331. Matchmaker Mindset: How to Make Yourself Memorable in Any Conversation

“Boredom is just the enemy of conversation.” Small talk doesn’t have to be boring. For matchmaker and dating coach Rachel Greenwald https://www.fastersmarter.io/guests/rachel-greenwald/, better conversations start with a little preparation and a willingness to move beyond predictable questions toward the stories that make people memorable. In this episode of Think Fast, Talk Smart https://www.fastersmarter.io/, Greenwald joins Matt Abrahams to share strategies for building stronger connections in dating, networking, and the workplace. From bridging small talk toward more meaningful topics to navigating taboo subjects and showing more vulnerability, she explains how to create conversations that bring out the best in others and ourselves. Takeaways: Better small talk starts with a little strategy. Preparing a few topics and finding natural bridges toward what makes you unique can turn routine exchanges into more memorable, meaningful interactions. Connection comes from stories, not just information. Asking questions that invite people to share experiences and emotions can reveal more than factual answers and help deepen relationships. Activity: Build a better bridge. Turn three standard small-talk questions into openings that lead somewhere more interesting. For example, instead of answering “How are you?” with “Good,” practice a response that naturally introduces a story, interest, or experience someone could ask you about. Printable Expanded Takeaways & Activities https://ae82bqismksvlodf.public.blob.vercel-storage.com/TFTS%20Rachel%20Greenwald-JFI7dn10akzoXHnbCBW4ZsIrIyLhKw.pdf To listen to the extended Deep Thinks version of this episode, please visit FasterSmarter.io/premium https://www.fastersmarter.io/premium/. Episode Reference Links: Rachel Greenwald https://www.fastersmarter.io/guests/rachel-greenwald/Ep.89 Listen, Listen, Listen: How to Build Deep Connections https://www.fastersmarter.io/89-listen-listen-listen-how-to-build-deep-connections/ Connect: Premium Signup >>>> Think Fast Talk Smart Premium https://www.fastersmarter.io/premium/Email Questions & Feedback >>> [email protected] Transcripts >>>Think Fast Talk Smart Website https://www.fastersmarter.io/331-matchmaker-mindset-how-to-make-yourself-memorable-in-any-conversation/Newsletter Signup + English Language Learning >>>FasterSmarter.io http://fastersmarter.io/Think Fast Talk Smart >>>LinkedIn https://www.linkedin.com/company/think-fast-talk-smart/,Instagram https://www.instagram.com/thinkfasttalksmart/, YouTube https://www.youtube.com/playlist?list=PL6caGRBUYZCmgDGM2RK6mxKB9jG_ccmm3Matt Abrahams >>>LinkedIn https://www.linkedin.com/in/maabrahams/ https://learning.fastersmarter.io/?redirect_from=podpageChapters: (00:00) - Introduction (00:50) - Strategic Small Talk (04:27) - Building Your Personal Brand (08:21) - Mastering the First 60 Seconds (10:54) - Starting in the Middle (12:17) - Navigating Taboo Topics (15:36) - The Final Three Questions (23:33) - 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. https://strawberry.me/quiz?isDirect=1&promotionCode=smart&utm_source=smart Get 50% off your first coaching session today at Strawberry.me/smart https://strawberry.me/quiz?isDirect=1&promotionCode=smart&utm_source=smart Join our Think Fast Talk Smart Learning Community and become the communicator you want to be. https://learning.fastersmarter.io/?redirect_from=podpage

Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.

• 0:00Matt Abrahams?

  Hi, Matt here. I wanted to remind you that for each episode, we provide English language learning support, where we share useful information to help you develop your English skills. Check out these English language learning and other resources along with our newsletter and deep dive videos at fastersmarter.io under Resources. And now, a word from our sponsors. Their support covers the cost of production, allowing us to bring you this episode free of charge.

• 0:28Matt Abrahams?

  The real value of coaching is what it helps you see and what it helps you do differently. I have been coached and I have coached others. And for me, the value is clarity. Seeing what you're doing well, where you're getting in your own way and what you can do differently. And if you're watching this, I'm guessing you're someone who wants to keep improving. That might mean communicating with more confidence, becoming a stronger leader or getting clearer about your next career move. Strawberry.me is like therapy for your career. They match you with a coach who fits your goals and gives you practical, personalized guidance you can actually use. It's all designed to make coaching more financially accessible. And because it's online, you can use it from anywhere in the world.

• 1:12Matt Abrahams?

  Visit strawberry.me/smart to get 50% off of your session and make sure you tell them Matt sent you.

• 1:23Matt Abrahams?

