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How to Listen Like You Mean It

For many of us, listening is simply something we do on autopilot. We hear just enough of what others say to get our work done, maintain friendships, and be polite with our neighbors. But we miss crucial opportunities to go deeper— to make connections that will endure for the long haul.

In this episode, researcher and author Ximena Vengoechea will share useful tools to self-assess your current listening habits and offer tried-and-true strategies to help you do better. Learn how to make simple adjustments that allow you to listen like you truly mean it, forge true connections that foster genuine relationships, grow your network and make advancements in your career and in life.


Ximena Vengoechea

Ximena Vengoechea

Ximena Vengoechea is a user researcher, writer, and illustrator. An experienced manager, she previously worked at Pinterest, LinkedIn, and Twitter. Her book Listen Like You Mean It: Reclaiming the Lost Art of True Connection tackles the timeless challenge of effective listening with veracity and offers practical concepts for work and real-life. The book has been named an Editor’s Choice from Porchlight Books and a Next Big Ideas Club Spring Nominee. Vengoechea is an experienced speaker and professional listener whose message resonates with companies and institutions across all industries. In her book and her lectures, Vengoechea outlines useful tools to help readers and audiences self-assess their current listening habits. Drawing from her own research sessions, as well as stories and interviews with marriage counselors, life coaches, filmmakers, podcast hosts, and other real-life listening experts, Vengoechea teaches audiences how to feel heard, connected, and understood in a world that keeps turning up the volume. Vengoechea has provided expert commentary on listening, workplace communication, and habit formation in publications such as The Washington Post, Good Housekeeping, The Muse, Fast Company, Inc., and Harvard Business Review. She also writes Letters from Ximena, a newsletter on tech, culture, career, and creativity and is known for her project The Life Audit.

Celeste Headlee

Celeste Headlee

Celeste Headlee is a communication and human nature expert, and an award-winning journalist. She is a professional speaker, and also the author of Speaking of Race: Why Everybody Needs to Talk About Racism—and How to Do ItDo NothingHeard Mentality, and We Need to Talk. In her twenty-year career in public radio, she has been the executive producer of On Second Thought at Georgia Public Radio, and anchored programs including Tell Me MoreTalk of the NationAll Things Considered, and Weekend Edition. She also served as cohost of the national morning news show The Takeaway from PRI and WNYC, and anchored presidential coverage in 2012 for PBS World Channel. Headlee’s TEDx talk sharing ten ways to have a better conversation has over twenty million total views to date. @CelesteHeadlee

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Photo credit: iStock/fizkes

Episode Transcript

Celeste Headlee:

So, looking at your resume, it leads me to the question of how you got involved in the subject in researching and working in the area of listening and conversation. How did that happen?

Ximena Vengoechea:

I certainly couldn’t have predicted it. I sort of fell into the role of user research, was not a role that I knew existed early in my career, but what really drew me to it was that it’s about meeting other people and getting to know their needs and motivations and perceptions. So, specifically, user researchers are part therapist, part coach, part detective, and it’s a role that exists within tech companies with the goal of understanding people in order to build better products. And so a lot of what I’m doing is having conversations with people about their lives and their routines, about their challenges and their needs, and figuring out ways that specific products could help make their lives just a little bit easier.

Celeste Headlee:

So how far did that research into conversation have to expand in order to include all of the other areas that you talk and write about, like making small talk with strangers you meet, relationships in your personal life, more in depth conversations? How did that your research change once you started expanding beyond that user research role?

Ximena Vengoechea:

Yeah. When you look at the topic of listening, it’s obviously much broader than just having a one-on-one conversation in a lab about a specific set of questions. So for me, a lot of that was realizing that some of the lessons that I had learned in that lab setting had begun to translate outside of it, and beginning to observe and talk to other folks about their experience as well. So just noticing, in a group setting or running a workshop or a meeting, what were some of the techniques that did and didn’t transfer over. Also speaking with therapists who are a different kind of professional listener, or people in radio, who also have a different kind of listening experience. And so I really started from what was the experience and the expertise that I had and was trained in, how did that apply to different setting, and then where might there be other expertise that could help round out my understanding?

Celeste Headlee:

Listening is hard, and I think a lot of people think that our technology that’s around us all the time makes listening really difficult, but listening has been tough for human beings for quite some time, even predating the smartphone. So how does one get better at it?

