Mastering the Art of the Interview | Polina Pompliano Returns!

26:11It was the most amazing experience. I could finally see what my friends from first grade are doing now. I would never call them, but I could see how their kid's soccer game did last night. Here's how I would do it. Sorry, sorry to interrupt you. I would, for example, I would say, you know, Mark, like Facebook is amazing for somebody like me because I get to, for the first time, you guys, you know, your company gave me the opportunity to connect with family in Bulgaria, where previously I had no contact with, like we couldn't share photos like this as easily, whatever. And then I would say, by the way, I noticed that my grandmother in Bulgaria is posting links to things that's definitely misinformation.

26:54information and it's kind of propaganda. How are you guys handling that with my grandmother? Something like that, where it's not as abusive. Right. Like, that's really good. Because then you could say like, does she need to be worried because the government in Bulgaria? And then what about, and then you could always bring that out. What about people here in the US? Is there this, is it different? Is it the same? Like, why are people worried about privacy here? Exactly. Yeah, that would have been good. And you know, all this stuff is important too for a job. Like, let's say you're just going for a job at some random bank.

27:26So it's like sort of generic. It's very important to research and figure out how to connect. Like why this bank? Why this person? Why are you sitting there? Like what's happening that's beyond just money and, you know, doing work that connects you to this experience? I think it's important to always think of these interview questions. Exactly. When I was interviewing at Fortune, you know, I go into interview for a job, but if I hadn't researched the person who was interviewing me, I would have never known that she got her PhD at the same university where I graduated from. That's a huge, like, connective, you know, thing that we could talk about.

28:06But if I hadn't done my research on her, I wouldn't have known that. And it would have just been like any generic interview she'd done that day. I'll tell you, like, that is incredibly valuable. thing that's going to come out of this particular podcast. Tell me. Just that type of thing when you research the people in advance that you're going to talk to in a job situation or some professional business situation. Of course, it's obvious that we do this in interviews or we should, but not everybody does that for a job interview or the first time you meet somebody in a professional setting. I've had companies actually acquired from me because I've done that level of research.

28:46which like one time I met the CFO of a company that was acquiring my company at the time. And I learned that he went to Grinnell College. And, you know, it was, we were both, you know, I had a finance company that I was selling. I said, you know, Grinnell College, of course. And I then, there was the CFO and the CEO in the room. I explained to the CEO, you got to really know that Grinnell College is an important case study because they have the fastest growing endowment because a young man by the name of Warren Buffett is sitting on their board of trustees. Wow. And so that ingratiated the CFO to me.

29:21You know, the CEO learned something. I was able to like, you know, show everybody I knew what I was doing. So stuff like that is really valuable. It's small, but it's like, I mean, we're human beings. It makes you more likable to me, you know? Yeah. And again, like no matter what an interview, the interviewee is nervous also they want to be at ease you only have an hour together you want them you want to be able to maybe interview them later like you said mark zuckerberg didn't go back to cariswisher for eight years i'm surprised he went back at all but i guess that's his job too to be the face of his company but it's it's important so okay no okay you got to set the tone number two uh by the way you mentioned you start mentioning larry king yeah and larry larry king is an excellent person to study because he specifically, and you mentioned he's conducted 60 ,000 interviews.

30:17That's crazy. Yeah. And he did not research on purpose the people he would interview because he wanted it to be fresh. Like the listener might not know who. But he really listened while the interview was going on. Yes. Yes. But what do you think of that approach of not doing any research at all? I think it works for some people. It would not work for me. I think I would be too nervous that I didn't touch on something that I should have touched on. And also I would be nervous that I'm just asking the same questions they've already been asked 10 billion times, but like the experts, the masters of their craft, you know, they know what they're doing and it's just, it works for some people, but you just got to know.

30:59Yeah. I, I don't know. I don't think it would work for me either, but sometimes when you do too much research, I have to make sure the listener knows what I'm talking about. The context, yeah. So sometimes it's a fine line to navigate, but I agree, I have to do the research. I'm impressed with Larry King, but there are some funny stories because Larry King does it this way. Like he famously asked Jerry Seinfeld in an interview, you know, how did you feel when your show was canceled? And Jerry Seinfeld was like, Larry, do you know who I am? Yeah, exactly. But like that makes for a great, great television.

31:37Yeah, it's true. Your second one's really interesting. Your second point is a good interviewer explores the gap between expectation and reality. So like, give me an example. Yeah. So, okay. I learned this from Brandon Stanton, who's the photographer behind Humans of New York. He interviews regular people on a daily basis. And he often has like 10 or 15 minutes with them. It's not, you know, two hours. So he's like, how do you build intimacy quickly? One of the questions that he asks is, how has your life turned out differently than you expected it to? And the reason that's such a powerful question is because it introduces conflict, like internal turmoil in the subject.

32:23They're like, oh man, I really thought my life would be this way, but then I got this drug addiction and now it's this way. And you see how like, it's almost like the life unlived, all the different possibilities of the way your life could have turned out and the way it actually did. So it forces the subject to kind of consider two realities and build a connection between them and be like, this is the reason why my life did not turn out this way. Yeah, that is really good. You know, I've never tried that question. That's a really good way to get fast intimacy. And you mentioned Ira Glass also in that.

