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Michael Ian Black is a good interviewer. His podcast, How to Be Amazing is a testament to the fact. From pop stars to scientists to chefs, Black talks to a wide swath of people and seems to do it with an inspirational ease. In my own selfish and personal quest to get better at my job, I spend my entire interview asking him how to be a better interview. If you’ve never interviewed anyone in your life (and don’t have any plans to) think of this as a lesson in how to be a good conversationalist, because as Black says, that’s really all their is to it.

Catch the live version of How To Be Amazing with Michael In Black at the Bentzen Ball Podcast Studio at the Kennedy Center on Thursday, July 20. Grab your tickets now. We’ll be there.

Can you remember the first time you interviewed someone and how it went?

That’s a good question… Do I remember the first time I interviewed someone and how it went? Oddly, I think the first time I actually interviewed someone in an interview format in any way, shape, or form was the first time I was guest hosting… Oh well. That’s not true.

You just remembered something else?

Yeah, I used to guest host sometimes on this NPR show. I can’t even remember the name of it… But I used to interview people for that. So it was probably some author or somebody and it probably went fine or I would remember. If it went horribly I would probably remember, but because I don’t, I’m assuming it went fine.

How did you cultivate this skill? Was it something you learned over many years? Did someone teach you? Or was it just purely natural?

Well, first of all, thank you for thinking I have this skill. Secondly, if there’s a skill at all, which, I’ll take the leap of faith and say this is a skill, it’s really twofold as far as I can tell. The first is doing your homework and researching and knowing who you’re talking to and why you’re talking to them. The second part is asking questions that you wish to know the answer and listening. I don’t think it’s any more complicated than that. At least in my experience.

That’s interesting because I always think it’s infinitely more complicated than that.

From your point of view, what’s hard about it? You’re just having a conversation with somebody and don’t you do that everyday?

Absolutely, but I do think you can be a bad conversationalist, right? I’m sure you’ve been stuck at a party or an event with someone who is the worst to talk to. I think interviewing can go the same way.

My technique for dealing with conversations that are going bad at parties is identical… Well, if I’m not in a position where I can say, “I’m sorry I need to take a poop” and then go away that way… If I find myself needing to have a conversation with somebody my strategy is no different than if I’m interviewing someone for the podcast, which is to just ask questions about them. Most people are happy to talk about themselves because they know the answers. I don’t think they’re necessarily full of themselves, but most people feel at ease thinking about themselves because you’re asking questions that they probably already know the answer, and that makes it easier for them. The difference in an interviewing setting is presumably the person wants to be there and they understand going into it what the ground rules are and the ground rules are generally that an interviewer is going to ask you questions and the interviewee is going to answer them.

If you approach it that way, which is how I approach it, it shouldn’t be that hard. That being said, I’ve had bad interviews where I feel like either I’m asking the wrong questions or whoever I’m speaking to is unwilling to give answers, and sometimes that does happen.

When you’re doing the research prior to an interview, are you ever worried that you won’t be able to come up with questions? Like, if they’ve already been interviewed a million times or you’re reading about them and nothing sparks inside your heart (or whatever your criteria for a good question is)? Does that ever happen to you?

It does. The latter question more than the former. Sometimes I’m worried I don’t know what we’re going to talk about for an hour, which is usually how long my interviews last. I’m always prepared with a lot of questions, which either I’ve written or my producers have written, so there is always stuff to talk about if the conversation isn’t proceeding in an organic way.

But the second question was, if I’m doing research and this person has been interviewed a thousand times, what do you do? I tend to focus on asking questions that I don’t know the answer to. If I’m reading about someone who I find is a well interviewed person, I generally stay away from, “Well, how did you get into xyz?” because I already know the answer to that. I understand that the person who is listening may not, in which case I provide a kind of sketch, an outline, of what that person needs to know… But I figure, if you find yourself, as a listener, wanting to know more about that person and I’ve discovered that they’ve been interviewed a thousand times, it will be easy enough for you to do the same. So I’m not particularly worried about giving the full picture of somebodies chronology in my podcast. I tend to focus on smaller things and then those smaller things can turn into bigger things, but I generally start with small things, details, and let that expand into their entire world.

Do you ever get nervous before an interview?

Yeah of course. I get nervous more than I don’t get nervous, I would say.

What do you do to relieve it?

I just trust that it’s going to be fine. I don’t always trust it, but so far it’s always been fine.

When have you not been nervous? When have you thought this is going to kill?

I’ve never thought, “This is going to kill”. I’ve never had the confidence to be like, oh I’m going to nail that. I mean in anything, not just in interviews.

I just interviewed Ina Garten, the chef and cookbook writer, and for whatever reason I thought, oh, we’ll get along. And we did. I don’t know why I felt that, but I felt some confidence that we would get along. I was very nervous going into interviewing Al Franken because with people I admire, I tend to get more nervous. Not that I don’t admire Ina Garten, but Al Franken is much closer to me in terms of career and the kinds of things he’s done. It’s maybe a little easier for me to talk to people who live in a separate professional world, because I know so little about those worlds maybe I feel freer to be dumb, I think.

