It may seem strange in a season devoted to questions to have a podcast and a blog on the topic of conversation. Upon reflection, however, I think you’d acknowledge that conversations live or die by the quality of the questions that drive them. Awkward conversations are usually the result of a failure to generate good questions.

Conversations are an ideal place to learn from the life experience of others. I don’t mean the inappropriate button-holing of physicians or financial advisors at parties. Everyone has life experiences that we can learn from. Most people blossom in conversation when they realize that the other person is really listening and really wants to know more as sign-posted by the questions they are asking.

It is so rare to have a conversation partner who is both a good questioner and a good listener. Perhaps that’s because it takes humility to really listen and not be thinking about what you are going to say in response.

If you meet a really humble man . . .probably all you will think about him is that he seemed a cheerful, intelligent chap who took a real interest in what you said to him.

C.S. Lewis in Mere Christianity

The accompanying podcast is available here and what follows is an approximate transcript of that show.

Mike: In today's podcast, we're going to be exploring questions as the key to good conversations and I have a guest with me; so you're not just going to listen to me today. You're going to be listening to a close personal friend, Laura. I'll not give her last name because she and her husband do mission work in Asia. Laura and I have known each other for probably going on 20 years now. Before I knew Laura on any other level, I knew Laura as a good conversationalist, and I haven't meant too many in my life. Her ability to ask good questions in a sequence that drew out the other person was intriguing to me.

Today we're going to explore the use of questions in that arena that we all have some experience with and maybe avoid at all costs because we feel we're not very good at conversation. But nonetheless, I think all of us would recognize that good questions are the key to the conversation moving forward in a helpful and non- awkward way. So, Laura, welcome to the podcast.

Laura: Thank you. It's wonderful to be here today.

Mike: Wonderful you can be here. What I guess we could start with is when you think about conversation, I think you've got kind of maybe triage is a really strong word, but at the outset of coming in contact with someone, with an opportunity for conversation, you have kind of a filter in mind, depending on the way the person fits within your life. Would you like to start there as maybe the basis?

Laura: Sure. I guess if I'm entering into a social conversation with someone, just a very relaxed environment for talking with them, basically, I would think in terms of three different environments in that way.

So the first would be, is this a family member or a very close friend? Someone that I've known for years, someone who knows me really well. So that would be the first context. And then the second would be maybe someone that I'm meeting for the first time, but I have the potential to see that person again and build a relationship with them in the future. And then I think the third group would be someone that is someone I'm meeting for the first time and very likely won't see them again. For instance, an Uber driver. But I'm in the vehicle with this person for maybe half an hour. So there's an opportunity within this enclosed space to get to know them a little bit within that time frame.

So I don't necessarily think that have this conscious attitude toward people in the moment. But as I look back and think about ways that I ask questions, I think there are three broad categories in the way that I do that.

Mike: So your goals for these three categories of people are different, and that shapes your question?

Laura: Not necessarily. I think probably the most significant difference would be the frequency of the questions. For instance, when I'm with a close friend or family member, maybe this is just laziness on my part, but I can tend to think of questions as being a little bit formal sometimes. And so maybe I'm more relaxed and I have more of an expectation that the other person will voluntarily share things with me. So maybe my questions are a bit fewer. But on the other extreme, if I'm with someone in a vehicle and on an Uber ride and I know I have a very limited time with that person, it feels almost like we're playing a game. And of course, that depends on how responsive they seem to be to my questions. They may not be interested at all, or we can have a very lively, interesting conversation within a short time frame. So there may be more questions that are asked within that time space.

Mike: Okay, so frequency of questions, but intent of questions that you're asking?

Laura: Sure. The intent of questions, definitely very different. Like I said with the Uber ride scenario, I'm not expecting great depth with the other person. But I have an assumption that whoever I'm speaking with is someone who is made in the image of God. And that makes them intrinsically interesting. They have a story to tell, whether they see themselves as storytellers or not. And whether they enter into a conversation with me really wanting to tell that story, maybe they'll find that there is something that they don't mind volunteering with a stranger within that context.

But then swinging back to the first category I mentioned speaking with a close family member or friend. Perhaps my questions well, hopefully my questions would deal with something that's a little bit deeper, something that has to do with probably recent circumstances in their lives and how they're interacting with those circumstances or how those are shaping them in some way. But that's just one scenario for that context.

