222. Discussing Through Discomfort: Why the Conversations You Avoid Cost You the Most

Some conversations are uncomfortable, but avoiding them comes with a cost. You want a more successful career, a more fulfilling relationship, a more meaningful life? What if all that’s standing in your way — are the conversations that you’re avoiding? “Most things that we want in life are on the other side of a difficult conversation,” says Jenn Wynn https://www.fastersmarter.io/guests/jenn-wynn/, a professor at NYU Stern School of Business and previously the director of education at the Obama Foundation. For nearly 10 years, she has taught a course on difficult conversations that equips people to communicate through discomfort in pursuit of what they want. “Sometimes it's a difficult conversation with a loved one, a colleague, a boss… sometimes it's a difficult conversation with myself,” she says. “Are you going to give up on your biggest dreams because you weren't willing to step out of your comfort zone?” In this episode of Think Fast, Talk Smart https://www.fastersmarter.io/, Wynn and host Matt Abrahams discuss how to build the “hard but worth-it skills” necessary for difficult communication. Whether it's asking for a raise, setting boundaries, or addressing conflict, Wynn’s insights show that the conversations you’re avoiding aren’t just holding you back — they’re keeping you from the life you really want. To listen to the extended Deep Thinks version of this episode, please visit FasterSmarter.io/premium https://www.fastersmarter.io/premium/. Episode Reference Links: Jenn Wynn https://www.fastersmarter.io/guests/jenn-wynn/The H. I. Note: Healing Inspirations from Life https://thehinotepodcast.buzzsprout.com/2270299/episodesEp.22 Under Pressure: How to Communicate Clearly and Timely During a Crisis https://www.fastersmarter.io/22-under-pressure-how-to-communicate-clearly-and-timely-during-a-crisis/ Connect: Premium Signup >>>> Think Fast Talk Smart Premium https://www.fastersmarter.io/premium/Email Questions & Feedback >>> [email protected] Transcripts >>>Think Fast Talk Smart Website https://www.fastersmarter.io/222-discussing-through-discomfort-why-the-conversations-you-avoid-cost-you-the-most/Newsletter Signup + English Language Learning >>>FasterSmarter.io http://fastersmarter.io/Think Fast Talk Smart >>>LinkedIn https://www.linkedin.com/company/think-fast-talk-smart/,Instagram https://www.instagram.com/thinkfasttalksmart/, YouTube https://www.youtube.com/playlist?list=PL6caGRBUYZCmgDGM2RK6mxKB9jG_ccmm3Matt Abrahams >>>LinkedIn https://www.linkedin.com/in/maabrahams/ Chapters: (00:00) - Introduction (00:52) - Understanding Difficult Conversations (03:09) - Developing Emotional Intelligence (04:09) - Self-Awareness, Pause, Reframe (06:24) - Common Communication Barriers (08:20) - Listening for Understanding (10:57) - Using AI for Communication (12:49) - Creating Psychological Safety (15:25) - The Final Three Questions (20:39) - Conclusion ******** Thank you to our sponsors. These partnerships support the ongoing production of the podcast, allowing us to bring it to you at no cost. Learn more about how Notion https://www.notion.com/?utm_source=podcasts&utm_medium=thinkfast can support your business at notion.com/thinkfast. https://www.notion.com/?utm_source=podcasts&utm_medium=thinkfast Join our Think Fast Talk Smart Learning Community and become the communicator you want to be. https://learning.fastersmarter.io/?redirect_from=podpage

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

• 0:00Matt Abrahams?

  In the moment, conflict is difficult for everyone. In our October newsletter, out now, you will learn ways to help yourself handle these challenges better. Not only do you get specific advice, we're also providing an infographic to help you remember. Find our newsletter on the Think Fast, Talk Smart LinkedIn page or at fastersmarter.io under Resources. Often, the things we really want are on the other side of a difficult conversation. 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 really looking forward to speaking with Jennifer Nguyen.

