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

Summary

Podcast Summary: Think Fast Talk Smart – Episode 222 Title: Discussing through Discomfort: Why the Conversations You Avoid Cost You the Most
Release Date: August 12, 2025

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In Episode 222 of Think Fast Talk Smart: Communication Techniques, host Matt Abrahams delves into the intricate dynamics of difficult conversations with esteemed guest Jennifer Wynn, a professor at NYU Stern School of Business. This episode, titled "Discussing through Discomfort: Why the Conversations You Avoid Cost You the Most," offers profound insights into navigating challenging dialogues that are often pivotal for personal and professional growth.

Introduction to Difficult Conversations

Matt Abrahams opens the discussion by highlighting the significance of difficult conversations, asserting that "the things we really want are on the other side of a difficult conversation." He introduces Jennifer Wynn, emphasizing her expertise in teaching strategies for handling such interactions effectively. Jennifer echoes this sentiment, stressing that emotions lie at the heart of what makes certain conversations challenging.

The Core of Difficulty: Emotions and Self-Awareness

Jennifer Wynn elaborates on why some conversations are tougher than others, pinpointing emotional reactivity as the central barrier. At approximately [01:02], she shares, "what makes a conversation difficult is much less the topic and much more the inner experience that each person is having." This perspective underscores the importance of self-awareness and emotional intelligence in managing difficult dialogues.

Key Takeaways:

• Self-Awareness: Recognizing one’s emotional triggers is crucial. Jennifer introduces the Self Awareness Pause Reframe framework, emphasizing the need to pause when emotionally triggered and reframe the conversation to perceive it as a learning opportunity rather than a threat.
• Emotional Regulation: Techniques such as envisioning a calming place or imagining a supportive friend can help regulate the nervous system, enabling a more composed and strategic response.

Strategies for Effective Difficult Conversations

The conversation shifts to practical strategies that facilitate productive difficult conversations. Jennifer outlines several key tactics:

1. Self Awareness, Pause, Reframe (SAP):

   • Self Awareness: Identify physical and emotional cues indicating stress or triggers. For instance, Matt shares, "when I'm ready for battle or feel like battle's coming, my whole chest gets tight" ([06:55]).
   • Pause: Take a moment to center oneself, utilizing techniques like imagining a serene place ([07:01]) or a supportive friend.
   • Reframe: Shift perspective from viewing the conversation as a threat to seeing it as an opportunity for learning and growth.

2. Listening as a Core Skill: Jennifer emphasizes that listening is not just about hearing words but about seeking a shared understanding. She introduces the components of effective listening:

   • Inquiry: Asking open-ended questions to fully understand the other person’s perspective.
   • Paraphrasing: Reflecting back what the other person has said to ensure accurate comprehension.
   • Advocacy: Sharing one’s own perspective after fully understanding the other’s viewpoint.

   Notable Quote:

   “Dialogue is the free flow of meaning. Effective dialogue grows the shared pool of understanding between us.”
   — Jennifer Wynn [10:25]

3. Overcoming Common Barriers: Jennifer identifies major obstacles in having difficult conversations:

   • Avoidance: Fear of negative outcomes often prevents initiating necessary dialogues.
   • Lack of Goals: Without clear objectives, conversations can become unproductive.
   • Insufficient Listening: Failing to actively listen can hinder mutual understanding and resolution.

The Role of Artificial Intelligence in Enhancing Communication

Addressing the rising influence of AI, Jennifer discusses how tools like ChatGPT can aid in preparing for difficult conversations. Examples include:

• Tone Adjustment: Using AI to refine the tone of messages to ensure they are received as intended.
• Perspective Generation: Leveraging AI to explore different viewpoints and enhance understanding.
• Role-Playing Simulations: Practicing conversations with AI to build confidence and strategy.

Building Psychological Safety and Connection

Jennifer shares her approach from her own podcast, the High Note Podcast, where she fosters a safe environment by starting with affirmations. By expressing genuine appreciation for her guests, she creates a foundation of trust and openness, enabling deeper and more meaningful conversations about personal hardships.

She extends this concept to her classroom, where initial exercises focused on sharing strengths create a psychologically safe space. This approach not only enhances student participation but also cultivates a more supportive and brave learning environment.

Practical Tips for Continuous Improvement

As the conversation wraps up, Jennifer emphasizes the importance of practice in honing communication skills:

• Gradual Challenge: Start with low-stakes conversations and progressively tackle more challenging dialogues.
• Consistent Repetition: Regular practice builds and reinforces effective communication habits, much like muscle training.
• Incremental Difficulty: Each practice session should introduce slightly more complexity to continuously develop skills.

Notable Quote:

“The goal is not perfection. It doesn't exist. The goal is continual improvement.”
— Jennifer Wynn [19:13]

Conclusion and Final Insights

The episode concludes with Jennifer highlighting Michelle Obama as a communicator she admires for her authenticity and connection. Her ability to relate through storytelling and humor exemplifies the impactful communication techniques discussed throughout the episode.