Mike: So you've got a relative, let's say, and you know some of their circumstances, whether those are something you view as a challenge to them or something that might be source of joy to them, what's your aim for that person in asking those questions? Just to acknowledge their joy or grief or beyond that?

Laura: I think initially, sure, acknowledging the joy or the grief, but also trying to understand them more as a person, which, particularly with my siblings, these are people that I grew up with. And I have a certain idea about who they were as children, of who I was interacting with them as a child. But they're adults now. They have very different lives from the way that we grew up. And so I meet them and I see them not just as siblings with shared history, but I see them really as friends. And we can converse on a number of different levels. But I think central to all of that is I want to get to know them better, get to know who they are as adults, get to know where their hearts are what's most important to them. What are the goals they have personally for their family and how those things relate to their relationship with God and so forth. Yeah.

Mike: It occurs to me that people who kind of take the relationship as a given and don't ask those questions face the real likelihood that they will grow apart from that person. That over time, they won't recognize who that person has become because they haven't been asking questions that would give us some insight into the decisions that they've made or the way in which circumstances have affected them. I think a lot of families experience that and wonder how it happened that we grew apart from one another. And from hearing you, part of the answer is we didn't ask enough questions as we had opportunity. We took for granted the relationship and failed to grow in our understanding of the other person. So I think there's a dimension to that. That's also true with people with whom we might have increased contact in the future. What's the motivation for this group of people that you have the potential to develop relationships with? Maybe that one's more obvious than our own family members. You want to speak to that group of people?

Laura: Wow. So someone that I'm meeting for the first time but have the potential to get to know more in the future. I'm thinking within a couple of different contexts. Maybe this might be a colleague at work, for example, or a fellow church member, maybe someone new to my church.

And so context, I think, will dictate a little bit how the conversation starts out, but again, just not necessarily finding out what their interests are and their hobbies. But I don't think there's necessarily anything wrong with that. There is kind of an ice breaker element to questions like that. I think they're very safe. They're things, you know, that the other person will certainly have in some form or fashion. And it just gives me an opportunity, as the question-asker, to kind of test the waters a little bit and see does this person even respond to me to any question. So starting with something fairly simple and safe I think is kind of good just in that small talk arena. So it's a little bit insipid. There's nothing really exciting happening there.

Mike: You want to give an example of small talk, because I think a lot of people get stymied right on the front end. Maybe I ask one question, and I got a short response. I don't know if this person wants to talk or not. And I don't know that I have another follow up question. Thank you. We've got this awkward silence. So what does small talk look like? And I'm asking because I would say the weakest part of my interaction with people is small talk.

Laura: Okay, well, I would have to agree with you there. Honestly, I'm not strong with small talk either. But I'm thinking of a situation that happened a couple of weeks before Christmas where I did exactly this, where I met many people who were new to me in a church context. So this is a church that my husband and I are visiting, that my parents attend regularly. It was a Christmas function for a community group that we're likely to join. So we will see these people again, very likely.

So we are seated at the table with eight other people, all of them strangers to us. So we're meeting them for the first time, and there's one other man at the table who's non-Asian like I am. So there's that point of connection and just starting out the conversation, if I recall correctly, it was just something very simple, like, where have you traveled? Actually, even as I say that, I think there must have been something that happened prior to that to make us aware that he had traveled. But as we moved forward, it was fairly simple because he had been to South Korea, had lived there for eight or nine years, and in fact, my husband and I had also lived in South Korea for about a year and a half. So we were able to work from that shared history of having been in the same country, not at the same time, had very different experiences there. But through these questions, in this back and forth exchange, I think we were starting to build some trust and show that we were interested in each other, show that we were listening to each other. And that just kept generating more questions as the night went on. So that's one recent example.

Mike: Maybe you could ask a question behind this kind of thing. Why go through the effort? Because I know you're an introvert. Why go through the potential difficulty of trying to see if there's a point of connection and start a conversation? What motivates you to enter these kinds of conversations?

Laura: I don't know if this is a good point to maybe mention that my motivation has changed over the years. So I could briefly mention that here. When I was younger, as an introvert and feeling very nervous and very cautious entering conversations with anyone, I used questions as kind of a defense mechanism. It was a way of me being in control of the conversation and me not having to answer questions.