• 0:41Matt Abrahams?

  Jen is a professor at NYU Stern School of Business, where she's taught a class on difficult conversations for nearly 10 years. Previously, she was the Director of Education at the Obama Foundation. Additionally, Jen hosts the High Note Podcast and runs a consultancy focused on organizational transformation, change leadership, and repair. Welcome, Jen. I'm really excited for our conversation. Thanks for being here.

• 1:05Speaker 01

  Thanks for having me, Matt. I'm excited to be here with you and the listeners, which include my executive MBA students.

• 1:11Matt Abrahams?

  Yes, absolutely. Well, shall we get started?

• 1:13Speaker 01

  Yes.

• 1:14Matt Abrahams?

  So you teach a course on difficult conversations, and I'm curious, what makes conversations so difficult? Is it the topic, the emotions, the circumstances? Where's the difficulty come from?

• 1:24Speaker 01

  I want to say all of the above, but at the core, it's the emotions. It's the emotional reactivity. So a quick way to think about this, in my first class of the difficult conversations course that I teach, I ask folks to call out topics that are difficult for them to discuss. And while they're calling it out, I'm typing the list into the slide deck. And we very quickly, not only fill the page with topics, but then you come to see that what's really difficult for one person is not that difficult for someone else. And in fact, some people enjoy it. So a topic like negotiations will terrify someone. I don't want to negotiate my salary, or getting a promotion, or negotiating fees with a client.

• 2:07Speaker 01

  And someone else will say, oh, I love a good negot- Let me take your negotiation on for you. Or saying no when a team member or direct report wants extra resources, or a loved one asks you for help and you've got to say no. And it's so interesting because not only are people really unique, even idiosyncratic, it shows you that what makes a conversation difficult is much less the topic and much more the inner experience that each person is having. And so effective communicators, effective leaders, know that they've got to be self-aware of that inner experience that they're having in the moment. When I say inner experience, I mean what you're thinking and feeling, but not saying out loud.

• 2:51Speaker 01

  And what that makes you realize is if I can be aware in the moment that I'm triggered, then I can pause, I can re-center, I can regulate my nervous system, and that way I'll be able to choose a better response. And I say to my students, your nervous system goes with you into every single difficult conversation. So if you can pause and regulate your nervous system, then you're going to be a better version of yourself at the time when you most need to be the best version of yourself. So the implication of all of that is self-awareness and emotional intelligence are essential for leading difficult conversations to productive outcomes.

• 3:31Matt Abrahams?

  So we really have to reflect on our own experience before we can actually be present and engage in the conversation. And I think the point you made about difficult conversations aren't the same for everyone. And in fact, we need to appreciate that. So it's really appreciating your own experience and the emotions you're feeling and finding a way to get yourself grounded and be centered and prepared before you go in.

• 3:56Speaker 01

  Yes, and open to hearing and understanding the other person's inner experience. Because if I happen to be the one who loves negotiations, but I'm sitting across from the person who's terrified by negotiations, I need to have the emotional intelligence to be aware of their inner state and help them manage that. And at the end of the day, the goal is for all members of the dialogue to move away from emotional reactivity towards choice.

• 4:23Speaker 01

  I want to choose the better, more strategic path, not the reaction that came out of an emotional trigger. It's more choicefulness.

• 4:31Matt Abrahams?

  So it sounds to me like one of the key elements, or a couple of the key elements of managing difficult conversations first starts with self-awareness, being other-aware, and accepting, doesn't mean agreeing, but accepting. And it sounds almost like there's an invitation involved, where you're inviting the other person to share their inner experience so that you can meet them and then ultimately make choices in a choiceful way. Are there particular strategies or tactics people can use to help bring out that information in someone?