When you look back on your catalogue of interviews, are there any you can look back on and say, “I did a great job, this is one of the highlights”?

Sometimes. There are a couple moments that stick out but I rarely ever give myself credit for that, so much as I give the other person credit for being willing to open up. I did an interview with Tim Gunn where he was really vulnerable and he opened up emotionally about where certain things in his life come from and he was connecting some dots for himself he maybe hadn’t connected before. I asked David Sedaris how much money he makes and he told me, that I’ll give myself credit for, I felt pretty good about that.

How do you get people to be vulnerable?

Well, I don’t think the goal can be “I want you to be vulnerable,” it has to be “I want to ask you questions that are interesting to me,” and hopefully you’re willing to walk down that road with me. That may lead to you opening up, and if not, I don’t know… But I hope it does.

I often find that vulnerability, or the most interesting thing about a person… The core of what makes them fascinating… You get to by doing the same thing. People don’t want to be vulnerable for obvious reasons, but people also don’t want to talk about what makes them unique, for reasons that are not so obvious. They’re nervous, they don’t want people to think it’s dumb etc. Have you noticed anything like that?

I suspect you’re right. I’ve never asked anybody that question, “Why aren’t you willing to be vulnerable with me?” That would be a very intimate and weird question to ask and probably would very much put that person on the defensive, but I suspect that you’re right. I also suspect, I’m thinking of one particular case, but I’m not going to name names… Somebody I interviewed I feel like was kind of living a lie about how that person conducts themselves and their motivations for doing what they do. It was purely speculative on my part, I have no idea, but I sensed that I would get to a certain point with that person and they would kind of deflect and shut down. And that’s frustrating, but understandable if they’re dealing with something deeply held that they’ve never addressed with themselves. I’m not going to get them to address it in a podcast.

What do you do when you catch someone in a lie? Does that change the tone of the interview for you? Or do you try to soldier on past the topic?

I will try to approach it from a different angle. I’ll try to get the same information, by approaching it differently. I’ll try to circle back to it. It’s a real stumbling block. I don’t think this happens often, but I think sometimes people are unwilling to be forthright, for whatever reason, and I will push back on it if I feel like it’s coming from a place of… You know, it can come from different places.

Sometimes it feels like it’s coming from a place of somebody has an agenda, not necessarily in a nefarious way, but there is something they’re trying to accomplish with the interview that doesn’t necessarily align with what I’m trying to accomplish with the interview. They may have a very specific goal they’re trying to achieve, whether it’s promoting something, or it could be a political goal. If they’re too on script about that thing, the interview gets very frustrating for me. I feel like I’m just hitting talking points and I’m not with the person.

When that happens, I will push back, not in a mean way or a confrontational way… Well, sometimes confrontationally. I think there is a way to be confrontational without being mean. I think there’s a way to be confrontational and just say, “I want to come back to this thing that I asked you about” or I could say, “I don’t think you’re being entirely forthcoming to me about this thing.” I guess I don’t have any problem confronting somebody when that happens, but my podcast in particular, I’m not doing the PBS NewsHour. It’s not a gotcha interview. It’s meant to be a positive and fun experience, so I’m only willing to go so far.

I know you said that you do quite a bit of research before you interview someone and you try and take a unique angle with your interviews, but has there been a guest that surprised you because they were infinitely more interesting than you thought?

I’m going to say no, but not in the way I think you mean. No in the sense that I’m pretty interested in everybody. I may be surprised by the way somebody speaks and the quality of their engagement and their emotional availability, but I haven’t felt, oh this person is so much more multidimensional than I thought, because I kind assume everybody is that way. I think everyone is multidimensional in their own way, and I think that my job as the interviewer is to let that person be their multidimensional fascinating self and to give them a forum and an opportunity to do that.

Do you think doing all of these interviews has made you a better person to interview?

Probably. I think I’m certainly more sensitive to the needs of an interviewer. I’ve certainly been more reticent in my past when it comes to speaking about myself and that had to do a lot with feeling like I wasn’t that interesting, which is what I think a lot of people feel. Like, I have nothing in particular to say. In interviewing people, I guess I’ve realized that everyone has something to say and it will be helpful to someone out there.

Is there someone you look up to in terms of an interviewer? Someone you would emulate, if possible?

Emulate is probably the wrong word, but there are things that I like about certain interviewers. Now that I’ve started to think about interviewing as a craft, which I never did before… I just never devoted any brain space to being an interviewer. Certainly when we were trying to figure out what this show was, we meaning my producers and myself, we were kind of aiming for the midway spot between Terry Gross and Marc Maron. I think we’ve landed pretty close to that.

