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

0:02Conversations 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.

0:34She's here on campus at Stanford to co-teach a class with Professor Tina Seelig 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. You're welcome. Thanks for having me back. Excellent. Shall we get started? Let's do it. 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.

1:02The 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?

1:33Yeah, 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.

2:09So 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 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.

2:47You know, you don't meet those hosts every day. What I want you to do is find a bridge that is gonna take you from a basic small talk question like, "How are you?" to something that allows you to talk about being a podcast host. 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.

3:20The 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 that makes you unique is that you're gritty.

3:47You, 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.

4:27So 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 Dorie 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.

4:52I 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?

5:28Would you like a table?" Or she could hand you a menu and essentially say, "What looks good here tonight on the menu?" 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, 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.

6:02And 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 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.

6:45Of 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?" You might be able to think in advance, uh, well, I'm gonna 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.

7:16And 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 a interesting menu to your conversation partner about something to talk about right away. I really like the idea of delineating your authentic differences in your brand as circles that overlap in a Venn diagram.

7:55A 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.

8:20Thank you. Many of us struggle in conversation in general, but the real struggle is that first beginning part, that first 60 seconds. 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. You're exactly right, that 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.

8:47But 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.

9:19And 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 for what 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 gonna ask how he became interested in fly fishing, and maybe that's gonna lead to a story about how his dad taught him to fly fish, and it was bonding, and that opens up conversation about his family.

10:06So 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 medias res. And in medias res 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.

10:46In 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. I remember the phone call. I don't remember this. 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.

11:13Toilet shopping for your mom? What on earth is the backstory to that? And you just launched into, in medias res, 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. 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, to take the time to do some preparation.

11:48And 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.

12:11As 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. I wanna 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.

12:37Can you share some tips and tools to help us talk about topics that might be taboo? 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.

13:20But really to focus on the stories and emotions behind those topics. So for example, if we use the taboo topic of money, um, 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 wanna 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?"

14:08So 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 topics a vehicle for deeper connection.

14:58So 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, 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.

15:26And I love the idea of just soliciting stories from people that allow you then to have, again, deeper conversations. Really good advice. 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 our, your previous visit. Are you ready for these?

15:52Absolutely. 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? 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.

16:34I 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 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.

17:08But if their answer was something more like, "Well, actually, he brought out my insecure side," or, "No, no, she brought out my competitive side," that's when I know it didn't go well. 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.

17:36I really like that. I appreciate that question. Question number two, who's a communicator that you admire, and why? I've thought about this since the last time I was on the show, and I'm gonna 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 our dinner tonight.

18:26I 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.

19:00And I think this is a really underutilized feature on our phones because it's not only 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 8 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.

19:41So I think those two things, appreciation and emotional connection, are really what make her a superstar communicator. 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?

20:10The 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, 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."

20:54And that kind 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.

21:31The second ingredient I would say is a acronym I use all the time, which is 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.

22:13Not just showing the polished version of yourself, but really telling a story that's real and 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.

22:41All 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.

23:11Rachel, like all of our conversations, I learn 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 have, and how we can bring out the best in others and ourselves, really important. Thank you. Thanks for having me. It was a pleasure as always. 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.

23:41This episode was produced by Katherine Reed, Ryan Campos, and me, Matt Abrahams. Our music is from Floyd Wonder, 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.

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