  Conversations can be brutal, but with a little preparation and bridging, you can have amazing communication. My name's Matt Abrahams and I teach strategic communication at Stanford Graduate School of Business. Welcome to Think Fast, Talk Smart, the Podcast. Today, I'm excited to have another conversation with my friend Rachel Greenwald. Rachel is an executive fellow at Harvard Business School and a professional matchmaker and dating coach. Rachel is an expert on communication and relationship building, not only in the dating arena, but also in the workplace. She's here on campus at Stanford to co-teach a class with Professor Tina Selig called Designing for Love. Welcome, Rachel. I am so glad you decided to revisit us and it's great to be in person this time. Thanks for being here.

• 2:06Speaker 01

  You're welcome. Thanks for having me back.

• 2:08Matt Abrahams?

  Excellent. Shall we get started?

• 2:10Speaker 01

  Let's do it.

• 2:10Matt Abrahams?

  All right. The last time you were here, we talked a lot about small talk and you gave very actionable, useful advice that I use to this day to start and to exit small talk. The white flag approach you taught was amazing. And I really quote you often with the point that small talk is about being interested and not interesting. And if any of you want to hear Rachel's advice on small talk, go back to episode 217. So if those were sort of the entry level, beginner level, small talk advice and tips, can you give us some advanced advice, black belt level, small talk tips to help us better communicate and help us avoid that dread we all feel?

• 2:53Speaker 01

  Yeah, everybody hates small talk because mostly it's so boring and awkward. So I think that moving up the scale to graduate level small talk advice is really about moving from playing defense to offense. So defense is more like coming up with good answers to basic small talk questions, which we talked about last time. But playing offense is more about being strategic with your small talk game to help your conversation partner learn something about you that might lead to a desired goal that you have. So this is really where your personal brand comes in, where I want you to find a bridge out of the initial stages of small talk

• 3:38Speaker 01

  that leads towards a topic that makes you unique and memorable. So here's an example. Maybe you're on a date or you're in a job interview. You want it to go well. So you think a little bit ahead of time, what is it that makes me unique from all the other dates that he's been on this week or all the other candidates he's interviewed this week? And in your case, Matt, maybe it's that being a podcast host is unique. You know, you don't meet those hosts every day. What I want you to do is find a bridge that is going to take you from a basic small talk question like, "How are you?" to something that allows you to talk about being a podcast host.

• 4:22Speaker 01

  So for example, if I say, "How are you?" You might say, "Oh, I'm actually doing great today. I just interviewed a really interesting guest on my podcast and she told me all about organic wine." And so now you've sort of bridged into this more interesting topic. The key, though, is that you have to have a plan going into these type of conversations because you can't expect to just come up with something like that on the spot. Think about if you're an athlete, you wouldn't just start exercising. You would do some stretching and warming up before the exercise. So all sorts of examples like this. For example, in a job interview, let's say one of the personal brand attributes

• 5:05Speaker 01

  that makes you unique is that you're gritty. You have a lot of grit. Maybe you walk into a job interviewer's office and he's got a photo of himself climbing a mountain behind him on the desk. And so you could do this bridge where you say, "Oh, I noticed that hiking photo over there. I'm curious where that hike is because actually I just climbed Kilimanjaro this year and it was so hard, but I did it." And so here, you're moving basic small talk into something that is strategic on your part, demonstrating your personal brand, that is grit in this case.

• 5:48Matt Abrahams?

  So what I really hear is it's about branding and bridging and how you connect those two. And what's required there is to be a little strategic and to think in advance about what are those things that make me unique? What advice do you have as we reflect on our personal brand? We've had Seth Godin and Dory Clark on the show and they've talked about personal brand as well. But as a matchmaker, I'm wondering if you have a specific way of thinking about brand that we could all benefit from?

• 6:13Speaker 01

  I do. I mean, I think the first thing to say about personal branding is that it gets a bad reputation as being manipulative or like you're bragging or showing off if you talk about something that makes you unique or special or memorable. So I think the first thing is you have to get that out of your head. That I think the better metaphor about personal branding is that it's almost like you're walking into a restaurant and the hostess is greeting you at the host stand. And she can either make basic small talk with you and say something like, "How are you? Would you like a table?" Or she could hand you a menu and essentially say, "What looks good here tonight on the menu?"

