Minisode: Get Better at Small Talk to Connect in a Hybrid World with Jenn DeWall

Get Better at Small Talk to Connect in a Hybrid World

Hi everyone. It’s Jenn DeWall, and we are wrapping up 2022 by talking about the fine art of small talk. We are doing a minisode today. This will be our new podcast episode of 2022, and we’ll bring you all new content in 2023. I will be talking about small talk, something I imagine many of you will be doing ALOT over the next few weeks.

But before we get started, I want to remind you that Crestcom offers a complimentary two-hour leadership skills workshop. If you or your team are thinking about how you want to approach 2023 to ensure that you are performing at your best and that you’re collaborating to the best of your abilities, head on over to We would love to know more about your organization and how we can help develop your leaders.

And also, if you don’t know, I just want to remind you that Crestcom also does free monthly webinars. They are complimentary and open to the public, all designed to give you the necessary skills that you can use immediately to be successful. Our next webinar is coming up on Thursday, January 26th, and we’ll discuss starting the new year with a growth mindset. So I hope you’re able to attend!

Why is Small Talk Necessary?

But now let’s get into the show. We’re talking about the art of small talk and how to connect in a hybrid world. And many of us might struggle with small talk. We might struggle because we feel like it’s so surface-level. Oh my gosh, I don’t know why I have to do this. There are a lot of grievances that people have around small talk. They might feel like it’s just a waste of time. They might feel like people don’t really have a meaningful connection, which is understandable. We need to be strategic about small talk if we actually want to have an impact with it.

So it’s natural to have those feelings. But for the podcast, we’re gonna talk about some of the benefits of small talk and how to navigate small talk. But before we get into it, let’s talk about what small talk is. And this is from “The Problem of Meaning in Primitive Languages” by Bronislaw Malinowski. And this was written in 1923, studying the benefits of small talk. And here, it was defined as:  Small talk— A great deal of talk does not serve any purpose of communicating ideas but instead serves to establish bonds, a personal union. So for those that might be thinking, Ugh, small talk is so frustrating. It’s a waste of time! I want to reframe that for you, to think about how you can use small talk to deepen connections and to build relationships because that’s really its purpose. But that also requires us to approach small talk in a different way.

Small Talk is the Foundation of Trust

And here’s another consideration, and this is from the Career Contessa. Think of small talk like bricks. One or two bricks don’t make much, but if you gather 10 bricks or 20 bricks and you start to establish a foundation, that’s when small talk serves as the foundation of building trust. So I know that initially, it might seem again that, oh, this is such a waste of time, but it’s something that we want to think of the long-term gain for maybe that short-term pain. And understanding that small talk is the starting point for a deeper connection. So I’m going to share with you some tips because as I was researching this, this is actually content that we used for a webinar that we offered in November on this. So again, I can’t recommend it enough— come to our webinars. We would love to have you. They’re open to the public.

But in my research looking at small talk and the art of small talk, one of the books that I picked up and read was The Fine Art of Small Talk. And this was written by Debra Fine. She is a speaker, and she works with individuals around the world on how to improve their art of small talk. And here within that book, and I would definitely recommend getting it, the book again is The Fine Art of Small Talk by Debra Fine, but she provides a worksheet, and I’m going to review or read a few different questions for you to consider and reflect on because we want to understand how often are you in situations that require small talk and what is typically your response.

Some Questions to Ask Yourself

So here are some questions for your consideration. And the full winning at small talk worksheet is available in her book. So one of the questions that you can consider is, “I have joined or participated in at least one club or group activity to meet new people this year.” Is that true for you? Do you find yourself maybe avoiding some of those things? Another statement, “in the past year, I’ve used my contacts to help at least two people get a job, date, connect with new clients or customers, or provide information for networking purposes.” Have you done that? Made a connection? Small talk is a way that we can build bridges to broaden and expand our network. Here are another few, but I would recommend getting her book and walking through this so you can reflect maybe where your areas of opportunity are or what your starting points are. I’ll give you one final reflection piece to ask yourself. When someone asks me what’s new, instead of saying, “Not much,” I often talk about something exciting in my life.

