Think Fast Talk Smart: Communication Techniques - 222. Discussing Through Discomfort: Why the Conversations You Avoid Cost You the Most

Episode Date: August 12, 2025

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, 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, 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.Episode Reference Links:Jenn WynnThe H.I. Note: Healing Inspirations from LifeEp.22 Under Pressure: How to Communicate Clearly and Timely During a Crisis  Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> [e-mail] Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedInChapters:(00:00) - Introduction (02:38) - Understanding Difficult Conversations (04:55) - Developing Emotional Intelligence (05:55) - Self-Awareness, Pause, Reframe (08:10) - Common Communication Barriers (10:06) - Listening for Understanding (12:43) - Using AI for Communication (14:35) - Creating Psychological Safety (17:11) - The Final Three Questions (23:39) - 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.Strawberry.me. Get 50% off your first coaching session today at Strawberry.me/smartJoin our Think Fast Talk Smart Learning Community and become the communicator you want to be. 

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Often the things we really want are on the other side of a difficult conversation. My name's Matt Abrams, 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 Wynn. 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. Thanks for having me, Matt. I'm excited to be here with you and the listeners, which include my executive MBA students. Yes, absolutely. Well, shall we get started? Yes.

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? 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 can, 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. And someone else will say, oh, I love a good negotiation. Let me take your negotiation on for you or saying no when a team member or a direct report wants extra resources or a loved one asks you for her. 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. 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. 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. 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. I want to choose the better, more strategic path, not the reaction that came out of an emotional trigger. It's more choicefulness. 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-aware. 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? 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? 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. 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 a 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 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. 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 Harbor Bridge. And when I get worked up, if I just envision that in what I felt like when I saw it, it's my place. 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 Gelfin, 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, 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. 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 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. 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 in the next one. You mentioned listening, and that's a skill that my wife is still encouraging. I'm curious, how do you help your students to be better listeners in these difficult conversations? 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 to 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 it back as a check for my understanding. A real humble attempt to say, this is my summary of what I think experience, 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. 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 skills, 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. 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.

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. And then recently I had a student really enjoyed 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. 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? So on the High Note podcast, we're talking about how people heal. 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 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 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 strength-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. 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, a quick word from one of our sponsors. Their support allows us to bring you this show free of charge. If you've ever felt like you're trying to do everything yourself, especially when the stakes are high, you're not alone.

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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? I think so. Yes, you're going to 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? 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, 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. 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. And I think that's absolutely dead on. We have to practice. I'll be curious to you. I'll be

curious to hear your answer. Who's a communicator you admire and why? 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. It's just a part of who she is. Courage is contagious, really profound, actually, and 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? 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 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. 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 and you have certainly increased our shared understanding and meaning.

Thank you for joining us and thank you for your time. Thank you for having me. This was fun. 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 Ibrahims, 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.

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