I admire both of those people for different reasons. I admire people who just ask good questions. I’ve gotten very frustrated lately with television interviews and what you see on the news because… I was going to say I’m mildly obsessed, but I’m just going to say I’m full on obsessed with the current administration. A lot of times what happens in television interviews is that because of the constraints of the television clock, you have eight minutes for a segment and you can only ask four or five questions before the time runs out. Interviewers have their questions written down and they’re going to ask those questions come hell or high water and the interviewee knows that. So all they have to do is filibuster their answers and nothing gets answered. I find it to be a very frustrating exercise to watch. There are some people who I think are very good at not getting away with it, Jake Tapper for example. I admire that type of persistence.

Would you ever want to do television interviews?

It would totally depend on the circumstances.

What would be the perfect circumstance?

Honestly the perfect circumstance would basically be what I do on my show, which is I have an hour, I sit down with somebody and I interview them. And that seems kind of perfect to me.

When you do the podcast live, does that change the your interview process? Because I imagine that would be similar to a televised version of your podcast.

We’ve only done a few live and I would say half of them have gone well and half of them have gone less well. The temptation for me as an interviewer, and I think sometimes the interviewee, is to play to the immediate audience. I know I have to resist my temptation as a comedian to do that. One of the things I really crave about these interviews and the way I conduct them is the intimacy of them. We record in this small studio, we’re sitting across from each other and it feels like two people having a conversation, because that’s what it is. Once you open that up to an audience, my feel is that the intimacy is lost and I feel like I must do what I can to keep that intact. That sometimes means resisting the desire to play to the audience.

Is there anything about your podcast now that you’re actively trying to improve on, or you want to change?

No. I’m just trying to get better at what I do. We’re always conscious of the kinds of people we interview, in terms of we want to get people from the widest possible spectrum of adjectives, or nouns. We’re trying to get people from creative endeavors and endeavors you might not necessarily think of as creative, although I think all endeavors are inherently creative. It’s always a balance between the right ratio of men to women and white people to people who aren’t white people, and we’ve only had one Asian guest on… We’re constantly trying to make sure we’re representing as many points of view as possible, and that’s our constant struggle.

It would be very easy for me to fall into only interviewing entertainment people, for example, because that’s what I know and that’s where my contacts are, but I’m not interested in doing that. It’s great that I can talk to someone like Deray, who I’m interviewing for this podcast, because he inherits a world that I know very little about. I look forward to conversations like those, where, as I said, I can feel freer to be dumb and I feel like I have the most to learn.

What is your criteria to have someone on the podcast?

It’s purely instinctual. if there’s somebody I want to talk to, or my producers want to talk to, we talk to them. If we can. We’ve been lucky lately that we’re starting to get people approaching us, we’re not constantly racking our brains to find people. That’s been a great new development, but from my point of view, there’s been no lack of amazing people. A lot of people will come in and I’ll say, “Welcome to How To Be Amazing,” and they’ll say, “I don’t know if I’m amazing,” and I say, it’s not for you to decide. I get to decide if you’re amazing. I’m telling you you’re amazing.

What does amazing mean to you though? Does it just mean interesting? Or is there another quality?

The easy answer, and I mean it, is to say that everyone is amazing on some level, but that doesn’t mean I necessarily want to interview everybody on the podcast. There’s something a little bit ineffable about the quality I’m looking for. Sometimes it has to do with longevity, somebody who has made a career out of doing something. Sometimes it’s precociousness, like Tavi Gevinson, who was one of our earlier interviews. She’s the founder of Rookie magazine, I think we talked to her when she was 19. It can be in the unusual way somebody approaches their work. It can be the nature of the work. It can be the way somebody conducts themselves in public. It can be any number of things. There’s no hard and fast rules and there’s no limit to it. Just somebody that I, or my producers, want to talk to and we feel like we understand why we want to talk to that person.

Sometimes we have to separate out, is this person amazing because of who they are or because of an organization they belong to? That’s a tricky line because sometimes we might admire… I’m just using an organization, I have nothing to do with them, but say the president of the ACLU or somebody. We may go, oh we love the ACLU, let’s talk to the head of the ACLU. This hasn’t happened by the way, this is purely hypothetical. Then we start looking at who the president of the ACLU is and we’re like, I don’t know if that person in and of themselves is amazing, but we love their organization. If we can’t find a compelling case for the person, then we’ll tend not to do the interview. I have no idea who the president of the ACLU is, by the way. That person might be amazing.

Me either! Do you have a white whale? Someone you desperately want to talk to, but for whatever reason it hasn’t worked out?

Not really. I mean, Cyndi Lauper’s people keep saying that she’ll do it but she doesn’t have time. We get a lot of those, which is kind of the polite brush off. I don’t know if my dream is to interview Cyndi Lauper but I’d like to. She’s a good example. I’ll say she’s my white whale for the moment. Why not?