Have an Intentional Strategy to Get Better at Small Talk

Are you one of the people that doesn’t necessarily talk or give much of a response, which can sometimes be the obstacle or barrier that we have to overcome with small talk? So leading into it, what are some of the small talk mistakes that people might make? And these are honest mistakes, but we want to think about small talk as an intentional strategy. And one of the mistakes that people make is when we ask the individual with whom we’re in conversation yes or no questions. When we ask the yes or no, do you like this? Have you been there before? Have you been here before? It doesn’t necessarily give you an opportunity to hear more, especially if that person doesn’t feel comfortable sharing more.

And so asking them open-ended questions such as, what do you like about coming to the events? What do you like about working here? That can be a better way to get more information from someone and to actually build on a foundation of that conversation. So one mistake to avoid is asking closed-ended questions because that will only elicit a one-word yes or no response.

Other small talk mistakes that people make is there’s no self-disclosure or talking or on the flip side. So you’re either saying too little, or you’re saying too much. Now the tip here with small talk is we want it to be this gradual self-disclosure where I might respond and answer a question, but then you are going to respond and answer a question. Or if you are the individual that’s running and managing that conversation, you’ll ask the question, but then you’ll also answer it in turn. When you have no self-disclosure, you’re not building trust, and that other person isn’t getting to know more about you.

On the flip side, if you’re only talking about yourself, someone might be thinking, holy cow, what’s my exit strategy? How do I get outta here? They don’t even care about me. And another small talk mistake that people make is being critical instead of curious. Let’s say that someone talks about their favorite restaurant or talks about a challenge that they have in the industry. You might be listening to learn, or you might be listening to judge based on your past experience. And if we’re critical, especially in this foundational opening conversation, it can be a turnoff for people, which might make them reluctant to want to talk and engage with you.

Avoid “Pitch-Slapping” in a Conversation

Another small talk mistake is interrupting people. This is a common mistake for extroverts. We have to slow down and allow people to finish their thoughts instead of assuming what they’re going to say. Another is “pitch-slapping,” also known as “getting networked on” by someone.

You go into that networking event, and you find that one person that’s only there to talk to you because they want to sell you. If you are that person, be mindful that you’re not building trust, you’re actually eroding it because they’d see you as someone that doesn’t necessarily care about them. You just care about yourself and your objectives. So be sure to ask some of those questions that you might think are actually fufu so you can deepen the level of trust, and then you could pursue and go into talking about what it is you do or potentially asking for a sale. And going into other small talk mistakes, avoid talking about controversial topics, those can be something that can instantly shut a conversation down.

Be Willing to Take the Lead to Get Better at Small Talk

Or how about not having anything to say or waiting for someone else to take the lead? Sometimes we don’t wanna be the one that is being vulnerable or owns the conversation, but when we think about what’s in a conversation, you know, typically what we’re doing in a conversation is we’re either exchanging information with someone, we might be exchanging power to try to influence someone to our point of view, or it might be transformational. We’re exchanging it. We’re exchanging energy. We’re just getting to know one another. But know that on the basic. And if you took our webinar, what you would see as a graphic of understanding that with all the conversational levels that I just talked about, that every level as we engage more and more or we add more bricks, going back to that career Contessa quote, we’re building trust. But initially, when we’re starting that conversation, it’s low trust for both people. So we might be a little skeptical of what you have to say. We might resist what you’re trying to say.

But as we’ve exchanged and done that gradual self-disclosure and gotten to know more about each other, then we’re building a conditional trust. And again, over time, as we’re listening and learning and going more, that’s when we can get to that high level of trust. So the starting point to be effective at small talk and is from Debra Fine’s book, the Fine Art of Small Talk, and I love this tip. There are two things that you can do to improve small talk. The first is to give yourself permission to take the risk of starting the conversation. Now that conversation or risk might be with a new employee in your organization. It might be with a new person that you’ve never met in a social setting. It might be at a networking event, but either way, give yourself permission to just take the risk and start the conversation. Too often, many of us avoid it because we might be uncomfortable. We tell ourselves we don’t have anything to say.