• 6:56Speaker 01

  So essentially, she's focusing the initial greeting on like the chef's specials and what are the signature items at the restaurant? Once you've got the right attitude about personal branding, the easiest shortcut to what is a personal brand is to come up with three traits or skills that makes you unique. Seth Godin talked about this in Purple Cow, about basically how to be unique and memorable. And I think you just come up with three things that feel authentic, but also unique. Kind of the Venn diagram of who you are, but what's unique about that? So maybe you're on a date, for example, and let's say your three personal brand traits

• 7:41Speaker 01

  are that you're adventurous. Maybe you once appeared on Shark Tank and you're from North Dakota. Being from North Dakota is not like being from New York or California. It's unique. So you will pick something that is part of that personal brand and find a bridge out of small talk into focusing on something that makes you memorable. Of course, you may not be the only one on Shark Tank. You're not the only one who's from North Dakota. You're not the only one who's adventurous. But you might be the Venn diagram of those three things. And that is a great place to start when somebody on a date might say to you, "What do you do?"

• 8:24Speaker 01

  You might be able to think in advance, "Well, I'm going to talk about being on Shark Tank because that's always good fodder for interesting conversation and the crazy things that happened that one time I was on TV." And so somebody says, "What do you do?" And you might start off by saying, "Well, I'm an entrepreneur, but I have to tell you, I've only had 15 minutes of fame. My company may not be doing very well right now, but once I was actually on Shark Tank and I have the craziest stories about Mr. Wonderful." So you brought up the topic and you've really served up an interesting menu to your conversation partner about something to talk about right away.

• 9:07Matt Abrahams?

  I really like the idea of delineating your authentic differences in your brand as circles that overlap in a Venn diagram. A lot of people say, "Just list out all the different things." But the physical representation and overlaps is what I think can be really interesting, because that is what makes you unique. There might be a lot of people who have tenacity and a lot of people who have deep knowledge in one area, but that overlap makes it unique. And I like that idea of helping us identify it that way. And then, thinking of yourself as a host or a hostess who has to focus that initial interaction, I really like that as well. Thank you. Many of us struggle in conversation in general, but the real struggle is that first beginning part, that first 60 seconds.

• 9:49Matt Abrahams?

  Do you have advice on how to maximize and set ourselves up to enjoy that beginning part? I feel like, once I get over that hump, it becomes much easier.

• 9:56Speaker 01

  You're exactly right. Those first 60 seconds are the worst. I think taking an improv class is always great, because that helps teach you to roll with any situation. But beyond that, there are two other things that I coach my dating clients on. So the first thing I tell people to ease that first minute is topic prep. So to think about in advance, again, you're like an athlete stretching and warming up for the exercises. Topic prep involves just taking a minute or two before you walk into a conversation. You're maybe going to a business networking event, or on a date, or a job interview, or even catching up with a friend.

• 10:40Speaker 01

  And you pause and think of three things that you're curious to ask in advance. So if it's a stranger you're meeting, you can Google them, or find their Instagram, or look for clues in some messages you've had so far they might be interested in. But for example, let's say you looked at their Instagram in advance of somebody you're meeting on a date, and you saw that this guy had a photo of himself fly fishing. So maybe that's one of your three topics that you've prepped in advance, and you are going to ask how he became interested in fly fishing. And maybe that's going to lead to a story about how his dad taught him to fly fish,

• 11:22Speaker 01

  and it was bonding, and that opens up conversation about his family. So I think being prepared is super important. There's another really interesting trick that works especially well in almost every situation, and it is a Latin phrase called "in media race." And "in media race" means literally "in the middle of things." So this is where you start a story in the middle. If you've ever seen a TV show where they start with a robbery in progress, and then the show cuts to a phrase on the screen that says "three days earlier," and it hooks the listener to show what led up to that moment.

• 12:06Speaker 01

  In conversation, starting a story in the middle is something that you actually did the last time you and I had a phone call. I don't know if you remember this.

• 12:15Matt Abrahams?

  I remember the phone call, I don't remember this.

• 12:17Speaker 01

  As soon as we got on the phone, I said to you something like, "Thanks for accommodating my schedule to talk on a Saturday." And you said, "There I was, toilet shopping with my mom, when the reminder for our meeting popped up on my phone." And so I was immediately hooked. Toilet shopping for your mom? What on earth is the backstory to that? And you just launched into "in media race," in the middle of a story, something that was unexpected and intriguing, and it really just helped us get over very quickly those awkward first 60 seconds of small talk.

• 12:54Matt Abrahams?

  I'm glad I demonstrated that. Let's just say it was an explosive situation that needed to be fixed, and we took care of it. Again, the advice is to do some preparation, even though conversations are spontaneous, to take the time to do some preparation. That reconnaissance, reflection, and research on the person or people you're interacting with can be really helpful. And the goal is not to script out the communication, but it's really to find the opening for further conversation, is what I heard you say. And that, to me, is a very different way of approaching. So it's not just, "What do I say to start it?" It's, "What do I say to open up the conversation?" And I like the idea of starting in the middle. As somebody who teaches people how to give presentations, that's definitely a technique that can be used, and I like that you apply it to conversation.