33:03Yeah, he does the same thing. He says, how did you think the situation was going to work out before it happened? And then how did it really work out? It's something in my book, I talk about Aaron Sorkin, who wrote The Social Network and a bunch of other films. But he talks about a good story has to have conflict and intent. And this is what this question has. It has conflict and has intent. What did you want to happen versus what actually happened because of all these challenges that stood in the way? And, you know, I wonder, like, so Ira Glass's version of this, as you just said, how did you think the situation was going to work out before it happened?

33:42And then how did it really work out? That's kind of a broader. that, you know, so Brandon Stanton's, how does your life turn out differently than you expected it to? The situation there is your life. But Ira Glass broadens it out. It could be any situation, not just your life. What's another, is there any other kind of way to bring up that kind of conflict real quickly like that? Well, I was going to say like that, so that I call that a gap question. Like how did this work out and how did you think it would work out and how did it actually work out? you could also get a lot out of the person and their decision-making if you dig a little deeper and be like, well, how, like, were you worried?

34:25What were you doing in that gap? Like, were you worrying about how it was going to turn out? Were you, you know, you were just like, eh, whatever, like, who cares? Like, it tells you a lot about the person's mentality and how they look at problems and how they solve problems. But I think another, to answer your question, another way to ask that could be like, because we're assuming that a person had a vision of something amazing that would have happened and it actually did not work out. But if you were to ask me that question, I would have said, I actually thought my life would be way worse than it turned out.

35:01You know what I mean? Yeah. I was wondering that when you were saying this, because a lot of this, like it's almost like when Brandon Stanton's interviewing people, everybody's mildly depressed that things didn't work out the way they thought. So but what you just said about, okay, so there's this gap, but then the follow-up questions, how do they deal with that gap? That's where the meat is. So it's like you open the gap and then that's where you're kind of, you know, getting the seeds and getting the real meat of the fruit there. In the article, I say exploring the gap can give you a window into how the subject feels about their life.

35:39Like, do they have regrets about the past or are they grateful for their present? Are they proud of the choices they made or do they wish they could have a do-over? So it's like it's introducing regret. Another good question is like, what is something in your life that you regret happened or that you regret a decision that you made? Something like that. So let me ask you about that because a lot of people say it's almost like a cliche for people to answer that. Oh, I have no regrets because otherwise I wouldn't. Yeah. And like people do really have regrets. Of course they do. Okay. Yes. If you did this differently in 2012, maybe your babies would be different.

36:19Right. Right. Since then. So I get that. Like in a science fiction sense, you have no regrets. but really like, so how do you, how do you dig deeper for that? How do you dig deeper for the actual regrets? I think you set the stage of assuming you would still end up in the same place. Do you have something that you regret that you wish you could do over? Yeah, that's a good way to do it. So you, you, you, you get rid of their objection. Yes. Because the one objection is that I don't really want anything right now to change, but you know, so, okay. So number three, And this is a good one because I always am trying to figure out Joe Rogan, who obviously has the most popular podcast on the planet.

37:02And I really enjoy the way he has conversations. And they are interviews, but they don't seem like it. So number three is a great interviewer mirrors to gather more intel. So maybe describe what that is. Yeah. I actually think you did it earlier, so we'll have to listen back. But basically, what Joe Rogan and a lot of really, really amazing interviews, interviewers do is a technique called mirroring, which is I'll say something and I'll stop. And then the interviewer will take the last phrase of my last sentence and turn it into a question. So the example I gave is somebody went on Joe Rogan's podcast and she said a statistic.

37:4642 % of the rising generation have had a mental health diagnosis. And then he said 42 % of kids have a mental health diagnosis. So he's just repeating back her statement as a question, expecting her to elaborate more. Yeah. And I think that is really valuable because, A, it shows that, you know, that's valuable in a couple different layers. One is, as you point out, that forces them to go beyond the statistic and add more context and information and so on and maybe tell a story. But it also makes Joe Rogan, in that specific case, the voice of the 10 million listeners or 50, however, you know, the millions of listeners.

38:30Because we're all skeptical of it too. Or we don't really, it's mind boggling. Or how do we understand, make sense of that statistic? And so he becomes the voice of all of his readers as opposed to being Joe Rogan interviewing somebody. Yeah. And it like, you're right. It asks a question out of genuine curiosity, but it also introduces skepticism. Is that true? And they end up looking it up on the show to see if it was true. How does he—like, a lot of times, he just gets into these just conversations with people, though. Like, he'll have—he'll have, like—I saw one recently, like, Louis C.K. was on his show.

39:09Uh-huh. And they were just talking about the benefits of cold showers. You know, the Wim Hof cold shower, you know, cold plunges method. And Joe Rogan was saying it was good. And Louis C.K. is like, I don't really care. And I guess he sort of trusted Louis C.K. as an interesting enough guest that they could talk about anything and it'll be interesting content, which is hard to do really for many podcasts and interviews. Like you can't just let the – you just can't let the topics be about anything. But Joe Rogan does it really well. Yes. And, but, but also like right now, the way we're talking, this is how we would be talking, even if this wasn't being recorded, but it's also because this is my, I think, third time on your show.

