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

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• Matt 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

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