LIFTOFF: The Art & Science of Conversation

6. HOW Part I: How to Ask Questions

• Ilana Gilovich • Season 1 • Episode 6

Share episode

LIFTOFF: The Art & Science of Conversation
Episode 6

In Episode 6, host Ilana Gilovich learns about the kinds of questions most likely to encourage scintillating conversation.

Featured Guests:

Mentioned Morsels:

Transcripts for all LIFTOFF episodes are available on Buzzsprout.

ILANA GILOVICH: [00:00:00] Matthew Yeager's poem. A jar of balloons or the uncooked rice is over 10,000 words long, and it is solely comprised of questions. Yeager's poem poses questions like, how are you at not losing pens? Do you tear into wrapped presents or open them neatly with the spoken intent to save the paper? What famous landmarks have you found especially disappointing?

Which do you or would you find more embarrassing? Crying in public by yourself on a bench or laughing out loud in public by yourself on a bench. When at the barber or hairstylist, do you tend to talk about hair or realize that people there must always talk about hair? How do you show love to what is yours by wearing it in or attempting to keep it pristine?

What are you usually doing when it occurs to you to clip your toenails? I am touched by these questions because of what they reveal an abiding interest in the human condition. Questions do that they interest themselves in what's around them. [00:01:00] Asking a great question can take conversations to places you've never imagined.

I. In this episode of Liftoff, we dive into a two episode exploration of Conversational How Beginning with this episode on how to ask questions, we'll learn about the different types of questions in conversation and why some kinds of questions are more effective in forging connection than others.

Personally, one of my favorite questions to pose is one that I stole from Andrew Horn, a social entrepreneur, writer, speaker, executive life coach, and the creator of a four question framework known as social flow. 

ANDREW HORN: So what are two things that you love about yourself? 

ILANA GILOVICH: What I like about this question is that everyone can answer it, but no one answers it with ease.

It's endearing to see how disarmed people become when pressed to express self-love in their quest for answers. However, people begin to light up having discovered or affirmed something powerful about themselves. Another question I love to ask is, can you describe one [00:02:00] meaningful encounter you've had with art?

Again, this is a democratic question. Everyone manages to summon a vivid memory of a dining experience concert, film, book, or museum visit. Their answers illuminate where art penetrates and therefore exists within the people themselves. We can think mindfully about the types of questions we ask and why.

For instance, here's Alejandro, founder of Alejo communication. 

ALEJANDRO RODRIGUEZ: There's a huge difference between like o like opening gambit questions such as. How's it going versus how are you feeling today versus what are you working on? You know, like there are these questions that we use to get conversations started, but there, and we sometimes don't respect the, the quite significant differences between them, but in some ways, I think a lot about what's the right aperture for this question, you know?

Oh, yes. Can I ask like a big, broad question [00:03:00] that gives that person lots of room to maneuver, how they wanna get started in this, and then we can find the container, the narrowing of the container together. But, but when I try to establish it too narrowly early on, I often impose where I'm at and who I am onto someone who I'm just trying to get to know.

ILANA GILOVICH: I asked conversational expert Alison Wood Brooks to speak about the different kinds of questions that are most fruitful to deploy in conversation. And she changed my freaking life by teaching me about the power of follow-up questions. 

ALISON WOOD BROOKS: So we started studying question asking at first by looking at people on speed dates.

Um, it's this amazing data set and people who ask more questions, um, get more second dates. 

It's just like a pretty amazing main effect. Um, the same is true when you look at negotiations. People who ask more questions, learn more information, they do better in their negotiations. I. So [00:04:00] there's this sort of very basic advice that which is like, just try to ask more questions.

Yes. Uh, don't leave a conversation having asked nothing that is a major faux pa Mm-Hmm. But then moving beyond. How many questions are you asking? You can start to think about the types of questions that you're asking. And there are a million different ways that you could categorize question types. One way that I find quite helpful, um, is thinking about what are the questions doing?

Like where are they taking you? 

Hmm. 

Um, so are you using a question to switch topics? So if I were like, Ilana, let's talk about ballet, right? Like, what? Tell me everything. What do you know about ballet? What's your experience as a dancer? Right? Yeah. That would be a major topic, switcher. As opposed to a follow up question, which is relying on something you've already said and digging deeper on it. 