Reframing How You View Small Talk

And instead of doing that, look for the reframe of saying, I’m just going to start this conversation and see what happens. And the second thing that you can do to improve small talk then assumes the burden of the conversation. Meaning if you notice lulls if you notice that someone maybe isn’t engaging, empower yourself to be more direct in your questions. How are you? What would you like to do? So on and so forth. So the two things to improve small talk is to start by giving yourself permission to take the risk to start the conversation. And then, second, give yourself the power to assume the burden of the conversation. This means that you also want to have a preparation list in some capacity of what types of questions you might ask.

And know that those questions are likely going to be different in a networking event versus at work versus outside work at a social event. But opportunities to practice that if you’re just looking to maybe improve it in a low stakes way, you could go and practice having basic conversations at the grocery store, maybe with the individual that’s checking you out or assisting you in finding a product. You could do the same at the mall or when you’re running errands, but look for opportunities to practice. That way, you’ll feel more confident and comfortable when you actually have a higher stakes conversation where you want to get to know that person and deepen the relationship and potentially partner, work with, or befriend them— whatever the outcome or objective is.

The Forgotten Name Problem…

Here’s a quick public service announcement, and I think this is great. This is again from Debra Fine’s book, um, the Fine Art of Small Talk. One of the things that she talks about is an obstacle that many of us have. If we find ourselves in a small talk situation, we might also notice that they’ve introduced themselves to us, but we’ve forgotten their name. And instead of listening to them going through your head and not actually listening because all you’re trying to do is recall their name, give yourself permission to just ask the name. What she would say is don’t wait for divine intervention or for someone to come up and be like, Hey Susie, hi Tachi, hi, whatever. We just have to ask, when you just take that power again, assume the burden, give yourself the power to take that risk and ask for the name again. That’s better than not listening to what they’re saying because you’re trying to recall it.

So that is one public service announcement. It’s totally okay. A lot of people forget names, especially at events where we’re meeting so many people. So give yourself permission to just ask in case you’ve missed it.

Dear Extroverts, Take a Breath and Listen More

And finally, I wanna give some tips if you are an introvert versus an extrovert because we need to approach it maybe in a different way. So my message for the extra extroverts would be to make sure that you’re taking a breath while you’re listening. Extroverts can sometimes come on a little too strong, which can be offsetting or off-putting for introverts or people that are maybe new or less familiar with small talk. And so make sure to breathe. You don’t wanna feel like you’re pushing all the information at them. Give yourself permission to ask questions, to slow it down. When you can ask those open-ended questions, you’re actually giving yourself permission to take a break and focus on that individual.

Another message for extroverts is to avoid oversharing. Know that if we’re just starting out in small talk, we are developing trust. Trust is not necessarily established, but sometimes a mistake that extroverts can make is by sharing too much when the trust isn’t established. And finally, make sure that you don’t assume what another person is going to say. This can lead extroverts into interrupting or maybe minimalizing what someone says, making them feel that you weren’t listening to them and you didn’t really care what you had to say. Or sometimes they might get the perception that you’re a one-upper or you’re just trying to show how great you are. And finally, the last message for extroverts is to stick with the conversation. Extroverts likely have a very easy time going from one topic to the next, but for people that may not, again, have that same experience or desire, it’s best to stick with that conversation and deepen it and just ask a deeper level of questions as you progress.

Introverts Can Get Better at Small Talk Too

And now, let’s go into introverts. So what you can do to feel more confident with small talk and feel like you are actually getting the benefit from it is to start by preparing conversational questions. What are potential go-to questions that you could have in a social setting, in a professional work setting, at a networking event, or at a family event? Create a list for each of those and start to think of potential questions that you might ask, but make sure that you’re also checking your mindset and your attitude. If you feel that small talk is a waste of time and it’s pointless, the individual whom you’re engaging in a conversation with will likely perceive that to be true. And so they’ll be less open to actually talking and deepening a relationship with you. So make sure that you’re reframing your opportunities for small talk as, Hey, this is a great chance to get to know more about them.