• 5:06Speaker 01

  Yes. So we'll start with that self-awareness piece, since it is the foundation. I tell my students, if you only remember one framework from this entire course, please remember self-awareness, pause, reframe. Okay, self-awareness, pause, reframe. So what does that mean? In the moment, am I aware of my physical cues, my cognitive and emotional cues that let me know, I'm triggered, I'm heated up in this moment, right? So for me, I get a lump in my throat or like a tightness in my chest. Some people get butterflies in their stomach. I'm curious, what is it for you, Matt?

• 5:42Matt Abrahams?

  So I resonate totally with a tight chest. When I'm ready for battle or feel like battle's coming, my whole chest gets tight.

• 5:48Speaker 01

  Yes. So each one of us think in advance, what's my tell sign, right? And once I know that, the moment I see it, I know, I've got to pause. And then here's the best thing. If I know my pause techniques, if I know what helps me metabolize my hormones, get that adrenaline out of my system, really regulate my nervous system, then I can be back to my center self. So a go-to pause technique for me is to imagine myself with my best friend Carla. Then I'm at ease, I'm centered. And that is our goal, that we lead these conversations to a productive outcome, both for the content, the matter at hand, and for the relationship. So that last step, reframe, is where I actually shift away

• 6:32Speaker 01

  from viewing this conversation as a threat to something I care about, and instead perceiving it as a learning opportunity. What good information can I get out of this? So self-awareness, pause, reframe is a framework I always ask my students to remember.

• 6:46Matt Abrahams?

  I really like the taking the time to check in with yourself. Both how am I feeling emotionally but physically? And use the physical as a trigger to help you. Pausing is wonderful. I love that you rely on a friend. I have a place I go to in my mind. There is a particular tree in Sydney, Australia, that faces the Opera House and the Harbour Bridge. And when I get worked up, if I just envision that and what I felt like when I saw it, it's my place of zen. That really helps calm me down. And then this notion of reframing from one of threat to one of learning, one of collaboration, one of imitation. One of my colleagues, Michelle Delphin, likes to say, mind your metaphors. And the metaphor you bring to the interaction helps determine how it's going to be. So if I see it as a learning opportunity,

• 7:30Matt Abrahams?

  this difficult conversation is going to go very differently than if I see it as a battle. So I really appreciate that. Share with us some of the other tips you have, especially if there are particular barriers that get in the way to doing this.

• 7:41Speaker 01

  Some of the most common barriers I see are not having the conversation at all. I'd say a second one, not having a goal. And a third, I'd say, not listening enough. Often when we don't have the conversation, it's because we assume it will go poorly. So we give up before we've even started. But here's the thing. Most things that we want in life are on the other side of a difficult conversation. Sometimes it's a difficult conversation with myself. Sometimes it's a difficult conversation with a loved one, a colleague, a boss. But a lot of those things that we really want and we've been longing for and haven't gotten yet are going to require us to get to the other side of a difficult conversation. So are you just going to give up on your biggest dreams in life because you weren't willing to take the time

• 8:26Speaker 01

  to step out of your comfort zone and practice a skill? Because that's the thing. You know this, Matt. Communication is a set of skills, learnable, growable skills. And difficult communication is a set of hard but worth it skills.

• 8:42Matt Abrahams?

  It is important to remember that these difficult conversations are one of many conversations that we will likely have with these people or in this environment. So we're not only trying to come to a mutually agreed to resolution in the short term for this situation, but we're setting ourselves up for the future and the next one. You mentioned listening, and that's a skill that my wife is still encouraging me to work on. I'm curious, how do you help your students to be better listeners in these difficult conversations?