Ximena Vengoechea:

I think that’s right. I think there are many things contributing to our challenges with listening. Some of them are recent, but some of them are really, frankly, just very human. Some of the things get that in the way are us, our own needs: how hungry we are, how tired we are, our emotions, whether we’re frustrated about something in a conversation, whether we’re bored by a topic. And so when it comes to improving our listening, I think there are many things that you can do, but one of the most important things to know is that the more you know yourself and what you are bringing to the table, what you’re bringing to a given conversation, the more self aware you can be about your own listening habits in conversation, the better you are going to be as a listener, because it really is about noticing I’m losing focus, I’m getting distracted, or my emotions are really starting to get the better of me right now and I can no longer hear what the other person is saying.

Ximena Vengoechea:

Or one area that I think is really helpful for this is identifying what I call your default listening modes. So this is something that we’re all bringing into conversation. This is just our natural intuitive way of listening. We all have them. They’re usually informed by our early relationships and our personalities, and they can be useful in some conversations and maybe less useful in others. And so just to get concrete, an example would be someone who comes into conversation with a problem solving listening mindset. Beautiful mindset, great to have a problem solver, great for generating ideas, removing roadblocks, however, if I come into every conversation listening for problems to be solved, listening for what can I do to help in this situation, I may be wrong sometimes. I’m bound to be wrong sometimes, because my conversation partner may not actually need help. They may not need advice. They may want something totally different, like validation, a cheerleader, someone to say they’re doing a great job, not someone to say, “Here’s how you solve that.”

Ximena Vengoechea:

And so once you are in tune with these modes and all those other things that I was mentioning, it really helps to become a more effective listener for a given conversation.

Celeste Headlee:

So if I’m in a conversation and I realize I’ve gotten to a place where I’m finding it difficult, emotionally or cognitively, to continue listening, what do I do?

Ximena Vengoechea:

It’s a great question. Usually where I start is starting by noticing, and then, depending on how comfortable you are with the other person, finding a way to gracefully pause. So if you are really at what I would call over threshold, you are emotionally not in a place where you can listen, have a clearheaded conversation, a pause is probably what’s going to be most productive. Sometimes we feel like we should just power through. We don’t want to admit that we are emotionally activated. We think we can just push our feelings aside and get through to the other side, usually that backfires on us and it can make maybe a small disagreement into a large argument, for example, or just increase our chances of misunderstanding.

Ximena Vengoechea:

So usually I recommend pausing. And if you have the safety and trust within a relationship where you can be vulnerable and say, “Hey, you know what? I’m noticing that I’m having a really strong emotional reaction to what’s being said to this conversation. It’s really important to me, and I want to make sure that we have this conversation, but I’m actually not able to do that right now. Can we come back to this and set a time? Can we come back to this in five minutes? Can we come back to this tomorrow? Next week?” And then closing that loop that so the other person doesn’t feel like you’ve just dropped the line on them. If you are not in a relationship where there is that kind of trust or vulnerability, or you don’t feel like you have permission to excuse yourself from the conversation in that way, which I think can happen depending on the relationship, particularly in professional settings where maybe you don’t have that kind of intimacy, then I think finding other ways to pause the conversation.

Ximena Vengoechea:

One of the most reliable is just to say, “Hey, are you okay if we hit a quick pause here? I just need to take a bio break,” or, “I need to grab some water,” whatever it may be. Usually the other person is not going to say, “No, you cannot take this five minute break to go and take care of that.” So finding ways to either, again, upfront, being able to say it aloud, or if there’s not that trust and safety, finding other ways to pause, and then being able to take some deep breaths and return to center before returning to that conversation.

Celeste Headlee:

You know, Ximena, I talk about conversation a lot, and one of the most common type of question I get from people is how do I change someone else’s behavior? People are always asking me how do you stop someone from interrupting you, what if they never listen to you, what if they run on and on and on and on? We all have a difficulty in acknowledging how we get things wrong in conversation, so when you talk about taking a moment and recognizing that you’re in a bad place or recognizing that maybe you’ve got it wrong, that can be tough too. How do you get yourself in the proper mindset so that your first reaction is not defensive?

Ximena Vengoechea:

Well, I think one of the things that’s really important to bring into these conversations is what I call a listening mindset, and that is really about bringing three qualities in, and that’s humility, curiosity, and empathy. So humility is part of what protects us against taking a position of defensiveness. Humility is really coming into the conversation from the position of I’m here to learn. So I’m going to be the student, not the expert. My goal is not to convince or to win the argument, it’s to understand the other person, and that’s usually not our default position. A lot of us are coming in with our opinions, our preconceived notions, our assumptions. Some of us like to debate, that’s really exciting to us. But humility is really about saying, you know what, it’s actually not about me right now. I am here to understand the other person and where they’re coming from and what their experience is. So starting there, I think, is crucial. Then you layer in curiosity. So there’s often this idea that to connect with someone we have to be really interesting, tell a great story, be funny, be charming.