Mike: My son in law, who's always the guy behind the camera, so he never shows up in any pictures, right?

Laura: Exactly. And that was a way of helping me to feel safe and secure. I had had an experience as a child where I felt like a relative sort of betrayed my trust by not listening to me. And I had become so cynical and thinking, well, if you're not going to listen to what I have to share with you, then I'm just not going to volunteer information about myself.

And so initially I had this very self-centered motivation for asking questions. But I think just in recent years and through this transformative process of hopefully becoming more and more like Christ, that motivation is changing. And maybe this sounds like a weird motivation, but I feel like it's an opportunity to show hospitality to people where even at this Christmas party which took place at church, it was not even my house. I wasn't in charge of anything. I was seated at the table. And if I'm asking the question, that kind of puts you in charge for a second and it gives you an opportunity to reach out to someone else who's there to acknowledge them, to show warmth, to show I'm offering you this moment, I'm offering you my attention. And I believe you have something very interesting to share with me, if you would like.

And so you just kind of serve it up that way. And whether the other person perceives up that way or not, I don't know. But in this particular instance of the Christmas party, this man seated across the table took that opportunity and so the conversation grew. And later, his wife, who is Korean, was very interested to meet my husband, who's from Asia. And so we're both cross cultural relationships and that was really interesting for the four of us to kind of continue to build on this conversation.

Mike: So hospitality is an interesting motivation. It's extending love on one level to somebody else. We all know the awkwardness of being in a new context and not having anybody offer to integrate us into their network of relationships. We're not quite sure what we should do as outsiders in that situation. Are there other kinds of motivations that factor in at other times, in other kinds of conversations? Perhaps?

Laura: I think in other contexts, again, because contexts differ so widely, I think the most basic common denominator for me in any conversation is just wanting to give the other person an opportunity to share who they are. And to build on that, to see that as something relational. Like, it's not just this person dispensing information like, here's who I am, but okay, you and I hopefully will be brought one step closer to each other. And maybe that's where we stay. Maybe we don't have many encounters in the future that will bring us any closer, but I think that it's important. Again, this is kind of a hospitality thing to always just have, hopefully this generous outreaching to whoever happens to be closest to you in proximity and just to see them and to have at least some small level of engagement with them.

Mike: Almost sounds like the question and who is my neighbor?

Laura: Yeah, I guess you could think of it that way.

Mike: Yeah. Well, in the process of respecting that this person is made in the image of God and has life experiences which probably differ from mine, maybe in small ways or maybe huge ways, there is the potential there for me to learn, to grow as a person, maybe to change some stereotypes that I have.

One of my emphases on this program is looking for patterns, and that is very helpful, and the brain is wired to do it. But sometimes we pigeonhole people, put them into a category which makes it convenient for us, but probably misrepresents them if we took the time to get to know them better. And we all develop stereotypes which may have some degree of justification but may also distort things. So there's an opportunity to learn on an entirely different level. When I'm interacting with a person face-to-face, is that something that you feel when you're in the middle of a conversation? That maybe my categories are being challenged? Or that, oh, I didn't realize that somebody could hold that view and be in this category or whatever combinations. That kind of thing. Has that learning occurred for you during a conversation?

Laura: That's a really interesting point about stereotypes. And I can't think of a specific example where I was aware in the middle of a conversation, wow, I have a stereotype that's being challenged right now. But I do absolutely agree with what you're saying as far as learning from the other person.

And maybe that's kind of what I was referencing earlier when I said that they have a story which that doesn't sound like I'm in a context where I'm learning, but just thinking of however they're relating their experiences or something about their lives. But I guess I could say particularly related to their expertise because that will often come up when you're speaking with someone. What do you then? Of course, they deploy this vocabulary or these other things that probably I've never even heard of before. So it's an opportunity for them to start defining some terms for me or to lay out probably for them, very basic foundational concepts related to whatever their field of expertise is. And there definitely have been times that that's happened. And I love it because it at least gives me a window into a new world that I've never dabbled in personally. But if they're really good at communicating that, I can hopefully understand it a little bit better, or I can at least appreciate that they're trying to help me get there.