• 9:11Speaker 01

  Yes. So, sometimes the issue is not listening enough, and sometimes it's not showing that we are listening. So, those are two distinct skill sets. At the end of the day, I think about dialogue as the free flow of meaning. And so, if I've done it well, effective dialogue grows the shared pool of understanding between us. I understand how you made meaning of a situation, and you understand how I made meaning of a situation. So, that means that I've got to inquire, I've got to ask enough questions to understand how you experienced that, that client meeting, that argument my husband and I may have had. And then, once I've listened, internalized the meaning you made, I've got to paraphrase

• 9:55Speaker 01

  it back as a check for my understanding. A real humble attempt to say, "This is my summary of what I think you experienced, but is that right? Fix what I'm missing. Is it half-right, and I miss the other half?" And, once we can paraphrase, this is a skill that honestly, I think it's like punching above its weight. Right? After I've taken all this time to really ask these open thoughtful questions, get curious, understand your perspective, make sure you show the person that you are internalizing what they said. And like you said, it's not agreeing, it's just acknowledging. And when they finally say, "Yes, that's it," then you've grown the shared pool of understanding, at least from their perspective, and then you can go share yours. And that's where you move into advocacy.

• 10:40Speaker 01

  But, at the end of the day, the balance you're looking for is inquiry, paraphrasing, and advocacy. And inquiry and paraphrasing are listening skills, both to understand what the other person experienced, and confirm with them that my understanding was correct of their experience. And the advocacy skill is the talking one, right? That's essentially a two-thirds, one-third ratio. And I don't mean it as an exact science, but I did have a student say to me one time, "Oh, so that's why my parents said you have two ears and one mouth for a reason." A lot more listening and confirming that I understood you correctly from your perspective before I dive into sharing mine.

• 11:19Matt Abrahams?

  I like your definition of listening as seeking shared understanding. And when you take that approach, it definitely puts you in a place of being present, of being humble, because you're checking, maybe I didn't get it right, in leveraging what I think is one of the most powerful communication skills, which is paraphrasing, because it does so much for us. I really appreciate that approach. I'd like to turn our conversation to a different topic. I know you are likely getting similar questions to me with artificial intelligence, AI, coming into things. How do you envision that AI could actually help us with some of these tricky communication situations?

• 11:59Speaker 01

  Yes, I have seen several of my students find some really great uses for AI. So I'll give some examples. Sometimes I have a student who wants to work on their tone. They've received feedback that their tone is getting in the way of their message being received. And so they'll type in what they want to say and say, make that tone more friendly, or make that tone more respectful, and get a sense for what some other language, some other word choice might be to help them still deliver an authentic message, but in a way that can be heard. So that's one interesting way. I think another is coming up with perspectives that I haven't considered, right? Here's the problem I'm dealing with. What other perspectives could there be? Or here's my take.

• 12:44Speaker 01

  And then recently, I had a student really enjoy the role plays that we did in class, but not have someone back in her apartment to role play with. And she actually asked ChatGPT to role play with her, which I thought was such a cool idea. And I just think at the end of the day, we have to keep in mind that this is one perspective based on Whatever data this particular LLM has been trained on and not take it as the final word, but just more options.

• 13:11Matt Abrahams?

  Practice for these situations can be so important, as with any communication, and using a tool to do that. And I really like this idea of having a tool help you see what other wording can affect tone in a way that you might not see. I like that a lot. Like me, you host a podcast, one that I enjoy very much. I'm curious to learn how you balance your inquiry to challenge your guests without turning your interviews into challenging conversations. In other words, how do you put your audience at ease enough to have the deep, meaningful conversations that you have?

• 13:43Speaker 01

  So on the High Note podcast, we're talking about how people healed from some really tough stuff. You know, childhood trauma, loss of loved ones, disease, goodness, toxic relationships, you name it. And so before I ask them to share about some of the toughest moments in their lives, I start by surprising them with three things that I love about them. And so this is not in the agenda that I send them ahead of time, but when we sit down to chat, I let them know three elements of who they are that I absolutely love. And it's amazing to see how not only pleasantly surprised they are, which is just a nice