We can see how we can partner together. Hey, this is a great chance to just, you know, see it. We have more in common than I ever realized. Choose the right mindset before going into the event. Otherwise, the individuals that you’re in conversation with will likely notice that you’re not that into the conversation. And just remember that curiosity is key as you think about those questions. Deepening it. Hey, what do you like to do for fun? And if they say, oh, I love playing volleyball, or I love playing football, you might say, oh, what do you like about those sports? Have you ever played those sports?

So deepen the conversation by being curious. And here’s a quick PSA. Be a little bit cautious when you use the conversational question, what do you do for work? You might run into a situation where someone might be unemployed or recently laid off or fired, and so you’re going to bring them into the pain of that situation.

So that’s one reason you might want to avoid that question. The second reason is you might want to avoid feelings of inferiority that can be created when you ask someone what they do. For example, if I am maybe a high-performing and successful business person and I’m talking to someone that maybe doesn’t have confidence in their career and what they do or feels a little less-than when I ask them what they do, then they might start to get into their head and feel like I’m not good enough to have this conversation. These people are way smarter than me. They are all of these things. So instead of asking the question, what do you do? You might say, what industry do you work in? What intrigues you about that industry?

Small Talk Only Works if You Also Listen

And now tips for the listener because that’s often the piece that we forget. We think about that initial approach of taking the risk and the conversation, assuming the burden of the conversation and what we can do to get our information to that other person in the conversation.

But what do you do when you are the listener? Well, be present. Make sure that you’re maintaining good eye contact, smile, and of course, be mindful of any cultural norms that exist in where you live. If you are in France, if you are in the UK, if you are in Morocco, these might have different cultural norms of what’s appropriate, but the non-verbal cues that you use are essential to the individual that is speaking because that lets them know that you’re in tune and connected with their message. And

Another tip for the listener, ask them a question. Always come up with a great follow-up question about the information that they shared. And you can also validate their responses. You can say, oh, what I heard you say is that you really enjoy volleyball and you love playing it with a team. Great, me too. And so just reiterating or what we would call mirroring, repeating back what someone had said to them to say, am I getting this right?

For Better Small Talk, Mind Your Body Language

And also, keep an open posture! Knowing that almost 60% of our communication is non-verbal, it’s very important to pay attention to the posture and those non-verbal cues that you’re using because sometimes it might show to someone that, again, you don’t care what they have to say. An example might be, and many of you likely have experienced this, think about if you’ve ever had a time when you were in a conversation with someone, and then they picked up their phone, or they looked at their watch to see what time it is. If I’m speaking and you do those things, I am going to assume that you don’t care what I have to say. Now, whether or not that’s true, that’s the information that I am getting from your nonverbal cues. So be very mindful of the information that you’re saying without words. Now, small talk tips, right?

Have a Go-To Conversation List

Think about your own conversation list. And this is more for building your own conversational list. I want you to just think about what are the topics that you feel comfortable with or you actually want to talk about. Maybe you have a particular hobby like making music or sewing or playing sports, whatever that might be. What are the topics that you feel comfortable with and actually want to talk about? Write down those topics. So then there are things that you can ask, and you can begin by just writing down a list of your interest. It might be sports books or podcasts, hobbies, TV shows or movies, whatever that might be. But if you can build a conversational list of the topics or general interests that you have, then you can use that to say, Hey, I’ve been listening to this podcast, the Leadership Habit, lately. What do you listen to for your own personal development? Are there any personal development topics that you think I should listen to? That’s how that might go.

Remember to Practice Good F.O.R.M.

Now, in Debra Fine’s book, the Fine Art Small Talk, she also gives an acronym of how to think about structuring or building that conversational list. And what she talks about is, are questions that you can ask typically follow the acronym of Form F O R M. The F in Form is about family. Hey, tell me about your family. Who’s your favorite member? Who’s, you know, how many children do you have? Are you married? Are you single? Now again, I would offer a pause to this, and that’s only from my own personal experience. I think it’s a great conversation. But no, there might be someone, just as I had an experience with an Uber driver where he shared with us that he actually doesn’t have any living family members left.

