Episode 25: Creating Meaningful Relationships and Eliminating Small Talk with Rachel Greenwald






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Brief summary of show:


This week on the podcast, I sit down with my go-to on all things relationships, Rachel Greenwald.

Rachel is one of the most successful matchmakers in the United States, responsible for 857 marriages in the past 20 years. She is the New York Times bestselling author of “Find a Husband After 35: Using What I Learned at Harvard Business School”.


Listen in as we talk about:

  • Rachel’s analogy of Penthouse people vs. basement people

  • How to decide which relationships you want to invest time and energy into

  • Tips to connect deeply with people virtually instead of in person

  • How to eliminate small talk and have more meaningful conversations


She has been featured widely in the media as a relationship expert, including The Today Show, CNN, The New York Times, Fortune Magazine, NPR, and many more. Her books have been translated into 18 languages worldwide, and have been optioned by Paramount Studios for a Hollywood film.

Rachel now uses the tactics she learned in the love business to help business leaders improve their professional relationships at work. She is currently doing an Executive Fellowship at Harvard Business School, and has conducted relationship coaching sessions at organizations like Google, Estee Lauder, Morgan Stanley, YPO groups, Stanford University and others.

She teaches two different workshops regularly at Canyon Ranch Spa in Tucson: one program is called “Relationships That Work” for executives, and the other program is called “Post-Divorce Bootcamp” for singles.




Resources mentioned in the episode


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Connect with Rachel Greenwald


Connect with Me





Podcast Highlights:


[00:03:56] Are you a penthouse or basement person?


