else is asking him.

Speaker 1 (45:02)

Yeah. That they couldn't read in the book or maybe a story in the book that they wish he would have ripped on more because that book, if you never read it, it is a great book or a great book to go into. It's probably one of my top five all time books because he acts out the book and the audio in the only way Matthew McConaughey can do it. And so it just made the whole experience even better.

Speaker 2 (45:22)

I'll have to check that out. That was a good closing question.

Speaker 1 (45:27)

He titles the book at the end or he claims it like he wanted to write this book and not as a self help book, but an approach book, an approach how to look for the green lights and void the red lights or when a red light hits how to find the green lights again, which is the name of the book, the green lights. So Matthew, that's wrapping it up from Studio Three here, wherever address you didn't like my 19216 eight. So I still have to work on the address part. But thank you, Mathew. We did a great topic here today and I think we did a good service to podcasting to help and ask better questions.

Speaker 2 (45:57)

Great questions today, sir. And thank you, as always for I would say for having me. But this is kind of our show. So that's thanks for being here with me. Sir welcome.