39:53So I feel very comfortable with you. If it was my first time, I would be like, well, number three says that they explore the gap, you know? So it's like, it's like, he's already, Louis C.K. is his friend. So it's like almost as if we are listening to a conversation between friends and that's the magic of it. I think that's right. And I think like my favorite podcast, I don't know. And I would probably have to say my best podcast have been where it's a repeat guest. And so I pretty early on, I learned the value of having repeat guests, like just continuing the conversation we've always been having.

40:29And that is a great technique. And that's what Joe Rogan does. He basically just has his friends on yeah and uh and they just have a fun time multiple times yeah i mean he's he he's the king of repeat guests and i guess like that's true for howard stern as well and because they because people are listening for for them like you listen you turn into joe rogan maybe in part for the guest but also largely because you know his listeners love him howard stern's listeners love him oprah's listeners love her almost doesn't matter who they're interviewing yeah Yeah. And it's also, there's something about the interviewing your friend thing where if you have some sort of relationship or connection or friendship before the interview, the interviewer, it's not as abrasive for them to ask a hard question.

41:20You know, like if somebody says something and they're my friend, I'd be like, come on, you know, that's complete BS. Can you tell the actual story? You know, like that's not as, versus if I didn't know them and I said that. yeah and and i think the goal in an interview let's say it's a first-time guest my goal always is to try to get to that point as quickly as possible in the interview and sometimes it's not easy like it's really hard to kind of get that level of intimacy in a first interview but i i try to get that but it's difficult yeah definitely

42:10now number four here is and this is one that is a critical one because i used to be accused of doing this when i first started my podcast people would say to me let your let your subject talk and so number four you have is the great a great interviewer masters the art of interruption The best interviewers know when to interject, and you have a great example. Can you talk about your example? Yes. So yeah, you have to interject. Otherwise, I personally really hate it when somebody goes on and on and on, and then they make so many points in that really long monologue, but the host hasn't stopped them to explore it, so they just go unexamined.

42:49A really good example is Oprah with her Prince Harry and Meghan Markle bombshell interview that everybody tuned in to watch. So Oprah going into this knows that this is going to be watched by millions of people. She's well aware of the pressure. She knows that she can't just let Meghan and Harry talk and say whatever they want. She has to interrupt him and examine every single thing that they say. So at one point, Meghan Markle says something like, Like, well, the palace was really concerned with what color skin my baby would have before he was born. And Oprah just, I don't think Megan meant, I think it just kind of came out.

43:28I don't think she planned to say this. You see her like starting to like fidget in her seat. She gets super uncomfortable. Oprah goes, hold. She like throws her hands up in there, says, hold on, hold on. She says, hold up, stop right now. And she goes, there was a conversation with you about how dark your baby is going to be. So she, again, mirrors, says exactly what Meghan Markle said in her last communication, but she does it in this like big showy manner. Now the spotlight is back on Meghan and Meghan's like, oh, actually, actually, no, it wasn't a conversation with me. It was with Harry. I wasn't there.

44:03Also, she says she didn't hear it directly from the source and she declines to reveal who said it because it may be too damaging. If Oprah hadn't stopped her, people would assume that somebody told Megan to her face, what color skin will your baby? Like, it's crazy. So it's in that way as an interviewer, you're almost like a, you're fact checking on the fly. And that's what Oprah did here. It was really, really well done. And also, I guess, Megan, if Oprah hadn't done that, maybe Megan would have been obsessing in her mind for the rest of the interview. Like, oh my gosh. Yeah. What did I say? Do I have to clarify this?

44:44So Oprah gives her a chance to kind of like soften it. Yeah. And, and, and that builds a rapport and a relationship. And you would give another example with Letterman and Kim Kardashian about her political views. And so good. Yeah. Like, you know, that's a, that's a bigger example, but, and you, you, you mentioned though that Letterman, Letterman is an interesting interviewer because he's so quirky. I'm not even quite sure that he is you know if it's a style you want to aspire to because his interviews are very quick and a lot of it is surfaced not so much in his Netflix show or his older Netflix show but in his main late night show that he did for so many years you know he's really just trying to get laughs from the audience and maybe a tiny spark in the interview so it's not that intense, but he does, I would say more than interruption, he does what I would call a pattern disrupt.

45:44It's like he'll do something weird. Yes, yes. And David Letterman, for me, is one of the weirdest. I have a really hard time watching his interviews because I'm like, he interrupts, I think, too much, but it's part of his thing. And then he'll say something about himself, and I'm like, David, I don't want to know this about you. I want to hear about Kim Kardashian. But that's part of his style. And again, it's very hard to imitate because it's him. It's very much him. And in this example, for the people listening who haven't read the article, he basically sits down with Kim Kardashian. He wants to ask her about her political loyalties because she's previously endorsed Hillary Clinton, but then she worked with Donald Trump to get this woman out of prison.

46:28So Letterman goes, do you feel like what's being done on behalf of sentencing reform now via this current administration in any way allows the balance of democracy back in a corridor of viability? And Kip Kardashian is like, I have no idea what you just said. He goes, I'll try again. I'm grateful for what you're doing, but it doesn't make me feel better about the current administration. And she starts answering, I understand. And he interrupts her very abruptly and goes, let me ask you, who are you voting for? And so like, I think part of his technique, and I don't even know if he does this consciously, he starts out in this very like confusing place.

