Think Fast Talk Smart: Communication Techniques - 217. Rethinks: How to Build Deep Connections

Episode Date: July 22, 2025

How to be a skilled conversationalist in work, love, and life.Whether you’re trying to build a romantic or professional connection, Rachel Greenwald’s advice is exactly the same. “Focus on how you make someone feel more than you focus on the words that you're saying,” she says. As a professional coach, Greenwald helps people develop better communication skills, from executives in the business world to singles in the dating world. Building deep connections may at times be challenging, but as Greenwald says, it’s ultimately not complicated. “You're demonstrating that you're interested in someone and that you like them,” she says.In this episode of Think Fast, Talk Smart, Greenwald and host Matt Abrahams discuss relationship-building tactics like small talk, active listening, communication blindspots, and more.Episode Reference Links:Rachel Greenwald Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [e-mail] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedInChapters:(00:00) - Introduction (03:38) - Don’t Be a Data Collector (07:04) - How to Start and End Small Talk (11:51) - Romance vs. Work Communication (15:12) - The Role of Humor and Light Banter (17:58) - Conversation Pitfalls (22:12) - The Final Three Question (27:58) - Conclusion ********Thank you to our sponsors.  These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

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Their support allows us to bring you quality content free of charge. If you've ever thought, I know I can do more, but something's holding me back. You're not alone. Whether you're navigating career growth, seeking better balance, or wanting to communicate with more confidence, coaching can help you bridge the gap between intention and action. At strawberry.comme, you'll get matched with a professional coach who's trained to help you clarify your goals, build lasting confidence, and make intentional choices professionally and personally. This is not therapy. It's not consulting. It's a thought partnership designed to help you take action with more clarity and purpose. I strongly believe in the value of coaching. All of us can benefit from the help of a coach.

Visit strawberry.combe slash smart to get matched up with your coach today. That's strawberry. dot me slash smart and get 50% off your first coaching session. It's the most affordable time ever to see if coaching is right for you. Think about your closest friends, not the virtual online ones, but the people you see in your everyday real life. How did you meet? I bet at least one or more of your friends you first met through small talk. Through small talk, big things happen. Yet many of us dread these conversations. Today we're going to open up the vault and explore interpersonal communication and conversations that allow us to connect, learn, and grow.

With my guest, Rachel Greenwald. Rachel teaches us valuable, practical skills, like how to focus on being interested, not interesting, along with how to exit small talk gracefully. I invite you to enjoy this Think Fast, Talk Smart, Rethinks episode. Forming relationships can be very challenging. at work in our personal lives, in our romantic lives. Today, let's learn some skills to help us.

I'm Matt Abrahams, and I teach strategic communication at Stanford Graduate School of Business. Welcome to Think Fast, Talk Smart, the podcast. I am super excited today to speak with Rachel Greenwald. Rachel is an executive fellow at Harvard Business School, and interestingly, a professional matchmaker and dating. coach. She's an expert on communication and relationship building in work, love, and life. At Stanford University, she's co-taught a seminar with past guest Tina Selegg at the D-School called Designing for Love. She also guest lectures with two of our other previous guests,

Allison Woodbrooks and Naomi Bagdonus. Welcome, Rachel. Thanks for being here. Hi, Matt. I am so excited for our conversation today. I am too. Let's go ahead and jump right in. you help people build relationships in two very different arenas. You coach executives in the business world and you coach singles in the dating world. What have you learned about one of the most challenging aspects of relationship building, small talk, that applies to both worlds? And how do you make small talk feel more comfortable when meeting someone at work or on a date? One big thing that I've learned about creating successful small talk, both at work and on dates, is simply this. Don't be a data collector. So what I mean by that is like asking, where are you from, what do you do? How many siblings

do you have? That is all so boring to ask and boring to answer. Well, in all my research, I just really discovered again and again that boredom is the enemy of small talk. So many people default to those predictable data exchange topics. So no wonder everybody hates small talk or dreads it. So your goal instead should just try to be intriguing so that someone wants to lean in and get to know you. I always say that in the space between the expected and the unexpected lies intrigue. If you want to be intriguing, you have to ask better questions. and you have to give better answers when someone asks you a boring question. So I'll try to think of an example here.

Like if you're on a first date and someone asks you a boring data collection question like, what do you do? Always what everybody asks the first thing. So instead of just stating the facts like I'm an engineer, you could turn it into an intriguing guessing game that could sound something like, What do I do? Well, let me give you two clues and see if you can guess. I had to get a master's degree for it and it usually involves avocados. So that's a very unexpected answer, right? It's intriguing. And what I like best about it is that it immediately signals to the other person. This is not going to be your standard boring small talk exchange. It's going to be much more enjoyable and memorable. it's just a better conversation for both people. I want to know what kind of engineer uses avocados.

