340. Rethinks: Why the Conversations You Avoid Cost You the Most

“Most things that we want in life are on the other side of a difficult conversation.”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? In this Rethinks episode of Think Fast, Talk Smart, Jenn Wynn, a professor at NYU Stern School of Business and previously the director of education at the Obama Foundation, joins Matt Abrahams to 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.Takeaways: Difficult conversations create opportunities for growth. Speaking up, setting boundaries, and addressing conflict can help us build stronger relationships and move closer to our goals.Confidence comes from communicating through discomfort. Developing the skills to navigate challenging discussions helps us overcome fear and approach difficult conversations with greater intention.Activity:Have the hard conversation. Identify a conversation you've been avoiding and write down what you want to achieve and what's holding you back. Then, take one step toward having it, whether that's scheduling a time to talk or practicing your opening words.Episode Reference Links:Jenn WynnEp.222 Discussing Through Discomfort: Why the Conversations You Avoid Cost You the Most Connect:Premium Signup >>>> Think Fast Talk Smart PremiumEmail Questions & Feedback >>> hello@fastersmarter.ioEpisode Transcripts >>> Think Fast Talk Smart WebsiteNewsletter Signup + English Language Learning >>> FasterSmarter.ioThink Fast Talk Smart >>> LinkedIn, Instagram, YouTubeMatt Abrahams >>> LinkedIn Chapters:(00:00) - Introduction (01:28) - Understanding Difficult Conversations (03:45) - Developing Emotional Intelligence (04:45) - Self-Awareness, Pause, Reframe (07:00) - Common Communication Barriers (10:04) - Listening for Understanding (13:11) - Feedback to Your Boss (17:04) - Reinforcing Good Behavior (20:04) - Using AI for Communication (21:31) - Lessons from the Obama Foundation (25:07) - Creating Psychological Safety (28:01) - The Final Three Questions (32:42) - 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.