47:07He confuses his interviewee. By the time they figure out what's going on, he just interrupts with a very direct question. And in this way, as the interviewee, you want to answer because you now understand the question. You know, and I wonder, I don't know if he does that consciously because I think he's a very like smart intellectual guy. So he might have been wondering, oh. The corridors of democracy. Right. Like he might be thinking like, oh, since she's like Hillary Clinton, what is she doing with Trump? So he's thinking in this very nuanced political way. Maybe he realizes in the interview that he really just wants to know who she's voting for.

47:47yes that could very much be it and also he realizes he's he's i don't want to say he's speaking above her head i'm sure she's very intelligent also but yeah he maybe he realized he wasn't being so clear and so then he's smart enough to get as direct as possible yes but by the way why can't she just because she likes one candidate i know why can't she do something effective for somebody who's president united states regardless of who they are that's how polarized we've become. We cannot have this dichotomy of Kim Kardashian and James. Right. Like, like people on both sides, people are willing to break the law to get their candidate in.

48:26And it's just like, just ridiculous how polarizing people have been, as opposed to wanting to just be, just do good in society. Exactly. I agree. Let's see. Number five, they make assumptions on purpose. And I think that's a little bit of the gotcha thing as well, but you use the Oprah example again. Yeah. And it doesn't have to be done in a gotcha way. It could be like, here's how I understand it. And then you let the person agree or disagree with you. I think in this one, I wanted to talk about how the interviewer is a representative of their reader or listener or whatever. So Oprah knew that and she kind of addressed the elephant in the room, which was she knew that the person watching at home is watching this.

49:13And Harry is kind of painting himself as the victim of the system. And she's like, oh man, oh man, I know what people are thinking. I have to ask it. And so she says, and it's not done in a very confrontational way, just kind of like, like in a funny way. She says, please explain how you, Prince Harry, raised in a palace in a life of privilege, literally a prince, how you were trapped. And so it's like, she makes it, you know, he, she addresses that. And then he, yeah. And then he responds with, oh, well, it's a system of wealth and all this stuff that you're trapped in, but she doesn't buy his response.

49:53So then she makes the assumption. She says, so the impression of the world, maybe it's a false impression, is that all these years before Meghan, you were living your life as a royal Prince Harry, the beloved Prince Harry, and that you were enjoying that life. We didn't get the impression that you were feeling trapped in that life. So she says, like, here's what we assumed. Is that true or not? And it forces him to take a stance. Yeah. And it's interesting, too, because as opposed to the Joe Rogan example where he he really becomes the voice of the listener like oh we're all all of us 10 million people are skeptical or or we want to know more about this thing she's almost like a translator like it's as if there's a gap between what her she understands there's a gap between what her audience thinks and what harry is saying and see she's trying to bridge that gap as opposed to as opposed to just being the voice of the listener, she's trying to translate what the listener might be thinking and what Harry might be thinking.

50:54So there's an intersection. Yeah. She keeps giving them the opportunity to explain themselves. And then I watched an interview with her about her interview and she said, that's all I was trying to do. I was just trying to let them explain their decision. And, you know, I think she did a great job. Yeah. And so Howard Stern, how does he, you I have my own thoughts on his style, but can you talk about the example you give for Howard Stern? Yeah, so I will admit I was not a big Howard Stern listener until I wrote this. And then a bunch of people told me to go watch and listen to his interviews. And what I noticed is that he…

51:37I don't know if he thinks that he knows these people or he just makes assumptions and lets them elaborate. but for example with Lindsay Lohan he said a bunch of stuff where he assumed things about how she thinks and he says you know when you see like an Emma Stone or Jessica Chastain they got a similar look to you I can tell you've thought about this when you see some of those movies don't you sit there and go oh I can effing do those movies it's got to be driving you nuts so he claims that he knows how Lindsay Lohan feels and she's like yeah that is exactly what I think you know that's interesting like kind of putting yourself on the on the side of the interviewee like the person you're interviewing yeah and he does that very good and they go along with it because look he's a very powerful guy so yeah and and and there he's kind of taking their side so he i think i think with him he's very interesting because i i think he tries to get dirt about everybody during the interview and they all at first i noticed in a lot of interviews people say no no i don't want to talk about that but then by doing this technique he kind of gets in their head enough and he's on their side and he's he's not the listener's voice he's their voice yes and finally they're like oh i'm talking to myself so finally they are able to like i saw him interview jonah hill once and he was like so when you had that your first role did you start like having sex with a lot of girls like even though you're kind of fat and like he's just very direct and he's like and don't jonah hill's really uncomfortable it's like uh howard i don't want to you know i don't want to talk about that can we just talk about the movie and but he like so so they they talk about the way and then he's doing this where he's like on their side but he keeps every now and then he'll ask like the real harsh question and Jonah Hill will be like, ah, I don't want to.

53:33But by the end, Jonah Hill's like listing all the girls he had sex with. No way. Yeah. Like he, he just works his way in and he just keeps poking, but then he'll get back to like, oh man, I'm on your side. I'm like, you know. Yeah. You know, and, and I think it's, he combines, he uses this technique that you're talking about to, to sort of get inside and, and the person's head. and then finally they're super comfortable. So they say, they forget they're on the radio and they, yeah. I watched, I forget which celebrity it was, but they were explaining the experience of why they shared so much on the show.

