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Matt Abrahams
Hi Matt here. Do you want to learn how to present better in groups? Then you should check out our July newsletter. Go to our LinkedIn page, or you can sign up for our newsletter at Fastersmarter IO Resources. Check it out. You'll be glad you did. 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 in 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 F 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 Selig at the D School called Designing for Love. She also guest lectures with two of our other previous guests, Alison Wood Brooks and Naomi Bagdonis. Welcome Rachel. Thanks for being here.
Rachel Greenwald
Hi Matt, I am so excited for our conversation today.
Matt Abrahams
We spend about a third of our waking hours working, but so many people feel stuck in their jobs they've outgrown. I've heard it all. What if the next move is even worse? I can't afford to take the wrong step. Who am I without the title I have? These feelings are real, but they're also why so many people feel stuck. That's where today's sponsor, Strawberry Me, comes in. They connect you with a certified career coach who helps you go from where you are to where you actually want to be. It's like therapy for your career. A coach helps you cut through the noise, define your next move, and turn vague goals into a real world plan with accountability that keeps you moving forward. Own your future with a coach in your corner. Go to Strawberry Me Smart to claim your $50 credit and get started. That's Strawberry Me Smart. Stop settling. Start building the career you Actually want. 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?
Rachel Greenwald
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's. 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, boring data collection question, like, what do you do? Always what? Everybody asks the first thing. So instead of just stating the fact 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.
Matt Abrahams
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. If it becomes an opportunity to engage and intrigue someone, that all of a sudden makes it much more interesting.
Rachel Greenwald
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.
Matt Abrahams
Absolutely. Absolutely. 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?
Rachel Greenwald
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 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, 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. 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 lap 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 end, 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 an 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, just make someone feel like you are genuinely listening to them. And, oh, by the way, you admired something about them.
Matt Abrahams
When you first said white flag, I thought you meant surrendering, like, I'm giving up. But. But I. I do know auto racing, and I do know the white flag analogy. I really like that idea. I. 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 in 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 at 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, but when I was in grad school, I published 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?
Rachel Greenwald
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 that everyone's judging them. So you could 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 work 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.
Matt Abrahams
I really like that advice. And as I was listening to, I was reminded of my 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 had 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 in 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 Bagdonis. 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.
Rachel Greenwald
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 felt, 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 say something like, I'm loving that woman's sweater over there. It's so Madonna circa 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 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. If you 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 is exhausting because you're humor too much in your communication style.
Matt Abrahams
I find the first point you made to be really true. When we try to be funny, it just invokes 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?
Rachel Greenwald
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 say. 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.
Matt Abrahams
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 co workers, the people we're 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 continue our conversation, but first, a word from our sponsors. Their support and yours helps make our show possible. You know, I'm a big supporter of sharing your messages and connecting with others, but only when you want your information out in the world. If you've ever searched for your name or address in Google, it's shocking to find how many results have your personal information. And it's not by chance. Data brokers and people search sites and collect your personal information. Your name, address, phone number, financial information, and much more. They sell and share it publicly without your consent. Thankfully, Incogni is here to put an end to that. Incogni hunts down these unethical sites and gets your info removed from the places that expose your private information. You don't have to email anyone, fill out forms or jump through any hoops. They handle the entire process for you. I use Incogni to help me control what information about me is out in the world. And I invite you to try it too. Go to incogni.comtfa that's I N C O G N I.comtfa and use the code TFA at checkout to get an exclusive 60% off an annual Incogni plan. Before we end, I'd like to ask you the same three questions I ask everyone. Are you up for that, Rachel?
Rachel Greenwald
Yeah, I'd love it.
Matt Abrahams
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?
Rachel Greenwald
I would call 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.
Matt Abrahams
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?
Rachel Greenwald
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, but if people aren't primed to come in being receptive to you, it's just really a missed opportunity.
Matt Abrahams
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 Cialdini about what he calls pre suasion, how you actually get people in the right space for you then to make the influence request that you have. 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.
Rachel Greenwald
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 to set up future conversations for success by communicating in advance what she hopes to accomplish.
Matt Abrahams
Absolutely. Question number three. What are the first three ingredients that go into a successful communication recipe?