• 13:38Matt Abrahams?

  I want to talk about how we did prepare for this interview on that phone call on that Saturday. You and I had a conversation about handling taboo topics, things like money, religion, sex. You have some really useful ideas about how to discuss these types of topics, which turn out to be really important as we develop deeper relationships with people. Can you share some tips and tools to help us talk about topics that might be taboo?

• 14:03Speaker 01

  People tend to avoid taboo topics because they're fearful of controversy or having awkward moments. But I would invite people, as they move away from small talk and start to grow and deepen a relationship with somebody, to reframe taboo topics as really a gateway to deepen connections. For example, what that looks like is not focusing on the facts of the taboo topic, not, "What do you think about it? Are you in favor of it or against it?" Those are facts about a taboo topic like money, sex, or religion. But really to focus on the stories and emotions behind those topics.

• 14:45Speaker 01

  So, for example, if we use the taboo topic of money, it's always somewhat awkward to talk about money for most people. So let's say you've been dating somebody for a few weeks or months, and you want to start assessing if your values align on an important topic like money. So instead of asking a factual-based question like, "Do you consider yourself frugal with your money, or do you spend lavishly?" You might ask a question that evokes a story, like, "What did your parents teach you about money when you were growing up?" Or you might ask a question like, "What's the first thing you bought with your own money, and why was that important?"

• 15:29Speaker 01

  So here you're getting at the why of what they feel, and not a factual black or white answer in terms of whether they align with what you think about the topic. So even though money is one of these topics that people argue a lot about in marriages, what's important is how you argue, not what you're arguing about, and not whether you're on the same page, but how you resolve conflict when it arises. Taboo topics and using those to get into storytelling about how someone's belief system was shaped, especially at a young age, is really this kind of gateway to making taboo

• 16:14Speaker 01

  topics a vehicle for deeper connection.

• 16:18Matt Abrahams?

  So several things there that I really like, that talking about topics that can be challenging actually deepen the relationship. And a great way to do it is through asking questions designed for people to explain why. Tell stories. Help me understand how you came to this, rather than what it is you believe. We had Wendy De La Rosa on, and we talked a lot about money, and she had similar advice, that talking about money in her case, but in all these topics, it's really an act of demonstrating care and concern, and that's what deepens those relationships. And I love the idea of just soliciting stories from people that allow you then to have, again, deeper conversations. Really good advice. We'll be right back to finish our conversation. But first, we're going to take a quick break for a word from our sponsors.

• 17:01Matt Abrahams?

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• 17:44Matt Abrahams?

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• 18:03Matt Abrahams?

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• 18:48Matt Abrahams?

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• 19:08Matt Abrahams?

  Well, Rachel, you've been here before. You know that before we end, I ask everybody three questions. One, I make up just for you, and two, I've been asking people for a long time. And feel free to repeat what you've said before or come up with different answers from your previous visit. You ready for these?

• 19:23Speaker 01

  Absolutely.

• 19:24Matt Abrahams?

  Excellent. As a matchmaker, your clients go out on dates every night all over the world, and the date outcome entirely hinges on them having a good or bad conversation. How do you evaluate a successful or unsuccessful date when you're not there yourself and you're just listening in to what they tell you? How do you assess a good conversation?

• 19:47Speaker 01

  Oh, I love that question. The truth is, I have one simple question that I reflect back to them, and I ask them, what side of you did they bring out? So what I'm not asking is information-based questions. I am not asking, did you like them? Or what information did you learn about them? Or was there a spark? You know, those are typical questions that your friends might ask you when you get back from a date. I'm asking, what side of you did they bring out to help me determine if this was a good or bad date? So if their

• 20:28Speaker 01

  answer is something like, he brought out my playful side, or maybe she brought out my confident side, then I know it was a successful date. But if their answer was something more like, well, actually, he brought out my insecure side, or, no, she brought out my competitive side, that's when I know it didn't go well.

• 20:52Matt Abrahams?

  I really like that question for assessing conversation, not just on dates, but in general. You know, what part of yourself showed up or was able to be shown off in the conversation? And I think we can all do that ourselves. We don't need to just go to somebody who's an expert like you and think about that. I really like that. I appreciate that question. Question number two, who's a communicator that you admire, and why?

