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

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.

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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:

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Chapters:

(00:00) - Introduction (02:27) - Understanding Difficult Conversations (04:44) - Developing Emotional Intelligence (05:44) - Self-Awareness, Pause, Reframe (07:59) - Common Communication Barriers (09:55) - Listening for Understanding (12:32) - Using AI for Communication (14:24) - Creating Psychological Safety (17:00) - The Final Three Questions (23:45) - Conclusion

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