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.
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insights INSIGHT
Emotions Drive Conversation Difficulty
Emotions and emotional reactivity make conversations difficult.
Recognize your inner experience to pause and choose a better response.
volunteer_activism 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.
insights 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.
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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.
Think Fast Talk Smart: Communication Techniques