It's a really big for me to be like, how are things in Brooklyn? Right? Like you already said that you live in [00:05:00] Brooklyn and I can follow up on that. 

Those just, that difference is gonna make a, is gonna be sort of a profound difference between what those questions are gonna lead us towards next in the conversation.

Um, they're both quite important in our research. We find that asking more follow-up questions makes, helps you learn more information and makes you more likable so people are willing to go on more dates with you, um, and you learn more information, let's say in a negotiation. So follow-up questions are a major superhero.

If you're looking to up your question asking game, trying to ask even just one more follow-up question per conversation will make a really big difference. 

Um, in my class, I have my students play this, uh, do do an exercise called Never Ending Follow-ups. And you can try it too. 

It's sort of what an interviewer does.

As part of the norm of doing an interview, but you can do it in your real life too, where you try and every time you talk, you try and end with a follow up question. To your partner, [00:06:00] um, and like see what happens and see how long it takes for them to notice if they notice at all. And many of my students find that, number one, it's so easy to do.

Yeah. 'cause you don't even really have to think about anything. You just keep following up with what they're saying. Number two, it's a lot less awkward and more fun than you think. Yeah. And number three, your partner is gonna like, love it. 'cause most people love talking about themselves and they feel.

When you ask a follow up question, they can tell that you're listening to them. They feel heard, they feel like you wanna hear more from them. So it creates this very, um, sort of for some people who are not natural question askers. It's a very eye-opening. Yes. For people who already do that in their lives.

I think they're just sort of like, yeah, I know. This is my whole life. 

This is what I do every day. All day. Okay. And then you asked about Boomer asking, so I love this. So where follow up questions are, are a superhero, and you should ask more follow up questions. Boomer asks are kind of like the opposite of a, of a [00:07:00] follow up.

The villain, the total villain. Um, and we've all experienced this in our lives where, um. Somebody asks us a question and we answer and then they bring it right back to themselves. Right. They're So, it would be like, Ilana, like, tell me about Brooklyn. You tell me about Brooklyn. And then I'm like, let me tell you about when I lived in Brooklyn.

Um, and so it makes you feel like, I didn't actually wanna hear what you had to say. Yes. Um, even if, and even if I really did wanna hear, and I'm doing this out of this sort of ecocentric tendency or this habit, it still is just like not a great move. Yes. You know, if you're gonna bring it back to yourself, at least wait a little bit before you share your own disclosure.

We call it a boomer ask because it followed the arc of a boomerang. Yeah. Like, like throwing the boomerang out. You ask the question, you let the other person answer, and then it kind of flies rip right back to yourself. 

ILANA GILOVICH: To engage in an enriching, [00:08:00] joyous conversation. Peppered with great questions. I contacted Paula Marantz Cohen, distinguished professor of English and Dean of Drexel University.

Paula is the author of many nonfiction books on literature, film, and culture, as well as six novels. Her latest books are of human kindness, what Shakespeare teaches us about Empathy and Talking Cure, an essay on the civilizing power of conversation. One thing I love about Paula is that she isn't afraid to really dive headfirst into the sandbox of conversation and get her hands dirty.

PAULA MARANTZ COHEN: I like the tension of disagreement, especially with people that you know well, um, where, you know, you can't believe they don't like this and you like it. Try and figure out why they don't like it or they, you know, try and explain to them why you don't like something that they really like. Um, it's a real exercise in, um, in analysis, which I, yes, [00:09:00] very exciting.

As a critic, I will say that some of my conversational loves annoyed my children because they felt that I was always parsing things. . That can get weary some. Sometimes 

just, uh, as a child of a parent that nothing is ever okay or great or awesome as it's always well, but you know, or I, this is good, but I see that and that's part for me.

I enjoy that, but not everybody does. So I do acknowledge that. 

ILANA GILOVICH: Yeah. That's beautiful. That's a beautiful self-reflection. I, and I'm curious, I wanna even double click a little bit about what you were just sharing with your friend, because. It sounds like the difference in and of itself and the exploratory process of difference, enhancing your analytical understanding of a, a piece of work.