Mike: So it seems like maybe that one of the targets of small talk is to try and get enough of a response from this person that I recognize something that they would like to talk about—to a stranger. And probably if it's not something I have experience with, I've got questions if I'm a good listener. Now, I think that gets on to another piece of conversation when I ask good questions. The reason that they're good is contextual. It's not that I have these fabulous questions and I regularly deploy my top ten on whoever I meet.

Laura: Absolutely. I think for me, if I were to give conscious attention to this every time, which I don't, but when I do pay attention to conversations that I have with people, I am aware after the fact of how tired I feel. And it's not because there was anything that broke down or went wrong, but it is so exhausting to be that active in your listening to try to understand everything that they're saying and then hold on to those key points that could lead into a follow up question.

Or if you reach a point in the conversation where there's kind of a lull and it's easy to sprinkle that moment with a word like okay, I see, interesting, and so the conversation maybe dies or doesn't advance in that direction. I think those are really good opportunities for a timely good question to land to either project that conversation a little bit further or maybe if I've been listening well, maybe there was something sprinkled in a little bit earlier and now I can rabbit trail over to something else that apparently is interesting to this person because they've mentioned it already.

Mike: So a good conversation is never one-sided.

Laura: No.

Mike: Or the person will feel that you're interrogating them, right. Which is going to shut most people down or get a negative reaction anyway. So how do you balance— you talked about these lulls in the conversation. How do you balance you talking and the other person talking?

Laura: Wow, that's a really good question. I think this is an area where I need to grow a lot, maybe grow the most in my own conversing with other people, because it's still really instinctive to me to just keep asking questions and kind of want to hide behind that and never volunteer anything about myself or that would help the other person get to know me.

So if you're thinking about a good conversation being like a seesaw, there has to be back and forth. Both people have to be equally invested with speaking and listening for this conversation to really go forward. So that doesn't necessarily mean that both people are asking the same kinds of questions or the same number of questions. But I think you have to pace yourself sometimes and recognize opportunities.

Maybe when the other person seems like they've talked a really long time and they just need a rest, then you can insert yourself into the conversation a little bit more and either talk about your experience that is either similar or different or start volunteering things about you just so that it is two-sided. It's not one dimensional. And you show that you are trusting the other person by volunteering things about yourself just the way you're expecting that trust in return.

Mike: Yeah, that's helpful. We talked about lulls in the conversation. How do you sense that maybe we've gone as far as we need to go this time and bring conversations to a close without feeling like it was an abrupt cut off? How do you steer things toward, like, okay, that was a helpful conversation to me, and I hope it was to them. And I'm sensing positive things from the other person and I don't want to monopolize their whole evening, for instance, if it's an event or they've got other things, maybe we're on a plane and they've got work that they need to do. So are there any things that mean we're not actually talking about a lull? We're talking about trying to wrap up this conversation?

Laura: I think there are probably a lot of good ways to do that. I think depending on the context and how well you know the person, it might be appropriate to thank them for their time, thank them for what they've shared. Share something that you genuinely learned from them if that's what you feel happened in the conversation. I learned blank. Fill in the blank with what you learned so that it's genuine, it's not some sort of platitude that you're dropping in at the end of the conversation.

Yeah, I think there are a lot of ways that I think maybe most importantly is just to share something that's genuine. It doesn't have to be lengthy. In fact, I think probably the shorter the better to just signal that maybe I have an obligation. My phone is ringing or my baby's crying, or maybe the other person has something that's come up.

So this is also something that I'm not naturally good at because I kind of hang there for a little bit and feel like the other person should show initiative and lead the way in either ending the conversation or walking away. But then that creates this sort of awkwardness where both of you are standing there and no one's doing anything. So I am trying to get better about being hopefully not abrupt or aggressive, but just if it seems very clear to both of us the conversations over, just walk away from it after a final remark. Yeah.

Mike: And maybe even with one of your categories here where somebody you might have an opportunity with in the future. Invite them. Like maybe we can continue this conversation or maybe I need to read a little bit and then I have some more questions for you about this one major thing that we spent a lot of time talking about. You piqued my interest, maybe even can you recommend something for me to read, for me to explore this a little bit further in more depth that we have time together for? Which, again, shows I'm interested in learning about this. This isn't just a technique here, but I'm asking you for recommendations from your life experience so that I can move this forward and know more about it if we have another opportunity to talk about this.