• 21:15Speaker 01

  I've thought about this since the last time I was on the show, and I'm going to tell you about a personal friend of mine named Katrina. And the reason I admire her so much is that she always makes me feel good when I talk to her. And she does two specific things that always make me feel good. First of all, she has a signature expression that she uses all the time. And the expression is, it's not lost on me. So she'll say something like, it's not lost on me that you have an early morning tomorrow and you didn't cancel

• 21:56Speaker 01

  our dinner tonight. I really appreciate that you came out and spent this time with me. So she's just finding a way to show appreciation. And it makes me feel so good, especially when it's something so minor. You know, it's not lost on her that I didn't cancel our date. Like, that's a pretty low bar, but here she is feeling so appreciative. So I think that expression is something that everybody should use more of. And then the second thing she does is she leaves a lot of voice notes for me instead of texting me. And I think this is a really underutilized feature on our phones, because it's not only

• 22:40Speaker 01

  unique from everybody else that's texting you, but it's more personal, and it creates an emotional connection when I hear her voice. And so I would say eight out of 10 times that I communicate with her is her leaving me a voice note. Now, I also appreciate that it's not as intrusive as a phone call, because that would be her interrupting something else I'm doing. But you know, the voice note is just that beautiful, happy medium where I get personal and emotional connection with her, but it's on my own time when I listen to it. So I think those two things, appreciation and emotional connection, are really what make her a superstar communicator.

• 23:20Matt Abrahams?

  I'll start by saying it's not lost on me that you spent a little time thinking about this deeply, and I appreciate that. And taking the time to express appreciation and finding a unique way to connect with somebody where your true voice, in the case of a voice memo, comes out, I appreciate that. Well, the final question, Rachel, what are the first three ingredients that go into a successful communication recipe?

• 23:42Speaker 01

  The first ingredient is mood. I think not enough people think about how they make someone feel when they're talking to them. And so the idea here is that if somebody says something to you like, I love to ski, you might respond by saying something like, me too, if you're the mirror, or you might respond by saying something factual, a question like, where's your favorite place to ski? That would be a very legitimate response. But a mood-based response to somebody who says they like to ski is more like saying to them, tell me the last time you went skiing and you really loved the day. And that kind

• 24:27Speaker 01

  of evokes a time for them when they felt good. And you're invoking a positive memory by asking a question that is focused on them telling a story. It's promoting connection, and it's not garnering information, but really creating a moment between the two of you where they're affiliating the positive mood they are calling up from their memory with almost like conflating it with you, because you're the one that's experiencing that with them. The second ingredient, I would say, is an acronym I use all the time, which is

• 25:08Speaker 01

  DBB, Don't Be Boring. I think not enough people use DBB, Don't Be Boring, as a lens to filter their conversation. And if you can start to remember that every time you go to answer a question in a conversation, first do a quick check, is this boring? And if it is, come up with something more interesting, because boredom is just the enemy of conversation. And last, I guess the ingredient I would say is probably vulnerability, not just showing the polished version of yourself, but really telling a story that's real and

• 25:51Speaker 01

  humble, maybe self-deprecating. You could talk about a challenge you're having. You could talk about an embarrassing moment. You could talk about a regret. And it's not about bringing the mood down or being negative, but really just being aware that the polished version of you, where everything's great and you're amazing, is a lost opportunity for connection.

• 26:13Matt Abrahams?

  All of your three ingredients have to do with connection. I really like the idea of setting the mood through the things you ask and the interaction you have. And that mood does transfer from, if I'm having a good time telling you a story, I'm having a good time with you. And this notion of, as you begin to respond in a conversation, you have choices of what to say. Choose the option that's less boring. And then finally, being vulnerable, being authentic, really powerful. Rachel, like all of our conversations, I learned so much from you. I really appreciate it. This notion of thinking first and planning before we go into conversation, considering how we bridge into the topics we want to

• 26:56Matt Abrahams?

  have, and how we can bring out the best in others and ourselves, really important. Thank you.

• 27:01Speaker 01

  Thanks for having me. It was a pleasure, as always.

• 27:05Matt Abrahams?

  Thank you for joining us for another episode of Think Fast, Talk Smart, the podcast. To learn more from Rachel Greenwald, please listen to episode 217. This episode was produced by Catherine Reed, Ryan Campos, and me, Matt Abrahams. Our music is from Floyd Wunder, with special thanks to Podium Podcast Company. Please find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Also, follow us on LinkedIn, TikTok, and Instagram. And check out fastersmarter.io for deep dive videos, English language learning content, and our newsletter. Please consider joining our Think Fast, Talk Smart learning community at fastersmarter.io/learning. You'll find video lessons, learning quests,

• 27:45Matt Abrahams?

  discussion boards, an AI coach, and book club opportunities. Again, that's fastersmarter.io/learning to become part of our learning community.

• 27:56Matt Abrahams?

  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, Talk Smart.