That in and of itself is rich. It doesn't sound like either of you were trying to change [00:10:00] the other person's mind, and it sounds like maybe you don't, you don't feel like the experience was diminished if you didn't come away having come to his perspective or vice versa. It was really about a kind of productive friction that helps you delve deeper into the.

PAULA MARANTZ COHEN: That's really well put, Ilana, I think you're right. I mean, we would get frustrated when we tried to change each other's mind. 

Yeah. But we 

would enjoy it. I mean, there would be times, I mean, he and I would fight a lot and I, each of us would sometimes just leave the table in a huff. It does happen. I mean, you know, and I think the best, and I think of my sister too.

Um, we've had many fights over the years, but we also have great conversations. I don't think you can always balance it perfectly, but the best kinds are when you're not trying to change the other person's. But at the end, or perhaps even. Later or even years later, you realize that their ideas have impressed themselves on [00:11:00] your psyche so that you're not, again, and I guess that's what makes me such a contrarian to, to my children, is that I always see a little bit of that other side, even as I'm arguing a position, having had this in-depth conversation with somebody who sees differently.

Yes. So in politics, I'm always seeing. Something of the other side and find it hard to take those very, you know, stark views that many of my friends do. 

ILANA GILOVICH: Paula is a naturally curious person with a gift for asking questions. Throughout our interview, Paula asked an astonishing number of questions given that I was the interviewer.

PAULA MARANTZ COHEN: So, uh, what is your field? What do you plan to do with that? That's where you are now in Greenpoint. And you're in a what? One bedroom. Yeah. So you took a lot of French in school, 

ILANA GILOVICH: given Paula's penchant for asking questions, it [00:12:00] wasn't surprising to learn that we share a pet peeve in conversation. One of my pet peeves in conversation is when I feel that someone doesn't ask any questions and exhibits.

No curiosity about, yeah, and I just feel as if I'm, it 

PAULA MARANTZ COHEN: happens a lot, doesn't it, Ilana? It is shocking. Amazingly. 

ILANA GILOVICH: It's one of the main motivators for this podcast actually, because I think it's not that people lack the care or lack the curiosity, but they don't have the skillset to, to connect the dots between, I'd like to know this person, but how could that be?

I mean, 

PAULA MARANTZ COHEN: do they, they don't have the skillset or they don't have the curiosity or they too frightened at that moment, although they don't seem frightened. Um, I cannot understand. It baffles me. My sister and I talk about it all the time. 

ILANA GILOVICH: I'm, I'm curious about that because I have people in my life who express, and I, and I won't reveal their [00:13:00] identity, but people that I, I know sort of well, but not too well, and that they keep saying, I really wanna get to know you more deeply or spend more time with you.

But I keep thinking. Why, but you, you say this, but there's been no, it's always talking at me and anything that I offer, there's no sense of, oh, would follow up. You expand on that or, and so I, I. I've been fascinated by that concept because I'm going, okay, so they do want to know more about other people, but it seems as though they don't know how, or they don't know that they have a failed me expert.

What if you said 

PAULA MARANTZ COHEN: to them, because I, I don't know that I have anyone that has actually said that I wanna get to know you better, but doesn't ask me any question. I wanna say to them, why don't you ask? Why aren't you more curious about me? Would you feel that that would be so? Painful or so, uh, wounding of them if you said that.

No, I mean, it's accusatory. 

ILANA GILOVICH: I actually think it's beautiful and I think there's something [00:14:00] really special in kind of what you talk about a lot in the book about feeling the safety to be direct. 

PAULA MARANTZ COHEN: Mm-Hmm. 

ILANA GILOVICH: And I actually really like that idea because if it's done with a, a gentleness and it with, it's done with an invitation.

I, Hey, I'm realizing that you've expressed this very kind desire to get to know me further and I, I would like to share more of myself with you, and I'm realizing that you don't seem very curious or you haven't asked me a lot of questions, and I would like to open up a conversation about that. That might be an interesting way to go.

Actually did 

PAULA MARANTZ COHEN: it very well. I think it fits with your personality. 

ILANA GILOVICH: Yeah. 