Laura: I think that's particularly true in context, that I'm often interacting with people who are foreigners, people who are new to America, and I think that there's a very common perception that Americans really don't care about people from other countries. We don't know about them, we don't speak their languages, and we are not proactive about asking questions.

And so I think exactly in a context like that, if you're meeting someone here on US soil who's possibly a new immigrant, just finding out more about their country, trying to learn some of the language and making those connections exactly like you just said, what can I read? What can I learn about your country so that I am better informed the next time I see you and we can talk more about it?

Mike: Thanks, Laura. There's lots more we could talk about, and maybe we'll have another opportunity also. But I think it's clear that there are multidimensional reasons for entering into conversations. Even if you're an introvert, even if it doesn't come naturally to you, that the effort is worth it, that it shows that we love other people, that we're interested in them, and that we think we have things that we can learn from their life experience. So thank you for being with us today.

Laura: Thank you very much.

Mike: Join me in two weeks as we begin a three episode series on the components of thinking. A visual artist, a scientist, and a historian can have profitable conversations if they recognize that each person in the group comes from a unique point of view that motivates them to answer a group of questions appropriate to their knowledge domain. Questions that intrigue the artist are likely to be quite different from those that captivate the scientist, but that need not mean that there is no hope of mutual understanding. The historian may be unfairly stereotyped by the other two due to the way that they were taught history, but was their exposure a fair representation of what motivates a historian?

We'll consider all of this in two weeks. It would help the cause of learning if each of you who listen would like, comment on, or share this podcast with one other person. If you want to explore conversation in more depth, please check out my blog at deepanddurableable.com, where you'll find links to some great conversations that have been recorded on YouTube.

A significant part of catalyzing generous enlightening conversations is the ability to listen well. This is something that you can cultivate.

Here is a YouTube interview with Carolyn Coughlin called “The Secrets to Listening Well”: https://www.youtube.com/watch?v=TNyaaUF0hwE&t=2910s Join the interview at 48:30 if you don’t have time for the whole thing. Coughlin identifies three kinds of listening:

1. Listening to win

2. Listening to learn

3. Listening to fix

It is particularly important to cultivate listening to learn! Listening to win is not very healthy. Listening to fix is what men tend to default to while women are more prone to listening to learn without an expectation that the conversation is going to fix anything.

I love this quote from Thuli Madonsela: “I need to listen well so that I hear what is not said.”

There are some great conversations recorded at Actors on Actors in YouTube. There are also some that are stilted or one-sided. Kate Winslet is a very skilled conversationalist. Here’s a link to a conversation she had with Saoirse Ronan:

https://www.youtube.com/watch?v=NzyN5kcbusY

and here’s another in a longer conversation she had with Gary Oldman:

https://www.youtube.com/watch?v=kqSfLfJKVI0

 Here’s a perceptive comment on the interview with Gary Oldman (from B. b. Gun). Notice that some of the same elements of conversation are highlighted that we noted in the podcast and blog above.

“This conversation SURPRISED me! Not the fact that it was fascinating because come on! They’re perhaps the best male and female actors today. The surprise was the ease with which they conducted this interview “conversation.” It had such a natural flow and you didn’t feel like they were asking what they thought they should but instead real questions due to mutual interest. Usually these actors on actors conversations feel unnatural. Because the setup is forced! (I still love them!) Even the really good ones like the one with Nicole Kidman and Ewan McGregor who know each other well from working closely together and have such great chemistry, there's an awareness that it’s an interview instead of a genuine back and forth. Goes like this: “My turn.” “Okay now your turn.” Even Tom Hanks who excels when it comes to being natural in any setting and Viola Davis who is as real as they come, still had a bit of a forced feeling at times. They didn’t just freely carry on. I’m not really sure how Gary and Kate managed to give us an authentic conversation but I’m grateful because they gave us a real peek at the inner selves of two incredibly gifted artists. I assume that it’s because they admired each other so much that they truly wanted to learn about the other so they weren’t just doing this for us but also for themselves. Which resulted in them getting lost in each other the way people who click carry on in real life.”