You've definitely got me intrigued. But this notion of engaging and building intrigue applies not just in the dating world, but I think in all of our interactions, when we talk at work about a project we're on, rather than just giving the facts, as you suggest, we could make it intriguing. We could share the potential value it brings. I really, really like that idea.

And it helps us as communicators reframe the whole. purpose. Because as you said, so many of us dread small talk. And if it becomes an opportunity to engage and intrigue someone, that all of a sudden makes it much more interesting. Yeah, absolutely. Just don't try to collect data about the other person. Just try to think that how would I like to spend these next few minutes myself? I'm sure the other person feels the same way. Let's try to make this fun and intriguing. Absolutely. Absolutely. When it comes When it comes to small talk, Rachel, in particular, I find it, and I know many people find, the initiation of the small talk and how you get out of the small talk, how you end it to be

really challenging. Can you share ways you coach people to start and end small talk? Sure, absolutely. The start and the ending are the toughest part. So if you're someone that struggles with initiating small talk, it's probably because you're worried about finding that intriguing question like we were just talking about. So if that's your obstacle, then I'd say just forget about asking a question entirely. Take that pressure away. And instead, think about simply making an observation about something in your environment. So an observation is essentially a bid for connection and it can create a feeling of instant familiarity, like sort of a conspiratorial vibe just between two people.

So what's an example? Like you could say to someone standing next to you at a networking event, you know, hey, that brownie over there on the buffet should have a big sign that comes with it that says, this requires 75 minutes on the Peloton. You have something, just any observation, it doesn't have to be funny, but just something about your mutual environment can create a space where the two of you can smile about something right in front of you before. launching into the business of getting to know each other.

So that's the beginning of the small talk exchange that I would suggest to make it easier. And that ending is super important also. I use actually in coaching both my daters and my executives at work, I use this technique that I call the white flag. And the white flag is something that people who know race car driving will probably recognize the white flag in a race car situation is where somebody stands at the finish line as the cars are going around and around, and the person with a white flag right before the last laugh of the race will throw down the white flag. And that says the race is almost over, but there's one more lap.

So for example, if you're at a function, a party, whatever, you could say to somebody towards the And as you're trying to wrap up your conversation, you could say, before I go get a drink, I have one last question because it was so great hearing about your trip to Alaska. I wonder if you have a favorite hike to recommend in Anchorage, just in case I get out there one day. So then you listen to what they recommend, their favorite hike. And then as you're walking away, you say something like, I really enjoy talking to you. And by the way, I love your shoes. So this is something that's important to remember that ending small talk is something in social psychology that is called the recency effect, where people will rate and experience more

positively if the last part of the experience is pleasant. So ending your conversation with this tactic like, I have one last question and then giving a compliment, a sincere compliment, of course, As you're walking away, it just makes someone feel like you were genuinely listening to them. And, oh, by the way, you admired something about them. When you first said white flag, I thought you meant surrendering. Like, I'm giving up. But I do know auto racing and I do know the white flag analogy. I really like that idea.

I can totally see how I could use that in conversation to say, I need to go over there. I need to go do this. But before I do, I'd like to learn one more thing. I think that's a wonderful technique. and really reminding everybody of the recency effect, that is how we feel at the end of an interaction really matters. So doing something at the end that's positive, I think is great, rather than that awkwardness that many of us feel

where we just say, I need something more to drink and step away from the person. I really appreciate that advice. And I have an upcoming social event for work, and I'm going to use that technique right away. In terms of starting, I like that idea of finding some kind of common ground or common connection.

I can imagine it a work function talking about a keynote speaker or a certain goal that was just discussed as a way of getting people to initiate that conversation and together be working towards getting the conversation moving. So very, very helpful. I took copious notes on what you just said and hope to put them into practice in the very near future. I know you and I talked about this once when we first met each other, Rachel. When I was in grad school, I published really.

research on flirtation and relationship initiation. This is a topic that really fascinated me then and still fascinates me now. And it was also really helpful because I met my wife while I was studying flirtation in grad school. Now, as a matchmaker, you help many people initiate and start relationships. What advice do you give daters about effective communication? And is there different advice you give people who are seeking romantic partners versus those who are looking for platonic and professional relationships. Matt, it is exactly the same advice in romantic or professional context. It's not different at all. And the advice is simply to focus on how you make someone feel more than you focus on the words that you're saying. So that's reminiscent of that Maya Angelou quote

where everyone knows this quote, I'm sure, but people will forget what you said. forget what you did, but never forget how you made them feel. So instead of, for example, trying to impress someone with your own stories or your credentials, you want to lean into their stories, their credentials, and make them feel smart or feel funny or even just feel accepted instead of judged, which is how most people walk around feeling every day is and everyone's judging them. So you can have comments like somebody tells you something and say something I don't know, like, wow, I never would have thought of doing that. How'd you come up with that idea?