PAULA MARANTZ COHEN: I don't know if I could do it, because when I say about the safety, generally it's with somebody. I've already established that intimacy with, in other 

words, 

I mean this, the types of people that wouldn't ask me questions would not be people that I would feel I knew.

Well, yes, even though they may tell me everything [00:15:00] about themselves, that doesn't mean unless I'm telling about myself as it connects to them, I don't feel I know them well. I mean, I don't know them as reciprocal people, so, but you may have a different. Vibe with these people where you feel that safety, you know what I'm saying?

Yes. And it also may have to do with your age and your, your peer set 

ILANA GILOVICH: as well. Mm-Hmm. Yes. Well, these are actually people from an older generation. But what's interesting, what feels like the. Again, maybe I'm mapping on my family dynamic where it was all about conversation and curiosity and, and really getting into it together.

But in this context, what I've noticed is that these people will share stories. Then there'll sort of be a silence and another person will share a story. Yes. So there'll be monologue, monologue, monologue, back and forth, but there's no sense of what you described so well in the book as each element of the conversation starting to building, enrich the other and building so that it's actually, there's something shared or [00:16:00] there's something made between the, the different people and dialogue.

I 

PAULA MARANTZ COHEN: realize as you're talking. That I'm not crazy about those stories. You know, if I have a dinner party and someone, there's always a story and people seem to like that. Mm-Hmm. And I enter into the glee, but I don't really like it. I mean, what I like Yeah. Is that where everyone is involved in the making of the conversation, which goes back, I guess, to my father and the making of the idea.

ILANA GILOVICH: Hmm. And it's, 

PAULA MARANTZ COHEN: it's a, it's a creative act. In which everyone is involved, and that's what a seminar is. You can't. You know, you can't get rid of somebody if the or the idea won't be complete. It has to be everyone adding to it. And really, when a seminar works, everyone speaks and the quiet person will add something that takes it to another level, and then other people will chatter and they will take it, [00:17:00] and everyone's personality will add, um.

That's very different from an amusing story or anecdote, which, you know, it can be a lot of fun. But I see that as only a segue to this other thing, which is the maybe the liftoff piece in the conversation to use your vocabulary. 

ILANA GILOVICH: And I, I'm just so, I'm so stirred by what you're saying with a seminar, with every person is vital, is a vital piece of that conversation.

'cause the philosophical underpinning of that is like everyone has value and everyone's necessary to this project. Absolutely. And what a beautiful way. Like that's the world I wanna live into. 100%. 

PAULA MARANTZ COHEN: Right. And you don't have to distort your personality to be part of it. You bring yourself. 

ILANA GILOVICH: In this particular conversation, I could feel precisely how Paul's natural inquisitiveness and rich life experience contributed to the beautiful flow state we achieved together.

PAULA MARANTZ COHEN: Thank Paul. I have a Shakespeare read aloud that is a conversation [00:18:00] every week for three years. It started during Covid and we meet every week and it's people from 17 to 80. And we talk. We read, I give out parts, and they read for a little while and then we stop and we do it. And we're reading Romeo and Juliet now.

Oh. And we do an in depth discussion. And then it moves into things like romantic love and you know, adolescent infatuation and how, and then people tell their stories a little bit, but we move back to the text. It's the most wonderful thing. And we have a group of about 14 people that don't miss, including someone from England who's in his seventies, who it went to Cambridge in mathematics.

I mean, the whole thing is so wonderful. Um. 

ILANA GILOVICH: I want the film rights to this, I feel like could make a great movie. Great. And, and 

PAULA MARANTZ COHEN: I, I think I mentioned it in the book actually, you do, somebody from the New Yorker came and listened and I think he was just puzzled by the whole thing. [00:19:00] Nothing came of it, but, um, but Rosalyn, we did as you like it as a group.

And of course everybody loved Rosalind. 

ILANA GILOVICH: How could you not call in love? Yeah. It's, um, I'm curious actually about that container because. I can understand why conversation can soar when it has no constraints. Mm-Hmm. And has the ability to wander every which way. And I can also see how having a springboard, 

PAULA MARANTZ COHEN: yes, 

ILANA GILOVICH: having some kind of substance, like a Shakespeare text from which to explore things like romantic love or death or, um, feuds would be helpful.