54:08And they were like, it almost feels like you enter this like different thing and there's no cameras, there's nothing. You forget that all this stuff is around you and you're just having a conversation and then it ends and you're like, what did I just say? You know, it's like that feeling of what just happened. And that's the best interviewers make it seem like time just flies by and you don't even know what's going on. Yeah, I've heard that too from people who have been on Stern's show that at first they tell themselves in advance, I'm not going to talk about X, Y, and Z. And by the end, they can't figure out how it happened, but they talked about all those things they didn't want to talk about.

54:47Crazy. So number six here is the great interviewers remove barriers to enhance intimacy. And I love this example of Sean Evans. Sean Evans, yeah. So usually the obvious example is you remove chairs and you remove tables and things like that in between the interviewer and interviewee to build intimacy quickly. So Oprah will sit on the same couch, like things like that. But it's not just physical objects that you can remove to build intimacy. It's sometimes like Sean Evans with the hot ones where they eat progressively hotter chicken wings throughout the interview. it's, you're removing like the barrier of like, you're breaking down the guest composure because everybody comes in like super glam, ready to do this interview.

55:34And then by the end, when they're eating a really spicy chicken wing, like they're crying, their nose is running, their throat is burning. You know, a lot of them just can't handle it. And you see like Tyra Banks had a ridiculous reaction on this show. You see their true, true colors. So, you know, I included this clip of Sydney Sweeney, but she's really trying so hard to hold on to her composure. And she's like, please, like, her voice is shaking. It's super high pitch. It's fascinating to watch. So what do you do? Like, like, I used to do podcasts in person before COVID, but since COVID, very rare that I do a podcast in person.

56:15And you probably interview on the phone or Zoom or whatever. Like, how do you do this technique if there's a lot of like built in barriers? Yeah, I mean, it's super hard to do because normally the best interviews, especially the ones like magazine profiles, for example, you're often doing an activity with the person. So whether you're at a restaurant having dinner, you see how they move through the world, how they treat the waiter, all this stuff, context clues that they can't just tell you, I'm a generous person. Well, you didn't even leave a tip, that kind of thing. um but like this is hard because i can tell you how great i am but you unless you see me in my natural habitat it's hard um i don't know i don't know what do you think what i think it's i think it's the repeat guest thing is one way so you so you're gonna have a hard time that first time but then it gets easier i think the pre-interview like you know you're on for a little bit and you're just chatting.

57:16And, but I think, I think it's really hard or sometimes I'll try to do an activity and then a week later do an interview. And, but that's, that's rare. So it's hard to do that. And also, um, one interesting thing, it could be that, uh, you found out a really interesting piece of information about the person and you bring it up like in the middle of the interview, it's kind of like a small bomb that goes off where it's like, oh, wow, how did you know this? And that breaks down the little, like the facade a little bit. That I try to do. So I try to find like odd things in their background that I could bring up and then connect with things they might be saying now.

58:03I don't really have a good example, but you know, like you mentioned before how like you read some, you know, or you knew someone did their PhD at your university. So I might go as far as to read the PhD, the thesis they wrote, and try to find some connection between that thesis and what's going on in their lives right now. And, or, or relate it to, you know, relate it to something they're doing now in a way that they might not even have thought of. And so I'll try to kind of like, you know, confuse them with over-researching. Exactly. Exactly. Just like something that's unconventional, they're not expecting.

58:43Yeah. Now, this is a really important one. And number seven here is a great interviewer strives to capture the juice of the story. And yet Barbara Walters interviewing Monica Lewinsky, and there's a lot of different angles. It's like, you know, it's a president of the United States. It's this sexual thing. So everybody wants to hear like the sexiest details, as sordid as it might be. But with this example you give about Monica Lewinsky and Barbara Walters, it really is the juice of the story, like how she was worried about what her mother would think. And we can all relate to that, doing something that's going to be public and like, oh, what are people going to think if they find this out?

59:28And that's, you know, Barbara Walters is really good at that. Yes. And it's like, it's, um, oh, it's such a good interview for so many reasons, but it's mainly because Barbara Walters knows that she doesn't go there. I mean, she asks all the direct newsworthy questions, but what she does is like, she gets into Monica's head. And by the end, you're like, I get it. I get why she's in love with Bill Clinton. But also at the same time, you're like, I cannot believe this happened. It's, it's, it's fascinating. It's like a masterclass in interviewing. And she humanizes Monica to the point where you're like, wow, like, you know, young girl, bad decision making, all this stuff, irresponsible president.

1:00:14But you, it's like, she refers to the juice is the details of the story that humanize the person that you're interviewing. And Barbara says, don't be so intent on getting just the facts that you take out all the juice. Yeah. And it's interesting because she kind of layers into this. So like, you know, like Lewinsky says, I felt very responsible. And Barbara Walters says, responsible for what? Exactly. And by the way, that was, there's a nuance there because she didn't say, why do you feel responsible? That would have taken it in a completely different direction. Lewinsky say, well, I agreed to go into his office, blah, blah, blah.