• 14:27Speaker 01

  moment of pure joy and connection, but also to see how, once they feel seen as a whole person and in a strengths-based and affirming way, they become more generous in what they share. And the conversations go deeper, and I learn such amazing insights because they've really let down any walls or any pretense and just shared from the heart. And it's been a beautiful gift to see how powerful asset-based framing is, and I've brought that over into my classes. So for difficult conversations and for the other courses I teach, in the very beginning, in the first session, I'll ask folks to gather up in trios

• 15:09Speaker 01

  and do an exercise that I call "At Your Best." And so they'll share in trios times they were at their best. During a difficult conversation and then the feedback that they give one another is strengths based. So this action that you took had a tremendously positive impact. Do that again. Or wow, I'm really impressed how you shifted your mindset right there in the middle of being triggered and now I'm going to go do that as well. And students say that they not only feel seen after that exercise, but that the classroom environment is more psychologically safe and enables them to be more brave in the rest of the course.

• 15:47Matt Abrahams?

  I love that as an opening activity. I'm going to borrow it if you don't mind to have people think about in my course, a time where they were able to communicate strategically in a way that was successful and then to get that positive affirmation. I really like this idea of leading with connection. You sharing the three things that you really appreciate about the person is a way of connecting and saying, I see you, I know you, and I respect you. And that opens up the door to perhaps more challenging or deeper conversations. Thank you for that. We'll be right back to finish our conversation. But first, we're going to take a quick break for a word from our sponsors. Their support covers the cost of production so we can bring you this show for free. This podcast is sponsored by Squarespace.

• 16:32Matt Abrahams?

  The best communicators don't just get their message across, they make it easy for people to know what to do next. Your website can do the same thing. With Squarespace, you can build a polished online presence that clearly shows people who you are, what you offer, and how they can work with you. If you offer coaching, consulting, classes, or other services, Squarespace lets you showcase those offerings, take payments, and use Acuity Scheduling so people can book time with you directly. And with built-in analytics, you can see how people are finding and engaging with your site, helping you make smarter decisions about where to focus. So your online presence doesn't just look professional, it helps people take action. Go to Squarespace.com/thinkfast for a free trial.

• 17:16Matt Abrahams?

  And when you're ready to launch, use offer code THINKFAST to save 10% off your first purchase of a website or domain. Hi, Matt here. Sometimes the biggest obstacle to getting something done isn't the idea, the plan, or even the budget. It's finding the right person to help you execute. And the longer that takes, the easier it is to lose momentum. That's where today's sponsor, Upwork, can help. Upwork gives businesses fast access to highly skilled freelance professionals across areas like marketing, design, software development, AI, and business operations. And with Business Plus, you can access the top 1% of talent on Upwork. AI-powered shortlisting gives you a curated list of freelancers matched to your goals in under six hours.

• 18:01Matt Abrahams?

  So you can spend less time searching for the right person and more time actually moving the work forward. Visit upwork.com right now and post your job for free. That's upwork.com to connect with top talent ready to help your business grow. That's U.P.W.O.R.K. dot com. Upwork.com.

• 18:22Matt Abrahams?

  Well, as you know, as someone who listens to the podcast, I end every episode with three questions. One, I make up just for you, and two, I ask everybody. Are you ready for that?

• 18:30Speaker 01

  I think so.

• 18:31Matt Abrahams?

  Yes, you're gonna do great. I'm going to ask you the unfair question that I always get asked because I'll be curious about your answer. So people will often ask me, what's the one thing I can do to improve my communication? As if there is one magic key. But I'm asking you this question because I hope it gives you an opportunity to talk about something that we haven't talked about because we've talked about a lot of really deep, meaningful communication bits of advice. Know your audience, know yourself, paraphrase. Is there something that we haven't covered that you think is important?

• 19:00Speaker 01

  Practice. At the end of the day, the goal is not perfection. It doesn't exist. The goal is continual improvement. I want to keep getting better and better. And so the way to do that, of course, like any muscle-building activity, is practice. And so I really do not only create a lot of practice opportunities for my students in class, but I give them ideas of how they might continue practicing after the class is over. And my suggestion is to make it a little more challenging each time. So Start with the low-stakes day-to-day stuff. When you're chatting with your roommate, ask a few more questions than you might have otherwise asked, so that you build that inquiry muscle.

