Career & Success

Listen, Listen, Listen: How to Build Deep Connections

Rachel Greenwald shares how to be a skilled conversationalist in work, love, and life.

May 09, 2023

Whether you’re trying to build a romantic or professional connection, Rachel Greenwald’s advice is exactly the same: “Focus on how you make someone feel more than you focus on the words that you’re saying.”

As a professional coach, Greenwald helps people develop better communication skills, from executives in the business world to singles in the dating world. Building deep connections may at times be challenging, but as Greenwald says, it’s ultimately not complicated. “You’re demonstrating that you’re interested in someone and that you like them,” she says.

In this episode of Think Fast, Talk Smart, Greenwald and host Matt Abrahams discuss relationship-building tactics like small talk, active listening, communication blindspots, and more.

Think Fast, Talk Smart is a podcast produced by Stanford Graduate School of Business. Each episode provides concrete, easy-to-implement tools and techniques to help you hone and enhance your communication skills.

Full Transcript

Matt Abrahams: Forming relationships can be very challenging, at work in our personal lives, in our romantic lives. Today, let’s learn some skills to help us. I’m Matt Abrahams and I teach Strategic Communication at Stanford Graduate School of Business. Welcome to Think Fast Talk Smart, the podcast. I am super excited today to speak with Rachel Greenwald. Rachel is an executive fellow at Harvard Business School and interestingly, a professional matchmaker and dating coach. She’s an expert on communication and relationship building in work, love, and life at Stanford University. She’s co-taught a seminar with past guest Tina Seelig at the d.School called Designing for Love. She also guest lectures with two of our other previous guests, Allison Wood Brooks, and Naomi Bagdonas. Welcome Rachel. Thanks for being here.

Rachel Greenwald: Hi Matt. I am so excited for our conversation today.

Matt Abrahams: 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. 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. If you’re on a first date and someone asks you a boring data collection question like, ‘what do you do?’ Always what everybody asks the first thing. So instead of just stating the 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. This notion of engaging and building intrigue applies not just in the dating world, but I think in all of our interactions when we talk at work about a project we’re on, rather than just giving the facts as you suggest, we could make it intriguing. We could share the potential value it brings. I really, really like that idea and it helps us as communicators reframe the whole purpose. Because, as you said, so many of us dread small talk, and if it becomes an opportunity to engage and intrigue someone that all of a sudden makes it much more interesting.

Rachel Greenwald: Yeah, absolutely. Just don’t try to collect data about the other person. Just try to think ‘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 away and instead think about simply making an observation about something in your environment. So an observation is essentially a bid for connection and it can create a feeling of instant familiarity, like sort of a conspiratorial vibe just between two people. So what’s an example? You could say to someone standing next to you at a networking event, you know, ‘Hey, that brownie over there on the buffet should have a big sign that comes with it that says, this requires 75 minutes on the Peloton.’ You know, 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 the ending is super important, also. I use in coaching both my date 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, like 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 makes someone feel like you were 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 can totally see how I could use that in conversation to say, if I need to go over there, I need to go do this, but before I do, I’d like to learn one more thing. I think that’s a wonderful technique and really reminding everybody of the recency effect that is how we feel at the end of an interaction really matters. So doing something at the end that’s positive I think is great, rather than that awkwardness that many of us feel where we just say, I need something more to drink and step away from the person. I really appreciate that advice and I have an upcoming social event for work and I’m going to use technique right away.

In terms of starting, I like that idea of finding some kind of common ground or common connection I can imagine in 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 trying to impress someone with your own stories or your credentials, you wanna 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’ve 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, I was reminded of my late mother-in-law was an expert at small talk and getting to know people. When she would come to visit, she would have to fly and the first half hour of our conversations when she would arrive would be about all the new friends she made on the flight over. And she 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. And her superpower was being able to ask the question, ‘Tell me more, I’d like to learn more. What more can you tell me about that?’ And she would use that all the time to really get conversations going and to signal that she was really interested.

I really appreciate what you said and, and I wish we would’ve known each other back when I was in grad school studying this, you would’ve helped me really hone in on the things I was interested in studying. You worked closely at times with some of our most popular previous guests, Alison Wood Brooks and Naomi Bagdonas, my interviews with them looked into humor. 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-filled and it really accomplishes the same goal, which is to lighten the mood. So for example, we talked earlier about finding observations in your environment that are unexpected or playful, and I think that’s a great starting point for light banter. Observations could be something like standing in a crowded room and you turn to the person next to you and you see something like, ‘I’m loving that woman’s sweater over there. It’s so Madonna circa in 1985.’ Or just something. It doesn’t have to be funny, it’s just sort of a light comment.

But as you bring up humor, I also want to caution people that there’s a dark side to using humor in conversations. Most people don’t think about humor in any negative way, but it really can be if it’s used incorrectly. So I conducted a one-year dating research project where I compiled a list of thirteen 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 eat 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 using 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 thirteen 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. 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 gonna 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 thirteen types that I found, you are doing yourself a disservice because you’re almost trying to impress the other person. 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 the meta message of what I heard you share, Rachel, is that we constantly have to be thinking about how we’re making our conversation partners, our coworkers, the people 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.

Before we end, I’d like to ask you the same three questions I ask everyone. Are you up for that, Rachel?

Rachel Greenwald: 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 gonna 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. Her work focuses on re-imagining how we spend our time together to create more meaning. 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. 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. 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. 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, 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: Ooh, I love that question. The first thing that comes to mind is the expression I’m gonna 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 gonna say the same is similar in communication, which is ‘listen, listen, listen.’ That is so important that it bears repeating three times.

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 what, 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 from Stanford Graduate School of Business. 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.

For media inquiries, visit the Newsroom.

Explore More