Think Fast Talk Smart: Communication Techniques

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

355 snips

Aug 12, 2025

Jenn Wynn, a professor at NYU Stern and former director of education at the Obama Foundation, dives into the power of tackling uncomfortable conversations. She argues that the success and fulfillment we seek often lie just beyond those tricky discussions. Wynn emphasizes the importance of self-awareness and emotional intelligence in navigating tough talks, whether with a colleague or oneself. She also shares practical tips on starting with low-stakes conversations to build confidence, highlighting that these skills are transformative for both personal and professional growth.

Ask episode

AI Snips

Chapters

Transcript

Episode notes

INSIGHT

Emotions Drive Conversation Difficulty

Emotions and emotional reactivity make conversations difficult.
Recognize your inner experience to pause and choose a better response.

ADVICE

Self-Awareness, Pause, Reframe

Remember the simple framework: self-awareness, pause, reframe.
Notice physical triggers, pause, and reframe the interaction as a learning opportunity.

INSIGHT

Goals Often Sit Behind Hard Talks

Many of the things we want in life require navigating a difficult conversation.
Avoiding those talks often means giving up on important goals and relationships.

Get the Snipd Podcast app to discover more snips from this episode

Get the app

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:

Connect:

Premium Signup >>>> Think Fast Talk Smart Premium
Email Questions & Feedback >>> hello@fastersmarter.io
Episode Transcripts >>> Think Fast Talk Smart Website
Newsletter Signup + English Language Learning >>> FasterSmarter.io
Think Fast Talk Smart >>> LinkedIn, Instagram, YouTube
Matt Abrahams >>> LinkedIn

Chapters:

(00:00) - Introduction
(01:55) - Understanding Difficult Conversations
(04:12) - Developing Emotional Intelligence
(05:12) - Self-Awareness, Pause, Reframe
(07:27) - Common Communication Barriers
(09:23) - Listening for Understanding
(12:00) - Using AI for Communication
(13:52) - Creating Psychological Safety
(16:28) - The Final Three Questions
(23:30) - Conclusion

*****
Thank you to our sponsors. These partnerships support the production of the podcast, allowing us to bring it to you at no cost.

This episode is brought to you by Babbel. Think Fast Talk Smart listeners can get started on your language learning journey today- visit Babbel.com/Thinkfast and get up to 55% off your Babbel subscription.

Support Think Fast Talk Smart by joining TFTS Premium.