So comments have to be genuine, though. Like, that's really important. You can't fake interest in someone. People can smell a fake a mile away. So try to have in your head this mantra that in every gathering, every person in this room has something to teach me. And then your interest and leaning into their stories will feel more genuine. You mentioned the word flirtation.

in your question and whether you use the word flirtation in a dating context or whether you label it something different in a word context like relationship initiation, it's basically the same thing. You're demonstrating that you're interested in someone and that you like them. And it's the universal truth that most people will like you if you like them first. I really like that advice. And as I was listening to, I was reminded of my late mother-in-law was an expert at small talk and getting to know people. When she would come to visit, she would have to fly. And the first half hour of our conversations when she would arrive would be about all the new friends she made

on the flight over. And she used what I heard one of the techniques you were talking about was genuine curiosity. She was very interested in people and really liked getting to know people. And you could feel that. And her superpower was being able to ask the question, Tell me more. I'd like to learn more. What more can you tell me about that? And she would use that all the time to really get conversations going and to signal that she was really interested. So I really appreciate what you said. And I wish we would have known each other back when I was in grad school studying this. You would have helped me really hone in on the things I was interested in studying. You work closely at times with some of our most popular previous guests, Alison Wood Brooks and Naomi

back Donus. My interviews with them looked into humor and I'm curious to get your take on using humor in conversations in our personal lives and our professional lives. To me, the word humor is always stressful and I think it is to a lot of people too because it feels daunting like there's this pressure to be funny. So I, and I don't think of myself as a funny person. So I try to rephrase that word humor and I coach people on specifically using. light banter in conversation, which to me just sounds much easier, less pressure-filled, and it really accomplishes the same goal, which is to lighten the mood. So, for example, we talked earlier about finding observations in your environment that are unexpected or playful,

and I think that's a great starting point for light banter. Observations could be something like standing in a crowded room and you turn to the person next to you and you said something like, I'm living that woman's sweater over there. It's so Madonna circa in 1985 or just something. It doesn't have to be funny. It's just sort of a light comment. But as you bring up humor, I also want to caution people that there's a dark side to using humor in conversations. Most people don't think about humor in any negative way, but it really can be if it's used incorrectly. So I, I, conducted a 10-year dating research project where I compiled a list of 13 bad conversation habits. And one of the bad habits I found, I called the comedian. And the comedian is someone in

conversation who gets a lot of laughs because they have jokes or they are self-deprecating. And at first, that's fun. But soon your conversation partner might crave a deeper connection than just all the laughs. And someone who's the comedian can use their humor like a shield. And your conversation partner can't penetrate that shield, which will feel frustrating to them. You sort of feel like, as the conversation partner, you're an audience, kept at a distance from the performer. And the comedian always reminds me of crashing after a sugar high, you'd feed too much chocolate. you might just suddenly afterwards feel tired or unsatisfied. And so you have to remember that the goal of communication is to create connection and make a

favorable impression. So obviously you don't want someone to feel like talking to you as exhausting because you're using humor too much in your communication style. I find the first point you made to be really true. When we try to be funny, it just invoked. so much stress. So I like your reframing of, hey, this is just light banter and that takes pressure off. And by taking pressure off, I think it frees us up to actually be funnier and more connecting. I am really curious to know. You said you found 13 bad conversation habits. Can you just share with us

two or three more beyond the comedian? Yeah, absolutely. One of the most common bad habits people have was something I called the mirror. And the mirror is the dynamic where whatever you say, the other person has a similar story to mirror back to you. Like, oh, wow, same thing happened to me, just waiting their turn politely until you stop speaking so they can reflect on their own relatable experience. And that's understandable because I think we're taught when you're younger or maybe even in some kind of sales training programs. They teach you that you're supposed to find a point of connection where you can relate to somebody. But actually, I find it to be the opposite. I find that the mirror habit can deflate conversational energy or make it feel choppy.

So the exchange can feel superficial and you don't feel heard. There's all sorts of other ones like the interrupter, somebody who's just interrupting you before you can finish your sentence and they try to finish your sentence for you. They're sure they already know what they're going to So they have that dirty four-letter word dynamic going on, the K-N-O-W, and the other person just feels annoyed. They don't feel heard. So all these conversation bad habits are really about the feeling you create in your conversation partner.

So whether you're trying to be the one-upper or you're the humble bragger or any of these 13 types that I found, you are doing yourself a disservice because. you're almost trying to impress the other person. Like I can understand why they're behaving the way they are. But the end result is that your conversation partner doesn't feel good talking to you. Thank you for sharing those. And as you were going through each of those bad communication behaviors, I saw in my mind's eye people who do those skills and how they make me feel.