1:00:51Instead, she says, responsible for what? and that led to the discussion of her mother. But then that allows her to get enough intimacy with Monica that she says, Monica, are you still in love with Bill Clinton? Right. And she uses Monica's name. She says, Monica. She doesn't say, are you still in love with Bill Clinton? So it's more personal when she uses the name. And if she had started off with, are you still in love with Bill Clinton? I think that would have been a different answer, a different interview then. Yeah. The whole interview builds on itself. It's fascinating to watch. I think that's really hard.

1:01:24I think, and as you mentioned later, the only way to get that skill is doing lots of interviews. Yeah, it's true. And it's like, you notice so many things as you're watching it. Like at one point, Monica Linsky, I didn't include this, but in the interview, she says, you know, at one point, my mom, like I couldn't shower alone. My mom would sit in the bathroom with me while I showered because they were all afraid that I might do something. She's obviously talking about like, you know, might take her own life. But Barbara Walters is very skilled at like knowing when to dig deeper and knowing when to kind of back off.

1:02:02And she says this in another interview, Barbara Walters says this, she's like, you know, for the really, really painful stuff, I'm not going to keep digging until I break you, basically. I'm going to like get there and then back off. And that's skill and that's like a you know social awareness skill that not everybody has and also knowing that she could go back to it later like she's patient barbara walters and again it's she's almost become a cliche interviewer i mean not her but like just the way people think about her but i think people underestimate her full her full power as an interviewer barbara walters totally i mean because then later on she's doing stuff like The View and all that.

1:02:46But you give an example in the next thing, challenging a subject's perspective with genuine curiosity. She interviewed the Shah of Iran right before he's getting overthrown. She was like the biggest interviewer on the planet at that point. I know. I know. And it's interesting, a lot of times she became friends. I think that was kind of like, wait a second. She became friends with the people that she interviewed. She became friends with Monica Lewinsky, and I believe the Shah of Iran. But it's interesting because I do think a really in-depth human interview has no choice but to leave the people like, oh, we know each other on a different level.

1:03:27Yeah, I think when you really are able to go a couple layers deep and then she was trying to ask him and talk to him about his views on women. and coming from a Muslim country and so on. In 1977. Yeah, which was, on the one hand, I don't know how completely we treat women differently now, but at least at that point in the 70s was the height of Gloria Steinem's original feminism movement and things like the Equal Rights Amendment were being discussed. And so it was a different conversation, but it was still a very big conversation in America, maybe for the first time. And I don't know, it might've actually been, you know, then a year later, he's overthrown and the US really didn't help him.

1:04:19And we got left with what we have now, this kind of, you know, religious, you know, super religious government in Iran that most of the people don't like. Most of the people wanted the Shah of Iran in Iran. And now most, you know, 80 million people in Iran are secular and they're ruled by this super religious establishment. I don't know any of this. Okay. Oh, yeah. Like Iran does not like their government. Like the people there, and that's why they literally beg the outside world to understand this because they don't want to get bombed if their government does something. Like they prefer not to be, they were a completely Western country under the Shah, almost, not completely, but almost.

1:04:58And now they're not, but they don't want people to know that so that they don't get blamed. If like Iran bombs Israel, They don't want to get bombed back because they're not like their government. I'm going to do some research after this. Yeah. And I think that was a mistake for Jimmy Carter at the time to not help the Shah a little more. Because, yeah, we didn't like some of the things he did. But that's like every country in the world. We don't like most of the things the French do either. But we're still their ally. Oh, that's fascinating. There's so many layers here. Yeah. Yeah. And Barbara Walters is, you know, I think she understood that like he's a dictator, but he was still kind of our friend.

1:05:43And then we, you can't condone, you don't condone everything your friends do, obviously, and particularly at that geopolitical level, but he was certainly much better than what happened. Yeah. You know, number nine is they know all humans seek genuine validation. And this is really important too. Yeah. This I found fascinating because Oprah talks about how pretty much every person that she's interviewed, including George W. Bush, Barack Obama, Beyonce, anybody she's interviewed, after the interview ends, they always ask her, I bet you get this question too. They're like, ooh, was that good? Was that okay?

1:06:23And she's like, what do you mean? You're a Beyonce. Of course it was okay. But like everybody has that small piece of them. That's like, did you like what I said? And do you think this will resonate with people? And I think a great interviewer's job is to make the person feel validated, um, in like, in like actually listened to during the interview. Yeah. And I think this happens at every level. Like, so for many years I did standup comedy and then I owned part of a standup comedy club. So I I would see all these great comedians perform on stage. You know, they'd be trying out material for their special or whatever.

1:07:00And no matter how famous the comedian was, like, they always ask that too. Like, was that okay? Was that good? Did you think the audience liked me? And people are human. They want to know. They want to be liked. Exactly. I thought that was really like, I was like, I would have never thought. But yeah, I do it too. It's crazy. Have you interviewed any like hardcore criminals? Oh my God. No, I don't think so. Like anybody who's gone to jail? Yes. I interviewed, oh my gosh. The guy who Leonardo DiCaprio played in Catch Me If You Can. Oh yeah. Frank Abagnale. Frank Abagnale. I interviewed him as well.