Rachel Greenwald
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.
Matt Abrahams
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 coworkers, potential romantic partners, and platonic friends. I appreciate your time. I appreciate your input. Thank you.
Rachel Greenwald
Oh, you're so welcome.
Matt Abrahams
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 Abrahams. Our music was provided by Floyd Wonder. For more information 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. I wanted to share with you that over the past few months I've had the amazing opportunity of talking to listeners across the globe about the impact the podcast has had on them. I love learning how people are applying the principles and concepts that we cover on the podcast and the impact that it has had on their lives. It is truly inspiring. Speaking on behalf of all of us that bring you the show, we thank you for your support. We look forward to bringing you new episodes, new techniques and deeper knowledge and we ask for your support. It takes time and effort to put this show on the air. Please keep your ideas coming and if you can, we'd love for you to join our premium. Thank you. And here's to another 200 episodes.
Release Date: July 22, 2025
Host: Matt Abrahams
Guest: Rachel Greenwald, Executive Fellow at Harvard Business School, Professional Matchmaker, and Dating Coach
In Episode 217 of Think Fast Talk Smart, host Matt Abrahams delves into the intricacies of building deep connections with Rachel Greenwald. Rachel brings a wealth of expertise from both the professional and dating worlds, offering actionable strategies to enhance interpersonal communication.
Small talk often serves as the gateway to meaningful relationships, yet it is frequently dreaded due to its superficial nature.
She advises against the mundane exchange of facts like “Where are you from?” or “What do you do?” Instead, she encourages making conversations intriguing to foster genuine interest.
Initiating small talk can be daunting, but Rachel provides practical methods to ease into conversations.
For example, commenting on the décor or a shared experience at an event can set a comfortable tone.
Concluding a conversation on a positive note ensures lasting good impressions.
This involves signaling the end of a conversation with a final question and a genuine compliment, enhancing the recency effect where the last interactions influence overall perception.
Rachel asserts that the fundamentals of effective communication are consistent across different relationship types.
This aligns with Maya Angelou’s wisdom:
“People will forget what you said, forget what you did, but never forget how you made them feel” (12:02).
Active listening is paramount in establishing meaningful connections.
She advises against merely hearing words, advocating for engaging with the speaker’s story and demonstrating genuine interest.
While humor can lighten conversations, it must be used thoughtfully to avoid creating barriers.
She warns against the “comedian” trap, where overuse of humor can prevent deeper connections:
“The comedian can use their humor like a shield” (16:31).
Recognizing detrimental communication behaviors is essential for fostering positive interactions.
These habits often stem from a desire to impress rather than to engage, ultimately leaving conversation partners feeling undervalued.
Rachel wraps up with key principles for successful communication:
Everyone Knows It But You:
“You have a communication blind spot, but you don't know what it is” (22:06). Seeking feedback is crucial for self-improvement.
Admiration for Priya Parker:
Rachel highlights Priya Parker’s concept of “pre-communicating” to set the tone for interactions, aligning with Robert Cialdini’s idea of “pre-suasion” (23:04; 25:29).
Communication Recipe – Listen, Listen, Listen:
Active listening is the cornerstone of effective communication, surpassing the importance of what is said (26:02).
Episode 217 offers a comprehensive exploration of building deep connections through strategic communication. Rachel Greenwald’s insights bridge the gap between professional and personal interactions, providing listeners with practical tools to enhance their relational dynamics. By focusing on genuine curiosity, active listening, and thoughtful engagement, individuals can transform small talk into meaningful conversations that leave lasting positive impressions.
Rachel Greenwald:
“Don't be a data collector. So what I mean by that is like asking, where are you from? What do you do. [...] boredom is the enemy of small talk” (05:42).
Rachel Greenwald:
“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” (05:42).
Rachel Greenwald:
“Active listening is about encouraging someone to elaborate” (26:02).
Rachel Greenwald:
“You have a communication blind spot, but you don't know what it is” (22:06).
This summary encapsulates the key discussions and insights from Episode 217 of Think Fast Talk Smart. For a deeper dive into effective communication techniques, listen to the full episode here.