Final Thoughts:

• Audience Intent & Listening: Understanding the audience’s needs and actively listening are foundational to successful communication.
• Shared Understanding: Striving for mutual comprehension fosters stronger relationships and more effective interactions.
• Continuous Practice: Consistently applying learned strategies ensures ongoing improvement and adaptability in diverse communication scenarios.

Key Quotes and Timestamps

• Jennifer Wynn on Emotions in Conversations:

  "What makes a conversation difficult is much less the topic and much more the inner experience that each person is having."
  — [01:26]

• Jennifer on Dialogue:

  "Dialogue is the free flow of meaning. Effective dialogue grows the shared pool of understanding between us."
  — [10:25]

• Jennifer on Continuous Improvement:

  "The goal is not perfection. It doesn't exist. The goal is continual improvement."
  — [19:13]

• Jennifer on Michelle Obama:

  "Courage is contagious."
  — [21:14]

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Episode 222 offers a comprehensive exploration of the complexities surrounding difficult conversations, providing listeners with actionable strategies to transform discomfort into opportunities for growth and connection. By emphasizing self-awareness, active listening, and continuous practice, Matt Abrahams and Jennifer Wynn equip individuals with the tools necessary to navigate and excel in challenging dialogues.

Transcript

[Matt Abrahams]

Hi Matt here. As September approaches, many of us are heading back to school and work to help get you back in the groove and hone your communication skills. Check out daily Back to basic videos we'll be publishing each day. In August, we have identified a weekly communication topic and we'll share a short, helpful video each day at 7am Pacific on our YouTube, Instagram and TikTok channels. Please check out these practical, helpful videos and be sure to follow us to get your daily dose of Think Fast, Talk Smart. You can you can see a complete calendar at fastersmarter IO Basics.

Often the things we really want are on the other side of a difficult conversation. My name is 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 Wynn. Jen is a professor at NYU Stern School of Business, where she's taught a class on difficult conversations for nearly 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.

[Jennifer Wynn]

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

[Matt Abrahams]

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Yes, absolutely. Well, shall we get started?

[Jennifer Wynn]

Yes.

[Matt 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 from?

[Jennifer Wynn]

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. 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 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. 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 recenter, 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 gonna 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.

[Matt 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.

[Jennifer Wynn]

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.

[Matt 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?

[Jennifer Wynn]

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?

[Matt Abrahams]

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

[Jennifer Wynn]

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.

[Matt 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 invitation. One of my colleagues, Michelle Gelfin, likes to say, mind your metaphors and the metaphor you bring 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.

[Jennifer Wynn]

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 gonna require us to get to the other side of a difficult conversation. So are you just gonna 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.

[Matt 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 resol 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 me to work on. I'm curious, how do you help your students to be better listeners in these difficult conversations?

[Jennifer Wynn]

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 to, 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 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. 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 2/3, 1/3 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.

[Matt 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. And 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?

[Jennifer Wynn]

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. 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 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.

[Matt 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?

[Jennifer Wynn]

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 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 learned 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 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.

[Matt 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.

Before we finish our conversation, a quick message from our sponsors. Their support helps us bring you our show. This episode is sponsored by BetterHelp. As someone who is always trying to learn and improve, I know firsthand how hard it can be to figure out exactly what will work. In a world where information overload is all around us about mental health and wellness, it can be a struggle to know what's true and what actions we should take. I believe everyone should leverage the support of therapists and coaches to help figure out what's right for us. Using trusted resources and talking to live therapists can get you personalized recommendations and help you break through the noise. As the largest online therapy provider in the world, BetterHelp can provide access to mental health professionals with a diverse variety of expertise. Talk it out with BetterHelp Think Fast. Talk Smart listeners get 10% off their first month at betterhelp.com thinkfast that's betterhelp.com thinkfast hi Matt, here. What if you could learn a new idea that sparked your curiosity every day? Well, you can, with the iconic podcast from ted. TED Talks Daily. Listen in and get a new TED Talk every day from the world's greatest thinkers. Find out why good people become bad bosses. Hear the case for everyone to be able to vote on their phone. Learn about what being on the autism spectrum actually means. Plus, you'll get great communication in action. Check out TED Talks Daily wherever you get your podcasts.

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?

[Jennifer Wynn]

I think so.

[Matt Abrahams]

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?

[Jennifer Wynn]

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. 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, and 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.

[Matt 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?

[Jennifer Wynn]

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's 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.

[Matt Abrahams]

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?

[Jennifer Wynn]

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.

[Matt Abrahams]

So, audience 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.

[Jennifer Wynn]

Thank you for having me. This was fun.

[Matt 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, Kathryn Reed and me, Matt Abrahams at the 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 fastersmarterio for deep dive videos, English language learning content and our newsletter. I wanted to share with you that.

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