And so know that you might run into something like that. And that’s totally normal. That is the life of of some people, and we want to be mindful and sensitive to that. So if you do get a response like that, you can also say, I am so sorry to hear that. Um, you know, I, I like to ask this question because it’s typically what lights people up, but I can understand where maybe this isn’t the question that you would want to answer. It’s totally okay to switch directions.

The O in FORM stands for occupation. What industry are you in? How long have you worked in it? What industries have you ever worked in? You could even ask questions such as, what was the best job that you ever had? What was the worst job that you ever had? I can tell you my worst job was as a newspaper delivery girl, and I had a bike. And when I was delivering Sunday papers, that was extremely heavy and I would often tip over.

The R in FORM is for Recreation. What do you like to do outside of work? What do you like to do for fun? And then of course, miscellaneous, maybe something that supports the fam family, occupation, and recreation, or maybe something completely different. That goes back to one of the conversational topics that you previously identified. The M is for miscellaneous topics, which could be books, movies, trivia, what ever you like.

So just remember that, you know, when we’re thinking about small talk, whether you’re doing this at the holiday table or at a networking event, every single person is nervous to some extent. And why is that? Because we don’t wanna be judged. We want to be liked, and we want to be safe. And when we go into these small talk conversations, we can feel that this is really vulnerable. What if they think that what I say is stupid, or they don’t like me or they don’t like my vibe, whatever that might be? Know that all of us have a little bit of head trash that’s making small talk seem a little bit scarier over than what it actually is, so know that it’s nervous.

Keep Building Your Small Talk Muscles

But in closing, I want you to keep in mind how you can build that conversational muscle. So I want you to create and build your conversational checklist. Create three to five questions that might be your go-to, questions that you ask. And you can always, for advice, start a conversation with a statement or an observation. If you’re meeting at a networking event, for example, oh, I love these events. What’s your favorite event that you’ve ever attended? Or you could talk about the weather, but typically people don’t necessarily want to talk about the weather right now. So you could say the weather is perfect outside, but what’s your favorite season? Now, there’s one thing that I would actually add to this, and it kind of goes back to the what do you do for a living? Talking about the basic topics such as, oh, what’s the weather like by you aren’t necessarily responses that elicit you to or that prompt you to provide a high level of information.

Yeah, it’s sunny. Cool. We’re not really deepening the connection there. And so that’s where a question such as, the weather is perfect outside right now, but what’s your favorite season is actually going to allow for a deeper conversation. So be mindful of typical questions that you likely hate answering because you feel like you do it all the time. Those might be what do you do for a living? Where do you work? What’s the weather like?

Avoid some of those because many of us are asked those repeatedly and we have very scripted responses, which causes us to kind of go into autopilot in the conversation and not be as engaged. And finally, tips for work and business events. Of course, know your audience of what’s appropriate to talk about and inappropriate to talk about. Maintain great eye contact, and smile. And when you’re going to that event for the first time and thinking about where do you start?

Find the person that seems approachable. Look for body language. Are they open? Do they seem engaging? And make sure that you give your name and also ask theirs. Sometimes we just walk up and start a conversation without introducing ourselves.

Questions to Start a Conversation Anytime, Anywhere

And questions that you can ask at business and work events. How did you get started in your career? And know that these are partially from Debra Fine’s book The Fine Art of Small Talk. How did you get started in your career? What trends have you noticed in your field? What projects are you working on right now? What does a typical workday look like for you? What professional organizations or associations are you a member of? What books or podcasts have you read or listened to lately? If you’re going to a social event, you might ask, what’s the highlight of your week so far?

What’s your favorite movie? Why? What is something you own that you wish you had never purchased? Now, this is a question that I have asked multiple times, and it typically elicits a fun and playful response. It allows for us to be a little bit self-deprecating, which can actually build trust between the person we’re speaking with and us. So if I was to answer that question, I might say, as much as I hate saying this because I wish I used it more, it’s my road bike. It has been in my garage, hung up for about two years, and it is a constant reminder that I actually bought that, bought all of the coinciding and extra bike apparel to go with it, the shorts, the jersey, and I never used it. I should have just bought that or bought something else, and saved that money. But typically, many of you have examples of something that you own that you thought you had to have, and now you’re like, why did I buy that?