[00:07:38] Tips to have more fulfilling relationships


[00:11:51] Meaningful ways to connect with people virtually


[00:17:33] Rachel's mission to eliminate small talk



Click Arrow to see Full Transcript of this Episode

[00:00:00] Natalie: I'm Natalie tysdal a journalist who decided enough is enough. I left a career that looked glamorous to do what I was scared of doing, going out on my own. I'm a married working mom of three on this podcast. We're going to talk about issues that really matter. Why am I not sleeping? What's up with that diet everyone's talking about. [00:00:19] Are my kids falling behind? How do I leave that job and start over? Welcome to the Natalie pistol podcast. I'm so glad you're here. [00:00:30] [00:00:30] We [00:00:30] Natalie: are all trying to find our normal again, back to life, back to [00:00:35] Rachel: school. [00:00:35] Natalie: And part of that is our relationships. Finding those, not be parts of our relationships and the fulfilling parts of those relations. Are you looking for more energy? If you're like me, the answer is always yes. Being a working mom. I do everything I can to eat healthy, get enough sleep, be more present for my kids. But you know, I've come to realize that I actually have to do even more. And I have found that taking electrolytes and immune building supplements that has helped me more than anything. [00:01:04] I put that electrolyte powder in my water every morning. It tastes like lemonade. It's really good. And doing this first thing in the morning, it helps me throughout the day. Now the line of products that I use is from seeking health. I've tested them, I believe in them. And I now recommend them to my listeners and viewers. [00:01:22] You can find a link in the show notes, or you can go to seeking help. Dot com that's their website and use the promo code, Natalie at checkout, you'll get a discount. I, by the way, we'll get a small cut, but this in no way will cost you any more. And you're supporting this show and my efforts to help people live healthier lives. [00:01:40] Again, it is seeking health.com. Use the promo code, Natalie. Joining me today for the podcast is New York times bestselling author matchmaker, dating coach, and executive fellow at Harvard business school. [00:01:53] Rachel Greenwald, Rachel, when it comes to relationships straight to you. [00:01:58] Rachel: Oh, it's so great to be here, Natalie. Thanks so much for inviting me. [00:02:02] Natalie: our relationships that have paid the price over the last year, in not having those, those special times face to face with people on a regular basis, it's really it's changed. [00:02:12] And that, I mean, our relationships with our friends, um, maybe with our coworkers, different groups that we were a part of. So I want to talk today about finding ways to help those relationships thrive. Again. What tips do you [00:02:27] Rachel: have for me? Well, I think there's a tendency to think that getting back to normal means going back to something that was really fantastic and perfect. [00:02:38] And of course we all know that our lives before COVID. Perfect and fantastic. And, and especially not every relationship was really great. So I think the first question is to ask what relationships do I want to reignite and which relationships do I want to shed from my life? Because we probably all fell into a routine where we went out with people. [00:03:06] Suggested Saturday night dinner and we didn't know how to say no. Or, you know, we participated in gatherings because we felt obligated to not because we wanted to. And so figuring out which relationships are really worth investing in is, the first step because, you know, I think we. Took up a lot of our energy and time with things that we didn't even like. [00:03:31] So it's not about getting back to what we used to do. It's about moving forward with the things we curate that we really want to reinvest in. [00:03:43] Natalie: So in a sense, it's, it's given us a chance to push the reset button to really look at what's important and to be. Time and energy into those relationships. [00:03:54] Rachel: Yeah, that's really well said. [00:03:56] I feel like in life, there are only two kinds of people and those two types of people in my language, I call penthouse people and basement people, penthouse people are the ones that elevate your mood. When you're with them, they raise up your mood and they make you feel. Elevated like you're in a penthouse and the other type of people, I call basement people. [00:04:23] Those are the people who deflate your mood and bring you down to the basement. And it's not that they are basement or penthouse people. They are basement or penthouse people to you personally because of your own psychology and your own childhood and your own insecurities. So this is a really important categorization that I use when I decide which relationships I want to spend more time, deepening and investing in. [00:04:53] And it's, it's really tricky to figure that out because. let me give you an example from the dating world. I have single clients who will say something to me. Like I want to date somebody who's really smart. I want someone with, you know, a graduate degree or someone who went to a top university because I really love to learn, and I have a strong education background. [00:05:15] But when I unpack their dating history, they have not been happy around really smart people because smart people have tended to make them feel insecure about their own intelligence. And you unravel the layers further and you realize maybe they had a parent who always. Put them down or, you know, their grades were never good enough for the parent or whatever their childhood dynamic was. [00:05:43] There was always a tension around, intelligence and needing to prove how smart you were. And so being in a relationship with someone who's really smart for this individual, maybe a basement person to them for these sort of hidden. Uh, dynamics from their childhood. And yet they seek something that makes them feel bad. [00:06:06] So identifying which people and which relationships in your life are penthouse people, penthouse relationships is really a great sorting tool to know where to invest your energy as you re-emerge back into, you know, quote unquote, normal life. And [00:06:24] Natalie: that's just fantastic. And it's, it's almost like if you're coming out of a conversation with someone or a meeting with maybe a board you're on or GTO at the school, but you leave there feeling drained, which we know the tasks can be difficult, but you're not energized by it. [00:06:41] You're drained by it. That might be something even an organization that you need to step away from and think of where your energy. [00:06:50] Rachel: Yes. I love that you pointed out it doesn't have to just be a person. It could be an organization that brings your mood down or elevates your mood. It could be, experiences. [00:07:00] It could be anything but tapping into your mood to figure it out. You know, you have so few, hours in the day. And how do you want to invest your time? Which relationships? it's so crucial to your happiness. [00:07:18] Natalie: Let's talk about fulfilling relationships, the best friend that you didn't get to spend a whole lot of time with. [00:07:23] You're finally getting back out you're meeting you're going on