Ximena Vengoechea:

Really what helps us connect is to be curious, is to express interest in the other person, rather than focus on how we can be interesting to them. And so that’s asking open ended questions. It’s encouraging them to say more. You can literally say, “Oh, tell me more about that.” And you’re starting to get to know someone a bit better. And again, just as with humility, you’re shifting away from this conversation is about me or this moment is about me to it’s actually about the other person and what I can learn from them or about them. And then the third part of that listening mindset is empathy, and this is where we’re getting a little bit deeper to the level of emotions, so what is this person feeling in this experience? And I think often there’s a little bit of maybe confusion around empathy and the idea that, well, I can’t empathize with this person because I don’t know what they’re going through. For example, I’ve never been fired, so I don’t know how to respond to someone who is telling me about this big event.

Ximena Vengoechea:

But we all can empathize if we get beyond that context to the deeper emotion. So, okay, you’ve never been let go, but you’ve probably experienced some kind of loss in your life mixed with shock or surprise, possibly mixed with something like shame, and if you can get to that underlying feeling, that’s where that deeper understanding and, ultimately, connection comes through. And so when you can bring those three things into conversation and really do that with intention, because again, it’s not necessarily where most of us are starting from, intuitively, that’s really going to change the nature of the conversation that you’re having with someone, and ultimately help you build a better, stronger relationship with them.

Celeste Headlee:

So a better, stronger relationship, that’s maybe one of the benefits of doing all this, but what are the others? I mean, these are things that we’re doing in order to listen to other people really well. It can be difficult to stop talking and listening instead, so what’s the plus side, whether that be at work or in our personal relationships?

Ximena Vengoechea:

I mean the payoff is a lot of things run much, much smoother. So if you think about this in the workplace, if you have a better understanding of where your coworker is coming from, of what their need is, then you’re going to be able to work much more efficiently, and you’re going to be more strategically aligned quicker, and it’s just going to make working with them probably a little bit more pleasant. If I know that I am partnering with someone, there’s two ways that I can approach it. One is okay, they’re my partner on this project. We’re just going to divide and conquer. Fine, get the job done. But if I take the time to really understand, well, what are they trying to get out of this project, that might change how we, for example, divide up responsibilities.

Ximena Vengoechea:

Maybe I learned that they’d like to try a new skill. Okay, great. So what would that change about how we approach this project together? Or maybe I learned that their boss is breathing down their neck and they’re under a lot of pressure for this project. That is also going to change how I understand them and their behavior and how we collaborate. So anytime you can get to know somebody better and, again, get to that deeper level of the squishy stuff that a lot of us either don’t really want to go near or aren’t quite sure how to go near, it actually is going to make everything go faster. I think of it as sometimes you have to go slow to move fast. And listening, when it’s done well, it’s not fast. You have to take the time. However, if you take the time to really get to know that person and their context and their situation and their emotions, it does make everything else run smoother later on.

Celeste Headlee:

So, which of all the pieces of advice that you give, the tips, which of them have you personally struggled with the most? What’s the hardest?

Ximena Vengoechea:

Hmm. That’s a good question. I am a natural born interrupter. I am naturally impatient. I’m one of four girls, so I’m used to having to vie for attention and just throwing your voice out there. So that’s one that I’ve definitely had to learn to keep in check. And I’ve practiced a lot of what I preach in terms of doing that. Being aware of, for example, how much air time a group of people is getting. So, let’s say you’re in a meeting, making sure that I’m not the person who’s speaking, the most, being aware of passing the mic, and leaning into silence. I’m a talker, so that’s not my natural position. But recognizing that silence can be very rewarding. When you give people just a little bit of space, they tend to fill that space, in part because it’s uncomfortable to be quiet in conversation. We say, “Oh, there was an awkward silence, an awkward pause.” We call it awkward for a reason.

Ximena Vengoechea:

But also, giving that space allows people to finish their thought. Not everyone processes aloud. Not everyone is a smooth improviser. Not everyone likes speaking in a group. And so just giving a little bit of space and not rushing in to fill that space, those are one of the things that I practice myself, even if that’s just, okay, I’m going to count to 10 in my head, and by the time I hit 10 usually someone else has spoken. And so there are just really small things that you can do to, in my case or in many people’s cases, encourage ourselves to just lean back a little bit and see what happens.