And I got this, this question from a different individual. And his example was a fancy watch that he bought that he thought he really needed, but now it’s just a reminder that he wasted a bunch of money on something that he doesn’t need. So it’s a fun, playful question. Another thing, what’s your favorite thing about where you live? Why? Cats or dogs? How do you know blank?

And general icebreakers. You could think, what’s one thing that you want to own and why? These might be questions that you can ask in a group setting to your team. Tell me about one of your favorite relatives. What do you think is the perfect age? Why? What’s your favorite holiday? What was the first car that you drove? Who were your idols as kids? One of my favorite questions is, what is your favorite karaoke song? And another quick question that I like to ask is, what was one activity that you really enjoyed doing in high school?

This allows us to get into our more childlike experience and it can allow us to learn more and just get a little bit deeper into the conversation without asking them to maybe explain their whole life story. When I asked this one of my favorite questions or one of my favorite responses that I totally was surprised by, because this individual was very tough and direct and he was a lovely person to work with. But when I asked him, what was your favorite activity in high school? He said, oh, I was part of the prom decorating committee. I was so surprised by his response and it just brought about a laugh by all of us because none of us that had known him and worked professionally with him would’ve ever guessed that that actually would’ve been an interest. So that’s my personal one that I love to ask.

How to End a Conversation

Now in closing, I just want you to think about how you can start a conversation. Where are these opportunities that you can practice? And maybe a goal for yourself is to choose three new people a week to just strike up a conversation. Remember, it doesn’t have to be long. It could be a conversation with someone as you’re checking out your groceries. And in closing, of course, we know just as things have to end, sometimes the conversation needs to end. So here are some conversation exit lines to end your conversations on a positive note. One, you might discuss feature plans. Hey, this was so great. Maybe we can get together again to talk more about this. Make a plan to connect later and create a time constraint. If you find that you add that you either need to go because of a natural time constraint, or you feel like maybe that individual brought up inappropriate subjects and you just want to make sure that you’re getting out of there, you can put a time constraint on it.

For example, I have to go, I have to go in a few minutes, but I would love to hear one more story or one more thing before I go. When we’re signaling to them that we’re unlimited time, then it makes it easier for us to say, okay, well I have to go. And then you can take your time away. And how do you know when to end a conversation? Well, it’s when you’re bored or they look bored or when you run out of things to say. That’s why it’s important to have that conversational list when you need a break. This is especially true for introverts, knowing that these conversations can typically drain your energy. Give yourself permission to take breaks, or if they brought up controversial or inappropriate topics, do not keep yourself hostage in a situation where it’s uncomfortable. Give yourself permission to say, hi, I actually have to step outside and you know, take this call or send this note.

And an another appropriate time to end a conversation is when they’re rude or judgmental. You do not need to engage in a conversation where someone is offensive, so please give yourself the power to be able to exit those strategies so you don’t have to tolerate what might be very inappropriate, rude, or controversial conversations. So thank you so much for joining our many. So this month I hope you got many tips that can help you in the coming month as maybe many of you are out to go to more holiday events or family events or work events. And just know that the art of conversation is the art of hearing as well as being heard. And you can make friends, more friends in two months by becoming interested in other people than you can in two years by trying to get other people interested in you.

So if you want to have a genuine conversation and actually deepen the connection, practice that curiosity. Be genuinely interested in someone else.

Have a Great December— We’ll See You in 2023!

Thank you so much for joining this week’s Minisode. We would love to see you next year. Feel free to check out our webinar. It’s January 26th, and we are gonna be talking about how to start the new year with a growth mindset. We have complimentary one-hour webinars offered every single month with the exception of December, and we would love to see you there.

And, of course, if you need help with your leadership development needs, head on over to We offer a complimentary leadership skills workshop where we will come into your organization, either in person or virtually, and help you and your team develop a strategy to collaborate better, to communicate better, and just to overall create a place where everyone wants to work. I hope you have a great rest of your year. I’ll see you in 2023. Bye, everyone!