1:07:42Yeah, exactly. So fascinating. He was a big criminal, but then he worked for the FBI. So I don't know if that counts. Yeah. No, and a lot of times, you know, I interviewed someone recently who committed a fairly big fraud, like$400 million Ponzi scheme. And he went to jail for nine years. And I think it was very important for me interviewing him that I didn't treat him like someone who did something really bad. but I still wanted to make sure my listeners knew that it was clear this person did something bad and I was against it. So it sometimes is a tricky thing. Yeah, yeah, yeah. Because you're trying to be empathetic but there has to be a clear line of like, you know, this is, I mean, we can all agree that what you did was not right.

1:08:34You know, it was tricky too. Like I interviewed Andrew Tate. Okay. And, you know, and Andrew Tate, Oh man. Obviously, that's a whole mess. If you're trying to be liked by everybody, don't interview Andrew Tate because nobody will. Everybody's going to make a judgment. Oh, you must agree with everything he says or you must like him or he used you or whatever. So sometimes the interviewer has to balance all of these things too. Yeah, it's so hard. It's like, you know, these people's views would never go challenged if I didn't interview them. You know what I mean? Like for anybody interviewing a dictator, are you just quote unquote giving them a platform?

1:09:17Or are you interviewing them and challenging what they think so that more people can like hear that it's BS? I don't know. It's really difficult. Like let's say you had to interview Putin. Okay. Okay. So now, okay. So there's so many layers in which you could get - I'm from Bulgaria. He's from Russia. This will be a tough one, James. Right. Like, so your family, they might say, don't talk to him or - Right. And then people might think you're, will make a judgment about whether you're a Democrat or Republican. Right. Oh, you know, only Republicans would talk to Putin. But obviously he would be a fascinating person to interview.

1:09:55I mean, he's on, you know, he's a leader of Russia. He's conducting a war. Whether you agree with that war or not, no matter what he did, I would interview him. Yeah. Well, it's so tricky. It's like the whole point of journalism in general is to interview people who are doing things that are newsworthy, that are affecting the world, all this stuff. By ignoring someone doesn't make them go away. In fact, it actually fuels them more. I don't know. There's a whole philosophical discussion on this. Yeah, it gets back to the thing of you have to join a team and then only talk to the people that that team approves.

1:10:43Exactly. And it's like I'm on nobody's team. I just want to hear the information and then challenge that information. Yeah, like I was once on the podcast talking to Mehdi Hassan, who had this show on MSNBC. Yes, there's a profile on him right now. Oh, yeah, I have seen that. And I told him I'm neutral. I really try very hard to be neutral so I could talk to everybody and not feel biased. And he said there's no way to be neutral. He challenged me on that. And we were going to follow up at some point. And he was going to prove to me that I wasn't neutral. And maybe I'm not, I don't know. But that's the thing.

1:11:21I mean, I guess nobody's truly neutral, but I also completely reject the idea that you're either a Republican or a liberal. I don't fall into any category. It's really hard. Maybe you're not neutral. You're just not part of any one group. Yeah, where you have to do everything that group says. Yeah, exactly. But then I wonder, look, the podcasts that are the most popular take a stance and are really biased. That's true. I'm just not like that. Yeah. That's not your style. And the good thing with what you do is that you could profile anybody. Yeah. So you're trying to take lessons from them. And so you could choose.

1:12:05They don't – you seldom will profile like a political person. That's the thing. I truly believe that you can learn from awful people about what not to do. You know, like there's lessons in everybody. It's not just like the good, moral, whatever people that we put on these like pedestals. It's also the people like, oh my God, look at how their life turned out. I don't want that at all. Yeah. Like, who would you say is like the worst person in the world right now? Would you interview that person? Oh my God. I don't even know. It's also like, you know, nobody is like only evil or only good, but there are some pretty bizarre people.

1:12:49Some people are insane. So like they are mentally ill and bad. Okay. Here's an example. So right now I'm working on an article that's similar to this Interviewing Techniques, but it's on public speaking. And on Twitter, I asked who is the greatest public speaker of all time. And of course, people came up with Hitler, Mussolini, a bunch of cult leaders, a bunch of other dictators. And I'm like, I get it. But in my article right now, I'm saying like, I understand that these people are probably amazing public speakers. I'm not going to include them just because I do not want to like feature their stories, but the world's greatest speakers all use similar techniques.

1:13:31That's not to say they did or did not use this. It's just, I'm choosing my editorial style is choosing not to include dictators and cult leaders in this article. But it's really interesting because like, you know you're right they all use similar techniques and that that's going to be a fascinating article when you write it and i i've written a lot about public speaking as well because it is another thing like interviewing where you're trying to win over just like in an interview you're trying to win over an audience and and there's there are specific techniques to do it and you to be as genuine and sincere as possible as well.

1:14:10But like a dictator will, you know, for instance, a dictator uses Robert Cialdini's consistency technique. Yeah. Like they'll use all his techniques. Like, you know, someone like Hitler might say something like, you know, you know, wasn't your life awful before, you know, when bread was like a gazillion marks and people would say yes. And then, and then when I became leader, wasn't your life better? And then it's a bigger, so it's like that consistency, like getting them to say a small yes to get them to a bigger yes. He was very effective at doing things like that. Um, you know, and, and cult leaders are like that as well.