And so. For you, do you have a preference about, I'd love a thematically grounded conversation. I'd love a structured conversation. Or do you prefer just like sitting down for coffee and, and chatting? 

PAULA MARANTZ COHEN: It depends on the people. I mean, a seminar is by definition, a structured conversation to some extent. Hmm.

And I think, uh, when you're dealing with people maybe you don't know too well, um, [00:20:00] it's a good way to spark. Material that you might not get at, uh, otherwise, and especially people perhaps, are on different sides of issues. To have something neutral like a poem or a play or something else 

ILANA GILOVICH: Yes. To 

PAULA MARANTZ COHEN: talk about is a way where you feel safe to express ideas without antagonizing.

So it depends. Yes. Um, but generally a good conversation, you often come with. Something to talk about. Mm-Hmm. I mean, my friend, he was a, uh, Catholic Jesuit 

who 

was sort of lapsed, but as he said, never fully lapsed. And I would say, let's talk about the virgin birth. Can you explain that to me? And it would go other places, but I mean, I love having something like that, a question or an idea that I'd like to have elucidated.

ILANA GILOVICH: And 

PAULA MARANTZ COHEN: discuss. I think that is [00:21:00] a really nice way to get a conversation going. 

ILANA GILOVICH: Yes, you're questing together, which is so beautiful. Mm-Hmm. I actually wanna read, there's a, I mean, I could quote from your book forever, but I, I, there were such beautiful lines in here that, that felt deeply philosophical and it reminded me, 'cause you were talking about Catholicism, deeply spiritual, the way that you think about conversation.

You describe conversation as a form of verbal sustenance, not just a seasoning to life, but one of its great pleasures. And like anything precious, it is not easy to come by. And you describe conversation as retrospectively poignant in that it exists in a particular moment and that is gone. If we think of conversation as an art, then it is more like food and theater than it is like poetry and film.

Though, in fact, it is like neither that even in a meal and a theatrical production have a blueprint, whereas a conversation happens spontaneously. It is an improvisational art form. And finally you say something. [00:22:00] So that gave me goosebumps when I read it. That dialogues model, that sense of eternal possibility of more material, always waiting, that fuels the best sorts of conversations.

So I'd love to talk to you about the kind of rapturous perspective that must have penned these lines in how you think about conversation. 

PAULA MARANTZ COHEN: Um, I, I love this idea that there's always more to be had, that it's never, there's no closure, so to speak. Hmm. And you know, when I, I'm also a writer and writer.

Fiction and there, you know, I try and move to a place of closure. 

Mm. You and 

I do love Jane Austen, and I love the idea of the courtship plot, the marriage, and then end. 

ALISON WOOD BROOKS: Yeah. 

PAULA MARANTZ COHEN: Of course things don't end there, but, you know, I think it's Carolyn Halburn, who was the great Columbia professor who said, uh, marriage in, uh, in 19th century fiction is [00:23:00] like death.

It's the end for these women, um, or for many women it was. And because we don't get anything after marriage in those novels, it sort of becomes the culmination point of the life. And that's a problematic thing to give women, which I think they've struggled with. They've struggled with, yes. But my my point is that conversation opens things.

There's, it's, you know, you, you end it because you have to end it. Either you have to go do an errand or you have to go to bed or you have whatever it is, it does, you can pick up again or you can start a new conversation. And I think that's very, I. Affirmative. Um, and it also fits with some of this postmodern theory of, you know, the play of the signifier where everything always leads to, there's no final, there's no overarching narrative, there's no final reference.

Mm-Hmm. And you are. Moving always to [00:24:00] something else, which can be very frustrating to some people. Mm-Hmm. But, which I kind of like, it never ends. And again, that's somewhat frustrating to my children because I'm always seeing another piece to another point. Well, let's stop talking already. It's enough. You know, I, I, I, you know, I get the point, but I wanna keep on talking because I think that it opens up new vistas.

ILANA GILOVICH: I love that. Feels like in a deeply abundant mindset, and also connects back to what you were saying about the seminar where each person is crucial to the collective endeavor. And if you feel that there's infinite food for conversation, then everything you do in your life, positive or negative is fodder for fodder or kind of dialogue you can have with someone else, which is so beautiful.