• 19:42Speaker 01

  But then, when you have a disagreement with a colleague, if you think, this might actually make a difference if I shared this one perspective, try out stating your intention, sharing your perspective, and then asking for a greater understanding on their perspective. And as we continue to have more and more repetition, right, as we build in the reps, we're not only going to build the muscle, which feels good, but then it's going to be ready for us to flex when the moment counts. When we're in the most consequential conversation, we will have already built up those great question-asking muscles, those great paraphrasing muscles, those great intention-stating muscles, and so on and so forth. So, practice, practice, practice, and make it a little more challenging each time along the way.

• 20:26Matt Abrahams?

  And I think that's absolutely dead-on. We have to practice. I'll be curious to hear your answer. Who's a communicator you admire, and why?

• 20:33Speaker 01

  Michelle Obama. Her authenticity is palpable. When she is sharing, it's not only real and true for her and others in the room, it's the heart of the matter. She's not being authentic about things on the fringe. She's getting to that piece that lands in the pit of my stomach, that I may not have had the courage to share. And she has so many great quotes, one of which is, "Courage is contagious." And I feel that in her presence, or when I'm watching a speech of hers. And then, of course, her ability to connect. She's fantastic at connection through relatable storytelling and humor, and I've seen that in her most casual and impromptu moments, and in her prepared speeches.

• 21:17Speaker 01

  It's just a part of who she is.

• 21:19Matt Abrahams?

  Courage is contagious. Really profound, actually, in connection, and the ability to connect. Storytelling is a key tool for that. All right. What are the first three ingredients that go into a successful communication recipe?

• 21:35Speaker 01

  Audience, intent or goal, and listening. We've already spoken about the importance of knowing where the other person is at and how to meet them where they are at, right? Emotionally, during that time of day or in their schedule, what matters most to them, understanding how to create a shared goal, right? Which goes into the second piece. And then the last piece, you might have thought it'd be something around know what your message is, or be clear on what your message is. But the reason I think it's listening is because if I'm really growing the shared pool of understanding, if I'm really hearing your perspective and understanding it to

• 22:17Speaker 01

  a level that I didn't understand before, I may actually have a new idea, right? I've heard the quote, "Dialogue is the birthplace of synergy." Your information and the way you made meaning of that information might create not just a new perspective within me, but a new meaning-making, a new understanding of what matters most and therefore what I most want to drive home. So, audience, intent or goal, and listening.

• 22:46Matt Abrahams?

  So, audience and intent and listening. Jen, this has been a fantastic conversation. You have equipped me and hopefully our listeners with many tools they can use, and you have certainly increased our shared understanding and meaning. Thank you for joining us and thank you for your time.

• 23:00Speaker 01

  Thank you for having me. This was fun.

• 23:04Matt Abrahams?

  Thank you for joining us for another episode of Think Fast, Talk Smart, the Podcast. To learn more about difficult conversations, listen to episode 22 with David Demarest. This episode was produced by Ryan Campos, Catherine Reed, and me, Matt Ibramz, at Spotify Studios in New York City. Our music is from Floyd Wonder. With special thanks to Podium Podcast Company. Find us on YouTube and wherever you get your podcasts. Be sure to subscribe and rate us. Also, follow us on LinkedIn and Instagram. And check out FasterSmarter.io for deep dive videos, English language learning content, and our newsletter.

• 23:42Matt Abrahams?

  Before we wrap up, I just want to say thank you for listening. It really means a lot to hear how people all over the world are using these ideas in their own lives. It inspires me and the whole team that brings you this show. If you want more episodes and resources, feel free to follow, subscribe, and explore past conversations. We're grateful for your support of Think Fast, Talk Smart.