Celeste Headlee:

So another thing that you advise, in terms of encouraging people to open up and continue with their stories, is asking the right questions, and I don’t think a lot of people put much thought into crafting the question, so what does that mean, the right question? It implies there’s a wrong type, right?

Ximena Vengoechea:

Yes. So what I would say is that many of us are asking leading questions or biased questions or questions that have a particular response baked in, and they’re usually narrower than we realize. So this is the opposite of asking an open ended question, which allows someone to take the reins and let us know where they want to go. And so what I usually recommend is to shift from these more closed ended questions to more open-ended questions. And what that sounds like is let’s say someone has a big presentation coming up. Instead of saying, “Hey, are you nervous about that big talk you’re giving,” which implies that maybe they have a reason to be nervous, and also really only suggests yes or no as the answer. Instead of asking something like that, you might just make it more open ended by saying, “Hey, how are you feeling about that presentation coming up?” Now we are giving them more room to say, “You know what? I’m really excited about it,” or, “I feel anxious, but I’m super prepared,” or, “I am really nervous and I don’t know what to do.”

Ximena Vengoechea:

And so one way of beginning to check your own questions is to see if you can shift them from beginning with “are”, so, “Are you nervous,” or “do”, or “is”, those tend to lead to yes or no responses. Shifting from that to how or what questions, which are much more open ended in nature. The other questions that I really like don’t even sound like questions, but function as questions because they are prompting the other person to respond, and those sound like saying things like, “What else?” You can use that in pretty much any conversation. “So, what else do you have on your mind? What else?,” or, “Tell me more about that,” or, “Say more.” One I particularly like is, “And that’s because…” And I dot, dot, dot. You add that ellipsis and you just wait for the other person to fill it in.

Ximena Vengoechea:

So if you feel that somebody is getting to a point and hasn’t fully expressed it, or is chewing on something and working their way through it as they process, when you can hear that there’s a little bit more to be said, you can just add these encouraging nudges that, again, don’t sound like questions but really are opening things up just a little bit more to help that person open up.

Celeste Headlee:

So how about conversations that have a very distinct purpose? And I’m specifically talking about networking and trying to start conversations when the whole point is to create new relationships with people, or sometimes the point of networking is to tell someone how great you are, what you’ve accomplished, really brag about yourself. Those people find very, very difficult. How does one navigate a conversation like that?

Ximena Vengoechea:

I think going back to one of the things that I was mentioning earlier of, especially in networking, there often is a lot of pressure to put your best foot forward, tell the best story, really present yourself in a way that does get at your resume highlights. Bang, bang, bang. You’ve got them all out there in two minutes or less. But going back to what I mentioned earlier of it’s in terms of making connections quickly. It is usually less about you than it is about the other person. So setting aside your perfect pitch, it’s great to have that, but setting it aside for a moment and seeing what you can learn about the person in front of you and getting really curious about them is going to make a more lasting impression than if you rattle off your resume. Also, if you make a true connection, you’re probably going to follow up on LinkedIn or somewhere digitally anyway, so your resume will be there if you need it.

Ximena Vengoechea:

But leading with your resume is usually not going to help you form a good connection. Really going back to asking questions and trying to understand this person as a person, as opposed to as a title, usually will lead to them wanting to know the same about you, and I think that’s really important. The other thing I would say about networking, this is true, I think, in every conversation, but especially relevant for networking, is recognizing that every conversation carries within it a need. We don’t usually think of conversations this way, but conversations, there’s a reason for them. There’s a reason that someone is venting to you or gossiping or giving an update. There is usually some underlying reason for it. There is a need. They need visibility, they need support, they need validation, whatever it may be. And so your job in a conversation is to understand what is that underlying need, and usually it is underlying. It’s not explicit. Sometimes it is, but usually it’s not.

Ximena Vengoechea:

And so when it comes to networking also thinking about, well, what might this person need out of this conversation, what might they be seeking from this event, what are they trying to get out of this, because maybe you can meet that need, and if you can’t meet it today maybe you can meet it in the future. And that is part of the give and take of beginning to build not just a connection, but also a network of folks who you can help and hopefully can help you in the future.