Um. 

PAULA MARANTZ COHEN: You know the famous Nora Efron, I interviewed her before her death. Oh, she was, her mother gave her this, um, uh, advice. Everything is copy. [00:25:00] Um, so, and I have to say that's true of conversa. I actually have always felt that that's true for my writing as well. Mm-Hmm. So I understand that although I've exhausted at this point in my life, I feel, I don't feel driven to write anymore.

I've written a tremendous amount and I used to write essays constantly. Anything that struck me, 

I realized maybe it was. I wanted to really talk about it, but sometimes if you talk about it, you use it up and you can't write about it. Um, so I would be writing constantly and all of a sudden, well, not all of a sudden, but in the last year or so, I really lost that urge to write.

But I have more than ever that urge to converse. So I think. That's interesting. I don't know what to do. It's What do you make of it? 

ILANA GILOVICH: Well, I, I, huh? It's funny, I [00:26:00] now thinking about the title of your book, which I wanted to ask you about, but Talking Cure. It's so specific and it's so vivid, and there's something about an essay or a novel.

Those curative properties feel different than the curative properties. Yes. In a, in a vocal conversation or assigned conversation with someone else. Mm-Hmm. And so. Yeah. How, what, what do you think does draw you to conversation? Are there certain topics you would rather speak about with someone else versus write?

PAULA MARANTZ COHEN: Um, I mean, the thing that's great about writing is that it seems to be, you feel like you're creating something permanent. Um, that, and, you know, Shakespeare, sonnets are all about that. Um. So long lives this and this gives life to thee. Yes. Um, but conversation with another person is with another person.

And is that your [00:27:00] time on earth diminishes? You begin to see that these so-called permanent things are not so permanent, and who's gonna, does it really matter? And that the relationship with another living person has. Value because of its transits, because it's so impermanent. And you, you want more of that?

I think, I mean, I'm, I'm improvising here as I'm talking to you. Yeah. Yeah. I think that is what it is, that you want to maximize your human contact before you have you cease to have that. 

ILANA GILOVICH: My new theory that I'm trying on right now when I think about death 

is, is. I want to go into that state feeling like I learned something.

And that's sort of it. That's sort of the one story that if I, I'm able to just like Ian characters end in, in marriage. Yeah. I wanna end in knowledge acquisition, whatever that [00:28:00] means. Emotionally, spiritually, intellectually. And there's something really beautiful about. What you're saying with conversation that there isn't this impulse to record and memorialize, it's just, it can live as it is and you become the archive that represents the knowledge that's been exchanged and the, the, hopefully the fun that's been exchanged too.

PAULA MARANTZ COHEN: Yeah. That's wonderful. I like that. And um, yeah, it just feels less selfish too because yeah. Engaging with another person to create whatever ephemeral thing that you're creating. 

Writing is, is a kind of, um, it's narcissistic in so many ways. Right? 

ILANA GILOVICH: Right, right. It's really true. And I find with writing too, when I.

When I can really get out of my own way and be the conduit for the ideas. Mm-Hmm. 

PAULA MARANTZ COHEN: Yeah. 

ILANA GILOVICH: I feel that my writing is much more generous and much more clear, but when I'm trying to be the agent of [00:29:00] something, the writing just isn't as good because it's more narcissistically driven. I. Thanks to Paula. I will never underestimate the power of a good question.

As an expedition guide, a question can escort us to vistas of breathtaking beauty and perspective. Questions are testaments to our human capacity for curiosity and wonder. It's a phenomenal human practice. We get to wonder things and formulate that wonder into queries, and perhaps even get answers back in your next conversation, see if you can challenge yourself to ask more, follow-up questions than reflect on how you feel and how your partner may have felt after the conversation concludes on the next episode of Liftoff, we learn how to listen in deeper and more dynamic ways.

Liftoff was created and directed by Ilana Gilovich and produced by Greg Hanson. The featured guests on this episode were Andrew Horn, Alejandro Rodriguez, Alison Wood Brooks, and Paula Moranz Cohen. If you like liftoff, [00:30:00] please share it with your friends and be sure to subscribe wherever you listen to podcasts, so the power of potent and playful conversation can continue.