walks. Maybe you're meeting for a drink, whatever that is. you're the relationship expert. So getting the most out of that relationship with the best friend, maybe a coworker and making sure that they are fulfilling relationships. [00:07:38] Rachel: Yeah, so surely taps into some research that I've been doing. [00:07:43] as you mentioned in the introduction, I'm an executive fellow this year at Harvard business school and I've been doing. Some research on conversation and I've identified 13 bad conversation types. And these are dynamics in everyday conversation with people in your personal life or your professional life that I'm creating. [00:08:07] experiences where you're not really connecting with someone. So an example is a conversation type. I call the mirror and this is one of 13 types. And the mirror is basically, that whatever you say, somebody else has a similar story to repeat back to you. So for example, you know, you see. Uh, wow. I had a really bad, session with my boss today. [00:08:34] And the person you're talking to says, oh my gosh, me too. I had the worst conversation at work and here's what happened to me. And so they're almost like. Not listening to you in the conversation. They're just waiting for their turn politely until you stop speaking. So they can reflect on their own relatable experience. [00:08:54] So that dynamic can really deflate conversation energy and make it feel choppy and make it feel so that you know, it's superficial and the other person doesn't feel heard. And so when you are. Trying to reconnect with someone that you care about. You've decided that this is a penthouse person in your life, and you really want to get close to them again in, in real life. [00:09:17] And not just through a video platform, like talking to them on zoom, you really have to watch out for that mirror situation. And I'm sure you know, that when somebody brings up a topic, it's because it's important to them and we have a tendency and this isn't a bad thing, but you just have to be aware of the negative effects it has on the conversation. [00:09:40] We have a desire to relate to that person and to show that. I understand what you're saying, because I feel that way too. That's a natural human tendency, but it has a really negative conversation dynamic and so practicing good conversation hygiene, as I like to say. A really great, reminder that connecting with someone is within your control. [00:10:07] It's not just about FaceTime and, and being with them either in the video medium or in real life. But it's about understanding that. If they have a topic that they bring up, it's worth going into and asking more probing questions, you know, probing questions sound like really, that's so interesting or, wow. [00:10:32] Tell me more about that. Or, you know, what did you say next? Or what were you thinking when that happened? I'm so curious, you know, those are the language that. Really deepens the conversation. Yeah. [00:10:47] Natalie: That's the best advice I remember. I'm going to remember all of those things you just said early on in marriage advice. [00:10:54] I'm sure you've heard it many have, understand before being understood. So Understand what that person is going through or what they're trying to tell you before you feel like you need to make yourself understood. Um, and it's hard. It can be very hard to do that, especially if relationships, um, have suffered or struggled over the last year with remote and, uh, for a lot of people that, that kind of leads me into what I want to talk to you about next. [00:11:21] A lot of people aren't comfortable getting back out, you know, they've had a nice summer, or maybe they're slowly getting back out, but they've kind of found a comfort zone in just being home. Um, and there we're certainly seeing more online meetings. Across the board online conversations, we're doing it more often with our families, even on zoom or face time. [00:11:43] So let's talk about ways that you can connect with people virtually where you can have those relationships that aren't in person. [00:11:51] Rachel: Yeah. I think, figuring out how to optimize your virtual. Experiences with people is a great way to think about getting back out there, getting back out there. It doesn't have to mean face-to-face. [00:12:07] It could really just mean getting back to a deeper connection with people and it doesn't necessarily matter what the medium is. So. Probably about three or four emotional levers that I always try to help people think about when they're trying to deepen a relationship on, you know, for example, a zoom meeting or Microsoft teams or FaceTime, whatever the video platform is. [00:12:33] the first one is self disclosure. You know, I feel like small talk is the enemy of human connection and that's true, whether it's in real life or in a digital platform. And so if you can just avoid things like, um, you know, the small talk, like how are you? Good, thanks. How are you that kind of stuff? I feel like giving about maybe 30 seconds of thought prior to turning on the video platform about what is it I really want to share today with this person. [00:13:07] That's important to me, something that I care about and it can be tailored to whatever the relationship is. Yeah. That person, it doesn't, you know, if it's a work colleague, you don't have to share your deepest, darkest secret, but you know, so here's an example. let's say that you are, you know, meeting someone for the first time in a, in a zoom business setting and somebody gets on and says, how are you? [00:13:32] Well, Given some thought in advance to something about like, what do they really love doing yesterday? And you realize that it was cooking. You know, again, it doesn't have to be really deep. It could just be an activity that you love. So instead of saying, you know, I'm good. Thanks. You could say something like, oh, I'm great. [00:13:52] Because Wednesdays are always the day. Geode posts a new recipe on her blog and it was a mint pistachio soup today. I don't know if you know this about me, but I love to cook. So, you know, right there it's, it's basic, but it launches into some follow-up conversation about personal passions and ultimately that small self-disclosure is going to create some type of bonding. [00:14:18] Natalie: That is fabulous. And that little bit of thought before the conversation, especially virtually, and you could definitely use this as you just go out and have meetings or coffee or what the difference [00:14:31] Rachel: too. but I love that on the virtual side though, because it [00:14:34] Natalie: does give you more of a connection that is just harder to have when you're not in person. [00:14:40] Rachel: Yeah, it's really true. You have to give it a little more time and thought and intentionality, but the result is that, you know, you're just gonna make things so much more fulfilling when you're talking about something you really care about, instead of things like the weather or, you know, something Monday. [00:14:59] What [00:14:59] Natalie: we all tend to go to right away. So getting past that right away, uh, will lead to more fulfilling relationships across the board. Rachel, you're so fun to talk to. I always get so much out of our conversations and, um, I have two questions that I like to ask of guests. And, the first one is, Productivity and