Celeste Headlee:

I mean, all of this advice that you’re giving is probably really going to help people learn from those they speak to in a way that perhaps they have not done in the past. And so many people are focused on telling what they know to others. But what about those times when you really need to be heard? How do you approach conversations when what you really need to say is someone is, “I don’t need advice. I just need to be heard. I just need a witness.”

Ximena Vengoechea:

Mm-hmm. I think the way you just put it is wonderful, and most of us don’t do that. So my advice here in terms of how we can be heard is to be much more explicit about our needs. So we often think that we have expressed a need clearly. So, for example, let’s say we say to our boss, “Oh, I have so much work on my plate.” For us, translation, that means please take something off our plate. But our manager hears that as she’s busy, but she’s handling it. That’s a totally different interpretation. If I were to say to that same manager, “I feel like I have a lot of work on my plate. I’m starting to feel overwhelmed. I’m worried about getting burnt out. Can you please help me prioritize this?,” or, “Can you please help me deprioritize a set of projects or change the scope,” or whatever it may be.

Ximena Vengoechea:

So being really much clearer about our needs, being willing to use emotion words when we’re expressing those needs, so saying things like, “I’m struggling with this. I’m feeling overwhelmed by…” “What I need from you is just to listen. I don’t need advice,” or, “What I’m looking for here is a thought partner. I need to brainstorm some solutions. What I’m not looking for is a venting session,” whatever that may be. So to the extent that you can clarify so the other person doesn’t have to do quite as much detective work of, okay, what might be needed here, that’s going to be really useful for having your own voice and your own needs heard and met.

Celeste Headlee:

So, I mean, this is all really, really good advice. I mean, not all conversations need to be deep. Some of them are just quick exchanges of information. And I read some really interesting research that shows people avoid getting into conversations, especially with strangers, because they don’t know how to end the conversations. They’re afraid they’ll get stuck in them forever. What is your advice to people on how to end a conversation? How do you walk away?

Ximena Vengoechea:

Yeah. No, that’s great. I’m picturing a vortex of getting stuck in a conversation. I would say a few things. Let’s say there is someone who you know, they are prone to talking a lot, maybe someone at the water cooler, it’s a neighbor, whoever it may be. You can set the stage ahead of time and literally say, “Oh it’s so great to see you. I’ve got two minutes to catch up, and then I’ve got to run,” or, “I have such and such appointment at two, so I’m all yours until then.” So you’re really clarifying up front, these are the guardrails of this conversation, so that when it comes it doesn’t have to be awkward, because you’ve already said it. The other thing is that I think sometimes we make the problem in our minds a little bit larger than it needs to be of like, “Oh this is going to be so awkward. I have to leave. They’re still talking. How do I get myself out of this?”

Ximena Vengoechea:

Maybe we think we have to concoct some excuse. “Oh, I just forgot. The cake is in the oven. The dog needs to be let out,” whatever it may be. It really doesn’t have to be that complicated. I think just saying, “It was so great to catch up with you. I really need to run now,” or, “I’m so glad I ran into you. Let’s pick this up again sometime soon.” So you don’t have to provide an excuse for why you need to leave. You can just say you need to leave and just acknowledge that you enjoyed the moment that you had together and now it’s time to move on. Usually people aren’t going to follow up with a set of questions of, “Well, where are you going? What are you doing?” Usually they’re pretty good about taking that cue and saying, “Oh great. I’m so glad we had a chance to catch up, too.”

Celeste Headlee:

So what have I not asked you that I should have asked you?

Ximena Vengoechea:

I mean, I think one thing that often comes up is around power dynamics in conversations, and how that can change how we approach them, or affect how we approach them. And usually one of the questions that comes up is, “How do I manage this if I’m trying to have a conversation with someone in a higher position than me, or vice versa?” And what I would say in that case is really just trying to do your best to level the playing field. So if you are someone who has to have, let’s say, a difficult conversation with a manager or an executive, someone who has more power than you at the company, just doing your best to humanize them as an individual. Stripping away the title and just approaching it as a human to human interaction, as opposed to a resume to resume interaction, can help.

Ximena Vengoechea:

If you’re on the other side doing the same, but I think specifically if you are the person who wields a bit more power in that context or setting being able to set the other person at ease either by acknowledging or by sharing something. So, for example, by saying, “When I was in your position, I had a lot of challenges with this also,” or, “I remember this being really difficult.” Something that shows that you’re human and just like them, and you have these challenges just like them. So finding ways to level out the playing field for those conversations.

Celeste Headlee:

Ximena, thank you so much. Really appreciate it.





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