1:14:52Uh, it is just like up to the person, like maybe you really don't like me. I am not entitled to be on your show. You know what I mean? Like, it's just, I think that everybody, every person has like a freedom to have whoever they want on their platform. And if they want to interview Putin and ask him questions, it's their right. Like, you will not catch me not defending free speech. Yeah, good. Good thing. And look, let's see, and you say here, the only way to become a masterful interviewer is to interview. Larry King conducted more than 60 ,000 interviews in his career. Oprah has done more than 37 ,000.

1:15:38Joe Rogan has hosted more than 21 guests on his podcast. It's really true. You've got to do things. Yeah. And it's like, once you think about 60 ,000 interviews, that is so many or 20 or 37 ,000. And then people think about Joe Rogan, you know, oh, he has the biggest show, biggest podcast, but he's only done 2 ,100 recorded interviews on his show. So it's like, and you've done 1 ,500. So it's like, those are big numbers, but 60 ,000 is like a different universe. Yeah. And, you know, and again, like he does like Larry King, those specifically are interviews. And Joe Rogan, it does, it still feels so much like conversations.

1:16:24And I really almost aspire to that. But you have to use interview techniques. Like these are all really important techniques. But, you know, one thing I'm going to try at one point is just give everybody, like go on Twitter, give everybody the Zoom link and interview whoever just comes on. Oh, that's cool. Yeah, just to show that everybody's got a story. And like, of course, Brandon Stanton and Humans of New York does that really well. But - Yeah, there's a thing. Sorry, what I say is like, you don't have to have a podcast to do an interview or have a conversation. It's just like with any stranger, you can practice these skills and just become a better conversationalist.

1:17:06Yeah, and like, what do you think though? On TikTok or Instagram, I see all these guys who go up to people and say, hey, how much rent do you pay? And they say, oh,$15 ,000 a month in New York City. Can I get a tour of your apartment? And they give the tour. So what do you think of that style where it's like there's one question and then they ask everybody and then the interview is around that? I kind of like that. It's because it has an angle. So it's kind of like hot ones. The angle is I'm going to ask you these random questions while you eat spicy food. It's the same. It has a slight point of view so you know exactly what you're getting, but then it can go anywhere.

1:17:47Yeah. And there's this voyeurism aspect. Yeah. So it's like, can you show me? And it's the intimacy. It's like the most intimate thing you can show somebody is your home. Right. And the guy, the main guy I'm thinking of who does this, I mean, maybe there's more than one, but the main guy I'm thinking who I always see who does this, he always says, can I sit in your bed? Oh my God, I have not seen that. Yeah. And it's usually like some really beautiful beautiful woman who he goes up to and says, Hey, how much do you like, it usually starts there. So he's getting every voyeuristic aspect. And you kind of are left wondering, like, is he going to have sex with this girl?

1:18:23Like, Oh my God. It's the kind of interview sort of is in that direction. Um, but I kind of like the, or, or what, or there's the, what do you do for a living guy? Like, I like that guy too. Yeah. Yeah. No, that's what they're trying to do. They're trying to just like quickly build intimacy with someone in a way that's like, can I see your house? How much money do you make? What do you do for like all the things that people think make them who they are? And I guess it is also the consistency thing. Like if you answer, like obviously we don't see all the rejections these people do. They only show us the Instagram reels of, of the people who answer.

1:19:01But if so, if you're already answering, what do you do for a living? Or how much money do you make? Or, or what's your rent? You've already said something so personal that now it's wide open for the guy to ask anything. Yeah, but I also think those people probably have pre-interviewed these people to get there. I don't think anybody's like, oh, well, we happen to be on the block where my apartment is. Let's go check it out. I wonder. Or if we just happen, or if like nine times out of 10, he gets nothing, and then - Maybe. One time out of 100, maybe, he gets lucky, and the person pays$200 ,000 a month in rent, And we can see their apartment.

1:19:40You should have him on. Yeah, that would be a good idea. Jay, who's listening to this, let's get that guy on. I want to figure out. Because that's a little bit like what I used to do at this 3 a.m. idea I used to do for HBO in the 90s, which is, you know, why are you out at 3 in the morning? It was that kind of concept. And I always think I did the first podcast because I would put it on the internet, these interviews that I was given permission to do. so that's cool but polina pompliano thank you james such a great newsletter the profile i love all of your newsletter uh every episode edition that comes out i'm always a reader you know you always have at least one reader which is me as soon as you said it out and you also wrote the book hidden genius about some of your more interesting profiles and always great to have you on the podcast thank you so much and congratulate i don't know if you're if you said congratulations on on second baby thank you so much a lot going on these days yeah like how many how many additions do you put out a week um one i won every sunday and then sometimes one every wednesday okay yeah i i know i've seen more than one a week from you and uh and are you gonna keep like this is this it now for life like you're gonna just do this newsletter for life you're making money and it's all good?

1:21:04Well, I just, I really love the newsletter. I have no reason to not do it. But I really enjoy it. I've done it for the last seven years, every single week. But now my goal is to do more interviews. So if anybody listening needs, you know, moderating help or is hosting something where they need an interviewer, let me know. Very good call to action there. Thank you. And thanks so much, Polina, again. Thank you. Awesome. Thank you so much.