tools that you have your bestselling author, you have amazing retreats that people learn from which I want to ask you about quickly as well after this. [00:15:26] Rachel: but what [00:15:27] Natalie: we'll do you use in productivity that helps you in your success? [00:15:31] Rachel: Well, I have to admit to you, and I'm not proud of it, but it's so effective. I am very old school and I keep a paper calendar, and I want to explain why this is so productive because it's going to sound counter intuitive. But I feel like when you record, meetings or appointments or commitments in a digital calendar that. [00:15:55] It tends to feel like it's a bit removed psychologically and it's somewhere out in outer space. But when you are forced to write things down on a paper calendar, and you can physically open a calendar book and see. You know, much more, you know, physically how many things you're committing to. I feel like you're more inclined to put less on the calendar and therefore you're going to be more productive. [00:16:25] So for me, it's a visual, physical reminder not to overbook myself. And I don't know if it's because I'm in my mid fifties and I, you know, haven't used, um, digital calendar. Um, in my formative years, I'm more comfortable with it, certainly, but I do think it serves as a reminder that, you know, your life gets crowded. [00:16:49] And when there are only so many inches on the page to fill up, it's, it's a really good, trigger to not put too much on. You're right. [00:17:00] Natalie: People put things on your digital calendar for you. It just shows up often, but when you actually have to write it, you can feel that commitment, everything old is new. [00:17:09] Again, I'm hearing more and more people going back to traditional calendars. So it's really interesting that you say that I do both, which is probably too much of a time commitment, but I like to write it. And then I have my digital calendar too. That's probably dangerous. Um, okay. My second question what is your purpose? [00:17:25] And I know that's it. Question for the end of a podcast, but what is your purpose in life? When did you discover that purpose? [00:17:33] Rachel: You know, on a, on a very quick level. I think that I feel like I'm on a mission to eliminate small talk. So, you know, we touched on this earlier about small talk, um, being the enemy of human connection. [00:17:49] I feel like. What is zaps people's energy in relationships and socializing is the superficial reality of small talk. And it's so easily avoidable. So if I could, you know, eliminate small talk in the world, that would be my grand vision. But it's just to encourage people to go deep, faster and not get lazy and just default to the weather or, you know, another, uh, here, here's a quick example, which is if you don't have time, even 30 seconds to think of something before. [00:18:28] Bumping into somebody or meeting with somebody that you want to talk about strategically. Even if you just do this, this is a really tiny thing. But when you ask somebody, how are you instead of just those three words, how are you add a fourth word? How are you really. And even that one extra word just signals that I don't want to have a superficial conversation. [00:18:56] I really care how you are. And because most people don't use the word really at the end of that question, it's very different and it really creates such a different energy in a conversation and relationship with two people. So, Yeah, there are a lot of things I want to do in the world. And certainly, there are probably bigger missions that someone might have, but if I could just do that one little thing to do is to eliminate small tech. [00:19:23] I would be so happy. [00:19:24] Natalie: And you'll take people by surprise. When you say, how are you really? Or sometimes for me, it's was your family. You know, it just, it's the way that I re not saying it because I feel like I need to, but because I really care and I want you to know it. I want you to know right away when I see you that I'm not just saying that on the surface. [00:19:44] I really mean it. And how are you or how's the weather or any of those things? It's almost like we don't even hear the question it gets used. So calm. [00:19:52] Rachel: Yeah, exactly. It's, it's almost like a reflex, like a snake. [00:19:57] Natalie: Yeah. Great advice as always, Rachel, I love our conversations. Thank you so much. I got so much out of this podcast and I've taken notes. [00:20:05] I'm going to be sure they're all in the podcast notes. I do want to touch quickly on these retreats that you have. because I know I'll getting away for a weekend or just a short period of time can help push that reset button and help us all grow. Tell me about your. [00:20:20] Rachel: Yeah. Um, for the last couple of years, I've been doing two different types of retreats at canyon ranch spot in Tucson. [00:20:28] And, you know, not only is it just a beautiful setting there, and it's just an amazing resort experience. But these are specifically about relationships. And, the first one is called post divorce bootcamp, and it's for singles. any type of singles, you don't even have to be post divorced, you could be widowed or never married, but it's an opportunity to rejuvenate your love life. [00:20:51] And we have been doing it once in the fall and once in the spring. And there are, three days, uh, packed with all these different optional sessions to focus on the whole self, to figure out how your beliefs and attitudes about lots of things in your life, like nutrition and energy and exercise, feed into your quest to find the right partner in life. [00:21:15] And then I focus specifically on a lot of tactics on how to get there. Into dating, especially after you know, a certain age. it's really hard to meet people when all your friends are married. So we do a lot of great specific tactics about how to meet somebody and to meet the kind of people you're not normally meeting in your real life. [00:21:37] and then there's a second. One is called relationships at work and it's at the life enhancement center at canyon ranch, Tucson, where it's like a six day executive retreat for people of any age or stage in their life that just want to focus on improving their relationships, their relationships with themselves, their relationships with romantic partners, their relationships with friends and families and work colleagues. [00:22:02] And even relationships through a zoom window. So it's a really multi-faceted retreat and it's, it's really powerful. It's, it's one of these experiences that you leave really changed in how you think about, how you relate to all these different, components in your life that make you happy. [00:22:21] Natalie: I love that deep dive into those things. Well, thanks again again, I just love talking to you and getting your advice, and I'll be sure that I put a link to your website and that information in the show notes too. So hope to talk to you again soon. Thank you. Thanks so much, [00:22:36] Rachel: Natalie. [00:22:37] Natalie: Thank you for joining the Natalie Tisdale podcast, you can follow along on Instagram and@natalietisdel.com. Subscribe to the show to catch every new episode and leave a review so I can continue to bring you fresh content. See you next week. .


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