Jay sits down with Harvard Business School professor Alison Wood Brooks, author of Talk: The Science of Conversation and the Art of Being Ourselves, to explore what makes great conversations actually work and where most of us get it wrong. Together, they unpack how to choose better topics, embrace the messiness of real dialogue, master the three stages of listening, and give compliments that genuinely connect. Alison also reveals why admitting uncertainty builds more trust than having all the answers, and shares practical conversation games you can start using right away. With Love and Gratitude, Jay Shetty Learn to own the conversations that matter most in Alison Wood Brooks' new class on MasterClass: The Conversation Advantage With Alison Wood Brooks | MasterClass PURPOSE10 for 10% at altrarunning.com/onpurpose. Free Shipping and Free 30-Day Trial. Head to https://wayfair.com right now to shop all things home and get your space ready for less. JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast What We Discuss: 00:00 Introduction 01:51 Shifting Focus from Yourself In Conversation 05:31 Lowering Your Anxiety with Topic Prep 08:30 Is It Better to Be Interesting or Interested? 09:45 The Butterfly Net Metaphor 13:00 Low-Stakes Practice To Build High-Stakes Confidence 14:00 Debunking Traditional Rules of Persuasion 15:55 Building Conversational Safety Through Validation 17:06 Agenda-Free Relationships vs. Manipulative Networking 20:36 The Power of Follow-Up Questions 24:00 Embracing the Natural Messiness of Dialogue 26:11 Unrealistic Standards Set by Media and Podcasts 27:06 Alison's Top Three Small Talk Techniques 29:22 Balancing Leading vs. Following in Conversation 32:40 Does Your Mind Wander During Conversation? 33:40 The Power of Callbacks 34:00 The Attention Crisis and Screen Disruption 37:09 Strategies for Staying Present 39:00 Reciprocity and the Good-to-Great Question Shift 41:14 Intimate Openers and Stealth Topic-Switching 46:12 How to Respond to One Word Answers 47:35 Game 1: Spontaneous Depth and Sincerity 51:57 Game 2: Breaking Through Reserve 55:56 Talk Time Game: Battle of the Nice Guys 01:01:03 The Compliment Landmines to Avoid 01:04:00 This Is Damaging Your Potential Connections 01:09:48 The Best Way to Receive a Compliment 01:12:30 Talk Time Game: Admitting Uncertainty 01:21:30 Feel More Confident During Conversations 01:22:05 Dating Conversations and the First-Date Pause 01:26:20 Reviving a Dying Date Conversation 01:29:54 Deconstructing the "36 Questions to Fall in Love" 01:31:40 Defusing Heated Disagreements 01:32:22 Preparing for Difficult Conversations 01:34:00 When Distance Is Better Than Talking 01:37:45 Alison Wood Brooks on Final Five Learn more about your ad choices. Visit podcastchoices.com/adchoices