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:

• Jenn Wynn
• The H.I. Note: Healing Inspirations from Life
• Ep.22 Under Pressure: How to Communicate Clearly and Timely During a Crisis

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
• (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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How do you stay clear, calm, and precise when every word counts and there’s no room for error?

Staying calm and focused while translating high-stakes conversations in real time isn’t just a language skill — it’s a masterclass in communication under pressure. And for Giampaolo Bianchi, simultaneous interpreter for the United Nations and World Health Organization, it’s a challenge he meets with presence, precision, and a whole lot of preparation. In this expanded conversation from our Spontaneous Speaking series, Bianchi offers a behind-the-scenes look at how he prepares for — and performs in — moments where being calm, in control, and adaptable are essential.
“We don’t translate words — we translate ideas,” Bianchi explains, highlighting the mindset shift that allows interpreters to go beyond language and convey meaning with clarity and nuance. He shares the role of rigorous preparation, physical grounding, and mental focus in his work, and explains how tools like note systems, pre-session rituals, and active listening help manage cognitive load during live interpretation.
In this episode of Think Fast, Talk Smart, Bianchi and host Matt Abrahams explore how the principles of simultaneous interpretation apply far beyond the booth — offering valuable strategies for anyone who needs to communicate effectively under pressure, adapt in the moment, and ensure their smartest communication happens without a script.

Episode Reference Links:

• Giampaolo Bianchi
• Ep.197 Prep or Perish: Mastering In-the-Moment Communication (1 of 3)
• Ep.198 Pause and Effect: Mastering In-the-Moment Communication (2 of 3)
• Ep.199 Blunder Pressure: Mastering In-the-Moment Communication (3 of 3)
• Ep.203 No Script, No Problem: Final Secrets to Speaking Under Pressure (Bonus)

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
• (02:42) - Becoming a UN Interpreter
• (03:50) - Staying Calm Under Pressure
• (05:03) - Translating Emotion, Not Just Words
• (06:10) - Memory and Focus Techniques
• (07:51) - The Power of Preparation
• (09:17) - Pre-Meeting Rituals and Readiness
• (10:34) - Handling Mistakes in Real Time
• (11:44) - Interpreter Habits in Daily Life
• (12:45) - The Final Three Questions
• (17:02) - Conclusion

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Master the art of thinking on your feet and turning unpredictability into powerful communication.

Being quick on your feet isn’t just a performance skill — it’s a communication necessity. And for Peter Sagal, longtime host of NPR’s Wait Wait… Don’t Tell Me, it’s a craft he’s honed over more than two decades in front of a live audience. In this expanded conversation from our Spontaneous Speaking series, Sagal shares what it really takes to communicate with presence, flexibility, and confidence when the script goes out the window.
“My job was no longer to be funny — my job was to make funny possible,” Sagal explains, reflecting on the shift from performer to facilitator. He opens up about how structure and ritual prepare him to embrace chaos, why listening matters more than cleverness, and how he defines success not by what he says, but by what others are able to say because of him. “Preparation is key,” he notes, “but being willing to let go of that preparation and follow what’s happening in the moment is really important.”
In this episode of Think Fast, Talk Smart, Sagal and host Matt Abrahams discuss how to navigate speaking on the spot—whether you're managing meetings, leading teams, or handling high-stakes conversations—and offer a powerful reminder: the best spontaneous communicators don’t control the moment—they connect through it.

Episode Reference Links:

• Peter D Sagal
• Ep.197 Prep or Perish: Mastering In-the-Moment Communication (1 of 3)
• Ep.198 Pause and Effect: Mastering In-the-Moment Communication (2 of 3)
• Ep.199 Blunder Pressure: Mastering In-the-Moment Communication (3 of 3)
• Ep.203 No Script, No Problem: Final Secrets to Speaking Under Pressure (Bonus)

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
• (02:41) - Making Funny Possible
• (03:50) - Ditching the Script
• (07:05) - Pre-Show Rituals
• (09:20) - How to Introduce People Well
• (12:23) - Being Funny in the Moment
• (14:17) - Staying Present On Stage
• (16:37) - Gracious Communication
• (19:53) - The Final Three Questions
• (23:29) - Conclusion

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This episode is sponsored by Grammarly. Let Grammarly take the busywork off your plate so you can focus on high-impact work. Download Grammarly for free today
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