And the meta message of what I heard you share, Rachel, is that we constantly have to be thinking about how we're making our conversation partners, our coworkers, the people were interested in dating, feel, and not so much focus on our particular goal in that moment, which is to share my story as soon as you share yours. And that is a wonderful reminder of what makes for effective communication, be focused on the needs of the person you're talking to. We'll be right back to finish our conversation.

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to help your business grow. That's UPWORK.com. Upwork.com. And now back to our conversation. Before we end, I'd like to ask you the same three questions I ask everyone. Are you up for that, Rachel? Yeah, I'd love it. Excellent. I'm excited to hear your answers. If you were to capture the best communication advice you've ever received as a five to seven word presentation slide title, what would it be? I would call it. I would call it. this slide title, everyone knows it but you. What I mean by that is that you have a communication blind spot, but you don't know what it is. Everyone else knows and you don't. So maybe you even have more than one blind spot, but people are terrible judges of their own communication skills. They either

overestimate or underestimate them. They have no idea how someone feels when talking to you. So You're the last to know unless you ask for feedback. So this advice is all about trying to get feedback, and it's true in dating and friendship and business anything. I didn't know where you were going to take your slide title, but I love the point that we have to seek out feedback. We are not the best observers of our own communication. So for question number two, who is a communicator that you admire and why?

For that question, I am going to pick. someone kind of out of the standard communication arena and point to someone named Priya Parker, who some of you may know, others may not. She's the author of a book that is one of my all-time favorites called The Art of Gathering. And her work focuses on reimagining how we spend our time together to create more meaning. So she's not specifically in the field of communication, But she talks a lot about setting the tone for a gathering before it even begins. And this is a point on the continuum of communication that I think doesn't get enough attention. And I call that point the pre-communicating point, which is the idea that communication actually begins in subtle ways, even before you're in the same space with someone.

And space could be in person or like you mentioned earlier, it could be a digital space like Zoom. and even email or text. So space is broadly defined. But Priya Parker advocates that it's important to set the tone before you interact with someone. So is your upcoming conversation or your meeting going to be fun or do you want it to be serious or is the emphasis on being productive, whatever it is? So if you think about all the communication that happens before a business meeting, like calendar invites or even the first few minutes in a Zoom window as people are logging on before the meeting begins, what if you created a clever title for the calendar invite? Or what if you played a theme song on Zoom for the first 60 seconds that reflects whatever your intended mood is for this meeting? I really like her because I think in the big picture, you can have the best communication skills on the planet.

it. But if people aren't primed to come in being receptive to you, it's just really a missed opportunity. I really like Priya's work. I've read the book. I've heard her speak. And this notion of setting the table, if you will, priming people is really important. We had a wonderful discussion with Robert Chaldini about what he calls pre-suation, how you actually get people in the right space for you then to make the influence requests that you have. We don't spend enough time, things. We don't spend enough time, thinking about the context for the communication that we're about to have. And highlighting Priya Parker's work reminds us that we need to do that. We are going back to social psychology again.

And if you think about the primacy effect, so the primacy effect is that people remember the first piece of information they encounter, and that is better than information presented later on. So pre-communication is difficult to master, but Priya Parker knows how this set up future conversations for success by communicating in advance what she hopes to accomplish. Absolutely. Question number three, what are the first three ingredients

that go into a successful communication recipe? Oh, I love that question. The first thing that comes to mind is the expression I'm going to steal from real estate. So in real estate, you probably know the advice for buying a valuable property is location, location, location. So I am going to say the same as similar in communication. which is listen, listen, listen.

That is so important that it bears repeating three times. So people, whether it's business or dating, they put so much emphasis in communication on what to say, but really successful communication is about active listening. And I use the word active intentionally because I don't mean just listening like stop talking or be quiet or let the other person speak, but actively listening means things like,

don't plan your next response. Don't be listening to what somebody's saying and secretly thinking about how you're going to respond. And active listening means ask follow-up questions instead of shifting the topic back to yourself. And probably most

of all, active listening is about encouraging someone to elaborate. I love those ingredients. You know, Rachel, I really thank you for taking time to be with us and give us very specific advice on how we can connect better with co-workers, potential romantic partners, and

platonic friends. I appreciate your time. I appreciate your input. Thank you. Oh, you're so welcome. Thanks for joining us for another episode of Think Fast, Talk Smart, The Podcast. This episode was produced by Jenny Luna, Ryan Campos, and me, Matt Abrams. Our music was provided by Floyd Wonder. For more and episodes, find us on YouTube or wherever you get your podcasts. Thank you. And please make sure to subscribe and follow us on LinkedIn. Before we wrap up, I just want to say thank you for listening. It really means a lot to hear how people all over the world are using these ideas in their own lives. It inspires me and the whole team that brings you this show. If you want more episodes and resources, feel free to follow, subscribe, and explore past conversations. We're grateful for your support of Think Fast.

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